CA2307078A1 - Mint and/or fruit flavor compositions - Google Patents
Mint and/or fruit flavor compositions Download PDFInfo
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- CA2307078A1 CA2307078A1 CA002307078A CA2307078A CA2307078A1 CA 2307078 A1 CA2307078 A1 CA 2307078A1 CA 002307078 A CA002307078 A CA 002307078A CA 2307078 A CA2307078 A CA 2307078A CA 2307078 A1 CA2307078 A1 CA 2307078A1
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
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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
- A23L27/88—Taste or flavour enhancing agents
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- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Nutrition Science (AREA)
- Fats And Perfumes (AREA)
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Abstract
A flavor composition comprising 8-ocimenyl esters of the formula (see formula I) wherein one of the two radicals R1 and R2 is methyl and the other is vinyl and one of the two radicals R3 and R4 is methyl and the other is (see formula II) wherein R5 is hydrogen, alkyl or alkenyl. Such flavor composition can also be mint and/or fruit flavor compositions, wherein the 8-ocimenyl esters have a flavor-enhancing action.
Description
HR-218-US Mn/klu/NT
MINT AND/OR FRUIT FLAVOR COMPOSITIONS
FIELD OF THE INVENTION
The invention relates to mint and/or fruit flavor compositions which comprise ocimenyl esters and to their use in foods, tobacco products or for oral hygiene.
BACKGROUND OF THE INVENTION
In the fragrance and flavor industry, there is a great need for substances, which can be used in fragrance and flavor compositions to partially or completely replace na-tural substances, which, because of the laborious nature of their manufacture, are ex-pensive. Additionally, such natural substances are available only in limited amounts and, moreover, their properties are subject to considerable quality fluctuations, which arise because they are natural substances.
Of particular interest, then, are substances, which not only have excellent organolep-tic properties (i.e., properties perceptible only by the senses), but, because of their strength and richness, can be used to achieve notable effects even at extremely low concentrations.
However, in the flavorings and food industry, substances which, apart from the pro-perty of imparting a certain odor or taste, have additional properties which are in-creasingly important. These can, for example, be certain stimuli, which are transmit-ted over the trigeminal nerve and thus perceived. They can, however, also be effects, which reduce or enhance olfactory and gustatory sensations.
. CA 02307078 2000-04-28 rsn ~ ~ o r rr SUMMARY OF THE INVENTION
We have found mint and/or fruit flavor compositions, which comprise 8-ocimenyl esters of the formula R' ~~ R2 (I), Rs Ra wherein one of the two radicals R1 and R2 is methyl and the other is vinyl and one of the two radicals R3 and R4 is methyl and the other is -CHzO I_Rs O
1 S wherein RS is hydrogen, alkyl or alkenyl, in particular C1-C6-alkyl or C2-C6-alkenyl.
DETAILED DESCRIPTION OF THE INVENTION
Preference is given to mint and/or fruit flavor compositions, which comprise 8-oci-menyl esters of the formula T-TR _71 R_T TC
MINT AND/OR FRUIT FLAVOR COMPOSITIONS
FIELD OF THE INVENTION
The invention relates to mint and/or fruit flavor compositions which comprise ocimenyl esters and to their use in foods, tobacco products or for oral hygiene.
BACKGROUND OF THE INVENTION
In the fragrance and flavor industry, there is a great need for substances, which can be used in fragrance and flavor compositions to partially or completely replace na-tural substances, which, because of the laborious nature of their manufacture, are ex-pensive. Additionally, such natural substances are available only in limited amounts and, moreover, their properties are subject to considerable quality fluctuations, which arise because they are natural substances.
Of particular interest, then, are substances, which not only have excellent organolep-tic properties (i.e., properties perceptible only by the senses), but, because of their strength and richness, can be used to achieve notable effects even at extremely low concentrations.
However, in the flavorings and food industry, substances which, apart from the pro-perty of imparting a certain odor or taste, have additional properties which are in-creasingly important. These can, for example, be certain stimuli, which are transmit-ted over the trigeminal nerve and thus perceived. They can, however, also be effects, which reduce or enhance olfactory and gustatory sensations.
. CA 02307078 2000-04-28 rsn ~ ~ o r rr SUMMARY OF THE INVENTION
We have found mint and/or fruit flavor compositions, which comprise 8-ocimenyl esters of the formula R' ~~ R2 (I), Rs Ra wherein one of the two radicals R1 and R2 is methyl and the other is vinyl and one of the two radicals R3 and R4 is methyl and the other is -CHzO I_Rs O
1 S wherein RS is hydrogen, alkyl or alkenyl, in particular C1-C6-alkyl or C2-C6-alkenyl.
DETAILED DESCRIPTION OF THE INVENTION
Preference is given to mint and/or fruit flavor compositions, which comprise 8-oci-menyl esters of the formula T-TR _71 R_T TC
R' /w Rz (I), R3 Ra wherein one of the two radicals Rl and R2 is methyl and the other is vinyl and one of the radicals R3 and R4 is methyl and the other is -CH20C-R5 O
wherein RS is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or 2-butenyl.
Particular preference is given to mint and/or fruit flavor compositions, which com-prise 8-ocimenyl esters of the formula:
/ /
/ / /
/ / v s O
O C C
O O O
(la) (Ib) (Ic) (Id) in which RS is hydrogen, methyl or ethyl.
~
TAR _71 R_T TC
wherein RS is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or 2-butenyl.
Particular preference is given to mint and/or fruit flavor compositions, which com-prise 8-ocimenyl esters of the formula:
/ /
/ / /
/ / v s O
O C C
O O O
(la) (Ib) (Ic) (Id) in which RS is hydrogen, methyl or ethyl.
~
TAR _71 R_T TC
Surprisingly, the 8-ocimenyl esters enhance the olfactory and gustatory sensation in mint and/or fruit flavor compositions.
8-Ocimenyl esters for the mint and/or fruit flavor compositions according to the pre-sent invention can be prepared by reacting 6-ocimenyl chloride of the formula R' ~~R2 (II), CI
wherein R1 and R2 are as defined above, with a salt, in particular an alkaline salt, such as Na or K salt, of an aliphatic carb-oxylic acid, in particular a C2-C~-carboxylic acid.
The process is preferably carned out in an organic solvent, in particular in a dipolar-1 S aprotic solvent. Examples of such solvents are dimethylformamide, dimethyl sulph-oxide, N-methylpyrrolidone, diethylene glycol dimethyl ether and mixtures thereof.
The reaction is preferably carned out at a temperature from 50 to 150°C, more pref erably from 90 to 120°C, optionally under pressure.
The process, starting from the compounds of the formula (II), is preferably carned out in the presence of an alkali metal iodide or elemental iodine, more preferably in the presence of NaI, this addition preferably being used in catalytic amounts, prefe-rably in an amount of from 0.01 to 10% by weight, based on II.
In the process, the compound of the formula (II) can be used as the E- or Z-isomer or as any E/Z mixture.
HR-218-i JS
8-Ocimenyl esters for the mint and/or fruit flavor compositions according to the pre-sent invention can be prepared by reacting 6-ocimenyl chloride of the formula R' ~~R2 (II), CI
wherein R1 and R2 are as defined above, with a salt, in particular an alkaline salt, such as Na or K salt, of an aliphatic carb-oxylic acid, in particular a C2-C~-carboxylic acid.
The process is preferably carned out in an organic solvent, in particular in a dipolar-1 S aprotic solvent. Examples of such solvents are dimethylformamide, dimethyl sulph-oxide, N-methylpyrrolidone, diethylene glycol dimethyl ether and mixtures thereof.
The reaction is preferably carned out at a temperature from 50 to 150°C, more pref erably from 90 to 120°C, optionally under pressure.
The process, starting from the compounds of the formula (II), is preferably carned out in the presence of an alkali metal iodide or elemental iodine, more preferably in the presence of NaI, this addition preferably being used in catalytic amounts, prefe-rably in an amount of from 0.01 to 10% by weight, based on II.
In the process, the compound of the formula (II) can be used as the E- or Z-isomer or as any E/Z mixture.
HR-218-i JS
If the E/Z mixture of the formula (II) is used, i.e. a mixture of a compound (II) in which R1 is methyl and R2 is vinyl, and a compound (II) in which R1 is vinyl and R2 is methyl, then a mixture containing the compounds of the formulae (Ia)-(Id) is obtained.
Particular preference is given to the process using sodium acetate as salt of an ali-phatic carboxylic acid.
Particular preference is given to the process using sodium acetate as salt of an ali-phatic carboxylic acid.
6-Ocimenyl chlorides can, for example, be prepared by reacting ocimene of the for-mula wherein R' ~~R2 (III), R1 and R2 are as defined above, with hypochlorous acid or sulfuryl chloride (S02C12).
For the reactions with hypochlorous acid, the latter is usually generated in situ from salts of hypochlorous acid by acidification. For the preparation of 6-ocimenyl chlo-ride(II), it has proven advantageous to liberate hypochlorous acid from sodium hy-pochlorite solution by acidification with acetic acid. The reaction with ocimene then proceeds in a two-phase system; the presence of a solvent is not necessary.
The reac-tion temperature can be between 0 and SO°C; a temperature range from 10 to 20°C is preferable.
The chlorination is carried out using sulfuryl chloride, preferably in the presence of a base, more preferably in the presence of an alkali metal carbonate, such as sodium or potassium carbonate, which is used, in particular, in excess, based on sulfuryl chlo-HR _71 R-T T
ride. Possible solvents are compounds, which are inert towards sulfuryl chloride, such as hydrocarbons, preferably n-hexane or n-heptane, such as halogenated hydro-carbons, preferably dichloromethane or tetrachloromethane, or such as ethers, pref erably methyl tent-butyl ether. The reaction temperature is, in particular, from 0 to S 50°C, a range from 20 to 30°C being preferable.
The ocimene can be used here as cis-ocimene, as trans-ocimene or as a cis/trans mixture.
Preference is given to using a cis/trans ocimene mixture, a content of from 50 to 90%
by weight of trans-isomer and from SO to 10% by weight of cis-isomer being pre-ferable, from which a E/Z mixture of the compound of the 6-ocimenyl chlorides (II) can be prepared and therefrom, in turn, a mixture of isomeric 8-ocimenyl esters of the formulae (Ia)-(Id).
Mint compositions according to the present invention comprise mint flavor compo-nents and 8-ocimenyl esters.
Mint flavor components can, for example, be:
essential oils, such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil, clove oil, citrus oils, cinnamon bark oil, wintergreen oil, cassia oil, davana oil, spruce needle oil, eucalyptus oil, fennel oil, galbanum oil, ginger oil, camomile oils, caraway oil, rose oil, geranium oil, sage oils, yarrow oil, anise seed oil, thyme oil, juniper berry oil, angelica root oil, and the fractions of these oils.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, men-thol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, eucalyp-tol, limonene, eugenol, pinene, sabinene hydrate, 3-octanol, carvone, gamma-octa-lactone, gamma-nonalactone, germacren-D, viridiflorol, 1,3E,SZ-undecatriene, iso-r CA 02307078 2000-04-28 LT12 _71 R_T TC
_7_ pulegol, piperitone, 3-octyl acetate, isoamyl isovalerate, hexanol, hexanal, cis-3-hex-enol, linalool, alpha-terpineol, cis and trans carvyl acetate, p-cymene, damascenone, damascone, dimethyl sulfide, fenchol, cis-4-heptenal, isobutyraldehyde, isovaleral-dehyde, cis jasmone, anisaldehyde, methyl salicylate, myrtenyl acetate, 2-phenyl ethyl alcohol, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, cinnamaldehyde, geraniol, nerol.
Compounds having a physiological cooling effect such as for example menthol, menthoneglycerol acetal, menthyl lactate, substituted menthyl-3-carboxamides (e.g.
menthyl-3-carboxylic acid N-ethylamide), 2-isopropyl-N,2,3-trimethylbutanamide, substituted cyclohexanecarboxylic acid amides, 3-menthoxypropane-1,2-diol, 2-hy-droxyethylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, menthylhydroxycarboxylic acid ester (e.g. menthyl-3-hydroxy-butyrate), menthylsuccinic acid ester, 2-mercaptocyclodecanone and 2-isopropyl-S-methylcyclohexyl-5-oxo-2-pyrrolidinecarboxylic acid.
Sweeteners, such as for example aspartame, saccharin, Acesulfam-K~, sorbite;
xylite, cyclamates (such as for example sodium cyclamate), Sucralose~, Alitam°, Neotarri , Thaumatin~, Neohesperidine DC~, maltitol and lactitol.
Preferred mint flavor components are:
essential oils such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil, clove oils, citrus oils, wintergreen oil, cassia oil, davana oil, spruce needle oil, eucalyptus oil, fennel oil, galbanum oil, ginger oil, camomile oil, caraway oil, gera-nium oil, sage oils, yarrow oil, anise seed oils, thyme oil, juniper berry oil, angelica root oil, and the fractions of these oils.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, men-thol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, euca-HR-218-i 1S
_g_ lyptol, limonene, eugenol, pinene, sabinene hydrate, 3-octanol, carvone, isopulegol, piperitone, 3-octyl acetate, hexanol, hexanal, cis-3-hexenol, linalool, alpha-terpineol, cis and trans carvyl acetate, p-cymene, dimethyl sulfide, cis-4-heptenal, isobutyral-dehyde, isovaleraldehyde, cis jasmone, anisaldehyde, methyl salicylate, 2-phenyl ethyl alcohol, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, cinnamaldehyde, geraniol, nerol.
Compounds having a physiological cooling effect such as for example menthol, menthoneglycerol acetal, menthyl lactate, menthyl-3-carboxylic acid N-ethylamide, 2-isopropyl-N,2,3-trimethylbutanamide, 3-menthoxypropane-1,2-diol, 2-hydroxyeth-ylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, menthyl-3-hydroxybutyrate, menthylsuccinic acid ester and 2-isopropyl-5-methylcyclohexyl-5-oxo-2-pyrrolidinecarboxylic acid.
Sweeteners such as for example aspartame, saccharin, Acesulfam-K~, sorbite;
xylite, cyclamates (e.g. sodium cyclamate), Sucralose~ and Alitam ° .
Particular preference is given to the following mint flavor components:
essential oils such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil, wintergreen oil, and the fractions of these oils.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, men-thol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, euca-lyptol, limonene, sabinene hydrate, carvone, isopulegol, piperitone, 3-octyl acetate, hexanol, hexanal, cis-3-hexenol, linalool, alpha-terpineol, cis and trans carvyl ace-tate, p-cymene, dimethyl sulfide, cis-4-heptenal, isobutyraldehyde, isovaleraldehyde, cis jasmone, anisaldehyde, methyl salicylate, 2-phenyl ethyl alcohol, cinnamalde-hyde.
HR-21 R-i 1~
Compounds having a physiological cooling effect such as for example menthol, menthone glycerol acetal, menthyl lactate, menthyl-3-carboxylic acid N-ethylamide, 3-menthoxypropane-1,2-diol, 2-hydroxyethylmenthyl carbonate, 2-hydroxypropyl menthyl carbonate and 2-isopropyl-5-methylcyclohexyl 5-oxo-2-pyrrolidinecarbox ylic acid.
Sweeteners such as for example aspartame, saccharin, Acesulfam-K~, sorbite;
xylite, cyclamates (such as for example sodium cyclamate), Sucralose°, Alitam ° and Neo-tam~.
Fruit flavor compositions according to the present invention comprise fruit flavor components and 8-ocimenyl esters. Fruit flavor components can, for example, be:
essential oils such as, for example, citrus oils, buchu leaf oil, davana oil, cassia oil, cedarwood oils, geranium oil, grain fusel oils, lemongrass oil, ambrette seed oil, rose oil, cinnamon bark oil, clove oils, carrot seed oil, mace oil, massoi bark oil, sandal-wood oil, and fractions thereof. Extracts such as, for example, fruit juice concentrates from all common fruits, guarana extracts, elderflower extracts, iris absolute, broom absolute, jasmine absolute, liquorice extract, osmanthus absolute, iris root extract, vanilla extract, chicory extracts, cinnamon extracts, boronia absolute.
Distillates from all common fruits.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, all common saturated and unsaturated fruit esters from the lower aliphatic acids C
and the lower alcohols C1-C12, the aliphatic saturated and unsaturated acids C1-C14, the aliphatic saturated and unsaturated alcohols C3-Clq., the aliphatic saturated and unsaturated aldehydes C2-C 14, the saturated and unsaturated gamma-lactones CS-C14, damascenone, alpha-ionone, beta-ionone, raspberry ketone, 2,5-dimethyl-4-hy-droxy-3(2H)-furanone, limonene, linalool, linalool oxide, phenylacetaldehyde, phen-ylacetic acid, 2-phenylethanol, maltol, vanillin, eugenol, 2-methyl-4-propyl-1,3-oxathiane, 3-methylthiohexanol, 4-methyl-4-mercapto-2-pentanone, methyleugenol, anethole, anise alcohol, anisaldehyde, guaiacol, cinnamyl alcohol, cinnamaldehyde, citral, citronellal, citronellol, nerol, geraniol, ethylvanillin, benzyl alcohol, all com-mon cinnamyl esters, all common benzyl esters, damascone, diacetyl, diethyl malo-nate, dihydrocoumarin, beta-7,8-dihydroionone, dimethyl anthranilate, methyl an-thranilate, 2(5)-ethyl-S(2)-methyl-4-hydroxy-3(2H)-furanone, ethylmaltol, eucalyp-tol, farnesal, farnesol, heliotropin, all common cis-3-hexenyl esters, alpha-iron, menthol, menthyl acetate, ethyl decadienoate, methyl dihydrojasmonate, methyl cin-narrate, ethyl cinnamate, methyl salicylate, lactic acid, myrcene, neryl acetate, geranyl acetate, nootkatone, 2,3-pentanedione, all common 2-alkanones, 3-thiohexa-nol, 8-thiomenthan-3-one, rose oxide, 4-ketoisophorone.
Preferred fruit flavor components are:
essential oils, for example, citrus oils, buchu leaf oil, davana oil, cassia oil, cedar wood oil, lemongrass oil, rose oil, cinnamon bark oil, clove oils, carrot seed oil, mace oil, massoi bark oil, sandalwood oil, and fractions thereof. Extracts such as, for ex ample, fruit juice concentrates from all common fruits. Distillates from all common fruits.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, all common saturated and unsaturated fruit esters from the lower aliphatic acids and the lower alcohols C1-C12, the aliphatic saturated and unsaturated acids C1-C14, the aliphatic saturated and unsaturated alcohols C3-C 14, the aliphatic saturated and unsaturated aldehydes C2-C14, the saturated and unsaturated gamma-lactones CS-C14, damascenone, alpha-ionone, beta-ionone, raspberry ketone, 2,5-dimethyl-4-hy-droxy-3(2H)-furanone, limonene, linalool, linalool oxide, phenylacetaldehyde, phen-ylacetic acid, 2-phenylethanol, maltol, vanillin, eugenol, 2-methyl-4-propyl-1,3-oxathiane, 3-methylthiohexanol, 4-methyl-4-mercapto-2-pentanone, methyleugenol, anethol, anise alcohol, anisaldehyde, guajakol, cinnamyl alcohol, cinnamaldehyde, citral, citronellal, citronellol, nerol, geraniol, ethylvanillin, benzyl alcohol, all com-mon cinnamyl esters, all common benzyl esters, damascone, diacetyl, diethyl malo-nate, dihydrocoumarin, beta-dihydroionone, dimethyl anthranilate, methyl anthrani-late, 2(S)-ethyl-5(2)-methyl-4-hydroxy-3(2H)-furanone, ethylmaltol, heliotropin, all common cis-3-hexenyl esters, alpha-iron, ethyl decadienoate, methyl dihydrojasmo-nate, methyl cinnamate, ethyl cinnamate, methyl salicylate, nootkatone, 8-thiomen-thanone-3, rose oxide, ketoisophorone.
Particular preference is given to the following fruit flavor components:
essential oils such as, for example, citrus oils, buchu leaf oil, cassia oil, cedarwood oil, lemongrass oil, carrot seed oil, mace oil, massoi bark oil, sandalwood oil, and fractions thereof.
Extracts such as, for example, fruit juice concentrates from all common fruits.
Distillates from all common fruits.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, all common saturated and unsaturated fruit esters from the lower aliphatic acids and the lower alcohols C1-C12, the aliphatic saturated and unsaturated acids C1-C14, the aliphatic saturated and unsaturated alcohols C3-C 14, the aliphatic saturated and unsaturated aldehydes C2-Clq., the saturated and unsaturated gamma-lactones CS-C14, damascenone, alpha-ionone, beta-ionone, raspberry ketone, 2,5-dimethyl-4-hy-droxy-3(2H)-furanone, limonene, linalool, phenylacetaldehyde, 2-phenylethanol, maltol, vanillin, eugenol, 2-methyl-4-propyl-1,3-oxathiane, 3-methylthiohexanol, 4-methyl-4-mercapto-2-pentanone, anethol, anise alcohol, anisaldehyde, guajakol, cin-namyl alcohol, cinnamaldehyde, citral, citronellal, citronellol, nerol, geraniol, ethyl-vanillin, benzyl alcohol, anisaldehyde, all common cinnamyl esters, all common TAR-71 R-T T,C
benzyl esters, damascone, diacetyl, dihydrocoumarin, beta-dihydroionone, dimethyl anthranilate, methyl anthranilate, 2(S)-ethyl-S(2)-methyl-4-hydroxy-3(2H)-furanone, ethylmaltol, heliotropin, all common cis-3-hexenyl esters, alpha-iron, ethyl deca-dienoate, methyl dihydrojasmonate, methyl cinnamate, ethyl cinnamate, nootkatone, 8-thiomenthanone-3, rose oxide, and ketoisophorone.
It is also possible to use mint and fruit flavor compositions and the various flavor components together.
The addition of solvents and/or carriers (adsorbent or fine dispersion medium) to the flavor compositions and/or fragrance compositions gives ready-to-use flavors, which are usually added in this dilute form to foods, tobacco products and to products for oral care. These ready-to-use flavors can comprise additives and auxiliaries.
Such additives and auxiliaries can be preservatives, dyes, antioxidants, flow agents, thick eners, emollients etc.
In the mint and/or fruit flavor compositions according to the present invention, the amount of 8-ocimenyl esters used is generally from 0.01 part by weight of 10 parts by weight, more preferably from 0.1 part by weight to 5 parts by weight.
The mint and/or fruit flavor compositions according to the present invention, and the ready-to-use flavors can be in liquid, semi-dried or in encapsulated form.
The spray-dried form is prepared from the liquid compositions by preparing an emul-sion with the addition of specific amounts of a carrier, for example, biopolymers such as starch, maltodextrin and gum arabic. This emulsion is dried in spray driers by very fine dispersion with the simultaneous use of heat. This results in a powder having the desired loading of liquid flavor.
The encapsulated form is likewise prepared from the liquid compositions by adding a Garner. There are various technologies, which can be used to prepare flavor capsules.
T~R-71 R-T TR
The most common is extrusion, spray granulation and coacervation. The particle si-zes usually range from 10 ~m to 5 mm. The most common capsule materials are va-rious starches, maltodextrin, gelatin. The liquid or solid flavor is enclosed in these capsules and can be released by a variety of mechanisms such as the application of S heat, a shift in pH or the pressure of chewing.
Such flavors can be used throughout the entire food sector, tobacco products and in products for oral hygiene. In particular, they can be used for the flavoring of fatty products, bakery products, yogurt, ice cream, sweets, chewing gum, alcoholic and non-alcoholic beverages, tobacco, toothpaste and mouth washes. The concentration of such flavors is preferably from 0.0005 to 2% by weight, more preferably from 0.01 to 1 % by weight, based on the finished foods, tobacco products or the oral hy-giene products.
1 S A principal use of the flavors according to the present invention is in sweets, chewing gum and products for oral hygiene (toothpaste, mouth washes). The mint flavors usu-ally consist of peppermint oils (Mentha piperita), mentha-arvensis oils and/or spear-mint oils (Mentha spicata and Mentha cardiaca) and fractions thereof with the addi-tion of synthetic and natural flavor substances and other natural extracts or essential oils. These mint flavors impart a minty odor and taste to foods and oral hygiene compositions flavored therewith and ensure freshness in the mouth and of the breath.
An important part of the taste profile of peppermint oil (Mentha piperita) are the sweet, hay-like notes (which some test subjects also referred to as tobacco notes), which are desired particularly for the flavoring of sweets and chewing gum.
The taste profile of a pure peppermint oil in chewing gum is given below and confirms this statement.
Taste profile of a peppermint oil (Mentha piperita) in chewing gum (sugar-free, concentration 1.2 %) Flavor profile Intensity (1-10) impact 6 fullness 8 freshness 6 coolness 6 eucalyptus 5 menthol 5 menthone 4 green 2 spicy 6 tea 8 hay 7 camomile S
floral 4 coumarin 5 sweet 7 soft 8 earthy 1 mushroom-like 1 Surprisingly, it has now been found that the mint flavors according to the present invention, as soon as they comprise the esters of 8-ocimenol (Ia)-(Id), can bring S about markedly enhancing taste effects. Whilst the 8-ocimenyl esters (Ia)-(Id) in pure form have the above-described olfactory and gustatory properties "fresh, fruity, gal-banum-like, green, pineapple, ester-like and floral", in mint compositions, they are able to significantly enhance the "sweet" and "hay" notes. In addition, it has time and again been established that test persons have found that the esters of the present in-vention "increases the gustatory impression of naturalness". A further finding is that said compounds are able to reduce bitter notes.
EXAMPLES
The invention was developed in systematic sensory experiments with the synthetic S mint flavor compositions of the formula given below by way of example, into which the 8-ocimenylester (Ia)-(Id) were either added or omitted from the composition.
1-Menthol 350 Menthone/Isomenthone 280 1-Menthyl acetate 40 Eucalyptol 30 Piperitone 30 Alpha-terpineolS
Linalool S
Myrtenyl acetate2 Sabinene hydrate2 Eugenol 1 Mint lactone 1 Cis jasmone 0.5 Cis-3-hexenol 0.3 Dimethyl sulfide0.2 3-Octanol 0.2 Isovaleraldehyde0.2 Alcohol, 96% 252.6 v/v Total 1000 Replacing 0.1-1 g of the alcohol with 1 g of the ocimenyl esters (Ia)-(Id) resulted in a marked increase in the sensory impression of the "sweet" notes, and to an increase in the "naturalness".
The mint flavors were incorporated into sugar-containing and sugar-free chewing gum bases in concentrations customary in practice (1 to 1.5% by weight) and tasted after storage for approximately 4 weeks. A comparison of the mint flavors with and without 8-ocimenyl esters showed that the compounds in the flavors according to the present invention have an enhancing effect and, in particular, "enhance the sweet-ness, increase the naturalness of the flavor, enhance the hay notes, mask the menthol, have a rounding action, and help to mask the slight bitterness of the base".
The sen-sory chewing experiments were carned out for 30 minutes.
The experiments with oral care products were carned out in toothpaste. In this ex-periment, use was made of both calcium carbonate and also silicate bases. The bases were sweetened with 0.2% of saccharin. Also, use was made of the synthetic mint flavors in which the 8-ocimenyl esters were added or omitted from the composition.
A comparison of the mint flavors with and without the 8-ocimenyl esters showed that the mint flavors according to the present invention with the compounds have a fla-vor-enhancing effect and, in particular, enhance the impact, enhance the sweetness, increase the naturalness of the flavor, enhance the herbaceousness, mask the sharp-ness of the menthol, have a rounding effect, and help to mask the slight bitterness of the base.
This finding is of great importance particularly for chewing gum since, as is known, because of the chewing gum composition and also the menthol in mint compositions together with the long chewing time (sometimes more than half an hour), some test subjects reported bitter notes, which would preferably be suppressed by the mint fla-vors according to the present invention. In addition, it can be shown that the mint composition according to the present invention has a taste-prolonging action.
- ~ CA 02307078 2000-04-28 rm ni o rm In summary, it can be established that the mint flavors according to the present in-vention in chewing gum have the following aroma-enhancing properties: they - increase the sweet, hay notes - increase the naturalness - increase the impact - reduce the bitterness - prolong the peppermint taste, - mask unpleasant aftertaste These properties were evident particularly between the 3ra and 5'h minute of the chewing operation, during which, for about 3 minutes, the bitterness was reduced, the sweetness increased and, as a result, stimulation of the trigeminus nerve by the sharpness of the menthol was moderated.
In mint compositions for toothpaste, the flavor compositions according to the present invention have the following flavor-enhancing properties: they - increase the naturalness - increase the impact - reduce the bitterness - round off the menthol sharpness Although the invention has been described in detail in the foregoing for the purpose of illustration, it is to be understood that such detail is solely for that purpose and that variations can be made therein by those skilled in the art without departing from the spirit and scope of the invention except as it may be limited by the claims.
For the reactions with hypochlorous acid, the latter is usually generated in situ from salts of hypochlorous acid by acidification. For the preparation of 6-ocimenyl chlo-ride(II), it has proven advantageous to liberate hypochlorous acid from sodium hy-pochlorite solution by acidification with acetic acid. The reaction with ocimene then proceeds in a two-phase system; the presence of a solvent is not necessary.
The reac-tion temperature can be between 0 and SO°C; a temperature range from 10 to 20°C is preferable.
The chlorination is carried out using sulfuryl chloride, preferably in the presence of a base, more preferably in the presence of an alkali metal carbonate, such as sodium or potassium carbonate, which is used, in particular, in excess, based on sulfuryl chlo-HR _71 R-T T
ride. Possible solvents are compounds, which are inert towards sulfuryl chloride, such as hydrocarbons, preferably n-hexane or n-heptane, such as halogenated hydro-carbons, preferably dichloromethane or tetrachloromethane, or such as ethers, pref erably methyl tent-butyl ether. The reaction temperature is, in particular, from 0 to S 50°C, a range from 20 to 30°C being preferable.
The ocimene can be used here as cis-ocimene, as trans-ocimene or as a cis/trans mixture.
Preference is given to using a cis/trans ocimene mixture, a content of from 50 to 90%
by weight of trans-isomer and from SO to 10% by weight of cis-isomer being pre-ferable, from which a E/Z mixture of the compound of the 6-ocimenyl chlorides (II) can be prepared and therefrom, in turn, a mixture of isomeric 8-ocimenyl esters of the formulae (Ia)-(Id).
Mint compositions according to the present invention comprise mint flavor compo-nents and 8-ocimenyl esters.
Mint flavor components can, for example, be:
essential oils, such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil, clove oil, citrus oils, cinnamon bark oil, wintergreen oil, cassia oil, davana oil, spruce needle oil, eucalyptus oil, fennel oil, galbanum oil, ginger oil, camomile oils, caraway oil, rose oil, geranium oil, sage oils, yarrow oil, anise seed oil, thyme oil, juniper berry oil, angelica root oil, and the fractions of these oils.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, men-thol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, eucalyp-tol, limonene, eugenol, pinene, sabinene hydrate, 3-octanol, carvone, gamma-octa-lactone, gamma-nonalactone, germacren-D, viridiflorol, 1,3E,SZ-undecatriene, iso-r CA 02307078 2000-04-28 LT12 _71 R_T TC
_7_ pulegol, piperitone, 3-octyl acetate, isoamyl isovalerate, hexanol, hexanal, cis-3-hex-enol, linalool, alpha-terpineol, cis and trans carvyl acetate, p-cymene, damascenone, damascone, dimethyl sulfide, fenchol, cis-4-heptenal, isobutyraldehyde, isovaleral-dehyde, cis jasmone, anisaldehyde, methyl salicylate, myrtenyl acetate, 2-phenyl ethyl alcohol, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, cinnamaldehyde, geraniol, nerol.
Compounds having a physiological cooling effect such as for example menthol, menthoneglycerol acetal, menthyl lactate, substituted menthyl-3-carboxamides (e.g.
menthyl-3-carboxylic acid N-ethylamide), 2-isopropyl-N,2,3-trimethylbutanamide, substituted cyclohexanecarboxylic acid amides, 3-menthoxypropane-1,2-diol, 2-hy-droxyethylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, menthylhydroxycarboxylic acid ester (e.g. menthyl-3-hydroxy-butyrate), menthylsuccinic acid ester, 2-mercaptocyclodecanone and 2-isopropyl-S-methylcyclohexyl-5-oxo-2-pyrrolidinecarboxylic acid.
Sweeteners, such as for example aspartame, saccharin, Acesulfam-K~, sorbite;
xylite, cyclamates (such as for example sodium cyclamate), Sucralose~, Alitam°, Neotarri , Thaumatin~, Neohesperidine DC~, maltitol and lactitol.
Preferred mint flavor components are:
essential oils such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil, clove oils, citrus oils, wintergreen oil, cassia oil, davana oil, spruce needle oil, eucalyptus oil, fennel oil, galbanum oil, ginger oil, camomile oil, caraway oil, gera-nium oil, sage oils, yarrow oil, anise seed oils, thyme oil, juniper berry oil, angelica root oil, and the fractions of these oils.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, men-thol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, euca-HR-218-i 1S
_g_ lyptol, limonene, eugenol, pinene, sabinene hydrate, 3-octanol, carvone, isopulegol, piperitone, 3-octyl acetate, hexanol, hexanal, cis-3-hexenol, linalool, alpha-terpineol, cis and trans carvyl acetate, p-cymene, dimethyl sulfide, cis-4-heptenal, isobutyral-dehyde, isovaleraldehyde, cis jasmone, anisaldehyde, methyl salicylate, 2-phenyl ethyl alcohol, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, cinnamaldehyde, geraniol, nerol.
Compounds having a physiological cooling effect such as for example menthol, menthoneglycerol acetal, menthyl lactate, menthyl-3-carboxylic acid N-ethylamide, 2-isopropyl-N,2,3-trimethylbutanamide, 3-menthoxypropane-1,2-diol, 2-hydroxyeth-ylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, menthyl-3-hydroxybutyrate, menthylsuccinic acid ester and 2-isopropyl-5-methylcyclohexyl-5-oxo-2-pyrrolidinecarboxylic acid.
Sweeteners such as for example aspartame, saccharin, Acesulfam-K~, sorbite;
xylite, cyclamates (e.g. sodium cyclamate), Sucralose~ and Alitam ° .
Particular preference is given to the following mint flavor components:
essential oils such as, for example, peppermint oil, spearmint oil, mentha-arvensis oil, wintergreen oil, and the fractions of these oils.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, men-thol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, euca-lyptol, limonene, sabinene hydrate, carvone, isopulegol, piperitone, 3-octyl acetate, hexanol, hexanal, cis-3-hexenol, linalool, alpha-terpineol, cis and trans carvyl ace-tate, p-cymene, dimethyl sulfide, cis-4-heptenal, isobutyraldehyde, isovaleraldehyde, cis jasmone, anisaldehyde, methyl salicylate, 2-phenyl ethyl alcohol, cinnamalde-hyde.
HR-21 R-i 1~
Compounds having a physiological cooling effect such as for example menthol, menthone glycerol acetal, menthyl lactate, menthyl-3-carboxylic acid N-ethylamide, 3-menthoxypropane-1,2-diol, 2-hydroxyethylmenthyl carbonate, 2-hydroxypropyl menthyl carbonate and 2-isopropyl-5-methylcyclohexyl 5-oxo-2-pyrrolidinecarbox ylic acid.
Sweeteners such as for example aspartame, saccharin, Acesulfam-K~, sorbite;
xylite, cyclamates (such as for example sodium cyclamate), Sucralose°, Alitam ° and Neo-tam~.
Fruit flavor compositions according to the present invention comprise fruit flavor components and 8-ocimenyl esters. Fruit flavor components can, for example, be:
essential oils such as, for example, citrus oils, buchu leaf oil, davana oil, cassia oil, cedarwood oils, geranium oil, grain fusel oils, lemongrass oil, ambrette seed oil, rose oil, cinnamon bark oil, clove oils, carrot seed oil, mace oil, massoi bark oil, sandal-wood oil, and fractions thereof. Extracts such as, for example, fruit juice concentrates from all common fruits, guarana extracts, elderflower extracts, iris absolute, broom absolute, jasmine absolute, liquorice extract, osmanthus absolute, iris root extract, vanilla extract, chicory extracts, cinnamon extracts, boronia absolute.
Distillates from all common fruits.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, all common saturated and unsaturated fruit esters from the lower aliphatic acids C
and the lower alcohols C1-C12, the aliphatic saturated and unsaturated acids C1-C14, the aliphatic saturated and unsaturated alcohols C3-Clq., the aliphatic saturated and unsaturated aldehydes C2-C 14, the saturated and unsaturated gamma-lactones CS-C14, damascenone, alpha-ionone, beta-ionone, raspberry ketone, 2,5-dimethyl-4-hy-droxy-3(2H)-furanone, limonene, linalool, linalool oxide, phenylacetaldehyde, phen-ylacetic acid, 2-phenylethanol, maltol, vanillin, eugenol, 2-methyl-4-propyl-1,3-oxathiane, 3-methylthiohexanol, 4-methyl-4-mercapto-2-pentanone, methyleugenol, anethole, anise alcohol, anisaldehyde, guaiacol, cinnamyl alcohol, cinnamaldehyde, citral, citronellal, citronellol, nerol, geraniol, ethylvanillin, benzyl alcohol, all com-mon cinnamyl esters, all common benzyl esters, damascone, diacetyl, diethyl malo-nate, dihydrocoumarin, beta-7,8-dihydroionone, dimethyl anthranilate, methyl an-thranilate, 2(5)-ethyl-S(2)-methyl-4-hydroxy-3(2H)-furanone, ethylmaltol, eucalyp-tol, farnesal, farnesol, heliotropin, all common cis-3-hexenyl esters, alpha-iron, menthol, menthyl acetate, ethyl decadienoate, methyl dihydrojasmonate, methyl cin-narrate, ethyl cinnamate, methyl salicylate, lactic acid, myrcene, neryl acetate, geranyl acetate, nootkatone, 2,3-pentanedione, all common 2-alkanones, 3-thiohexa-nol, 8-thiomenthan-3-one, rose oxide, 4-ketoisophorone.
Preferred fruit flavor components are:
essential oils, for example, citrus oils, buchu leaf oil, davana oil, cassia oil, cedar wood oil, lemongrass oil, rose oil, cinnamon bark oil, clove oils, carrot seed oil, mace oil, massoi bark oil, sandalwood oil, and fractions thereof. Extracts such as, for ex ample, fruit juice concentrates from all common fruits. Distillates from all common fruits.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, all common saturated and unsaturated fruit esters from the lower aliphatic acids and the lower alcohols C1-C12, the aliphatic saturated and unsaturated acids C1-C14, the aliphatic saturated and unsaturated alcohols C3-C 14, the aliphatic saturated and unsaturated aldehydes C2-C14, the saturated and unsaturated gamma-lactones CS-C14, damascenone, alpha-ionone, beta-ionone, raspberry ketone, 2,5-dimethyl-4-hy-droxy-3(2H)-furanone, limonene, linalool, linalool oxide, phenylacetaldehyde, phen-ylacetic acid, 2-phenylethanol, maltol, vanillin, eugenol, 2-methyl-4-propyl-1,3-oxathiane, 3-methylthiohexanol, 4-methyl-4-mercapto-2-pentanone, methyleugenol, anethol, anise alcohol, anisaldehyde, guajakol, cinnamyl alcohol, cinnamaldehyde, citral, citronellal, citronellol, nerol, geraniol, ethylvanillin, benzyl alcohol, all com-mon cinnamyl esters, all common benzyl esters, damascone, diacetyl, diethyl malo-nate, dihydrocoumarin, beta-dihydroionone, dimethyl anthranilate, methyl anthrani-late, 2(S)-ethyl-5(2)-methyl-4-hydroxy-3(2H)-furanone, ethylmaltol, heliotropin, all common cis-3-hexenyl esters, alpha-iron, ethyl decadienoate, methyl dihydrojasmo-nate, methyl cinnamate, ethyl cinnamate, methyl salicylate, nootkatone, 8-thiomen-thanone-3, rose oxide, ketoisophorone.
Particular preference is given to the following fruit flavor components:
essential oils such as, for example, citrus oils, buchu leaf oil, cassia oil, cedarwood oil, lemongrass oil, carrot seed oil, mace oil, massoi bark oil, sandalwood oil, and fractions thereof.
Extracts such as, for example, fruit juice concentrates from all common fruits.
Distillates from all common fruits.
Individual flavor substances (in the case of chiral compounds as racemate or as in-dividual enantiomer or as enantiomer-enriched mixture) such as, for example, all common saturated and unsaturated fruit esters from the lower aliphatic acids and the lower alcohols C1-C12, the aliphatic saturated and unsaturated acids C1-C14, the aliphatic saturated and unsaturated alcohols C3-C 14, the aliphatic saturated and unsaturated aldehydes C2-Clq., the saturated and unsaturated gamma-lactones CS-C14, damascenone, alpha-ionone, beta-ionone, raspberry ketone, 2,5-dimethyl-4-hy-droxy-3(2H)-furanone, limonene, linalool, phenylacetaldehyde, 2-phenylethanol, maltol, vanillin, eugenol, 2-methyl-4-propyl-1,3-oxathiane, 3-methylthiohexanol, 4-methyl-4-mercapto-2-pentanone, anethol, anise alcohol, anisaldehyde, guajakol, cin-namyl alcohol, cinnamaldehyde, citral, citronellal, citronellol, nerol, geraniol, ethyl-vanillin, benzyl alcohol, anisaldehyde, all common cinnamyl esters, all common TAR-71 R-T T,C
benzyl esters, damascone, diacetyl, dihydrocoumarin, beta-dihydroionone, dimethyl anthranilate, methyl anthranilate, 2(S)-ethyl-S(2)-methyl-4-hydroxy-3(2H)-furanone, ethylmaltol, heliotropin, all common cis-3-hexenyl esters, alpha-iron, ethyl deca-dienoate, methyl dihydrojasmonate, methyl cinnamate, ethyl cinnamate, nootkatone, 8-thiomenthanone-3, rose oxide, and ketoisophorone.
It is also possible to use mint and fruit flavor compositions and the various flavor components together.
The addition of solvents and/or carriers (adsorbent or fine dispersion medium) to the flavor compositions and/or fragrance compositions gives ready-to-use flavors, which are usually added in this dilute form to foods, tobacco products and to products for oral care. These ready-to-use flavors can comprise additives and auxiliaries.
Such additives and auxiliaries can be preservatives, dyes, antioxidants, flow agents, thick eners, emollients etc.
In the mint and/or fruit flavor compositions according to the present invention, the amount of 8-ocimenyl esters used is generally from 0.01 part by weight of 10 parts by weight, more preferably from 0.1 part by weight to 5 parts by weight.
The mint and/or fruit flavor compositions according to the present invention, and the ready-to-use flavors can be in liquid, semi-dried or in encapsulated form.
The spray-dried form is prepared from the liquid compositions by preparing an emul-sion with the addition of specific amounts of a carrier, for example, biopolymers such as starch, maltodextrin and gum arabic. This emulsion is dried in spray driers by very fine dispersion with the simultaneous use of heat. This results in a powder having the desired loading of liquid flavor.
The encapsulated form is likewise prepared from the liquid compositions by adding a Garner. There are various technologies, which can be used to prepare flavor capsules.
T~R-71 R-T TR
The most common is extrusion, spray granulation and coacervation. The particle si-zes usually range from 10 ~m to 5 mm. The most common capsule materials are va-rious starches, maltodextrin, gelatin. The liquid or solid flavor is enclosed in these capsules and can be released by a variety of mechanisms such as the application of S heat, a shift in pH or the pressure of chewing.
Such flavors can be used throughout the entire food sector, tobacco products and in products for oral hygiene. In particular, they can be used for the flavoring of fatty products, bakery products, yogurt, ice cream, sweets, chewing gum, alcoholic and non-alcoholic beverages, tobacco, toothpaste and mouth washes. The concentration of such flavors is preferably from 0.0005 to 2% by weight, more preferably from 0.01 to 1 % by weight, based on the finished foods, tobacco products or the oral hy-giene products.
1 S A principal use of the flavors according to the present invention is in sweets, chewing gum and products for oral hygiene (toothpaste, mouth washes). The mint flavors usu-ally consist of peppermint oils (Mentha piperita), mentha-arvensis oils and/or spear-mint oils (Mentha spicata and Mentha cardiaca) and fractions thereof with the addi-tion of synthetic and natural flavor substances and other natural extracts or essential oils. These mint flavors impart a minty odor and taste to foods and oral hygiene compositions flavored therewith and ensure freshness in the mouth and of the breath.
An important part of the taste profile of peppermint oil (Mentha piperita) are the sweet, hay-like notes (which some test subjects also referred to as tobacco notes), which are desired particularly for the flavoring of sweets and chewing gum.
The taste profile of a pure peppermint oil in chewing gum is given below and confirms this statement.
Taste profile of a peppermint oil (Mentha piperita) in chewing gum (sugar-free, concentration 1.2 %) Flavor profile Intensity (1-10) impact 6 fullness 8 freshness 6 coolness 6 eucalyptus 5 menthol 5 menthone 4 green 2 spicy 6 tea 8 hay 7 camomile S
floral 4 coumarin 5 sweet 7 soft 8 earthy 1 mushroom-like 1 Surprisingly, it has now been found that the mint flavors according to the present invention, as soon as they comprise the esters of 8-ocimenol (Ia)-(Id), can bring S about markedly enhancing taste effects. Whilst the 8-ocimenyl esters (Ia)-(Id) in pure form have the above-described olfactory and gustatory properties "fresh, fruity, gal-banum-like, green, pineapple, ester-like and floral", in mint compositions, they are able to significantly enhance the "sweet" and "hay" notes. In addition, it has time and again been established that test persons have found that the esters of the present in-vention "increases the gustatory impression of naturalness". A further finding is that said compounds are able to reduce bitter notes.
EXAMPLES
The invention was developed in systematic sensory experiments with the synthetic S mint flavor compositions of the formula given below by way of example, into which the 8-ocimenylester (Ia)-(Id) were either added or omitted from the composition.
1-Menthol 350 Menthone/Isomenthone 280 1-Menthyl acetate 40 Eucalyptol 30 Piperitone 30 Alpha-terpineolS
Linalool S
Myrtenyl acetate2 Sabinene hydrate2 Eugenol 1 Mint lactone 1 Cis jasmone 0.5 Cis-3-hexenol 0.3 Dimethyl sulfide0.2 3-Octanol 0.2 Isovaleraldehyde0.2 Alcohol, 96% 252.6 v/v Total 1000 Replacing 0.1-1 g of the alcohol with 1 g of the ocimenyl esters (Ia)-(Id) resulted in a marked increase in the sensory impression of the "sweet" notes, and to an increase in the "naturalness".
The mint flavors were incorporated into sugar-containing and sugar-free chewing gum bases in concentrations customary in practice (1 to 1.5% by weight) and tasted after storage for approximately 4 weeks. A comparison of the mint flavors with and without 8-ocimenyl esters showed that the compounds in the flavors according to the present invention have an enhancing effect and, in particular, "enhance the sweet-ness, increase the naturalness of the flavor, enhance the hay notes, mask the menthol, have a rounding action, and help to mask the slight bitterness of the base".
The sen-sory chewing experiments were carned out for 30 minutes.
The experiments with oral care products were carned out in toothpaste. In this ex-periment, use was made of both calcium carbonate and also silicate bases. The bases were sweetened with 0.2% of saccharin. Also, use was made of the synthetic mint flavors in which the 8-ocimenyl esters were added or omitted from the composition.
A comparison of the mint flavors with and without the 8-ocimenyl esters showed that the mint flavors according to the present invention with the compounds have a fla-vor-enhancing effect and, in particular, enhance the impact, enhance the sweetness, increase the naturalness of the flavor, enhance the herbaceousness, mask the sharp-ness of the menthol, have a rounding effect, and help to mask the slight bitterness of the base.
This finding is of great importance particularly for chewing gum since, as is known, because of the chewing gum composition and also the menthol in mint compositions together with the long chewing time (sometimes more than half an hour), some test subjects reported bitter notes, which would preferably be suppressed by the mint fla-vors according to the present invention. In addition, it can be shown that the mint composition according to the present invention has a taste-prolonging action.
- ~ CA 02307078 2000-04-28 rm ni o rm In summary, it can be established that the mint flavors according to the present in-vention in chewing gum have the following aroma-enhancing properties: they - increase the sweet, hay notes - increase the naturalness - increase the impact - reduce the bitterness - prolong the peppermint taste, - mask unpleasant aftertaste These properties were evident particularly between the 3ra and 5'h minute of the chewing operation, during which, for about 3 minutes, the bitterness was reduced, the sweetness increased and, as a result, stimulation of the trigeminus nerve by the sharpness of the menthol was moderated.
In mint compositions for toothpaste, the flavor compositions according to the present invention have the following flavor-enhancing properties: they - increase the naturalness - increase the impact - reduce the bitterness - round off the menthol sharpness Although the invention has been described in detail in the foregoing for the purpose of illustration, it is to be understood that such detail is solely for that purpose and that variations can be made therein by those skilled in the art without departing from the spirit and scope of the invention except as it may be limited by the claims.
Claims (14)
1. Mint and/or fruit-flavor compositions comprising 8-ocimenyl esters of the formula wherein one of the two radicals R1 and R2 is methyl and the other is vinyl and one of the two radicals R3 and R4 is methyl and the other is wherein R5 is hydrogen, alkyl or alkenyl.
2. Mint- and/or fruit-flavor compositions according to Claim 1, wherein R5 is C1-C6-alkyl or C2-C6-alkenyl.
3. Mint- and/or fruit-flavor compositions according to Claim 1, wherein R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tent-butyl or 2-butenyl.
4. Mint- and/or fruit-flavor compositions according to Claim 1, comprising 8-ocimenyl esters of the formulae wherein R5 is hydrogen, methyl or ethyl.
5. Mint- and/or fruit-favor compositions according to Claim 1, comprising from 0.01 to 10% by weight of 8-ocimenyl esters based on said flavor composition.
6. Food products comprising flavor compositions comprising 8-ocimenyl esters of the formula wherein one of the two radicals R1 and R2 is methyl and the other is vinyl and one of the two radicals R3 and R4 is methyl and the other is wherein R5 is hydrogen, alkyl or alkenyl.
7. Food products according to Claim 6, wherein R5 is C1-C6-alkyl or C2-C6-alkenyl.
8. Food products according to Claim 6, wherein R5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or 2-butenyl.
9. Food products according to Claim 6, wherein said flavor composition comprises 8-ocimenyl esters of the formulae wherein R5 is hydrogen, methyl or ethyl.
10. Food products according to Claim 6, comprising from 0.0005 to 2% by weight of said flavor composition based on said food product.
11. Food products according to Claim 6, wherein said flavor composition is a mint flavor.
12. Food products according to Claim 6, wherein said flavor composition is a fruit flavor.
13. Food products according to Claim 6, wherein said flavor composition is a mint and fruit flavor.
14. Oral hygiene products comprising flavoring compositions comprising 8-ocimenyl esters of the formula wherein one of the two radicals R1 and R2 is methyl and the other is vinyl and one of the two radicals R3 and R4 is methyl and the other is wherein R5 is hydrogen, alkyl or alkenyl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19920147.1 | 1999-05-03 | ||
| DE19920147A DE19920147A1 (en) | 1999-05-03 | 1999-05-03 | Mint and / or fruit flavor compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2307078A1 true CA2307078A1 (en) | 2000-11-03 |
Family
ID=7906711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002307078A Abandoned CA2307078A1 (en) | 1999-05-03 | 2000-04-28 | Mint and/or fruit flavor compositions |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1050574A3 (en) |
| JP (1) | JP2000351988A (en) |
| CA (1) | CA2307078A1 (en) |
| DE (1) | DE19920147A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2407146A1 (en) * | 2010-07-15 | 2012-01-18 | Nutrinova Nutrition Specialties & Food Ingredients GmbH | Use of acesulfame K as a flavour modulator |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7763238B2 (en) * | 2002-01-16 | 2010-07-27 | Monell Chemical Senses Center | Olfactory adaptation and cross-adapting agents to reduce the perception of body odors |
| AU2006330915B2 (en) * | 2005-12-23 | 2011-02-03 | Intercontinental Great Brands Llc | Compositions providing a sensation substantially similar to that provided by menthol |
| JP4896680B2 (en) * | 2006-11-27 | 2012-03-14 | 高砂香料工業株式会社 | Perfume composition, product containing the perfume composition, and novel ester compound |
| JP5493730B2 (en) * | 2009-11-06 | 2014-05-14 | ライオン株式会社 | Dentifrice composition |
| JP5493732B2 (en) * | 2009-11-06 | 2014-05-14 | ライオン株式会社 | Oral composition |
| JP5690811B2 (en) * | 2010-03-19 | 2015-03-25 | ライオン株式会社 | Liquid oral composition and method for producing the same |
| CN109480330A (en) * | 2012-01-25 | 2019-03-19 | 日本烟草产业株式会社 | The smelly implication of cigarette improves spice composition |
| JP6230780B2 (en) * | 2012-09-28 | 2017-11-15 | サッポロビール株式会社 | Non-alcoholic beverage and method for producing the same |
| US10933039B2 (en) | 2016-05-05 | 2021-03-02 | Symrise Ag | Coolant mixtures |
| EP3624757A1 (en) * | 2017-05-15 | 2020-03-25 | Firmenich SA | Compositions comprising essential oils |
| JP7377647B2 (en) * | 2019-08-14 | 2023-11-10 | サッポロビール株式会社 | Beer-taste beverage, method for producing beer-taste beverage, and method for improving flavor of beer-taste beverage |
| JP2023523290A (en) * | 2020-05-01 | 2023-06-02 | ザ プロクター アンド ギャンブル カンパニー | mint flavor composition |
| JP2025017588A (en) * | 2023-07-25 | 2025-02-06 | 高砂香料工業株式会社 | Fragrance composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4510319A (en) * | 1982-07-01 | 1985-04-09 | Fritzsche Dodge & Olcott Inc. | Functionalization of terminal trisubstituted alkenes and derivatives thereof |
| JPH07145398A (en) * | 1993-11-24 | 1995-06-06 | Lotte Co Ltd | Method for improving flavor of mint perfume and mint perfume composition |
| DE19532886A1 (en) * | 1995-09-06 | 1997-03-13 | Haarmann & Reimer Gmbh | Open-chain olefinically unsaturated compounds, process for their preparation and their use as fragrances |
| DE19748774A1 (en) * | 1997-11-05 | 1999-05-06 | Haarmann & Reimer Gmbh | 8-Ocimenyl esters and their use as fragrances and flavorings |
-
1999
- 1999-05-03 DE DE19920147A patent/DE19920147A1/en not_active Withdrawn
-
2000
- 2000-04-26 EP EP00109007A patent/EP1050574A3/en not_active Withdrawn
- 2000-04-28 CA CA002307078A patent/CA2307078A1/en not_active Abandoned
- 2000-05-01 JP JP2000132530A patent/JP2000351988A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2407146A1 (en) * | 2010-07-15 | 2012-01-18 | Nutrinova Nutrition Specialties & Food Ingredients GmbH | Use of acesulfame K as a flavour modulator |
| WO2012007170A1 (en) * | 2010-07-15 | 2012-01-19 | Nutrinova Nutrition Specialities And Food Ingredients Gmbh | Use of acesulfame k as a flavour modulator |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1050574A3 (en) | 2003-05-02 |
| DE19920147A1 (en) | 2000-11-09 |
| JP2000351988A (en) | 2000-12-19 |
| EP1050574A2 (en) | 2000-11-08 |
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| EEER | Examination request | ||
| FZDE | Dead |