WO2019140253A1 - Composés, compositions et procédés de modulation du goût salé - Google Patents

Composés, compositions et procédés de modulation du goût salé Download PDF

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Publication number
WO2019140253A1
WO2019140253A1 PCT/US2019/013289 US2019013289W WO2019140253A1 WO 2019140253 A1 WO2019140253 A1 WO 2019140253A1 US 2019013289 W US2019013289 W US 2019013289W WO 2019140253 A1 WO2019140253 A1 WO 2019140253A1
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WIPO (PCT)
Prior art keywords
composition
compound
salt
compounds
formula
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PCT/US2019/013289
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English (en)
Inventor
Stuart Hayden
Ryan LOY
Dennis Sawchuk
Melissa WOLFF
Wa ZHANG
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Chromocell Corp
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Chromocell Corp
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/40—Table salts; Dietetic salt substitutes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present disclosure relates to flavor enhancers in foods, beverages, pharmaceuticals, and other edible compositions. More specifically, the present disclosure relates to compounds for use in edible compositions for increasing the perception of saltiness in comestible products.
  • the present disclosure provides comestible compositions comprising carnitine salts, betaine salts, and combinations thereof.
  • the present disclosure provides compounds that modulate salty taste, edible compositions comprising such compounds, blends of such compounds, and methods of using and preparing such edible compositions.
  • the present disclosure also provides methods of reducing the amount of sodium in an edible composition.
  • the present disclosure further provides a method of enhancing, modulating or potentiating the salty taste of an edible composition, such as a food, consumer or pharmaceutical product, in a subject.
  • the present disclosure further provides a method of enhancing, modulating or potentiating the salty taste of an edible composition comprising a salt, wherein the salt is at least one selected from a sodium, lithium, potassium, ammonium, magnesium, or alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate.
  • the present disclosure also provides methods of replacing an amount of one salt, selected from, but not limited to sodium chloride (NaCl), potassium chloride (KC1), ammonium chloride (NH 4 Cl), magnesium chloride(MgCl2), and calcium chloride (CaCk), or combinations thereof with at least one compound as disclosed herein, without producing an off-taste.
  • the present disclosure also provides a method of modulating, particularly enhancing or potentiating the activation of a salty taste receptor.
  • the present disclosure also provides a method of modulating, particularly enhancing or potentiating the activation of an ENaC receptor.
  • a further aspect of the present disclosure provides compounds or blends with taste improving compounds , such as bitter-blockers.
  • one or more of the compounds that modulate, enhance, or potentiate salty taste or saltiness intensity of an edible composition are synthesized. In one aspect of the present disclosure one or more of the compounds that modulate, enhance, or potentiate salty taste or saltiness intensity of an edible composition are biosynthesized. In a further aspect of the present disclosure one or more of the compounds that modulate, enhance, or potentiate salty taste or saltiness intensity of an edible composition are bio-converted. In another aspect of the present disclosure one or more compounds that modulate, enhance, or potentiate salty taste, saltiness intensity or perception of saltiness intensity of an edible composition is separated from its naturally occurring environment, if it is derived from a natural source or product. In another aspect of the present disclosure one or more compounds that modulate, enhance, or potentiate salty taste, saltiness intensity or perception of saltiness intensity of an edible composition is isolated and purified.
  • One aspect of the present disclosure provides edible compositions for modulating salty taste (e.g ., enhancing salty taste, enhancing saltiness intensity, perception of saltiness, or perception of saltiness intensity) of a salt or salty tastant.
  • the edible compositions comprise at least one compound of Formula (I), comestibly or biologically acceptable salts, solvates, enantiomers, diastereomers, or derivatives thereof, or combinations of any of the compounds.
  • the edible compositions comprise at least one compound of Formula (II), comestibly or biologically acceptable salts, solvates, enantiomers, diastereomers, or derivatives thereof, or combinations of any of the compounds.
  • the compositions comprise a compound of Formula (I), Formula (II), any one of Compounds 1 to 19, or any combination of the foregoing compounds.
  • the compositions comprise two or more compounds of Formula (I), Formula (II), any one of Compounds 1 to 19, or any combination of the foregoing compounds.
  • the comestibly or biologically acceptable salt of the compound(s) is selected from hydrochloride salt, calcium salt, potassium salt, ammonium salt, magnesium salt, tartrate salt, succinate salt, fumarate salt, and carbonate salt.
  • the compound is the inner salt of carnitine.
  • the compound is the inner salt of betaine.
  • the edible composition further comprises an organic or inorganic acid.
  • the organic acid is selected from hydrochloric acid, tartaric acid, fumaric acid, carbonic acid, and succinic acid.
  • the organic acid is tartaric acid.
  • the organic acid is succinic acid.
  • the salt is at least one selected from a sodium, lithium, potassium, ammonium, magnesium, calcium or alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate.
  • the salt is one selected from NaCl, KC1, NH 4 Cl, MgCh, CaCh or combinations thereof. In some embodiments, the salt is NaCl.
  • taste modulators as disclosed herein may be combined with any suitable salt selected from, but not limited to NaCl, KC1, NH 4 CL, MgCh, and CaCh or combinations thereof, to provide a composition having enhanced saltiness.
  • the compound is present at or below its saltiness threshold.
  • the compounds provided herein such as a compound of Formula (I), Formula (II), any one of Compounds 1 to 19, or combinations of thereof
  • the saltiness modulators may themselves provide salty taste at concentrations above a saltiness threshold level. It is noted that the saltiness modulators may be effective as enhancers even if present at concentrations above their saltiness threshold level. In such embodiments, there is major contribution of the saltiness enhancer to the saltiness of the composition via enhancement of the inherently salty taste attributed to a salt, where the salt is also present in the composition and the perceived saltiness is greater than the additive saltiness of the salt and the compound.
  • the present disclosure provides a method of modulating the saltiness or salty taste (e.g ., enhancing salty taste, enhancing saltiness intensity, perception of saltiness, or perception of saltiness intensity) of a salt comprising combining (i) at least one salt, such as NaCl, KC1, NH 4 CL, MgCh, or CaCh and (ii) one, two or more compounds according to Formula (I), Formula (II), comestibly or biologically acceptable salts, solvates, enantiomers, derivatives thereof, enantiomers thereof, any one of Compounds 1-19, or combinations of any of the foregoing compounds.
  • a salt such as NaCl, KC1, NH 4 CL, MgCh, or CaCh
  • Formula (II) comestibly or biologically acceptable salts, solvates, enantiomers, derivatives thereof, enantiomers thereof, any one of Compounds 1-19, or combinations of any of the foregoing compounds.
  • the compositions comprise a compound of Formula (I), Formula (II), any one of Compounds 1 to 19 or any combination of the foregoing compounds.
  • the comestibly or biologically acceptable salt of the compound(s) in the edible composition is selected from hydrochloride salt, tartrate salt, fumarate salt, carbonate salt, and succinate salt.
  • the comestibly or biologically acceptable salt is the inner salt of the compound.
  • the comestibly or biologically acceptable salt is a salt selected from calcium chloride salt, ammonium chloride salt, potassium chloride salt and Magnesium chloride salt of the compound.
  • the composition further comprises an organic acid.
  • the organic acid is selected from tartaric acid, fumaric acid, carbonic acid, and succinic acid. In some embodiments, the organic acid is tartaric acid. In some embodiments, the organic acid is succinic acid. In some embodiments, the edible composition comprises a blend of at least one first compound with at least one second compound as disclosed herein, wherein the first and second compound are different compounds.
  • the edible composition comprises a blend of at least one first compound selected from a compound according to Formula (I), Formula (II), any one of
  • the edible composition further comprises a third compound according to Formula (I), Formula (II), any one of Compounds 1 to 19 or any combination of the foregoing compounds, wherein the third compound is different form the first and second compound in the composition.
  • the edible composition further comprises an organic acid.
  • the second compound is an organic acid.
  • the third compound is an organic or inorganic acid.
  • the organic acid is selected from hydrochloric acid, tartaric acid, fumaric acid, carbonic acid, and succinic acid.
  • the organic acid is tartaric acid.
  • the organic acid is succinic acid.
  • the edible composition comprises a blend of Compound 1 and Compound 6. In some embodiments, the edible composition comprises a blend of Compound 1 and Compound 6. In some embodiments, the edible composition of the present disclosure comprises a blend of L-Camitine HC1 and L-Camitine Tartrate. In some embodiments, the edible composition comprises a blend of Compound 1 and Compound 8. In some embodiments, the edible composition comprises a blend of L-Carnitine HC1 and L-camitine succinate. In some embodiments, the edible composition comprises a blend of Compound 8 and Compound 14. In some embodiments, the edible composition comprises a blend of L-camitine Succinate and Betaine HC1. In some embodiments, the edible composition comprises a blend of Compound 1 and Compound 3. In some embodiments, the edible composition comprises a blend of
  • the edible composition comprises a blend of compound 4 and Compound 1.
  • the comestible composition comprises a blend of Acetyl -L-camitine (inner salt) and L- Carnitine HC1.
  • the comestible composition comprises a blend of Compound 3, Compound 1 and an organic acid.
  • the organic acid is tartrate.
  • the organic acid is succinate.
  • the comestible composition comprises a blend of L-Camitine (inner salt)), L-Carnitine HC1 and tartrate.
  • the comestible composition comprises a blend of L-Camitine (inner salt)), L- Carnitine HC1 and succinate. In some embodiments, the comestible composition comprises a blend of Compound 14 and succinate. In some embodiments, the comestible composition comprises a blend of betaine HC1 and succinate.
  • the present disclosure provides a method of modulating or enhancing the saltiness or salty -taste of a salt comprising combining (i) at least one salt, such as but not limited to NaCl, KC1, NLLCL, MgCh, or CaCh and (ii) a compound of the present disclosure, such as a compound of Formula (I), Formula (II), any one of Compounds 1-19, or comestibly or biologically acceptable salts, solvates, enantiomers, or derivatives thereof, or enantiomers thereof, or combinations thereof.
  • the compositions comprise a compound of Formula (I), Formula (II), any one of Compounds 1 to 19, or any combination of the foregoing compounds.
  • the compositions comprise Compound 1. In some embodiments, the compositions comprise Compound 6. In some embodiments, the compositions comprise a blend of Compound 1 and Compound 6.
  • the method as disclosed herein may further comprise combining at least one salty taste improving composition. In some embodiments, the method may further comprise adding an organic acid to one or more compounds as disclosed herein. In some embodiments, the method comprises adding an organic acid to two or more compounds as disclosed herein.
  • the organic acid is one selected from as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl) benzoic acid, cinnamic acid, mandelic acid, methanessulfonic acid, ethanesulfonic acid, l,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzensulfonic acid, 4-chlorobenzenesulfonic acid, 2- naphthalenesulfoic acid,4-tokuenesulfonic acid, comphorsulfonic acid, 4-methylbicyclo[2.2.2]- octo-2-ene-l-carbolyclic acid, glucoheptonic
  • the organic acid is one selected from tartaric acid, fumaric acid, succinic acid, and carbonic acid.
  • the methods as disclosed herein may comprise adding an inorganic acid to one, two or more of the compounds as disclosed herein.
  • the inorganic acid is selected from hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like.
  • Compounds as disclosed herein or blends thereof may be added in an amount at or below their saltiness threshold. In some embodiments, the compounds or blends thereof may be added above their saltiness threshold.
  • the Compounds in the blend are added at various ratios.
  • Compound 1 and Compound 6 are added in a ratio of at or about 2: 1, or 1 : 2, respectively.
  • Compound 1 and Compound 6 are added in a ratio of at or about 1 : 1, respectively.
  • the Compound are added in a ratio at or about 3 : 1 or 1 :3, respectively.
  • compositions such as food products, pharmaceutical preparations and table-top salts comprising the compositions of the present disclosure; methods for preparing an edible composition; methods for reducing the amount of a salt in an edible composition; methods of enhancing activation of a salty taste receptor, methods of enhancing an ENaC receptor, methods of synthesizing the compounds of the present disclosure from natural sources, and methods of preparing the compounds of the present disclosure using biosynthetic methods as they occur in nature.
  • the method may further comprise combining at least one comestible composition as disclosed herein.
  • the compounds or blends of said compounds such as compounds defined by Formula (I), or (II), or any one compounds 1-19
  • the compounds or blends of said compounds may be added in an amount at or below their saltiness threshold.
  • the compounds or blends thereof as disclosed herein such as compounds defined by Formula (I), or (II), or any one compounds 1-19
  • the compounds as disclosed herein do not impart undesirable characteristics as described with other salt replacers (e.g. KC1).
  • the compounds provided herein can be added to low sodium, or reduced sodium food and beverage products to enhance the saltiness and palatability of these products, ultimately increasing consumer acceptability of such products.
  • Low sodium, or reduced sodium food and beverage products may further comprise a salt selected from KC1, NFLCL, MgCh, or CaCh .
  • the compound(s) disclosed herein that elicits an increased perception of saltiness is included in a comestible composition, such as food or beverage products, pharmaceutical products, nutritional products, dietary supplements, over-the-counter medications, or non-comestible composition, such as oral care products, hygienic products, cleansing products, or cosmetic products.
  • a comestible composition such as food or beverage products, pharmaceutical products, nutritional products, dietary supplements, over-the-counter medications, or non-comestible composition, such as oral care products, hygienic products, cleansing products, or cosmetic products.
  • compositions such as food products, pharmaceutical preparations and table-top salts comprising the compositions of the present disclosure; methods for preparing an edible composition; methods for reducing the amount of a salt in an edible composition; methods of enhancing activation of a salty taste receptor, methods of synthesizing the compounds of the present disclosure from natural sources, and methods of preparing the compounds of the present disclosure using biosynthetic methods.
  • a composition comprising: one or more carnitine salt or one or more betaine salt, or combinations thereof; and at least one salt, selected from sodium, lithium, potassium, ammonium, magnesium, calcium, or alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate; wherein said compositions is edible and capable of modulating or enhancing the taste of said salt, when compared to a composition not comprising said carnitine or said betaine salt.
  • composition comprising:
  • Ri is each independently H, CH 3 , C 2 H 5 , C 3 H 7 , or aryl
  • R 2 is H, COCH 3 , COC 2 H 5 , COC 3 H 7 , or COaryl;
  • R3 is absent, H, CH 3 , C 2 H 5 , C 3 H 7, or aryl;
  • n l or 2
  • Xi absent, Cl, tartrate, fumarate, succinate, or carbonate
  • X 2 absent, NH 4 , K, Ca, Mg;
  • Ri is each independently H, CH 3 , C 2 H 5 , C 3 H 7 , or aryl;
  • R 2 is CO2R3, CH2CO2H, C2H5CO2H, CO2COCH3, CO2COC2H5, CO2COC3H7, or CO COaryl;
  • R3 is absent or H
  • n l or 2;
  • Xi absent, Cl, tartrate, fumarate, succinate, or carbonate
  • X 2 absent, NH 4 , K, Ca, Mg;
  • composition is edible and capable of modulating or enhancing the salty taste of said salt, when compared to a control composition.
  • composition according to any of paragraph 21, 22 or 23, wherein n l. 25. The composition according to any one of paragraphs 21-24, wherein Xi is absent.
  • composition according to paragraph 27, 28 or 29, wherein n l.
  • composition according to paragraph 57, wherein R 2 is H. 59.
  • composition according to paragraph 57, 58 or 59, wherein n l.
  • composition according to Formula (II) of paragraph 2 wherein Ri is -CH 3. 81.
  • composition according to paragraph 92, 93 or 94, wherein n 2.
  • composition according to paragraph 98, 99 or 100, wherein n l.
  • composition according to paragraph 110, 111 or 112, wherein n l.
  • compound(s) is separated from its naturally occurring environment if it is derived from a natural source or product.
  • said composition according to paragraph 2 wherein said compound is one or more selected from Compound 1, Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, Compound 8, Compound 9, Compound 10, Compound 11, Compound 12, Compound 13, Compound 14, Compound 15, Compound 16, Compound 17, Compound 18, and Compound 19 or any combination of the foregoing Compounds, having the structure:
  • compositions is edible and capable of enhancing the perception of saltiness intensity of said salt
  • the salt is at least one selected from a sodium, lithium, potassium, ammonium, magnesium, or alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate.
  • composition according to paragraph 121, wherein the salt is MgCk.
  • composition according to paragraph 127 wherein said organic acid is selected from tartrate, succinate, carbonate, or fumarate.
  • compound(s) is present at or about at least 50 ppm and less than at or about 1500 ppm in the composition.
  • composition according to any one of the preceding paragraphs comprising: (a) a first compound, selected from a compound according to Formula (I), Formula (II), or any one of Compounds 1-19; and
  • composition according to claim 131 further comprising:
  • a second compound selected from tartrate, succinate, carbonate, and fumarate.
  • composition according to paragraph 131 or 133 wherein the first compound and the second compound in the composition are present in a ratio of at about 1 : 1, 2: 1, 3: 1, 1 :2, or 1 :3, respectively, and further wherein said composition can enhance the perception of saltiness intensity of said salt when compared to a composition not comprising said first and said second compound or when compared to a composition not comprising said first or said second compound.
  • composition according to claim 113 or 133 wherein the first compound is in the range of at or about 10-1500 ppm and the second compound is in the range of at or about 10-1500 ppm.
  • composition according to paragraph 132, wherein the third compound is in the range of at or about l0-l500ppm.
  • composition according to paragraph 132, wherein the first compound is
  • composition according according to any one of paragraphs 1, or 2-146 wherein said composition is capable of modulating or enhancing salty taste when compared under the same conditions to a composition not comprising said compound(s).
  • perception of salty taste of said salt is enhanced by at least about 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or 75% in an edible composition.
  • perception of salty taste of said salt is enhanced by at least about 1.1, 1.15, 1.2, 1.25, 1.3, 1.35, 1.4, 1.45, 1.5, 1.55, 1. 6, 1.65, 1.7, 1.75, 1.8, 1.85, 1.9, 1.95, or 2.0-fold in an edible composition.
  • composition according to any one of paragraphs 1, or 2-147, wherein the edible composition further comprises one or more salty taste improving additive(s).
  • improving additive is selected from yeast extract, hydrolyzed vegetable protein, IMP, GMP, MSG, monopotassium glutamate, calcium diglutamte, calcium lactate, sodium lactate, adenosine- 5 '-monophosphate, DHB (2,4-dihydroxybenzoic acid), lactose, sodium gluconate, amino acids, and vitamins. .
  • composition according to paragraph 152 wherein said carrier is selected from propylene glycol, ethanol, water, an alcohol-water mixture, triacetin, a triglyceride, and oil.
  • composition according to paragraph 153 wherein the carrier comprises starch.
  • the carrier comprises a
  • carbohydrate a maltodextrin, cyclodextrin or other dextrin, or a liposome.
  • ENaC epithelial sodium channel
  • composition according to any one of paragraphs 1, or 2-157 wherein the edible composition is selected from a food product, a consumer product, and a pharmaceutical composition.
  • composition according to paragraph 159 wherein the at least one amino acid forms a peptide bond with one or more compounds according to the compound of Formula (I), Formula (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, enantiomer, or derivative thereof, or a combination of any of the foregoing compounds.
  • alanine selected from alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine,
  • proline serine, threonine, tryptophan, taurine, and valine.
  • arginine selected from arginine, glycine, lysine, taurine, aspartic acid, methionine,
  • a method of enhancing the perception of saltiness intensity of one or more salt(s) in an edible composition comprising:
  • the salt in the edible composition is at least one selected from a sodium, lithium, potassium, ammonium, magnesium, and alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate.
  • a method for reducing the amount of one or more salts, selected from a sodium, lithium, potassium, ammonium, magnesium, and alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate, by about 1% to 95% or more in an edible composition comprising: adding an effective amount of one or more compound(s) of Formula (I), Formula (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, enantiomer, diastereomer thereof, or a combination of any of the foregoing compounds.
  • composition comprises:
  • the first compound in the composition is different from the second compound in the composition; and further wherein the composition is capable of modifying or enhancing salty taste, reducing bitter taste, and/or reduce off-taste.
  • composition further comprises a third compound.
  • said third compound is at least one organic acid selected from tartrate, fumarate, succinate, and carbonate.
  • composition comprises: (a) a compound according to Formula (I), (II), compounds 1-19, or a comestibly or biologically acceptable salt, solvate, enantiomer, diastereomer thereof, or a combination of any of the foregoing compounds; and
  • composition is capable of modifying or enhancing salty taste.
  • the compound is in the range of at or about 10-1500 ppm and the second compound is in the range at or about 10-1500 ppm.
  • a method of preparing an edible composition comprising:
  • composition is capable of modifying or enhancing salty taste.
  • composition is selected from a food product, a consumer product, and a pharmaceutical composition.
  • a tabletop salt composition comprising a salt and one or more of the compounds according to Formula (I), Formula (II), any one of Compounds 1-19, a comestibly or biologically acceptable salt, solvate, enantiomer, diastereomer, or derivative thereof, or a combination of any of the foregoing compounds. .
  • the tabletop salt composition according to paragraph 200 further comprising at least one bulking agent, additive, anti-caking agent, functional ingredient or a combination thereof.
  • a delivery system selected from the group consisting of a co-crystallized flavor composition with a salt, an agglomerated flavor composition, a compacted flavor composition, a dried flavor composition, a particle flavor composition, a spheronized flavor composition, a granular flavor composition or a liquid flavor composition, wherein the flavor composition comprises a compound selected from the compounds according to Formula (I), Formula (II), any one of Compounds 1-19, a comestibly or biologically acceptable salt, solvate, enantiomer, diastereomer, or derivative thereof, or a combination of any of the foregoing compounds.
  • a food product comprising:
  • said at least one compound is present in the food product in an amount sufficient to enhance a perception of salty taste of the food product and further wherein the salt in (a) is at least one selected from a sodium, lithium, potassium, ammonium, magnesium, and alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate.
  • Mac&Cheese a confectionary, a gum, a bakery product, an ice cream, a dairy product, a fruit snack, a chip or crisp, an extruded snack, a tortilla chip or com chip, a popcorn, a pretzel, a nut, a snack bar, a meal replacement, a ready meal, a soup, a pasta, a canned food, a frozen processed food, a dried processed food, an instant noodle, a chilled processed food, an oil or fat, a sauce dressing or condiment, a dip, a pickled product, a seasoning, a baby food, a spread, a chip or a crisp such as chips or crisps comprising potato, com, rice or other grain, vegetable (including raw, pickled, cooked and dried vegetables), a fruit, a grain, a soup, a seasoning, a baked product such as a ready-to-eat breakfast cereal, hot cereal or dough, an ice cream such as a frozen yogurt, a dairy products such as
  • the compound is present in the food product in an amount of at or about 10 ppm or greater.
  • a food product comprising two or more compounds selected from compounds 1-19, or a comestibly or biologically acceptable salt, enantiomer, diastereomer, derivative, or solvate thereof, or a combination of any of the foregoing compounds.
  • a food product comprising:
  • the salt is sodium, lithium, potassium, ammonium, magnesium, and alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate.
  • a pharmaceutical composition comprising:
  • salt in (a) is at least one sodium, lithium, potassium, ammonium, magnesium, and alkali salt with the anion of the salt being selected from chloride, phosphate, glutamate, nitrite, nitrate, bicarbonate, lactate, citrate and stearoyl lactylate.
  • Figure 1 depicts the biosynthetic scheme of biosynthetically or naturally produced L- carnitine.
  • Figure 2 depicts the effect of the taste modulating compounds (CPD) as disclosed herein on ENaC channel activity in the presence of NaCl compared to a control not comprising the taste modulating compounds.
  • CPD taste modulating compounds
  • the terms“a” and“an” do not denote a limitation of quantity, but rather denote the presence of at least one of the referenced item.
  • the term“or” or“and/or” is used as a function word to indicate that two words or expressions are to be taken together or individually.
  • the terms“comprsing”,“having”, Fincluding”, and“containing” are to be construed as open-ended terms (i.e., meaning“including, but not limited to”). The endpoint of all ranges directed to the same component or property are inclusive and independently combinable.
  • the use of“or” means“and/or” unless stated otherwise.
  • the use of“or” refers back to more than one preceding indepednent or dependent claim in the alteranaive only.
  • the temf’include” has the same meaning as“include, but are not limited to”
  • the term“includes has the same meaning as“includes, but is not limited to”
  • the term“including” has the same meaning as as“including, but not limited to.”
  • the term“such as” has the same meaning as the term“such as, but not limited to.”
  • any numerical range recited herein includes all values from lower value to upper value. For example, if a concentration range is stated as 1% to 50%, it is intended that sauch values as 2% to 40%, 10% to 30%, or 1% to 3%, etc. are expressly enumerated in this specification. These are only exampes of what is specifically intended, and all possible combinations of numerical values between and including the lowest value and the highest value enumerated are to be considered to be expressly stated in this application.
  • control refers to, unless otherwise stated, a product or composition not comprising or comprising only one of the compounds as dislcosed herein, wherein the composition is prepared using the same process as the process used to prepare a composition comprising the compounds.
  • saltiness or“salty taste” refers to the perception of the salty flavor of a product, such as a food or beverage product.
  • Saltiness is a taste produced by the presence of sodium
  • table salt is made is made up of sodium chloride (NaCl).
  • NaCl sodium chloride
  • Many products incorporate NaCl to enhance the perception of saltiness.
  • Comestible products are often labeled as“reduced sodium”,“low sodium”,“sodium-free”, or“no salt added”. Such products have reduced levels of NaCl, and as a result, the perception of saltiness or perception of saltiness intensity may be reduced.
  • Salts of the compound(s) possess the desired activity of the parent compound include, but are not limited to: (1) acid addition salts, formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like; or formed with organic acids such as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl) benzoic acid, cinnamic acid, mandelic acid, methanessulfonic acid, ethanesulfonic acid, l,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzensulfonic acid, 4-chlorobenzenesulfonic acid, 2-
  • Comestibly or biologically acceptable salts as disclosed herein that are capable of enhancing the perception of saltiness or the perception of saltiness intensity are different from the at least one salt of the composition.
  • the at least one salt of the composition is selected from NaCl, KC1, NH4CI, MgCh, and CaCh, or combinations thereof.
  • the at least one salt is NaCl.
  • aliphatic refers to straight chain or branched hydrocarbons that are completely saturated or that contain one or more units of unsaturation.
  • aliphatic groups include substituted or unsubstituted linear or branched alkyl, alkenyl, and alkynyl groups. Unless indicated otherwise, the term“aliphatic” encompasses both substituted and unsubstituted hydrocarbons.
  • alkoxy refers to O-alkyl substituent, wherein the alkyl portion may be optionally substituted.
  • alkoxy substituents include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy and n-butoxy.
  • O-alkenyl or O-alkynyl groups are also included within the scope of the term“alkoxy”. In all cases, the alkyl, alkene, and alkyne portions may be optionally substituted.
  • alkyl refers to both straight and branched saturated chains containing, for example, 1-3, 1-6, 1-9, or 1-12 carbon atoms. An alkyl group may be optionally substituted.
  • alkenyl refers to both straight and branched saturated chains containing, for example, 2-3, 2-6, 2-9, or 2-12 carbon atoms, and at least one carbon-carbon double bond.
  • An alkenyl group may be optionally substituted.
  • alkynyl refers to both straight and branched saturated chains containing, for example, 2-3, 2-6, 2-9, or 2-12 carbon atoms, and at least one carbon-carbon triple bond.
  • An alkynyl group may be optionally substituted.
  • aryl group is an aromatic carbocyclic group of from 6 to 14 carbon atoms having a single ring (e.g., phenyl) or multiple condensed rings (e.g., naphthyl or anthryl). In some embodiments, aryl groups contain 6-14 carbons, and in others from 6 to 12 or even 6 to 10 carbon atoms in the ring portions of the groups.
  • Aryls include, but are not
  • An aliphatic group may contain one or more substituents.
  • suitable substituents on a saturated or unsaturated carbon of an aliphatic group include, but are not limited to, halogen, -CF 3 , -R’, -OR’, -OH, -SH, -SR’, protected OH (such as acyloxy), -N0 2 , -CN, -NH 2 , -NHR’, -N(R’) 2 , -NHCOR’, -NHCONH 2 , -NHCONHR’, -NHCON( R’) 2 , -NRCOR’, -NHC0 2 H, -NHC0 2 R ⁇ -C0 2 R ⁇ -C0 2 H, -COR’, -CONH 2 , -CONHR’, -CON(R’ ) 2 , -S(0) 2 H, -S(0) 2 R ⁇ -S(0) 3 H, -S(0) 3 R’,
  • the compounds of the disclosure are intended to include all stereochemical forms of the compound, including geometric isomers ⁇ i.e., E, Z) and optical isomers (i.e., R, S). Single stereochemical isomers as well as enantiomeric mixtures of the present compounds are within the scope of the disclosure and are specifically contemplated.
  • formulas depicted herein are also meant to include compounds which differ only in the presence of one or more isotopically enriched atoms. For example, compounds having the present formulas except for the replacement of a hydrogen by a deuterium or tritium, or the replacement of a carbon by a 13 C- or 14 C-enriched carbon are within the scope of this disclosure.
  • compositions refers to any comestibly or biologically acceptable salt, ester, or salt of such ester, of a compound of the present disclosure, which, upon ingestion, is capable of providing (directly or indirectly) a compound of the present disclosure, or a metabolite, residue or portion thereof, characterized by the ability to enhance the perception of a salty taste attributed to a salt and/or reduce the perception of bitter taste due to a bitter tastant.
  • the term “comestibly or biologically acceptable derivative” refers to any comestibly or biologically acceptable derivative of a compound of the present disclosure, which, upon ingestion, is capable of providing (directly or indirectly) a compound of the present disclosure, or a metabolite, residue or portion thereof, characterized by the ability to enhance the perception of a salty taste attributable to a salt and reduce the perception of a bitter taste attributed to a bitter tastant.
  • the terms “comestible product”,“comestible composition”,“edible product”, and“edible composition” are used interchangeably herein and refer to a product or composition suitable for oral use, such as eating or drinking. Therefore, a comestibly acceptable compound is an edible compound.
  • such salt is preferably derived from inorganic or organic acids and bases.
  • examples of such salts are, but are not limited to: (1) acid addition salts, formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like; or formed with organic acids such as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4- hydroxybenzoyl) benzoic acid, cinnamic acid, mandelic acid, methanessulfonic acid,
  • ethanesulfonic acid l,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzensulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfoic acid,4-tokuenesulfonic acid, comphorsulfonic acid, 4-methylbicyclo[2.2.2]-octo-2-ene-l-carbolyclic acid, glucoheptonic acid, 3-phylpropionic acid, trimethylacetic acid, tertiary butylacetic acid, lauryl sulfuric acid, gluconic acid, glutamic acid, hydroxynaphtghoic acid, salicylic acid, stearic acid, muconic acid, and the like; (2) inner salt of carnitine.
  • solvate refers to a physical association of a compound of this disclosure with one or more solvent molecules that does not interfere with the biological activity of the compound. This physical association involves varying degrees of ionic and covalent bonding, including hydrogen bonding. In certain instances, the solvate will be capable of isolation, for example when one or more solvent molecules are incorporated in the crystal lattice of the crystalline solid.“Solvate” encompasses both solution-phase and isolatable solvates. Non limiting examples of suitable solvates include ethanolates, hydrates, and the like.
  • A“hydrate” is a solvate wherein the solvent molecule is water and includes a hemihydrate, a monohydrate, a sesquihydrate, a dihydrate, etc.
  • carrier refers to a diluent, adjuvant, excipient or vehicle with which a compound is combined.
  • a“food product” is a food produced by combining two or more edible ingredients.
  • an“isolated” or“purified” compound is a compound that is substantially separated from other components of the source of the compound.
  • an isolated or purified compound may be a compound that is separated from its naturally occurring environment. If the compound is synthesized, the compound may be separated from unreacted reagents, reaction byproducts, solvents, or the like.
  • diet collectively refers to the food products and/or beverages consumed by a subject.
  • a subject’s“diet” also includes any consumer products or pharmaceutical compositions the subject ingests.
  • modulator refers to a compound or a blen of compounds that, when added to an edible composition, such as a food product, changes the individual characteristics of a food flavor, such as odor or taste. Flavor modification effects can include increasing, decreasing, masking, eliminating, reducing, enhancing or changing the perception of relevant sensorial characteristics of flavor in the edible composition. The ability of flavor modifiers to modify flavor may be independent of their aromatic or taste characteristics.
  • An example of a modulator or flavor modifying compound is a saltiness or salty taste enhancing compound.
  • An“enhancer” as disclosed herein refers to a compound, or an ingestible salt or solvate thereof that modulates (increases) a flavor (e.g. saltiness) or the activation of a receptor, preferably the chemosensory receptor.
  • pharmaceutically active ingredient refers to a compound in a
  • composition which is biologically active.
  • replacement refers to substituting one compound for another compound in or in the preparation of, for example, an edible composition, such as a food product. It includes complete and partial replacements or substitutions.
  • a composition that includes a salt and one or more compound is perceived as imparting a quantity of saltiness equal to a substantially similar composition that does not include the compound but has a higher concentration of the salt.
  • the composition that includes the compound imparts a perception of saltiness equal to the substantially similar composition that does not have the compound when the composition has about 1% or less salt than the substantially similar composition.
  • the composition that includes the compound may impart a perception of saltiness equal to the substantially similar composition that does not have the compound when the composition has about 2% or less, about 5% or less, about 7% or less, about 8% or less, about 9% or less, about 10% or less, about 11% or less, about 15% or less, about 20% or less, about 30% or less, about 35% or less, about 40% or less, about 50% , about 60%, or about 70% or less salt than the substantially similar composition.
  • one or more compounds may be resent in a food product in an amount sufficient to reduce the amount of a salt, such as for example sodium chloride, by about 1% or more, about 2% or more, about 5% or more, about 7% or more, about 8% or more, about 10% or more, about 11% or more, about 12% or more, about 15% or more, about 20% or more, about 22% or more, about 25% or more, about 30% or more, about 35% or more, about 40% or more, about 45% , about 50% or more, about 55% or more, about 60% or more, about 655 or more, about 70% or more, about 75% or more, about 80% or more, about 85% or more, about 90% or more , or about 95% or more, or the like.
  • a salt such as for example sodium chloride
  • the reduced salt food product elicits the same or similar perception of saltiness as a substantially similar food product that does not include the one or more compound.
  • the composition may impart a perception of saltiness equal to the substantially similar composition that does have only one of the two compounds when the composition has about % or less, about 5% or less, about 7% or less, about 8% or less, about 9% or less, about 10% or less, about 11% or less, about 15% or less, about 20% or less, about 30% or less, about 35% or less, about 40% or less, about 50% , about 60%, or about 70% or less salt than the substantially similar composition.
  • a composition that includes a compound may be substantially similar to a composition that does not have the compound, if the components of the composition, other than the salt and the compound, are present in a substantially similar concentration.
  • a compound as disclosed herein (such a compound of Formula (I), Formula (II), or any one of Compound 1-19) that is derived form a“natural source or product” is a compound that is extracted from, for example, a fungal or microbial source as opposed to being produced synthetically. Extraction or isolation of the naturally-derived taste modulating or salty taste enhancing compound may be facilitated by simple chemical reactions such as acidification, basification, ion exchange, hydrolysis, and salt formation as well as microbial fermentation, and the like.
  • a taste modulating, or compound is derived from natural sources such as natural plant, fungi and bacterial sources.
  • a taste modulating, or compound is biosynthesized.
  • One aspect of present disclosure provides edible compositions comprising one or more compound of the present disclosure (such a compound of Formula (I), Formula (II), or any one of Compound 1-19), including food products, consumer products, and pharmaceutical compositions comprising said compounds, and methods of preparing such compositions.
  • the present disclosure also provides methods of reducing the amount of a salt, such as for example NaCl, KC1, NH4CI, MgCh, and CaCh, or combinations thereof in an edible composition, methods of enhancing or potentiating salty taste of a salt, methods of enhancing or potentiating the activity of a salty taste receptor, methods of synthesizing and/or extracting salty taste enhancers or modulators.
  • the present disclosure also includes reducing the amount of a salt in an edible composition or diet by replacing an amount of salt or the other salt with an amount of one or more compounds or one or more extracts containing compounds of the present disclosure.
  • the disclosure provides compounds for modulating salty taste (e.g ., enhancing or potentiating the salty taste of a salt).
  • the term“compounds” refers to flavor substances with taste modifying properties, such as a compound according to Formula I, Formula (II), or any one of Compound 1-19.
  • Saltiness or salty taste enhancers are understood to be a type of“compound” where perception of saltiness is increased in a manner not or not solely attributable to the inherent saltiness of the salty taste enhancer alone.
  • the term“salty taste enhancer” is understood to include at least compositions capable of enhancing or intensifying the perception of salty taste of salty compositions or salted compositions.
  • salty taste enhancer is synonymous with the terms“ compound,”“salty taste potentiator,”“saltiness potentiator,”“saltiness amplifier,”“saltiness enhancer”“perception of saltiness intensifier” and“saltiness intensifier.”
  • the compounds provided herein may enhance or potentiate the salty taste of salts without providing any noticeable salty taste by themselves at acceptable use levels (at or below their threshold level for saltiness); however, the saltiness enhancers may themselves provide salty taste at concentrations above a saltiness threshold level. It is noted that the saltiness enhancers may be effective as enhancers even if present at concentrations above their saltiness threshold level.
  • saltiness enhancer there is major contribution of the saltiness enhancer to the saltiness of the composition via enhancement of the inherently salty taste attributed to a salt, where the salt is also present in the composition.
  • the terms“saltiness threshold,” and“saltiness recognition threshold,” are used interchangeably, herein, and refer to the level at which the lowest known concentration of a certain salty compound is perceivable as salty by the human sense of taste.
  • This saltiness recognition threshold also encompasses the saltiness detection threshold, referring to the level at which the lowest known concentration of a certain salty compound is perceivable by the human sense of taste.
  • the saltiness threshold can vary from person to person.
  • the saltiness threshold can also vary from matrix to matrix (e.g ., different saltiness thresholds in water compared to a chicken broth. For example, a saltiness threshold level for NaCl in water could be around 1% or 1.5%.
  • the saltiness enhancers of Formula (I), Formula (II), Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds are used at concentrations below their saltiness threshold.
  • enhancement of the saltiness intensity is measured by comparing the perception of saltiness of a composition comprising the compounds as disclosed herein to a control composition.
  • the one or more compound of the present disclosure is a different compound from the salt of the composition.
  • Useful salts include, but are not limited to: NaCl, KC1, NH 4 Cl, MgCh, and CaCh, or combinations thereof. Accordingly, although an ingredient may be characterized as both a compound and a salt, in all embodiments of the disclosure, the compound (such a compound of Formula (I), Formula (II), or any one of Compound 1-19) and the salt are different ingredients, i.e., the compound and the salt are not the same compound.
  • compositions comprising compounds for modulating or potentiating the salty taste of a salt.
  • the compounds of this disclosure are capable of modulating or potentiating the salty taste of a salt.
  • the or potentiating compounds of this disclosure refer to salts of the compounds, which possess the desired saltiness or salty taste enhancing property.
  • the compound may have a molecular weight less than about 1000, about 500, or about 300 Daltons.
  • the compound is a compound selected from:
  • Ri is each independently H, CH 3 , C 2 H 5 , C 3 H 7 , or aryl
  • R 2 is H, COCH 3 , COC 2 H 5 , COC 3 H 7 , or COaryl;
  • R3 is absent, H, CH3, C2H5, C3H7 , or aryl;
  • n l or 2
  • Xi absent, Cl, tartrate, fumarate, succinate, or carbonate
  • X2 absent, NH 4 , K, Ca, Mg;
  • Ri is each independently H, CH 3 , C 2 H 5 , C 3 H 7 , or aryl;
  • R 2 is CO2R3, CH2CO2H, C2H5CO2H, CO2COCH3, CO2COC2H5, CO2COC3H7, or CO COaryl;
  • R3 is absent or H
  • n l or 2;
  • Xi absent, Cl, tartrate, fumarate, succinate, or carbonate
  • X 2 absent, NH 4 , K, Ca, Mg;
  • the comestible composition comprises a blend of a first compound according to Formula I, Formula II , or any one of Compound 1-19 and a second Compound according to Formula I, Formula II , or any one of Compound 1-19, wherein the first compound in the blend is different from the second compound in the blend.
  • the first and second compound in the blend are present in a ratio of at or about 1 : 1, 2: 1, 3 : 1; 1 :2; or 1 :3, respectively.
  • compositions of the present disclosure refers to any comestibly or biologically acceptable derivative of a compound of the present disclosure, which, upon ingestion, is capable of providing (directly or indirectly) a compound of the present disclosure, or a polymorph, metabolite, residue or portion thereof, or a combination of compounds as disclosed herein, characterized by the ability to enhance the perception of a salty taste attributed to a salt.
  • A“comestible product” is a product suitable for oral use, such as eating or drinking. Therefore, a “comestible product”, or“comestibly acceptable compound” is an“edible product” or“edible compound” compound, respectively.
  • the compounds a s disclosed herein synergize with salts, such as for example NaCl, KC1, NH4CI, MgCh, and CaCh, or combinations thereof, to enhance or potentiate the perception of salty taste due to the salt.
  • salts such as for example NaCl, KC1, NH4CI, MgCh, and CaCh, or combinations thereof.
  • the compounds as disclosed herein may synergize with salts to enhance or potentiate the perception of salty taste due to the salt.
  • the overall saltiness of a composition comprising a compound, or a combination of compounds, and a salty compound or salt is higher than the combined inherent saltiness due to each of the compounds, or the combination of compounds, and a salty compound.
  • the perceived saltiness of the resulting composition would be greater than that of a 6% NaCl solution -with any perceived saltiness greater than a 6% NaCl solution being attributable to the saltiness enhancing properties of the compounds.
  • Such an increase in perceived saltiness may be referred to as synergistic or super-additive, not additive.
  • an effective concentration and“effective amount” are used interchangeably herein and refer to an amount sufficient to produce a desired property or result.
  • an effective amount of a compound as disclosed herein is an amount capable of modulating (e.g ., enhancing) the perception of salty taste associated with a salt.
  • the term“effective amount” of a compound as disclosed herein, or a combination of the compounds of the disclosure also refers to an amount which, when added to an edible composition, enhances the salty taste of, e.g., a salt, thereby allowing for the maintenance of the perception of a desired salty flavor of the edible composition.
  • the term “effective amount” also refers to the amount of compound of the present disclosure, or a combination of the compounds of the present disclosure, capable of modulating (e.g, enhancing) the perception of a salty taste associated with either a salt in a food product or an inherently salty food product.
  • the compounds, or the combination of compounds, of the present disclosure may impart a saltiness or taste at certain concentrations and no perceptible saltiness or taste at other concentrations.
  • the compound, or the combination of compounds, as disclosed herein may be present in an amount such that the taste, such as saltiness, of the compound, or the combination of compounds, is imperceptible.
  • the compositions discussed herein include an effective amount of the compound, or the combination of compounds as disclosed herein.
  • An effective amount of the compound, or the combination of compounds, of the present disclosure includes an amount sufficient to enhance the perception of saltiness intensity of a salt.
  • a compound, or a combination of compounds, of the present disclosure e.g, a compound of Formula (I), Formula (II),), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds
  • the compound, or the combination of compounds, of the present disclosure enhances the saltiness of a salt when the compound, or the combination of compounds, is present at a concentration between about 10 ppm to about 50 ppm; about 50 ppm to about 100 ppm; about 100 ppm to about 200 ppm; about 200 ppm to about 300 ppm; about 300 ppm to about 400 ppm; about 400 ppm to about 500 ppm; about 500 ppm to about 600 ppm; about 600 ppm to about 700 ppm; about 700 ppm to about 800 ppm; about 800 ppm to about 900 ppm; about 900 ppm to about 1000 ppm; about 1000 ppm to about 1100 ppm;
  • the compound of the present disclosure e.g ., a compound of Formula (I), Formula (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds
  • the compound of the present disclosure e.g., a compound of Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds
  • one or more salty taste enhancing compound as disclosed herein can be combined with an organic acid, such as, but not limited to Tartaric acid, fumaric acid, succinic acid, and carbonic acid.
  • a composition comprising one or more compounds as disclosed herein and an organic acid enhances the saltiness of a salt when one or more compound and the organic acid is present at a concentration between about 10 ppm to about 50 ppm; about 50 ppm to about 100 ppm; about 100 ppm to about 200 ppm; about 200 ppm to about 300 ppm; about 300 ppm to about 400 ppm; about 400 ppm to about 500 ppm; about 500 ppm to about 600 ppm; about 600 ppm to about 700 ppm; about 700 ppm to about 800 ppm; about 800 ppm to about 900 ppm; about 900 ppm to about 1000 ppm; about 1000 ppm to about 1100 ppm; about 1100 ppm to about 1200
  • the terms“parts per million” and“ppm” are used in the food industry to refer to a low concentration of a solution.
  • one gram of solute in 1000 mL of solvent has a concentration of 1000 ppm and one thousandth of a gram (O.OOlg) of solute in 1000 mL of solvent has a concentration of one ppm.
  • a concentration of one milligram per liter i.e., 1 mg/L
  • a concentration of 1 mg% is 1 mg/lOOmL.
  • a concentration of 1 mg% is equal to 10 ppm.
  • the term“wt.%” means weight percent.
  • a wt.% of 0.2 wt.% is equal to 2000 ppm.
  • the compound, or the combination of compounds, of the disclosure may be combined with known naturally occurring and/or synthetic compounds when used in embodiments (e.g ., edible compositions and methods) described herein.
  • compositions and methods of the disclosure that comprise a salt may be one selected from, but not limited to NaCl, KC1, NFLCl, MgCh, and CaCh, or combinations thereof.
  • the salt is a natural or inherent component of an edible composition.
  • the salt may be an inherent component of a food product or of a food stuff, such as meat or seafood or a meat or seafood product (e.g., beef, shellfish).
  • the compounds, or the combination of compounds, of the present disclosure may be used in edible compositions to which no salt is added.
  • The“salt-like” characteristics of the compounds disclosed herein include any characteristic similar to that of NaCl and include, but are not limited to, maximal response, flavor profile, temporal profile, adaptation behavior, mouthfeel, concentration/response function, tastant/and flavor/salty taste interactions, spatial pattern selectivity, and temperature effects.
  • the“salt-like” characteristic refers to the flavor profile and temporal profile.
  • Low sodium when used herein to refer to a comestible composition, means the composition has 140 mg sodium or less per serving of the composition.
  • Reduced sodium when used herein to refer to a comestible composition, means the composition has at least 25% less sodium per serving than a similar comestible composition in which no effort has been made to reduce the sodium level.
  • Exemplary amounts of sodium in a single serving of certain foods in which no effort has been made to reduce the sodium level include: 890 mg in canned soup; 860 mg in chicken broth; 460 mg in Bloody Mary; 306 mg in white bread; and 150 mg in saltine crackers.
  • the content of sodium may be from any source, including sodium chloride.“No salt added,” as used herein, means that no sodium chloride is added during preparation of a comestible composition.
  • the comestible composition may inherently comprise an amount of sodium salt.
  • the comestible composition may inherently comprise sodium slat and one or more sodium replacement salt, such as KC1, MgCh, CaCh, or NH 4 CL.
  • the compound of the present disclosure is present in the composition in an amount greater than its saltiness threshold level.
  • the salt is present in an amount ranging from 0.01% to 99.9% by weight, relative to the total weight of the composition.
  • the at least one salt is present in an amount ranging from 2% to 50%, or for example from 4% to 50% by weight, relative to the total weight of the composition.
  • the at least one salt is present in about 5% to about 20% by weight.
  • the at least one salt is present in about 5% to about 15% by weight.
  • the at least one salt is present in about 5% to about 12% by weight in soups, for example, in chicken broth.
  • the compound, or the combination of compounds, of the present disclosure potentiates or enhances the saltiness of the salt.
  • the composition comprising the salt and the compound, or the combination of compounds, of the composition of the present disclosure has more saltiness intensity than a composition comprising the at least one salt without the compound, or the combination of compounds.
  • the composition comprising the salt and the compound, or the combination of compounds has more saltiness intensity than a composition comprising the at least one salt without the compound, or without the combination of compounds, when the compound of the present disclosure or combinations thereof is present at or below its saltiness threshold.
  • saltiness intensity is understood to mean any perceptible saltiness.
  • composition comprising the salt and the compound, or the combination of compounds, of the present disclosure is perceptibly saltier than a composition comprising the salt without the compound, or the combination of compounds.
  • a composition comprising the salt and the compound, or the combination of compounds, of the present disclosure may be slightly saltier, moderately saltier, or significantly saltier than a composition comprising the salt without the compound, or the combination of compounds.
  • the composition comprising the salt and the compound, or the combination of compounds, of the present disclosure is perceptibly saltier than a composition comprising the salt without the compound, or without the combination of compounds, wherein said compound or combination of compounds is present below its saltiness threshold.
  • any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds are used above their saltiness threshold, the increase in saltiness intensity is synergistic, not additive.
  • the saltiness of a composition may be based on (z.e., relative to) a known salty standard.
  • Salty compounds based on such salty standards include, but are not limited to, for example NaCl, KC1, NH 4 Cl, MgCh, and CaCh, or combinations thereof.
  • the saltiness of a composition may be based on a 5% NaCl solution.
  • a composition comprising the salt and compound according to the disclosure such as a compound of Formula (I), Formula (II), or any one of Compound 1-19), or a combination of the compounds, of the present disclosure may be perceived as having a saltiness equivalent to a 5.5% NaCl solution.
  • the composition comprising the salt and a compound, or a combination of compounds, of the present disclosure may be perceived as having a saltiness equivalent to a 6.0%, 6.5%, 7.0%, 7.5%, 8.0%, 8.5%, 9.0%, 9.5%, or 10% NaCl solution.
  • Suitable salt standards include, but are not limited to, NaCl standards, KCL standards, NH 4 Cl standards, MgCh standards, and CaCl standards. Each of these standards may be used at concentrations which include, but are not limited to, 0.5%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5%, 5.0%, 5.5%, 6.0%, 6.5%, 7.0%, 7.5%, 8.0%, 8.5%, 9.0%, 9.5%, or 10% solution.
  • the saltiness intensity of the composition comprising the salt and compound, or a combination of compounds, of the present disclosure increases the perceived saltiness based on a salt standard by greater than 10%, by greater than 20%, by greater than 30%, by greater than 40%, greater than by 50% or greater than by 60% compared to a composition comprising the salt without the compound, or the combination of compounds.
  • the perception of saltiness intensity of the salt i.e., the perception of salty taste of the salt in the edible composition
  • the perception of saltiness intensity of the salt is enhanced beyond 100%, for example, by 125%, 150%, 175%, 200%, 225%, 250%, 275%, 300%, 325%, 350%, 375%, 400%, 425%, 450%, 475%, 500% or increments in between those recited.
  • the perception of saltiness intensity is enhanced by up to 25%.
  • the perception of saltiness intensity is enhanced by up to 50%.
  • the perception of saltiness intensity is enhanced by up to 75%.
  • the saltiness intensity is enhanced by up to 100%. In some embodiments, the perception of saltiness intensity is enhanced by about 5% to about 100%, about 5% to about 90%, about 5% to about 80%, about 5% to about 70%, about 5% to about 60%, about 5% to about 50%, about 5% to about 40%, about 5% to about 30%, about 10% to about 30%, about 10% to about 25%. about 20% to about 80%, about 20% to about 70%, about 20% to about 60%, about 20% to about 50%, about 20% to about 40%, about 20% to about 30%, about 25% to about 80%, about 25% to about 70%, about 25% to about 60%, about 25% to about 50%, about 25% to about 40%, or about 25% to about 30%. These amounts are not meant to be limiting, and increments between the recited percentages are specifically envisioned as part of the disclosure.
  • the combination of at least one compound as disclosed herein and at least one salt may be carried out in any pH range that does not materially or adversely affect the taste of the salty composition or the salted composition.
  • a non-limiting example of the pH range may be from about 1.5 to about 9.0.
  • Further examples include a pH range from about 2.0 to about 8.5, from about 2.0 to about 8.0, from about 2.0 to about 7.5, from about 2.0 to about 7.0, from about 2.5 to about 7.0, and from about 3.0 to about 7.0.
  • pH ranges include from about 2.0 to about 4.0, from about 2.5 to about 4.5, from about 3.5 to about 5.5, from about 5.0 to about 6.0, from about 4.0 to about 5.5, from about 5.0 to about 6.0, from about 6.5 to about 7.5, and from about 6.0 to about 8.0.
  • the pH is about 3.0 or about 7.0.
  • the temperature of the composition may, for example, range from about -4° C to about 90° C.
  • One of ordinary skill in the art may combine the salt(s) and compound(s), or the combination of compounds, or combination of one or more compound and one or more organic acids in any manner.
  • salty taste improving composition and“salty taste improving additive” are used interchangeably herein and refer to any material that imparts a more salt-like temporal profile or salt-like flavor profile or both to a salted composition.
  • Suitable salty taste improving additives useful in embodiments of this disclosure include amino acids and salts thereof, poly- amino acids and salts thereof, peptides, nucleotides and salts thereof, organic acids, inorganic acids, organic salts including organic acid salts and organic base salts, inorganic acid salts (e.g ., sodium chloride, potassium chloride, magnesium chloride), acid salts (e.g., sodium citrate), bitter compounds, flavorants and flavoring ingredients, astringent compounds, polymers, proteins or protein hydrolysates, surfactants, emulsifiers, flavonoids, and alcohols.
  • amino acids and salts thereof include amino acids and salts thereof, poly- amino acids and salts thereof, peptides, nucleotides and salts thereof, organic acids, inorganic acids
  • salt-like characteristic “salt-like taste,”“salt-like salty,”“salty,” and “salt-like” are used interchangeably, herein, and include any characteristic similar to that of NaCl and include, but are not limited to, maximal response, flavor profile, temporal profile, adaptation behavior, mouth feel, concentration/response function behavior, tastant and flavor/salty taste interactions, and temperature effects. These characteristics are dimensions in which the taste of NaCl is different from the tastes of saltiness enhanced salted compositions. Suitable procedures for determining whether a composition has a more salt-like taste are well known in the art.
  • compositions of the present disclosure may also further comprise at least one additional additive, such as a salty taste improving composition, and/or a salty taste improving additive.
  • a salty taste improving composition such as a salty taste improving composition, and/or a salty taste improving additive.
  • the composition of the disclosure may comprise at least one salty taste improving composition for balancing the temporal and/or flavor profile of the saltiness enhanced salt composition.
  • Suitable salty taste improving amino acid additives for use in embodiments of this disclosure include, but are not limited to, aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (a-, b-, or g-isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, and their salt forms such as sodium or potassium salts or acid salts.
  • the salty taste improving amino acid additives also may be in the D- or L-configuration and in the mono-, di-, or tri-form of the same or different amino acids. Additionally, the amino acids may be a-, b-, g-, d-, and e-isomers if appropriate. Combinations of the foregoing amino acids and their corresponding salts (e.g ., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof, or acid salts) also are suitable salty taste improving additives in some embodiments.
  • the amino acids may be natural or synthetic.
  • the amino acids also may be modified.
  • Modified amino acids refers to any amino acid wherein at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl amino acid, N-acyl amino acid, or N-methyl amino acid).
  • modified amino acids include amino acid derivatives such as trimethyl glycine, N-methyl- glycine, and N-methyl-alanine.
  • modified amino acids encompass both modified and unmodified amino acids.
  • amino acids also encompass both peptides and polypeptides (e.g, dipeptides, tripeptides, tetrapeptides, and pentapeptides) such as glutathione and L-alanyl-L-glutamine.
  • Suitable salty taste improving polyamino acid additives include poly- L-aspartic acid, poly-L-lysine (e.g, poly-L-a-lysine or poly-L-a-lysine), poly-L-omithine (e.g, poly-L-a-ornithine or poly-L-e-omithine), poly-L-arginine, other polymeric forms of amino acids, and salt forms thereof (e.g, calcium, potassium, sodium, or magnesium salts such as L- glutamic acid mono sodium salt).
  • the salty taste improving poly-amino acid additives also may be in the D- or L-configuration.
  • poly-amino acids may be a-, b-, g-, d-, and e- isomers if appropriate.
  • Combinations of the foregoing poly-amino acids and their corresponding salts e.g, sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof or acid salts
  • the poly-amino acids described herein also may comprise co-polymers of different amino acids.
  • the poly-amino acids may be natural or synthetic.
  • poly-amino acids also may be modified, such that at least one atom has been added, removed, substituted, or combinations thereof (e.g, N-alkyl poly-amino acid or N-acyl poly-amino acid).
  • poly-amino acids encompass both modified and unmodified poly-amino acids.
  • modified poly-amino acids include, but are not limited to poly-amino acids of various molecular weights (MW), such as poly-L-a-lysine with a MW of 1,500, MW of 6,000, MW of 25,200, MW of 63,000, MW of 83,000, or MW of 300,000.
  • MW molecular weights
  • the taste improving amino acid additive is glycine, alanine, taurine, serine or proline. In such embodiments, the taste improving amino acid additive is present in a concentration of about 10 ppm to about 25,000 ppm or about 100 ppm to about 1000 ppm.
  • Suitable salty taste improving nucleotide additives include, but are not limited to, inosine monophosphate (“IMP”), guanosine monophosphate (“GMP”), adenosine
  • AMP monophosphate
  • CMP cytosine monophosphate
  • UMP uracil monophosphate
  • inosine diphosphate guanosine diphosphate
  • adenosine diphosphate cytosine diphosphate
  • uracil diphosphate inosine triphosphate
  • guanosine triphosphate adenosine triphosphate
  • cytosine triphosphate uracil triphosphate
  • nucleotides described herein also may comprise nucleotide-related additives, such as nucleosides or nucleic acid bases (e.g ., guanine, cytosine, adenine, thymine, and uracil).
  • nucleosides or nucleic acid bases e.g ., guanine, cytosine, adenine, thymine, and uracil.
  • Suitable salty taste improving organic acid additives include any compound which comprises a— COOH moiety.
  • Suitable salty taste improving organic acid additives include but are not limited to C2-C30 carboxylic acids, substituted hydroxyl C2-C30 carboxylic acids, benzoic acid, substituted benzoic acids (e.g., 2,4-dihydroxybenzoic acid), substituted cinnamic acids, hydroxyacids, substituted hydroxybenzoic acids, substituted cyclohexyl carboxylic acids, tannic acid, lactic acid, tartaric acid, citric acid, gluconic acid, glucoheptonic acids, adipic acid, hydroxycitric acid, malic acid, fruitaric acid (a blend of malic, fumaric, and tartaric acids), fumaric acid, maleic acid, succinic acid, chlorogenic acid, salicylic acid, creatine, caffeic acid, bile acids, acetic acid, ascorbic acid, al
  • suitable salty taste improving organic acid additive salts include, but are not limited to, sodium, calcium, potassium, and magnesium salts of all organic acids, such as salts of citric acid, malic acid, tartaric acid, fumaric acid, lactic acid (e.g, sodium lactate), alginic acid (e.g, sodium alginate), ascorbic acid (e.g, sodium ascorbate), benzoic acid (e.g, sodium benzoate or potassium benzoate), and adipic acid.
  • citric acid e.g, malic acid, tartaric acid, fumaric acid
  • lactic acid e.g, sodium lactate
  • alginic acid e.g, sodium alginate
  • ascorbic acid e.g, sodium ascorbate
  • benzoic acid e.g, sodium benzoate or potassium benzoate
  • adipic acid e.g, sodium benzoate or potassium benzoate
  • the examples of the salty taste improving organic acid additives described optionally may be substituted with at least one group chosen from hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfo, thiol, imine, sulfonyl, sulfenyl, sulfmyl, sulfamyl, carboxalkoxy, carboxamido, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximino, hydrazino, carbamyl, phospho, phosphonato, and any other viable functional group provided the substituted organic acid additives function to improve the salty taste of
  • suitable salty taste improving inorganic acid additives include but are not limited to phosphoric acid, phosphorous acid, polyphosphoric acid, hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen phosphate, and alkali or alkaline earth metal salts thereof (e.g, inositol hexaphosphate Mg/C a).
  • Edible compositions include but are not limited to phosphoric acid, phosphorous acid, polyphosphoric acid, hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen phosphate, and alkali or alkaline earth metal salts thereof (e.g, inositol hexaphosphate Mg/C a).
  • the disclosure provides an edible composition
  • an edible composition comprising a compound or a combination of compounds, of the disclosure for enhancing or potentiating the salty taste of a salt without imparting an unpleasant taste.
  • such edible compositions may comprise a compound of Formula (I), Formula (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds.
  • the edible composition may comprise a (i) salt; and (ii) a compound of Formula (I), Formula (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds.
  • Edible composition refers to a composition suitable for consumption, typically via the oral cavity (although consumption may occur via non-oral means such as inhalation).
  • Edible compositions may be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, lozenges, powders, gels, gums, pastes, slurries, syrups, aerosols and sprays.
  • edible compositions include food products, pharmaceutical compositions, and consumer products.
  • edible composition also refers to, for example, dietary and nutritional supplements.
  • edible compositions also include compositions that are placed within the oral cavity but not swallowed, including professional dental products, such as dental treatments, fillings, packing materials, molds and polishes.
  • professional dental products such as dental treatments, fillings, packing materials, molds and polishes.
  • the term“comestible” refers to similar compositions and is generally used as a synonym to the term“edible.”
  • Food product refers to any composition comprising one or more processed foodstuffs.
  • Food products include, but are not limited to, confectionaries, bakery products (including, but not limited to, doughs, breads, biscuits, crackers, cakes, pastries, pies, tarts, quiches, and cookies), ice creams (including but not limited to impulse ice cream, take-home ice cream, frozen yogurt, gelato, sorbet, sherbet and soy, oat, bean and rice-based ice cream), dairy products (including, but not limited to, drinking milk, cheese, yogurt, and sour milk drinks), cheeses (including, but not limited to, natural cheeses and processed cheeses), butter, margarine, sweet and savory snacks (including but not limited to fruit snacks, chips/crisps, tortilla/corn chips, popcorn, pretzels, chocolates, and nuts), hot and cold beverages (including, but not limited to, beverages, beverage mixes, concentrates, juices, carbonated beverages, non-carbonated beverages, alcoholic beverages
  • cheese sauces e.g, for macaroni and cheese
  • tomato pastes tomato purees
  • bouillon cubes stock cubes
  • table sauces bouillabaisse sauces
  • pasta sauces cooking sauces
  • marinades dry sauces
  • powder mixes ketchups
  • mayonnaises salad dressings, vinaigrettes, mustards, and dips
  • jellies jams, preserves, honey, puddings, recipe mixes, syrups, icings, fillings, infused foods, salt-preserved food, marinated foods and condiments (such as ketchup, mustard and steak sauce).
  • the food product is animal feed.
  • the food product may be a pet food product, i.e. a food product for consumption by a household pet.
  • the food product is a livestock food product, i.e. a food product for consumption by livestock.
  • Any salt that imparts a salty taste may be present or incorporated into a food product that contains a taste modulating, , or salty taste enhancing compound.
  • the most commonly used salt for food applications is sodium chloride (typically referred to as common table salt).
  • Other illustrative sources of sodium salts that may be present of incorporated into a food product include sodium phosphates, mono sodium glutamate, sodium nitrite, sodium nitrate, sodium bicarbonate, sodium lactate, sodium citrate, and sodium stearoyl lactylate. Similar lithium, potassium, ammonium or other alkali earth salts may be present or included in addition or as an alternative to one or more sodium salts.
  • a food product includes sodium chloride as a salt that imparts a salty taste.
  • Sodium chloride may be present in the food product at any suitable amount or concentration.
  • sodium chloride is present in the food product in an amount up to about 10.0 weight percent, more particularly, up to about 5.0 weight percent, even more particularly up to about 1.2 weight percent, or in the range of about 0.017 to about 1.2 weight percent, or about 0.1 to about 1, or about 0.4 to about 0.6 weight percent.
  • a food product that includes one or more taste modulating, , or salty taste enhancing compounds comprises no more than 0.04 weight percent, no more than 0.1 weight percent sodium, no more than 0.2 weight percent, no more than 0.25 weight percent sodium, no more than 0.3 weight percent, no more than 0.4 weight percent, no more than 0.5 weight percent sodium, no more than 0.75 weight percent sodium, no more than 1 weight percent sodium, no more than 5 weight percent sodium, or no more than 10 weight percent sodium.
  • a desired weight percent of sodium may vary depending on the type of food product. For example, it may be desirable for a seasoning to have higher weight percent sodium than a soup or a breakfast cereal.
  • a food product that includes one or more taste modulating or compounds comprises no more than 100 mg sodium per serving, no more than 250 mg sodium per serving, no more than 500 mg sodium per serving.
  • the term“foodstuff’ refers to an unprocessed ingredient or a basic nutrient or flavor containing element used to prepare a food product.
  • foodstuffs include: fruits, vegetables, meats, fishes, grains, milks, eggs, tubers, oils, herbs, snacks, sauces, spices and salts.
  • processed foodstuff refers to a foodstuff has been subjected to any process which alters its original state (excluding, e.g ., harvesting, slaughtering, and cleaning).
  • methods of processing foods include, but are not limited to, removal of unwanted outer layers, such as potato peeling or the skinning of peaches; chopping or slicing; mincing or macerating; liquefaction, such as to produce fruit juice; fermentation ( e.g .
  • beer beer
  • emulsification cooking, such as boiling, broiling, frying, heating, steaming or grilling; deep frying; baking; mixing; addition of gas such as air entrainment for bread or gasification of soft drinks; proofing; seasoning (with, e.g., herbs, spices, salts); spray drying; pasteurization; packaging (e.g, canning or boxing); extrusion; puffing; blending; and preservation (e.g, adding salt, sugar, potassium lactate or other preservatives).
  • cooking such as boiling, broiling, frying, heating, steaming or grilling
  • deep frying baking
  • mixing addition of gas such as air entrainment for bread or gasification of soft drinks
  • proofing seasoning (with, e.g., herbs, spices, salts); spray drying; pasteurization; packaging (e.g, canning or boxing); extrusion; puffing; blending; and preservation (e.g, adding salt, sugar, potassium lactate or other preservatives).
  • consumer product refers to health and beauty products for the personal use and/or consumption by a subject.
  • Consumer products may be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, capsules, lozenges, strips, powders, gels, gums, pastes, slurries, syrups, aerosols and sprays.
  • Non-limiting examples of consumer products include nutraceuticals, nutritional supplements, lipsticks, lip balms, soaps, shampoos, gums, adhesives (e.g, dental adhesives), toothpastes, oral analgesics, breath fresheners, mouthwashes, tooth whiteners, and other dentifrices.
  • the edible composition may comprise (i) a compound of the disclosure, or combinations thereof; and (ii) a salt.
  • the compound or the combination of compounds is a compound having a molecular weight less than about 1000, 500, or 300 Daltons.
  • the compound is a compound of Formula (I), (II), or comestibly or biologically acceptable salts, solvates, enantiomers, or derivatives thereof, or combinations of any of the foregoing.
  • the compound is any one of Compounds 1-19, or comestibly or biologically acceptable salts, solvates, enantiomers, or derivatives thereof.
  • the compound is a blend or combination of two or more compounds of Formula (I), Formula (II), any one of Compounds 1-19.
  • the salt taste enhancing composition is a blend or combination of Compound 1 and Compound 6.
  • the salt taste enhancing composition is a blend or combination of Compound 8 (L- Carnitine succinate) and Compound l(L- Carnitine HC1).
  • the salt taste enhancing composition is a blend or combination of Compound 4 (Acetyl -L-carnitine (inner salt)) and Compound l(L- Carnitine HC1).
  • the salt taste enhancing composition is a blend or combination of Compound 8 (L-Camitine Succinate) and Compound 14 (Betaine HC1).
  • the salt taste enhancing composition is a blend or combination of Compound 3 (L-camitine (inner salt)) and Compound 1 (L-Camitine HC1). In some embodiments, the salt taste enhancing composition is a blend or combination of Compound 3 (L-Camitine (inner salt)), Compound 1 (L-Carnitine HC1) and tartrate. In some embodiments, the salt taste enhancing composition is a blend or combination of Compound 3 (L-Carnitine (inner salt)), Compound 1 (L-Camitine HC1) and succinate. In some embodiments, the salt taste enhancing composition is a blend or combination of Compound 14 (betaine HC1) and succinate.
  • the edible composition naturally or inherently comprises a salt.
  • the salt may be an inherent component of a food product or of a food stuff, such as fruit or a fruit product ( e.g ., fruit sauce). Accordingly, the compounds, or the
  • combination of compounds, of the present disclosure may be added to edible compositions to which no salt is added.
  • the edible composition is a salted composition
  • a compound of the disclosure e.g., a compound of Formula (I), (II), any one of Compounds 1- 19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds
  • a salt e.g., a salt of a compound of the disclosure (e.g., a compound of Formula (I), (II), any one of Compounds 1- 19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds); and (ii) a salt.
  • the compound of Formula (I), (II), any one of Compounds 1- 19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds may be used to enhance the salty taste or perception of any salt, such as, but not limited to NaCl, KC1, NH 4 CL, MgCL 2 or CaCh.
  • the compound of Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds may have an inherent salty taste and is present at or above its saltiness threshold, but is not the primary salt in the composition.
  • the compound of Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds serves to enhance the salty taste of the salt.
  • the compound of Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds may be present at or below its saltiness threshold. In such cases, the compound, or combination of compounds, serves only to enhance the salty taste of the salt.
  • the edible composition further comprises functional ingredients.
  • the term“functional ingredient” refers to compound which provide a real or perceived heath benefit to the composition.
  • Functional ingredients include, but are not limited to, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydration agents, probiotics, prebiotics, weight management agents, osteoporosis management agents, phytoestrogens, long chain primary aliphatic saturated alcohols, phytosterols, and combinations thereof.
  • the functional ingredient is at least one antioxidant.
  • the at least one antioxidant may comprise a single antioxidant or a plurality of antioxidants as a functional ingredient for the edible compositions (e.g ., beverages) provided herein.
  • the at least one antioxidant is present in the edible composition (e.g., beverage) in a concentration sufficient to promote health and wellness.
  • antioxidant refers to any substance which inhibits, suppresses, or reduces oxidative damage to cells and biomolecules. Without being bound by theory, it is believed that antioxidants inhibit, suppress, or reduce oxidative damage to cells or biomolecules by stabilizing free radicals before they can cause harmful reactions. As such, antioxidants may prevent or postpone the onset of some degenerative diseases.
  • antioxidants for embodiments of this disclosure include, but are not limited to, vitamins, vitamin cofactors, minerals, hormones, carotenoids, carotenoid terpenoids, non-carotenoid terpenoids, flavonoids, flavonoid polyphenolics (e.g, bioflavonoids), flavonols, flavones, phenols, polyphenols, esters of phenols, esters of polyphenols, nonflavonoid phenolics, isothiocyanates, and combinations thereof.
  • bioflavonoids bioflavonoids
  • flavonols flavones
  • phenols polyphenols
  • esters of phenols esters of polyphenols
  • nonflavonoid phenolics isothiocyanates
  • the antioxidant is vitamin A, vitamin C, vitamin E, ubiquinone, mineral selenium, manganese, melatonin, a- carotene, b-carotene, lycopene, lutein, zeanthin, crypoxanthin, reservatol, eugenol, quercetin, catechin, gossypol, hesperetin, curcumin, ferulic acid, thymol, hydroxytyrosol, tumeric, thyme, olive oil, lipoic acid, glutathinone, gutamine, oxalic acid, tocopherol-derived compounds, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), ethylenediaminetetraacetic acid (EDTA), tert-butylhydroquinone, acetic acid, pectin, tocotrienol, tocopherol, coenzyme
  • embodiments of this disclosure include, but are not limited to, fruits, vegetables, tea, cocoa, chocolate, spices, herbs, rice, organ meats from livestock, yeast, whole grains, or cereal grains.
  • the functional ingredient is at least one dietary fiber source.
  • the at least one dietary fiber source may comprise a single dietary fiber source or a plurality of dietary fiber sources as a functional ingredient for the edible compositions (e.g, beverages) provided herein.
  • the at least one dietary fiber source is present in the edible composition (e.g, beverage) in a
  • polysaccharides polysaccharides, lignin, cellulose, methylcellulose, the hemicelluloses, b-glucans, pectins, gums, mucilage, waxes, inulins, oligosaccharides, fructooligosaccharides, cyclodextrins, chitins, and combinations thereof.
  • Polysaccharides are complex carbohydrates composed of monosaccharides joined by glycosidic linkages. Non-starch polysaccharides are bonded with b-linkages, which humans are unable to digest due to a lack of an enzyme to break the b-linkages. Conversely, digestible starch polysaccharides generally comprise a (1-4) linkages.
  • Lignin is a large, highly branched and cross-linked polymer based on oxygenated phenylpropane units. Cellulose is a linear polymer of glucose molecules joined by a b (1-4) linkage, which mammalian amylases are unable to hydrolyze.
  • Methylcellulose is a methyl esther of cellulose that is often used in foodstuffs as a thickener, and emulsifier. It is commercially available (e.g ., Citrucel by GlaxoSmithKline, Celevac by Shire Pharmaceuticals).
  • Hemicelluloses are highly branched polymers consisting mainly of glucurono- and 4-0- methylglucuroxylans.
  • b-Glucans are mixed-linkage (1-3), (1-4) b-D-glucose polymers found primarily in cereals, such as oats and barley.
  • Pectins such as beta pectin, are a group of polysaccharides composed primarily of D-galacturonic acid, which is methoxylated to variable degrees.
  • Gums and mucilages represent a broad array of different branched structures.
  • Guar gum derived from the ground endosperm of the guar seed, is a galactomannan. Guar gum is commercially available (e.g., Benefiber by Novartis AG). Other gums, such as gum arabic and pectins, have still different structures. Still other gums include xanthan gum, gellan gum, tara gum, psylium seed husk gum, and locust been gum.
  • Waxes are esters of ethylene glycol and two fatty acids, generally occurring as a hydrophobic liquid that is insoluble in water.
  • Food sources of dietary fiber include, but are not limited to, grains, legumes, fruits, and vegetables.
  • Grains providing dietary fiber include, but are not limited to, oats, rye, barley, wheat.
  • Legumes providing fiber include, but are not limited to, peas and beans such as soybeans.
  • Fruits and vegetables providing a source of fiber include, but are not limited to, apples, oranges, pears, bananas, berries, tomatoes, green beans, broccoli, cauliflower, carrots, potatoes, celery.
  • Plant foods such as bran, nuts, and seeds (such as flax seeds) are also sources of dietary fiber.
  • Parts of plants providing dietary fiber include, but are not limited to, the stems, roots, leaves, seeds, pulp, and skin.
  • dietary fiber generally is derived from plant sources, indigestible animal products such as chitins are also classified as dietary fiber.
  • Chitin is a polysaccharide composed of units of acetyl glucosamine joined by b(1-4) linkages, similar to the linkages of cellulose.
  • Sources of dietary fiber often are divided into categories of soluble and insoluble fiber based on their solubility in water. Both soluble and insoluble fibers are found in plant foods to varying degrees depending upon the characteristics of the plant. Although insoluble in water, insoluble fiber has passive hydrophilic properties that help increase bulk, soften stools, and shorten transit time of fecal solids through the intestinal tract. [0109] Unlike insoluble fiber, soluble fiber readily dissolves in water. Soluble fiber undergoes active metabolic processing via fermentation in the colon, increasing the colonic microflora and thereby increasing the mass of fecal solids. Fermentation of fibers by colonic bacteria also yields end-products with significant health benefits.
  • Acids produced during fermentation include butyric, acetic, propionic, and valeric acids that have various beneficial properties such as stabilizing blood glucose levels by acting on pancreatic insulin release and providing liver control by glycogen breakdown.
  • fiber fermentation may reduce atherosclerosis by lowering cholesterol synthesis by the liver and reducing blood levels of LDL and triglycerides.
  • the acids produced during fermentation lower colonic pH, thereby protecting the colon lining from cancer polyp formation.
  • the lower colonic pH also increases mineral absorption, improves the barrier properties of the colonic mucosal layer, and inhibits inflammatory and adhesion irritants. Fermentation of fibers also may benefit the immune system by stimulating production of T-helper cells, antibodies, leukocytes, splenocytes, cytokinins and lymphocytes.
  • the functional ingredient is at least one fatty acid.
  • the at least one fatty acid may be single fatty acid or a plurality of fatty acids as a functional ingredient for the salted edible compositions (e.g ., beverages) provided herein.
  • the at least one fatty acid is present in the edible composition (e.g., beverage) in a concentration sufficient to promote health and wellness.
  • fatty acid refers to any straight chain monocarboxylic acid and includes saturated fatty acids, unsaturated fatty acids, long chain fatty acids, medium chain fatty acids, short chain fatty acids, fatty acid precursors (including omega-9 fatty acid precursors), and esterified fatty acids.
  • long chain polyunsaturated fatty acid refers to any polyunsaturated carboxylic acid or organic acid with a long aliphatic tail.
  • omega-3 fatty acid refers to any polyunsaturated fatty acid having a first double bond as the third carbon-carbon bond from the terminal methyl end of its carbon chain.
  • the omega-3 fatty acid may comprise a long chain omega-3 fatty acid.
  • omega-3 fatty acid any polyunsaturated fatty acid having a first double bond as the sixth carbon-carbon bond from the terminal methyl end of its carbon chain.
  • Suitable omega-3 fatty acids for use in embodiments of the present disclosure can be derived from algae, fish, animals, plants, or combinations thereof, for example.
  • suitable omega-3 fatty acids include, but are not limited to, linolenic acid, alpha-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, stearidonic acid, eicosatetraenoic acid and combinations thereof.
  • suitable omega-3 fatty acids can be provided in fish oils, (e.g ., menhaden oil, tuna oil, salmon oil, bonito oil, and cod oil), microalgae omega-3 oils or combinations thereof.
  • suitable omega-3 fatty acids may be derived from commercially available omega-3 fatty acid oils such as Microalgae DHA oil (from Martek, Columbia, MD), OmegaPure (from Omega Protein, Houston, TX), Marinol C-38 (from Lipid Nutrition, Channahon, IL), Bonito oil and MEG-3 (from Ocean Nutrition, Dartmouth, NS), Evogel (from Symrise, Holzminden, Germany), Marine Oil, from tuna or salmon (from Arista Wilton, CT), OmegaSource 2000, Marine Oil, from menhaden and Marine Oil, from cod (from OmegaSource, RTP, NC).
  • omega-3 fatty acid oils such as Microalgae DHA oil (from Martek, Columbia, MD), OmegaPure (from Omega Protein, Houston, TX), Marinol C-38 (from Lipid Nutrition, Channahon, IL), Bonito oil and MEG-3 (from Ocean Nutrition, Dartmouth, NS), Evogel (from Symrise, Holzminden, Germany), Marine Oil, from tuna or salmon (
  • the functional ingredient is at least one vitamin.
  • the at least one vitamin may be single vitamin or a plurality of vitamins as a functional ingredient for the edible compositions (e.g., beverages) provided herein.
  • the at least one vitamin is present in the edible composition (e.g, beverage) in a concentration sufficient to promote health and wellness.
  • Vitamins are organic compounds that the human body needs in small quantities for normal functioning. The body uses vitamins without breaking them down, unlike other nutrients such as carbohydrates and proteins. To date, thirteen vitamins have been recognized, and one or more can be used in the functional salt and salted compositions herein. Suitable vitamins include, vitamin A, vitamin D, vitamin E, vitamin K, vitamin Bl, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B 12, and vitamin C.
  • pseudo-vitamins include, but are not limited to, compounds such as ubiquinone (coenzyme Q10), pangamic acid, dimethyl glycine, taestrile, amygdaline, flavanoids, para-aminobenzoic acid, adenine, adenylic acid, and s- methylmethionine.
  • the term vitamin includes pseudo-vitamins.
  • the functional ingredient is glucosamine.
  • glucosamine is present in the edible composition (e.g, beverage) in a concentration sufficient to promote health and wellness.
  • the edible composition e.g, beverage
  • the functional ingredient is at least one mineral.
  • the at least one mineral may be single mineral or a plurality of minerals as a functional ingredient for the edible compositions (e.g, beverages) provided herein.
  • the at least one mineral is present in the edible composition (e.g, beverage) in a concentration sufficient to promote health and wellness.
  • Minerals in accordance with the teachings of this disclosure, comprise inorganic chemical elements required by living organisms. Minerals are comprised of a broad range of compositions (e.g ., elements, simple salts, and complex silicates) and vary broadly in crystalline structure. They may naturally occur in foods and beverages, may be added as a supplement, or may be consumed or administered separately from foods or beverages.
  • Minerals may be categorized as either bulk minerals, which are required in relatively large amounts, or trace minerals, which are required in relatively small amounts.
  • Bulk minerals generally are required in amounts greater than or equal to about 100 mg per day and trace minerals are those that are required in amounts less than about 100 mg per day.
  • the functional ingredient is at least one preservative.
  • the at least one preservative may be single preservative or a plurality of preservatives as a functional ingredient for the edible compositions (e.g., beverages) provided herein.
  • the at least one preservative is present in the edible composition (e.g, beverage) in a concentration sufficient to promote health and wellness.
  • the preservative is chosen from antimicrobials, antioxidants, antienzymatics or combinations thereof.
  • antimicrobials include sulfites, propionates, benzoates, sorbates, nitrates, nitrites, bacteriocins, salts, sugars, acetic acid, dimethyl dicarbonate (DMDC), ethanol, and ozone.
  • Non-limiting examples of antienzymatics suitable for use as preservatives in embodiments of the disclosure include ascorbic acid, citric acid, and metal chelating agents such as ethylenediaminetetraacetic acid (EDTA).
  • ascorbic acid citric acid
  • metal chelating agents such as ethylenediaminetetraacetic acid (EDTA).
  • the functional ingredient is at least one hydration agent.
  • the at least one hydration agent may be single hydration agent or a plurality of hydration agents as a functional ingredient for the edible compositions (e.g, beverages) provided herein.
  • the at least one hydration agent is present in the edible composition (e.g, beverage) in a concentration sufficient to promote health and wellness.
  • Hydration products help the body to replace fluids that are lost through excretion.
  • Fluid loss is lost as sweat to regulate body temperature, as urine to excrete waste substances, and as water vapor to exchange gases in the lungs. Fluid loss can also occur due to a wide range of external causes, non-limiting examples of which include physical activity, exposure to dry air, diarrhea, vomiting, hyperthermia, shock, blood loss, and hypotension.
  • Diseases causing fluid loss include diabetes, cholera, gastroenteritis, shigellosis, and yellow fever.
  • Forms of malnutrition that cause fluid loss include the excessive consumption of alcohol, electrolyte imbalance, fasting, and rapid weight loss.
  • the hydration product is a composition that helps the body replace fluids that are lost during exercise.
  • the hydration product is an electrolyte, non-limiting examples of which include sodium, potassium, calcium, magnesium, chloride, phosphate, bicarbonate, and combinations thereof.
  • electrolytes for use embodiments of this disclosure are also described in U.S. Patent No. 5,681,569, the disclosure of which is expressly incorporated herein by reference.
  • the electrolytes are obtained from their corresponding water-soluble salts.
  • Non-limiting examples of salts for use embodiments include chlorides, carbonates, sulfates, acetates, bicarbonates, citrates, phosphates, hydrogen phosphates, tartrates, sorbates, citrates, benzoates, or combinations thereof.
  • the electrolytes are provided by juice, fruit extracts, vegetable extracts, tea, or teas extracts.
  • the functional ingredient is chosen from at least one probiotic, prebiotic and combination thereof.
  • the at least one probiotic or prebiotic may be single probiotic or prebiotic or a plurality of probiotics or prebiotics as a functional ingredient for the edible compositions (e.g ., beverages) provided herein.
  • the at least one probiotic, prebiotic or combination thereof is present in the edible composition (e.g., beverage) in a concentration sufficient to promote health and wellness.
  • Probiotics in accordance with the teachings of this disclosure, comprise
  • probiotics beneficially affect the human body’s naturally-occurring gastrointestinal microflora and impart health benefits apart from nutrition.
  • Probiotics may include, without limitation, bacteria, yeasts, and fungi.
  • the functional ingredient is at least one phytoestrogen.
  • the at least one phytoestrogen may be single phytoestrogen or a plurality of phytoestrogens as a functional ingredient for the edible compositions (e.g, beverages) provided herein.
  • the at least one phytoestrogen is present in the edible compositions (e.g, beverages) in a concentration sufficient to promote health and wellness.
  • the functional ingredient is at least one long chain primary aliphatic saturated alcohol.
  • the at least one long chain primary aliphatic saturated alcohol may be single long chain primary aliphatic saturated alcohol or a plurality of long chain primary aliphatic saturated alcohols as a functional ingredient for the edible compositions ( e.g ., beverages) provided herein.
  • the at least one long chain primary aliphatic saturated alcohol is present in the edible composition (e.g., beverage) in a concentration sufficient to promote health and wellness.
  • the edible compositions are beverages.
  • the beverage may be selected from the group consisting of broths, cocktail
  • the beverage may be a soft drink.
  • the beverage may be low sodium, or reduced sodium, or no salt added.
  • the beverage can also contain one or more functional ingredients, which provide a real or perceived health benefit to the composition.
  • Functional ingredients include, but are not limited to, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydration agents, probiotics, prebiotics, weight management agents, osteoporosis management agents, phytoestrogens, long chain primary aliphatic saturated alcohols, phytosterols and combinations thereof.
  • suitable additives to the edible compositions as disclosed herein include, but are not limited to emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts and are described above.
  • the amount of functional ingredient in the edible composition varies widely depending on the edible composition (e.g, beverage) and the desired functional ingredient. Those of ordinary skill in the art will readily ascertain the appropriate amount of functional ingredient for each beverage.
  • the edible composition further comprises a solubilizing agent, as discussed herein.
  • a solubilizing agent as discussed herein.
  • Compounds - such as compounds according to Formula (I), Formula (II), any one of Compound 1-19, or combinations thereof - have a particular solubility in aqueous solutions.
  • the solubility of a compound depends on a number of factors including, but not limited to, the chemical structure of the compound, the solvent, the pH of the solvent, etc. Solubilizing agents may be used to increase the amount of a compound, such as a compound, or the combination of compounds, that may be dissolved in a particular amount of solvent.
  • Solvents for dissolving the compound of the combination of compounds of the disclosure include, but are not limited to, 1, 3-butylene glycol, amyl acetate, benzyl alcohol, butane- 1, 3 -diol, castor oil, diethyl tartrate, diethylene glycol monoethyl ether, ethyl acetate, ethyl alcohol, glycerin, glycerol, glycerol diacetate, isopropyl alcohol, NEOBEE® M-5 oil, propylene glycol, and triacetin. Solvents may be used at concentrations between 0.001% to 50% to solubilize the compounds of the disclosure. In some embodiments, solvent concentrations in the final product range from about 0.05 to about 2%.
  • the edible composition further comprises a surfactant to increase or decrease the effectiveness of the compounds, or the combination of compounds, of the present disclosure as compounds.
  • Suitable surfactants include, but are not limited to, non-ionic surfactants (e.g ., mono and diglycerides, fatty acid esters, sorbitan esters, propylene glycol esters, and lactylate esters) anionic surfactants (e.g., sulfosuccinates and lecithin) and cationic surfactants (e.g, quaternary ammonium salts).
  • the edible compositions of this disclosure are prepared according to techniques well-known in the art.
  • an edible composition of the disclosure is prepared by mixing a component or ingredient of the edible composition, such as a salt, with a compound, or a combination of compounds, of the disclosure.
  • a compound, or a combination of compounds, of the disclosure can be added directly to the edible composition comprising a salt.
  • a salt is added simultaneously or sequentially with a compound, or a combination of compounds, of the disclosure. If sequentially, the salt may be added before or after the compound, or the combination of compounds, of the disclosure.
  • the edible composition is a food product.
  • the edible composition is a pharmaceutical composition. In some embodiments, the edible composition is a consumer product.
  • the edible composition is in the form of, for example, a gum, lozenge, sauce, condiment, meat matrix, meat slurry, paste, suspension, spread, coating, a liquid, a gel, an emulsion, granules, or seasoning.
  • the amount of both a compound, or a combination of compounds, of the present disclosure and a salt used in an edible composition depends upon a variety of factors, including the purpose of the composition and the desired or acceptable perception of saltiness. The amount may depend on the nature of the edible composition, the compound or combination of compounds added, the salt, other compounds present in the composition, the method of preparation (including amount of heat used), and the pH of the edible composition. Those of skill in the art will know how to determine the amounts needed to produce the desired taste(s).
  • a compound, or the combination of compounds, of the disclosure may be present at any of the concentrations effective for modulating the saltiness of a salt listed above.
  • the edible compositions are formulated as a concentrate, which is intended for dilution prior to consumption.
  • concentrates include syrups, frozen concentrates, dry mixes, and food additives.
  • the compounds, or the combination of compounds may be present in a concentrate - for later dilution - at concentration between about 1 ppm and about 5000 ppm.
  • the compound of the present disclosure may be present in a concentrate at a concentration between about 1 ppm to about 3000 ppm; about 10 p8pm to about 1000 ppm; about 50 ppm to about 500 ppm; about 50 ppm to about 250 ppm; about 50 ppm to about 100 ppm; about 100 ppm to about 500 ppm; about 100 ppm to about 1000 ppm; about 100 ppm to about 3000 ppm; about 500 ppm to about 1000 ppm; about 500 ppm to about 3000 ppm; or about 1000 ppm to about 3000 ppm.
  • the compound of the present disclosure may be present in a concentrate for dilution at a concentration of about 50 ppm to about 3000 ppm, about 50 ppm to about 1000 ppm or about 50 ppm to about 500 ppm.
  • the compound, or the combination of compounds, of the present disclosure may be present in a concentrate for dilution at a concentration of about 1 ppm to about 500 ppm; about 1 ppm to about 250 ppm; about 1 ppm to about 100 ppm; about 1 ppm to about 50 ppm; about 10 ppm to about 500 ppm; about 10 ppm to about 250 ppm; about 10 ppm to about 100 ppm; about 50 ppm to about 500 ppm; about 50 ppm to about 250 ppm; or about 50 ppm to about 100 ppm.
  • the edible compositions as disclosed herein, including solid or liquid concentrate compositions for preparing beverages enable the reduction in concentration of sodium chloride. In some embodiments, any one of the above may be low sodium, reduced sodium, or no salt added.
  • the one or more compound of the disclosure is added to an edible or comestible composition, such as a food or beverage, wherein the comestible composition is a low sodium, reduced sodium, or no salt added composition.
  • an edible or comestible composition such as a food or beverage
  • the comestible composition is a low sodium, reduced sodium, or no salt added composition.
  • one or more compounds can be added to a composition having less than about 140 mg of sodium per serving.
  • the one or more compounds can be added to a composition having about 25% or less sodium than a similar composition in which no effort has been made to reduce the sodium level.
  • the one or more compounds can be added to a composition having less than about 5 mg of sodium per serving.
  • the one or more compounds is used to enhance the perception of saltiness in the compositions that are low sodium, reduced sodium, or no salt added.
  • the one or more compounds can be added to a composition that is low sodium, reduced sodium, or no salt added that also is low in typical sodium chloride replacement salts, such as, for example potassium chloride, ammonium chloride, magnesium chloride, and calcium chloride, wherein the amount of potassium chloride, ammonium chloride, magnesium chloride, or calcium chloride is less than 140 mg per serving.
  • typical sodium chloride replacement salts such as, for example potassium chloride, ammonium chloride, magnesium chloride, and calcium chloride, wherein the amount of potassium chloride, ammonium chloride, magnesium chloride, or calcium chloride is less than 140 mg per serving.
  • the concentration of sodium in the composition is less than about 2 wt. %, less than about 1.8 wt. %, less than about 1.6 wt. %, less than about 1.4 wt. %,
  • the flavoring concentrate composition comprises i) one or more salt-enhancing compounds as described herein; ii) a carrier; and iii) optionally at least one adjuvant.
  • carrier denotes a usually inactive accessory substance, such as solvents, binders, or other inert medium, which is used in combination with the flavor modifying compound and one or more optional adjuvants to form the composition.
  • water or starch can be a carrier for a flavoring concentrate composition.
  • the carrier is the same as the diluting medium for reconstituting the flavoring concentrate composition; and in other embodiments, the carrier is different from the diluting medium.
  • carrier includes, but is not limited to, ingestibly acceptable carrier.
  • adjuvant and“functional ingredient” are used interchangeably denotes an additive which supplements, stabilizes, maintains, or enhances the intended function or effectiveness of the active ingredient, such as the compound of the present disclosure.
  • the one or more salt-enhancing compounds can be any of the compounds as disclosed herein or combinations thereof.
  • the at least one adjuvant comprises one or more ingredients selected from the group consisting of an emulsifier, a stabilizer, an antimicrobial preservative, an antioxidant, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts are described below.
  • the one or more salt-enhancing compound as disclosed herein is added to a comestible composition or formulation, such as a food or beverage, wherein the comestible composition or formulation contains normal sodium concentrations.
  • the one or more salt-enhancing compound can be added to a soup having around 800 mg or more of sodium per serving.
  • the one or more salt-enhancing compounds can be added to: broth having about 800 mg or more of sodium per serving; bakery products such as breads or desserts having about 400 mg or more of sodium per serving; or beverages having about 400 mg or more of sodium per serving.
  • the salt-enhancing compounds can be added to any composition having normal sodium levels to enhance the sodium flavor thereof.
  • the one or more salt-enhancing compound is added to a comestible composition, such as a food or beverage, wherein the comestible composition is a low sodium, reduced sodium, or no salt added composition.
  • the one or more salt-enhancing compounds is used to enhance the perception of saltiness in the composition that are low sodium, reduced sodium, or no salt added.
  • the one or more compounds can be added to a composition that is low sodium, reduced sodium, or no salt added that also is low in typical sodium chloride (NaCl) replacement salts, such as, for example potassium chloride (KC1), ammonium chloride (NH 4 CL), magnesium chloride (MgCh), and calcium chloride (CaCh), wherein the amount of potassium chloride, ammonium chloride, or calcium chloride is less than 140 mg per serving.
  • NaCl sodium chloride
  • KC1 potassium chloride
  • NH 4 CL ammonium chloride
  • MgCh magnesium chloride
  • CaCh calcium chloride
  • the concentration of sodium in the composition or composition is less than about 2 wt. %, less than about l.8wt. %, less than about 1.6 wt. %, less than about 1.4 wt. %, less than about 1.2 wt. %, less than about I wt. %, less than about 0.8 wt. %, less than about 0.6 wt. %, less than about 0.4 wt. %, less than about 0.2 wt. %, less than about 0.1 wt. %, less than about 0.08 wt. %, less than about 0.06 wt. %, less than about 0.04 wt. %, or less than about 0.02 wt.
  • the comestible composition comprise one or more salt-enhancing compounds described herein, wherein the amount of chloride salts in the composition, such as sodium chloride, potassium chloride, ammonium chloride, or calcium chloride or combinations thereof, is less than about 900 mg, 600 mg, 400 mg, 140 mg, or 5 mg
  • chloride salts in the composition such as sodium chloride, potassium chloride, ammonium chloride, or calcium chloride or
  • combinations thereof) is less than about 5 wt. %, less than about 4.5 wt. %, less than about 4 wt. %, less than about 3.5 wt. %, less than about 3 wt. %, less than about 2.6 wt. %, less than about wt. %, less than about 2.4 wt. %, less than about 2.2 wt. %, less than about 2 wt. %, less than about 1.8 wt. %, less than about 1.6 wt. %, less than about 1.4 wt. %, less than about 1.2 wt. %, less than about I wt. %, less than about 0.8 wt.
  • % less than about 0.6 wt. %, less than about 0.5 wt. %, less than about 0.4 wt. %, less than about 0.3 wt. %, less than about 0.2 wt. %, less than about 0.1 wt. %, less than about 0.08 wt. %, less than about 0.06 wt. %, less than about 0.04 wt. %, or less than about 0.02 wt. %.
  • the compound, or the combination of compounds, of the present disclosure may be present in a concentrate for dilution at a concentration of about 50 ppm, about 75 ppm, about 100 ppm, about 150 ppm, about 200 ppm, about 250 ppm, about 300 ppm, about 350 ppm, about 400 ppm, about 450 ppm, about 500 ppm, about 550 ppm, about 600 ppm, about 650 ppm, about 700 ppm, about 750 ppm, about 800 ppm, about 850 ppm, about 900 ppm, about 950 ppm, about 1000 ppm, about 1050 ppm, about 1100 ppm, about 1150 ppm, about
  • the edible composition further comprises a salty taste improving composition.
  • auxiliaries or carriers include maltodextrin, starch, natural or artificial polysaccharides and/or vegetable gums such as modified starches or gum arabic, coloring agents, for example permitted foodstuff dyes, coloring plant extracts, stabilizers, preservatives, antioxidants, viscosity-influencing substances.
  • the edible compositions may be included in a package.
  • the edible composition is packaged in bulk, in which the package contains more of the compositions than would typically be used for a single dish or serving of food or beverage.
  • Such bulk packages can be in the form of paper, plastic, or cloth bags or cardboard boxes or drums.
  • Such bulk packages may be fitted with plastic or metal spouts to facilitate the dispensing of the edible composition.
  • the package may contain an edible composition comprising a compound, or a combination of compounds, of the present disclosure and a salt. In some embodiments, the package contains an edible composition comprising a compound, or a combination of compounds, of the present disclosure. In some embodiments, the package contains an edible composition comprising a compound, or a combination of compounds, of the present disclosure and a salt selected from, but not limited to KC1, NH 4 CI, MgCk, and CaCk. In some
  • the package contains an edible composition comprising a compound, or a combination of compounds, of the present disclosure. In some embodiments, the package contains an edible composition comprising a compound, or a combination of compounds, of the present disclosure.
  • the edible compositions may be used for medicinal or hygienic purposes, for example, in mouthwash, medicines, pharmaceuticals, cough syrup, throat spray, toothpaste, dental adhesives, tooth whiteners, glues ( e.g ., on stamps and envelopes), and toxins used in insect and rodent control.
  • the salted composition is in a form of a tabletop salt composition
  • a tabletop salt composition comprising at least one compound according to Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds, and at least one salt, at least one bulking agent, and optionally at least one salty taste improving composition and/or anti-caking agent with and/or flavor profile.
  • the term“bulking agent” encompasses any non-toxic carrier which is non-gritty and releases substantially no electrolytes in water or when
  • the bulking agent is a water insoluble or low solubility food grade material with a bland taste.
  • Suitable non-gritty bulking agents include, for example, grain flours, starches, maltodextrins, dietary fibers, bleached all-purpose wheat flour, cellulosic materials and the like. Mixtures of bulking agents can also be employed.
  • anti-caking agent is understood to mean any composition which prevents, reduces, inhibits, or suppresses at least one salty taste enhancing molecule from attaching, binding, or contacting to another salty taste enhancing molecule.
  • “anti caking agent” may refer to any composition which assists in content uniformity and uniform dissolution.
  • non-limiting examples of anti-caking agents include cream of tartar, calcium silicate, silicon dioxide, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pa.), and tricalcium phosphate.
  • the anti caking agents are present in the tabletop salt composition in an amount from about 0.001 to about 3% by weight of the tabletop salt composition.
  • Tabletop salt compositions may be embodied and packaged in numerous different forms, and may be of any form known in the art.
  • the tabletop salt compositions may be in the form of powders, granules, packets, tablets, sachets, pellets, cubes, solids, or liquids.
  • the disclosure provides a method of preparing an edible composition.
  • the method comprises: (a) providing a salt; and (b) adding to the salt of (a) a compound of Formula (I), (II), any one of Compounds 1-19, as described herein, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds.
  • the compound of the disclosure has been solubilized prior to the addition step (b).
  • a solubilizing agent is added to the composition.
  • the salt of step (a) is provided in a comestibly acceptable carrier.
  • method steps (a) and (b) can be performed in any order - z.e., the method may comprise: (a) adding a compound, as described herein, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds; and (b) adding a salt to the Compound(s) of (a).
  • the method of preparing an edible composition of the disclosure comprises mixing a component or ingredient of the edible composition, such as a salt, with a compound, or a combination of compounds, of the disclosure.
  • a compound, or a combination of compounds, of the disclosure can be added directly to the edible composition comprising a salt.
  • the salt is added to the edible composition simultaneously or sequentially with a compound, or a combination of compounds, of the disclosure. If sequentially, the salt may be added before or after the compound, or a combination of compounds, of the disclosure.
  • solubilizing agents are utilized, the method includes the addition of the solubilizing agent at any point.
  • the solubilizing compound may be added as the first, second, or third component.
  • the solubilizing agent may also be added concurrently with any other component.
  • the methods of preparing an edible composition further comprise adding at least one additional additive, such as a salty taste improving composition, and/or a salty taste improving additive.
  • the edible compositions may be a food product, a pharmaceutical composition, or a consumer product.
  • the edible composition is in the form of, for example, a gum, lozenge, sauce, condiment, meat matrix, meat slurry, paste, suspension, spread, coating, a liquid, a gel, an emulsion, granules, or seasoning.
  • the disclosure provides a method of enhancing the perception of salty taste in a subject.
  • the method comprises the use of an edible composition of the present disclosure, where the edible composition comprises a compound according to Formula (I), (II), any one of Compounds 1-19, as described herein, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds.
  • the edible composition comprises (i) a compound according to Formula (I), (II), any one of Compounds 1-19, as described herein, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds; (ii) a salt; and optionally (iii) a solubilizing agent.
  • the compositions my further comprise one or more organic acids, selected from, but not limited to tartaric acid, fumaric acid, succinic acid and carbonic acid.
  • a subject refers to a mammal.
  • the subject is human.
  • a subject is a domestic or laboratory animal, including but not limited to, household pets, such as dogs, cats, pigs, rabbits, rats, mice, gerbils, hamsters, guinea pigs, and ferrets.
  • a subject is a livestock animal.
  • livestock animals include: alpaca, bison, camel, cattle, deer, pigs, horses, llamas, mules, donkeys, sheep, goats, rabbits, reindeer, and yak.
  • the methods as disclosed herein can be used to enhance or potentiate salty taste in any edible composition, including a foodstuff, food product, pharmaceutical composition or consumer product.
  • the edible composition may be in any form.
  • the composition is in the form of, for example, a gum, lozenge, sauce, condiment, paste, suspension, spread, coating, a liquid, a gel, an emulsion, granules, or seasoning.
  • the edible composition may be utilized by, for example, placement in the oral cavity or by ingestion.
  • the edible composition comprising a compound, or a combination of compounds, of the disclosure is placed in the oral cavity or ingested before an edible composition, such as a foodstuff, a food product, pharmaceutical composition or consumer product, comprising a salt
  • an edible composition such as a foodstuff, a food product, pharmaceutical composition or consumer product, comprising a salt
  • the edible composition comprising a compound, or a combination of compounds, of the disclosure is placed in the oral cavity or ingested after a salty food stuff, food product, pharmaceutical composition or consumer product.
  • a compound, or a combination of compounds, of the disclosure is placed in the oral cavity or ingested concurrently with a salty food stuff, food product, pharmaceutical composition or consumer product, either as a separate edible composition or by incorporation in the salty food stuff, food product, pharmaceutical composition or consumer product.
  • a compound, or a combination of compounds, of the disclosure can be combined with foodstuffs or food products to enhance or potentiate the salty taste of a foodstuff or food product.
  • a compound, or a combination of compounds, of the disclosure can be used, for example, in a lozenge or gum for use after exposure to a salty food stuff, food product, pharmaceutical composition or consumer product ( e.g ., to enhance or potentiate a salty aftertaste).
  • a salt such as NaCl, KC1, NH 4 Cl, MgCh, or CaCh
  • another aspect of the present disclosure provides a method of reducing the amount of a salt in an edible composition, such as a food product, a pharmaceutical composition or a consumer product.
  • An amount of the salt in the edible composition may be replaced with a compound according to Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds.
  • an amount of solubilizing agent may also be added to the edible composition, as described herein.
  • the term“replace” or“replacing” refers to substituting one compound for another compound in or in the preparation of, for example, an edible composition, such as food product.
  • the method comprises: (a) replacing an amount of a salt used in preparing an edible composition with an amount of a compound according to Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds.
  • a salt used in preparing an edible composition with an amount of a compound according to Formula (I), (II), any one of Compounds 1-19, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds.
  • the compound of the disclosure is added in the form of an edible composition comprising the compound, or a combination of compounds, of the disclosure.
  • an amount of solubilizing agent may also be added to the edible composition, as described herein.
  • the method of reducing the amount of a salt in an edible composition comprises the steps of: (a) ingesting a first edible composition, in which the amount of a salt has been reduced; and (b) ingesting a second edible compound, which comprises a compound, or a combination of compounds, of the present disclosure.
  • the first edible composition is ingested before the second edible composition.
  • the first edible composition is ingested after the second edible composition. In some embodiments, the first edible composition is ingested concurrently with the second edible composition. In such methods, an amount of solubilizing agent may also be added along with the compound, or a combination of compounds, of the present disclosure.
  • the edible composition is a food product.
  • the edible composition is a pharmaceutical composition.
  • the edible composition is a consumer product.
  • the salt being replaced may be selected from NaCl, KC1, NH4CI, MgCh, and CaCh, or combinations thereof.
  • the methods of reducing salt intake of a subject further comprise the step of identifying a subject in need thereof.
  • the skilled worker would be able to identify a subject in need of reducing salt intake.
  • Non-limiting examples of such subjects include for example subjects that suffer from hypertension, and/or chronic kidney disease.
  • the amount of the salt replaced in the edible composition is an amount sufficient to maintain or restore the health of a subject.
  • the amount of the salt replaced in the edible composition may be an amount sufficient to decrease hypertension and/or chronic kidney disease.
  • the amount of the salt replaced may be up to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or more.
  • the amount of the compound, or the combination of compounds, added is effective to enhance the perception of salty taste in the subject.
  • the amount of the compound, or the combination of compounds, added is sufficient to permit replacement of up to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% 75%, 80%, 85%, 90%, 95% or more of the amount of salt present in the edible composition.
  • the amount of the compound, or the combination of compounds, added is sufficient to permit replacement of up to 25% of the amount of the salt present in the edible composition.
  • the amount of the compound, or the combination of compounds, added is sufficient to permit replacement of up to 50% of the amount of the salt present in the edible composition. In other embodiments, the amount of the compound, or the combination of compounds, added is sufficient to permit replacement of up to 75% of the amount of the salt present in the edible composition. In yet other embodiments, the amount of the compound, or the combination of compounds, added is sufficient to permit replacement of up to 99% of the amount of the salt present in the edible composition.
  • the method of reducing the amount of a salt in an edible composition further comprises adding at least one additional additive, such as a salty taste improving composition, and/or a salty taste improving additive.
  • the disclosure provides methods of enhancing or potentiating the salty taste in an edible composition.
  • the edible composition may be a food product, a pharmaceutical composition, or a consumer product.
  • the method comprises: (a) adding an effective amount of a compound according to Formula (I), (II), any one of Compounds 1-19, as described herein or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds, to an edible composition comprising a salt such that the perception of saltiness intensity of the salt is enhanced.
  • the salt is either added to the edible composition before the compound, or the combination of compounds; concurrently with the compound, or the combination of compounds; or after the compound, or the combination of compounds.
  • the salt is naturally or inherently present in the edible composition when the compound, or the combination of compounds, is added. In such methods, an amount of solubilizing agent may also be added to the edible composition, as described herein.
  • the method comprises: (a) ingesting an effective amount of a compound according to Formula (I), (II), any one of Compounds 1-19, as described herein, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds, before, along with, or after the edible composition such that the perception of saltiness intensity of the salt is enhanced.
  • an amount of solubilizing agent may also be added to the edible composition, as described herein.
  • the perception of saltiness intensity of the salt is enhanced by up to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% 75%, 80%, 85%, 90%, 95% or 100%.
  • the perception of saltiness intensity of the salt is enhanced beyond 100%, for example, by 125%, 150%, 175%, 200%, 225%, 250%, 275%, 300%, 325%, 350%, 375%, 400%, 425%, 450%, 475%, 500% or increments in between those recited.
  • the perception of saltiness intensity of the salt is enhanced by up to 25%. In other embodiments, the perception of saltiness intensity of the salt is enhanced by up to 50%. In other embodiments, the perception of saltiness intensity of the salt is enhanced by up to 75%. In other embodiments, the perception of saltiness intensity of the salt is enhanced by up to 100%.
  • the perception of saltiness intensity of the salt is enhanced by about 5% to about 100%, about 5% to about 90%, about 5% to about 80%, about 5% to about 70%, about 5% to about 60%, about 5% to about 50%, about 5% to about 40%, about 5% to about 30%, about 10% to about 30%, about 10% to about 25%, about 20% to about 80%, about 20% to about 70%, about 20% to about 60%, about 20% to about 50%, about 20% to about 40%, about 20% to about 30%, about 25% to about 80%, about 25% to about 70%, about 25% to about 60%, about 25% to about 50%, about 25% to about 40%, or about 25% to about 30%.
  • These amounts are not meant to be limiting, and increments between the recited percentages are specifically envisioned as part of the disclosure.
  • the method of enhancing the salty taste attributed to a salt in an edible composition further comprises adding at least one additional additive, such as a salty taste improving composition, and/or a salty taste improving additive.
  • a salty taste improving composition such as a salty taste improving composition, and/or a salty taste improving additive.
  • Another aspect of the disclosure provides a method of enhancing or potentiating activation and/or signaling of a salty taste (ENaC) receptor.
  • the method comprises contacting a salty taste receptor with a compound according to Formula (I), (II), any one of Compounds 1-19, as described herein, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds, in the presence of a salt.
  • the salt can be one selected from NaCl, KC1, NH 4 CL, MgCh, CaCh or a combination of the foregoing salts.
  • the method comprises contacting a salty taste receptor with an edible composition comprising a compound, as described herein, or a comestibly or biologically acceptable salt, solvate, or enantiomer thereof, or a combination of any of the foregoing compounds, in the presence of a salt.
  • the edible composition may be a food product, a pharmaceutical composition, or a consumer product.
  • the salty taste receptor is an ex vivo or in vivo (ENaC) receptor present in, for example, an assay.
  • the salty taste receptor also may be an in vivo (ENaC) receptor present in a subject.
  • the salty taste receptor is typically present in the oral cavity or gastrointestinal tract of the subject.
  • An in vivo salty responsive assay means an assay where an assessment of increased perception of saltiness can be ascribed.
  • Such an assay may be, for example, but not limited to, a human sensory descriptive analysis panel, a human sensory discriminative panel, a consumer panel and/or an expert flavorist assessment.
  • Non-human assessments of salty response include, but not limited to, operant conditioned animal studies of saltiness taste perception and/or lick rate/amount bottle preference tests
  • An in vitro salty responsive assay refers to an assay where an assessment of increased salty response or interaction can be ascribed.
  • An example of such an assay may be, but is not limited to, in vitro (ENaC) receptor binding assays, in vitro receptor cell-based assays, and/or electronic tongue taste analysis.
  • L-camitine (inner salt) 4.0 g (24.8 mmol) is mixed with fumaric acid l.44g ( 12.4 mmol) in 10 mL of water (deionized). The solution is stirred at 95C for 2 hours in a round bottom flask. After reaction is complete maltodextrin 5.5 g is added and stirred for 5 minutes. Water is removed via roto evaporation and the semi -dry mixture is placed in a vacuum oven at 50C for 8 hours to yield 8.8 g of a dry semi crystalline solid powder product in 50% concentrate mp °C.
  • L-camitine (inner salt) 4.0 g (24.8 mmol) is mixed with succinic acid l.46g (12.4 mmol) in 10 mL of water (deionized). The solution is stirred at 95C for 2 hours in a round bottom flask. After reaction is complete maltodextrin 5.5 g is added and stirred for 5 minutes. Water is removed via roto evaporation and the semi -dry mixture is placed in a vacuum oven at 50C for 8 hours to yield 8.2 g of a dry semi crystalline solid powder product in 50% concentrate mp °C
  • L-camitine (inner salt) 3.5 g (21.7 mmol) is mixed with calcium chloride 0.8lg (10.8 mmol) in 6 mL of water (deionized). The solution is stirred at 95C for 2 hours in a round bottom flask. After reaction is complete maltodextrin 4.3 g is added and stirred for 5 minutes. Water is removed via roto evaporation and the semi -dry mixture is placed in a vacuum oven at 50C for 8 hours to yield 3.18 g of a dry semi crystalline solid powder product in 50% concentrate mp °C
  • L-camitine (inner salt) 1.5 g (9.3 mmol) is mixed with potassium chloride 0.69g (9.3 mmol) in 6 mL of water (deionized). The solution is stirred at 95C for 2 hours in a round bottom flask. After reaction is complete maltodextrin 2.1 g is added and stirred for 5 minutes. Water is removed via roto evaporation and the semi -dry mixture is placed in a vacuum oven at 50C for 8 hours to yield 2.1 g of a dry semi crystalline solid powder product in 50% concentrate mp °C
  • Betaine 7.5g is heated (80°C) with 28g of ethanol in a round bottom flask with stirring. Dissolved Tartaric acid 4.76g in l8.0g of warm ethanol is added slowly (dropwise) over 30 minutes and stirred for 1 hour at 80°C. The stirred solution is cooled to ambient temperature and a white precipitate occurs. The white product is filtered and washed 2X with 25 mL ethanol. The pure product is dried in a heated vacuum oven at 40°C for 8 hours to give 10.8 g (88% yield) of 100% betaine tartrate mp °C
  • Betaine 7.65g is heated (80°C) with 23g of ethanol in a round bottom flask with stirring.
  • Dissolved succinic acid 3.82g in 14.5 g of warm ethanol is added slowly (dropwise) over 30 minutes and stirred for 1 hour at 80°C.
  • the stirred solution is cooled to ambient temperature and a white precipitate occurs.
  • the white product is filtered and washed 2X with 25 mL ethanol.
  • the pure product is dried in a heated vacuum oven at 40°C for 8 hours to give 8.9 g (76% yield) of 100% betaine succinate mp °C
  • Betaine 10 Og is heated (80°C) with 39g of ethanol in a round bottom flask with stirring. Dissolved succinic acid 10. Og in 40.0 g of warm ethanol is added slowly (dropwise) over 30 minutes and stirred for 1 hour at 80°C. The stirred solution is cooled to ambient temperature and a white precipitate occurs. The white product is filtered and washed 2X with 25 mL ethanol. The pure product is dried in a heated vacuum oven at 40°C for 8 hours to give l3.55g (68% yield) of 100% betaine acid succinate mp °C
  • Betaine (inner salt) 10.0 g (84 mmol) is mixed with calcium chloride 6.22g (42 mmol) in 25 mL of water (deionized). The solution is stirred at 85C for 2 hours in a round bottom flask. After reaction is complete maltodextrin 16.2 g is added and stirred for 5 minutes. Water is removed via roto evaporation and the semi -dry mixture is placed in a vacuum oven at 40C for 8 hours to yield 30.0 g ( 90% yield) of a white crystalline solid powder product in 50% concentrate mp °C 1/2 Ca 2 ⁇ +
  • the compounds as disclosed herein can also be prepared as described in EiS Patent 7,718,414 B2 (May 18, 2010).
  • the biosynthetic scheme, which is also the way how L-camitine is produced in nature, is described in Figure 1.
  • test compounds used in the following examples are commercially available, may be obtained from the synthetic or biosynthetic methods, or may be extracted from a natural source, as disclosed above.
  • a concentration response curve for sodium was prepared in assay buffer in appropriate concentrations to achieve the final on-cell concentrations of in mM: 142, 128, 108, 88, 75, 55, 30, and 19. Cells were exposed to the full range of sodium chloride concentration response curve in absence (NaCl) and presence of the potential enhancing compound (NaCl + CPD). Data were analyzed by evaluating the signal over background (essentially max Relative Fluorescence ETnit (RFEi)-min RFET) for each
  • the taste test panelists used in the Example 4 were selected using a sensory acuity screening program.
  • Candidate taste panelists were recruited, with prescreening and personal interviews, and were assessed and for their ability to detect, recognize and differentiate basic taste attributes or mixtures thereof as part of a standardized acuity test. This included basic tastes of salty, sour, salty, bitter and umami, as well as having the capacity to focus on specific aspects of sensory character such as ranking the various tastes perceived and identifying the basic tastes presented at threshold levels.
  • Control sample 0.25% NaCl in water
  • Test Sample Compound 6 at l250ppm in water
  • test sample thirty responses of thirty-two indicated that the control sample was saltier. Two responses indicated that the test sample was saltier. Using a binomial distribution, p ⁇ 0.05 for the test sample. Therefore, the control sample is significantly saltier than the test samples. This would suggest that, up to maximum use level indicated above, the test sample is not inherently salty.
  • aqueous salt solution was prepared by adding NaCl (by weight), to reverse- osmosis (RO) water to achieve the desired concentration.
  • test compounds The intrinsic effect of test compounds on the perception of salty taste, in an aqueous solution, in humans was evaluated using 2AFC methodology. This test was a double-blinded, randomized study where taste panelists (n >15) evaluate a pair of aqueous solutions one at a time- one sample contains RO water plus compound (i.e. test) while the other contains RO water plus 42.5mM NaCl (i.e. control). Each test sample is compared against the aqueous NaCl solution to observe if the test is significantly less salty than the control sample.
  • Panelists were instructed not to eat or drink (except water) for at least lh before the test. During the test, panelists were instructed to sip each sample, swirl it around their mouth and then expectorate. After tasting each sample in the pair, panelists were instructed to record the sample that is“saltier” in taste. Panelists cleansed their palates by rinsing with water, eating an unsalted matzo cracker and waiting for an interval of about 5 minutes. Each pair was tasted twice. All samples were tasted at ambient temperatures. Data were analyzed using binomial probabilities.
  • test compound The effect of the test compound on the perception of the salty taste in three different food matrices, was evaluated using a descriptive analysis methodology with a group of trained panelists, as follows.
  • Candidate panelists were recruited, with prescreening and personal interviews, and were assessed for their ability to detect, recognize and differentiate basic taste attributes or mixtures thereof as part of a standardized acuity test. These candidate panelists were also assessed for their innate ability to identify flavors, and to rank on intensity scales. Other senses such as smell and vision were also included as part of the assessment. Candidates also were screened for their ability to use language to describe and articulate ideas about their taste, smell and visual perception of samples.
  • Selected candidates proceeded to training as a group in three phases: (1) Lexicon development, (2) Concept alignment, and (3) Scaling descriptors.
  • lexicon development panelists evaluated products appropriate for use in the study to generate and align on terms describing the flavor, taste, aromatic, trigeminal, and temporal attributes.
  • concept alignment the panel evaluated the products mentioned above to clarify and confirm the attributes that were generated during lexicon development using reference standards that appropriately define each attribute; these are either physical references (e.g. salt solutions) or verbal descriptions (e.g. overall flavor).
  • Product terms and concepts were validated during this portion of the study.
  • the panel used in this example was trained to reference salty attributes in an absolute manner, such that a particular concentration of NaCl is always measured by the panelists at the same point using a l5cm line scale where each cm represents a 0.08% increase in NaCl to cover the range of 0% to 1.2% NaCl.
  • the trained panel was then used for a descriptive analysis assessment for Compound in chicken bouillon, tomato sauce and cheese sauce matrices.
  • the compound blend was assessed at a dose of 525ppm / 225ppm for salt enhancement across all three of the matrices.
  • the Chicken Bouillon was prepared by reconstituting a low sodium dry chicken powder with RO water (by weight) to achieve the desired dilution according to the recipe.
  • the tomato sauce and cheese sauce were prepared by heating a frozen, prepared product until the desired temperature was reached, according to the package directions.
  • Compound was first prepared as a 500ppm concentrated stock solution in RO water. The concentrated stocks were then added to the chicken bouillon to result in a final compound concentration listed in Table 3.
  • Table 3 Illustrative results of this DA assessment are presented in Table 3.
  • Table 4 and Table 5 show results obtained in different matrices for blends of Compound 1 and 6.
  • Table 3. DA assessment of salt enhancing effects of individual and blends of compounds in chicken bouillon matrix.
  • Normalized fold values are used to account for sensory perceptual space rather than physical space.
  • the perception space is defined by the distance between the negative and positive controls. Since the perceptual space varies in contrast to the physical space (particularly in non linear regions of taste), utilizing the perceptual space eliminates the expected gap.

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  • Health & Medical Sciences (AREA)
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Abstract

La présente invention concerne des composés destinés à être utilisés en tant qu'agents de modification ou d'amélioration de goût salé, et destinés à être utilisés pour modifier ou améliorer l'arôme de produits à teneur réduite en sodium et augmenter la sapidité de produits qui peuvent avoir une teneur en sodium réduite. L'invention concerne également des procédés de modulation de la salinité perçue d'un produit par ajout de composés selon l'invention au produit.
PCT/US2019/013289 2018-01-12 2019-01-11 Composés, compositions et procédés de modulation du goût salé Ceased WO2019140253A1 (fr)

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WO2025168835A1 (fr) 2024-02-09 2025-08-14 Symrise Ag Bétaïne en tant qu'agent de masquage pour des notes atypiques indésirables dans un produit alimentaire à base de plantes et/ou de produits laitiers

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US20100227023A1 (en) * 2009-03-06 2010-09-09 Danisco A/S Seasoning blend

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US3629451A (en) * 1969-03-03 1971-12-21 Stanley Drug Products Inc Method of treating bacterial infections
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025168835A1 (fr) 2024-02-09 2025-08-14 Symrise Ag Bétaïne en tant qu'agent de masquage pour des notes atypiques indésirables dans un produit alimentaire à base de plantes et/ou de produits laitiers

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