WO2019079651A1 - Shelf-stable nitrogenous organic acid compositions - Google Patents
Shelf-stable nitrogenous organic acid compositions Download PDFInfo
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- WO2019079651A1 WO2019079651A1 PCT/US2018/056591 US2018056591W WO2019079651A1 WO 2019079651 A1 WO2019079651 A1 WO 2019079651A1 US 2018056591 W US2018056591 W US 2018056591W WO 2019079651 A1 WO2019079651 A1 WO 2019079651A1
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- creatine
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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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/38—Other non-alcoholic beverages
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/90—Preservation of foods or foodstuffs, in general by drying or kilning; Subsequent reconstitution
- A23B2/93—Spray drying
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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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/385—Concentrates of non-alcoholic beverages
- A23L2/39—Dry compositions
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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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
- A23L2/66—Proteins
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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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
- A23L2/68—Acidifying substances
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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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/238—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin from seeds, e.g. locust bean gum or guar gum
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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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
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- 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
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- 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
- A23V2250/00—Food ingredients
- A23V2250/18—Lipids
- A23V2250/184—Emulsifier
- A23V2250/1842—Lecithin
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- 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
- A23V2250/00—Food ingredients
- A23V2250/30—Other Organic compounds
- A23V2250/306—Creatine
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- 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
- A23V2250/00—Food ingredients
- A23V2250/50—Polysaccharides, gums
- A23V2250/51—Polysaccharide
- A23V2250/5112—Cyclodextrin
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- 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
- A23V2250/00—Food ingredients
- A23V2250/50—Polysaccharides, gums
- A23V2250/51—Polysaccharide
- A23V2250/5114—Dextrins, maltodextrins
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- 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
- A23V2300/00—Processes
- A23V2300/10—Drying, dehydrating
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- 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
- A23V2300/00—Processes
- A23V2300/26—Homogenisation
Definitions
- the present invention relates to compositions and methods for increasing nitrogenous organic acid solubility and stability. More specifically, the invention relates to methods for formulating products comprising creatine in a more soluble form with increased shelf stability in water even after high-heat processing, as well as compositions made by such methods.
- Creatine (A/-(aminoiminomethyl)-/V-methyl glycine) is a nitrogenous organic acid. About 95% of the creatine in the human body is found in the muscle tissue. Because creatine plays a significant role in muscle metabolism, it is a popular supplement for athletes. It has also been suggested to have beneficial effects for disease conditions such as heart disease, chronic obstructive pulmonary disease (COPD), and Parkinson's disease.
- COPD chronic obstructive pulmonary disease
- Creatine has become one of the most popular and widely used supplements in the sports nutrition market, with athletes often consuming loading doses as high as 20-30 g/day for 5-7 days. Reported annual sales of creatine supplements in the U.S. alone increased from $50 million in 1996 to over $400 million in 2001 (Bird, Stephen P., Creatine Supplementation and Exercise
- creatine monohydrate powder In its solid form, creatine monohydrate powder is very stable, showing no signs of degradation over years, even at elevated temperatures.
- its use in liquid products such as sports nutrition drinks, for example has been limited by its low solubility and its decreased stability in solution.
- creatine solubility may be increased at lower pH and higher temperatures (lower pH being common in drink formulations and higher temperatures being used for processing and packaging those products), under those conditions it also rapidly degrades by self-cyclizing into creatinine.
- the composition comprises acid stable protein isolates, or a combination or blend of protein isolates, concentrates and hydrolyzates and caseins in micellar forms, a suitable aqueous solvent or vehicle, a non-aqueous vehicle, a preservative, a physical stabilizing ingredient, one or more surfactants, and/ or one or more buffer salts that can render the composition pH stable.
- Owoc discloses in US20150238453A1 an alternative approach for addressing that concern, since, as Owoc observed in paragraph [0019], "[i]t is well known that chain length has an effect on the absorption of biologically active peptides from the Gl tract. Furthermore, we know that the potency of orally consumed peptides decreases as the chain length increases.”
- Owoc's alternate approach he creates N-acetyl or N-acyl creatine, wherein an acetyl or acyl group replaces an active hydrogen of the amino group in creatine, and creatyl peptides wherein an amino acid is bonded to acetylated or acylated creatine.
- Emulsions comprising creatine and medium chain triglycerides
- MCTs have been described, but the oil, at some point of storage, becomes oxidized and can become rancid.
- Powdered drink mix sales have reached approximately one billion dollars per year. Their attractiveness is due, in part, because they can be available to consumers in canister-type containers, in single-shot sleeves, often referred to as "sticks," in cap-mounted delivery systems, or in tablet form, for example. In these forms, the mixes may be carried by the consumer in a pocket, purse, gym bag, briefcase, or lunchbox. Creatine has typically not been a suitable ingredient for many of these products because it is very unstable in water and not sufficiently soluble to be readily mixed to form a solution from a powder mix.
- compositions and methods for providing creatine in a form that increases both its solubility and stability. Also needed are compositions and methods for providing creatine in formulations that do not undergo significant creatine degradation over shelf time, as well as compositions that provide creatine in a form that will not settle/recrystallize, agglomerate, or otherwise create a potential choking hazard in a product such as a beverage.
- the invention relates to a method for making a more shelf-stable form of at least one nitrogenous organic acid, the method comprising the steps of combining lecithin, water, and at least one polysaccharide to form a surfactant solution; admixing at least one nitrogenous organic acid with the surfactant solution to form a dispersion; and homogenizing the dispersion to produce a nitrogenous organic acid colloidal dispersion.
- the at least one polysaccharide is selected from the group consisting of polysaccharides with a dextrose equivalent (DE) value of from about 4.0 to about 12.0, polysaccharides with a bound galacturonic acid value of less than about 8g/100g, and combinations thereof.
- DE dextrose equivalent
- the at least one polysaccharide can be selected from the group consisting of polysaccharides with a dextrose equivalent (DE) value of from about 4.0 to about 12.0, polysaccharides with a bound galacturonic acid value of less than about 8g/100g, and combinations thereof.
- the at least one polysaccharide has a bound
- the method optionally comprises a step of drying the nitrogenous organic acid colloidal dispersion.
- the step of drying is performed by spray-drying.
- the invention also relates to products made by this method.
- the at least one nitrogenous organic acid is creatine, and in various embodiments the form of creatine may be chosen from among the group consisting of creatine monohydrate, creatine hydrochloride, buffered creatine, creatine magnesium chelate, di-creatine malate, creatine-magnesium chelate, creatine alpha-amino-N-butyrate, and combinations thereof.
- the lecithin can be soy lecithin.
- the polysaccharide is selected from the group consisting of gum acacia, gum Arabic, chitosan sulfate, maltodextrin, pectin, alginate and combinations thereof.
- alpha cyclodextrin is optionally admixed with the creatine and the surfactant solution to form the dispersion.
- the polysaccharide is maltodextrin, and in various aspects of the invention the ratio of lecithin to maltodextrin comprises from about 0.7 to about 1 .0 Lecithin/Maltodextrin.
- the creatine dispersion is homogenized at pressures of from about 500 to about 3000 psi. In various aspects, the homogenization pressure is about 500 psi (or 34 bar), and in various aspects the ratio of lecithin to
- polysaccharide to creatine is, for example, from about 1 :1 :2 to about 1 :1 :12, from about 1 :1 :2 to about 1 :1 :1 2, from about 1 :1 :2 to about 1 :1 :2.5, and in some specific instances, about 1 :1 :6.
- FIG. 1 is a graph illustrating the comparison between creatine stability for a product of the invention and for a second product, an emulsion comprising creatine and formed using medium chain triglycerides (MCTs). Creatine stability measurements were performed over a period of eleven (1 1 ) months, two (2) days.
- MCTs medium chain triglycerides
- composition which can be in liquid or dry form for use as an ingredient in products such as beverages and nutritional bars, for example, can be made using a straightforward method using a limited number of ingredients, all being generally recognized as safe (GRAS), thereby eliminating the need for numerous ingredients and/or chemical reactions to modify creatine to enhance its storage stability and bioavailability.
- GRAS generally recognized as safe
- the invention relates to a method for making a colloidal dispersion of at least one nitrogenous organic acid (e.g., creatine), the method comprising the steps of combining lecithin, water, and at least one polysaccharide to form a surfactant solution; admixing at least one nitrogenous organic acid (e.g., creatine monohydrate) with the surfactant solution to form a dispersion (e.g., a creatine dispersion); and homogenizing the dispersion to produce a nitrogenous organic acid colloidal dispersion (e.g., a colloidal dispersion comprising creatine).
- a nitrogenous organic acid e.g., creatine
- the at least one polysaccharide is selected from the group consisting of polysaccharides having a dextrose equivalent (DE) value of from about 4.0 to about 12.0, polysaccharides having a bound galacturonic acid value of less than about 8g/100g, and combinations thereof.
- the at least one polysaccharide will preferably be selected from the group consisting of polysaccharides having a dextrose equivalent (DE) value of from about 4.0 to about 12.0, polysaccharides having a bound galacturonic acid value of less than about 8g/100g, and
- the at least one polysaccharide will preferably have a bound
- the method optionally comprises the step of drying the nitrogenous organic acid colloidal dispersion.
- the step of drying is performed by spray-drying.
- the invention also relates to products made by this method.
- “Surfactants” are organic molecules which decrease the surface tension between two liquids or between a liquid and a solid.
- the term “surfactants” is used for agents that decrease the surface tension between a liquid and solid phase.
- the solid phase can be creatine monohydrate powder, which generally is insoluble, or has very low solubility, in water.
- the phrase "as in dispersion” indicates the concentration of an ingredient in the colloidal dispersion, before being dried into powder.
- a “colloidal dispersion” is a system in which particles of colloidal size (e.g., about 1 nm to about 1 ⁇ ) are dispersed in a continuous phase of a different composition.
- the phrase "as in powder” indicates the concentration of an ingredient in the dried (e.g., spray-dried) powder.
- Homogenization can be performed by methods known to those of skill in the art, and those of skill in the art will recognize that homogenization is generally performed until a substantially homogenized state is produced ⁇ i.e., a state in which the composition is homogenized as much as is readily achievable under normal processing conditions by the homogenization method selected).
- the combination of ingredients used to prepare the inventive composition can be formulated at lower homogenization pressures commonly used during commercial processing (i.e. 500-2500 psi), while providing excellent creatine stability for at least about 8-12 months.
- the selected polysaccharides provide effective encapsulating agents when used in the method of the invention, which may, in various embodiments of the invention, be substituted with, or combined with, one or more other food-grade ingredients such as gum acacia, gum Arabic, chitosan sulfate, pectin, alginate, combinations thereof, or other polysaccharides which may be chosen by one of skill in the art, given the information provided in the present disclosure.
- Polysaccharide(s) with either a dextrose equivalent (DE) value of from about 4.0 to about 12.0, or bound galacturonic acid value of less than about 8g/100g can be used for neutral beverage applications.
- Polysaccharide(s) used in high-acid beverage applications will preferably have a bound galacturonic acid value of at least about 8g/100g.
- Galacturonic acid is an oxidized form of D- galactose.
- Pectin for example, consists primarily of polymeric galacturonic acid (polygalacturonic acid).
- Galacturonic acid has an aldehyde group at C1 and a carboxylic acid group at C6.
- Galacturonic acid monomers that form part of a long chain polysaccharide are referred to as bound galacturonic acid units.
- bound galacturonic acid for identifying polysaccharides for use in the method of the invention has been determined by the inventor, through multiple experiments using different polysaccharides having different bound galacturonic acid values. It is known that the higher the surface charge on an encapsulated
- galacturonic acid has carboxylic acid groups, they tend to electrostatically enhance colloidal stability at pH values greater than its isoelectric point. At these pH values it has high negative charge due to ionization of carboxylic acid groups of the galacturonic acid moiety (Yokoyama A., Stabilization mechanism of colloidal suspensions by gum tragacanth: The influence of pH on stability, Journal of Colloid and Interface Science (1988) 126(1 ), 141 -149).
- the ionized carboxylic acid groups of the galacturonic acid moieties of the polysaccharide(s) complex with the positively-charged choline heads of lecithin e.g., soy lecithin
- lecithin e.g., soy lecithin
- the at least one nitrogenous organic acid is creatine.
- the lecithin is soy lecithin.
- alpha cyclodextrin is optionally admixed with the creatine and the surfactant solution.
- the ratio of lecithin to maltodextrin comprises from about 0.7 to about 1 .0 Lecithin/Maltodextrin. Examples of the ratio of lecithin to
- polysaccharide to creatine are from about 1 :1 :2 to about 1 :1 :12, from about 1 :1 :2 to about 1 :1 :1 2, from about 1 :1 :2 to about 1 :1 :2.5, or even more specifically, in some formulations about 1 :1 :6, the ratios for specific formulations being readily
- the creatine dispersion is homogenized at a pressure of from about 500 to about 3000 psi. In various aspects, the homogenization pressure is about 500psi/34bar.
- the inventive creatine compositions can be particularly useful for those for whom higher-dose creatine supplementation may be beneficial, such as athletes.
- creatine has been shown to reduce cholesterol by up to 15%.
- MD muscular dystrophy
- Creatine having been shown to reduce cholesterol by up to 15%.
- powders which may be successfully admixed into water, milk, fruit juice, or another type of beverage, or bottled or canned beverages, may provide a significantly better option for creatine administration than would other options such as, for example, ingestion of capsules.
- Creatine has been suggested to be more bioavailable if it is ingested in conjunction with both protein and carbohydrate, and drinks or drink mixes provide good options for accomplishing that goal.
- Powdered drink mixes can provide creatine supplementation in a very convenient form, as they can be packaged in small or large canister-type containers, zippered pouches, pouches with screw-top caps, and/or in single-shot sleeves ("sticks," or "slim-sticks”), for example. In these forms, the mixes may be carried by the consumer in a pocket, purse, gym bag, briefcase, or lunchbox.
- composition a solution of surfactants is made.
- surfactants comprise soy lecithin, and maltodextrin. Creatine monohydrate is added to the surfactant solution.
- a typical creatine concentration could be, for example, 23.7g/100g as in dispersion or 65.2g/100g as in powder.
- creatine monohydrate is used as the source of creatine, it may, for example, be incorporated at from about 15.5 to 23.7g/100g as in dispersion or 56.4 to 65.2 g/100g as in powder.
- Lecithin may be incorporated at up to about 7.7g/100g as in dispersion or 20.3g/100g as in powder.
- Alpha cyclodextrin can also be optionally added to enhance the effect on the performance of the formulation with regards to creatine shelf stability.
- This mixture is processed through a homogenizer at, for example, 500 psi/ 34 bar, 1 pass.
- lecithin, cyclodextrin, and maltodextrin are used in combination, the inventors believe that since creatine is almost hydrophobic, it is encapsulated by soy lecithin and cyclodextrin as the surfactants, with the maltodextrin (e.g., MD040) forming an additional wall material that surrounds the other ingredients.
- maltodextrin e.g., MD040
- a product formed by this method can, for example, be produced to provide about 61 .2 grams of creatine per 100 grams of spray-dried powder. That is, the method produces a creatine encapsulation efficiency of about 95% (based on the expected creatine levels of ⁇ 65g in 100g of spray dried powder).
- UHT ultra-high temperature processing
- hot-fill processing for high-acid beverages, which are often used to kill bacteria and extend shelf life of liquids, providing a significant advantage as compared to the processing limits associated with products such as emulsions formed using ingredients such as medium-chain triglycerides.
- Creatine compositions according to the invention may be formulated using various forms of creatine, including, for example, creatine monohydrate, creatine hydrochloride, buffered creatine, creatine magnesium chelate, di-creatine malate, creatine-magnesium chelate, creatine alpha-amino-N- butyrate.
- creatine analogs have been developed to improve the solubility of creatine.
- these analogs can also be provided in a form that significantly decreases the rate of creatine degradation in water, increases its shelf-life stability, and significantly improves stability under ultra-high temperature (UHT) or hot-fill processing.
- Creatine compositions made by the method of the invention may also comprise additional ingredients such as branched-chain amino acids (BCAAs), for example.
- BCAAs branched-chain amino acids
- Products of the invention include bottled and/or canned colloidal dispersions made by the method of the invention, with added flavors, coloring, etc., as desired, and/or powdered drink mixes made by spraying (e.g., spray-drying) one or more colloidal dispersions, the powdered mix being especially suited for mixing with water at or about neutral pH.
- the invention also provides creatine in a form that can be used in "dry,” semi-moist, and moist food products, such as nutritional bars, for example, increasing the shelf stability of the creatine in those products.
- Uzzan et al. reported that water activity affects creatine stability.
- Water activity (aw) refers to water in food which is not bound to food molecules, but it is not the same thing as moisture content.
- Foods may have the same moisture content and yet have quite different water activities.
- Bread for example, can have a water activity of about 0.95.
- the highest water activity (0.983) reduced the half-life of creatine to 43 days, while at the lowest water activity (0.31 ) the half-life of creatine was 182 days.
- the method of the invention provides creatine in a form that is more protected from the effects of water in the environment surrounding the creatine, which provides a distinct advantage for the formulation of aqueous-based products, as well as dry, semi-moist and moist products which may have a higher water activity that would generally reduce the half-life of isolated creatine in the products into which it is incorporated.
- Such products can include a variety of products formulated for human and/or animal consumption, such as breakfast bars, protein bars, dog or cat foods and/or treats, etc.
- a solution of surfactants was made by combining soy lecithin with 48-98% acetone insolubility (3.1 to 9.9 g/100g as in dispersion or 9.2 to 1 6.9 g/100g as in powder) in water (pH 7.0), with maltodextrin MD040 (Maltrin®, Grain Processing Corporation, 4.9-10.2 g/1 OOg as in dispersion or 1 2.4-1 7.7 g/1 OOg as in powder).
- the formulation was similar to that of the neutral pH application formulation described above, except that maltodextrin was replaced with polysaccharide with a bound galacturonic acid value of at least 8g/100g. Also, an amount of salt, Ca 2+ or Mg 2+ , was added (0.4 to 0.74 g/100g as in dispersion or 0.9 to 1 .3 g/100g as in powder) to enhance the flow property of spray- dried powder.
- polysaccharide along with Ca 2+ or Mg 2+ salts were dispersed in hot water (50-55°C), and then other ingredients were added in the following order: soy lecithin, Alpha-cyclodextrin, and micronized creatine monohydrate. This formulation was repeated, using different polysaccharides having different bound galacturonic acid values of at least 8g/100g.
- Spray-dried powder was analyzed to determine the amount of creatine (g) in 100g of spray dried powder. This value was compared with a theoretical amount of creatine in spray-dried powder, indicating that there was a -95- 100% creatine encapsulation, based on the expected creatine levels of -65-75 g in 10Og of spray-dried powder.
- the corresponding spray- dried powders produced from the slurry were used for determining the chemical stability of creatine monohydrate either in a neutral pH (6.8-7.0) drink or an acidic pH (3.3-3.7) drink formula.
- the creatine-containing beverages were prepared at their respective pH, using spray-dried powder. They were then bottled using either UHT conditions for neutral beverage applications or through hot- fill process conditions for acidic pH beverage applications. These bottles were stored at an ambient temperature of 22-25°C. Then the chemical stability of creatine was checked in these bottles at time intervals of days, using the HPLC-UV method for creatine and creatinine detection.
- This shelf stability curve was compared with another encapsulated creatine formula, and with non-encapsulated creatine monohydrate.
- a comparison of creatine shelf-stability in non-encapsulated creatine monohydrate and encapsulated formulas at neutral pH conditions is shown in Fig. 1 .
- the creatine stability increased (i.e. creatine levels stayed higher), when polysaccharides with higher bound galacturonic acid levels were used in the formula.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201880068339.1A CN111246748A (en) | 2017-10-18 | 2018-10-18 | Storage stable nitrogenous organic acid composition |
| KR1020207014149A KR20200145824A (en) | 2017-10-18 | 2018-10-18 | Storage stability nitrogen-containing organic acid composition |
| EP18869052.3A EP3697231A4 (en) | 2017-10-18 | 2018-10-18 | LONG-STORAGE NITROGENIC ACID COMPOSITIONS |
| MX2020003970A MX2020003970A (en) | 2017-10-18 | 2018-10-18 | Shelf-stable nitrogenous organic acid compositions. |
| AU2018351158A AU2018351158A1 (en) | 2017-10-18 | 2018-10-18 | Shelf-stable nitrogenous organic acid compositions |
| BR112020007883-2A BR112020007883A2 (en) | 2017-10-18 | 2018-10-18 | shelf stable nitrogenous organic acid compositions |
| JP2020542706A JP7321167B2 (en) | 2017-10-18 | 2018-10-18 | Storage-stable nitrogen-containing organic acid composition |
| CA3079527A CA3079527A1 (en) | 2017-10-18 | 2018-10-18 | Shelf-stable nitrogenous organic acid compositions |
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| US201762573995P | 2017-10-18 | 2017-10-18 | |
| US62/573,995 | 2017-10-18 | ||
| US201862726421P | 2018-09-03 | 2018-09-03 | |
| US62/726,421 | 2018-09-03 |
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| PCT/US2018/056591 Ceased WO2019079651A1 (en) | 2017-10-18 | 2018-10-18 | Shelf-stable nitrogenous organic acid compositions |
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| US (1) | US12568993B2 (en) |
| EP (1) | EP3697231A4 (en) |
| JP (1) | JP7321167B2 (en) |
| KR (1) | KR20200145824A (en) |
| CN (1) | CN111246748A (en) |
| AU (1) | AU2018351158A1 (en) |
| BR (1) | BR112020007883A2 (en) |
| CA (1) | CA3079527A1 (en) |
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| WO (1) | WO2019079651A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020058297A (en) * | 2018-10-11 | 2020-04-16 | 横浜油脂工業株式会社 | Creatine-containing water-dispersible powdery composition and method for producing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US12568991B2 (en) | 2017-10-18 | 2026-03-10 | Glanbia Dairy Nutrition Limited | Method for increasing the solubility and stability of organic compositions |
| DE102022114966A1 (en) | 2022-06-14 | 2023-12-14 | Alzchem Trostberg Gmbh | Water-soluble creatine agglomerate |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734401A (en) * | 1986-03-17 | 1988-03-29 | W. R. Grace & Co. | Process for spray drying amino acid compositions |
| US5929051A (en) * | 1998-05-13 | 1999-07-27 | Carrington Laboratories, Inc. | Aloe pectins |
| US5968544A (en) | 1996-05-31 | 1999-10-19 | The Howard Foundation | Compositions containing creatine |
| US6114379A (en) | 1999-07-07 | 2000-09-05 | Albion Laboratories, Inc. | Bioavailable chelates of creatine and essential metals |
| WO2003026439A1 (en) | 2001-09-25 | 2003-04-03 | Vitalstate Canada Ltd. | A starch-based delivery system for creatine |
| US20060151899A1 (en) * | 2003-08-06 | 2006-07-13 | Akira Kato | Process for producing drug ultramicroparticle and apparatus therefor |
| US20080020995A1 (en) | 2004-12-17 | 2008-01-24 | Martin Purpura | Use of Cyclodextrin Complexes Containing Lipoic Acid |
| US7432073B2 (en) * | 2002-10-31 | 2008-10-07 | Kirin Beverage Corporation | Method for detecting guaiacol producing bacteria |
| US20140066512A1 (en) | 2011-05-03 | 2014-03-06 | Patentnav Ireland Ltd | Oral compositions comprising creatine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10017102A1 (en) | 2000-04-06 | 2001-10-11 | Basf Ag | Process for the manufacture of solid creatine dosage forms and dosage forms obtainable thereby |
| US20040052852A1 (en) | 2001-09-25 | 2004-03-18 | Michael Farber | Carbohydrate-based delivery system for creatine and other bioactive ingredients |
| US20070087103A1 (en) | 2005-10-14 | 2007-04-19 | Riis Soeren B | Acidified milk products containing pectin |
| US20070116836A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-Potency Sweetener Composition for Treatment and/or Prevention of Osteoporosis and Compositions Sweetened Therewith |
| KR101022599B1 (en) * | 2008-08-26 | 2011-03-16 | 씨제이제일제당 (주) | Method for producing a creatine-containing beverage composition ensured quality stability and safety |
| US20100055178A1 (en) | 2008-08-29 | 2010-03-04 | Adel Vilallobos | Enteric-coated creatine compositions and methods of use thereof |
| CN101536993A (en) * | 2009-04-21 | 2009-09-23 | 浙江花园生物高科股份有限公司 | Vitamin D3 microcapsule and preparation method thereof |
| US8445466B2 (en) | 2010-04-08 | 2013-05-21 | John H. Owoc | Stable aqueous compositions comprising amide-protected bioactive creatine species and uses thereof |
| CN102908337B (en) * | 2012-10-12 | 2014-03-05 | 大连医诺生物有限公司 | Microencapsulated amino-acid composition and preparation method of microencapsulated amino-acid composition |
| CA3108628A1 (en) | 2013-06-12 | 2014-12-18 | Anabio Technologies Limited | A process for producing microcapsules comprising an active component encapsulated, protected and stabilised within a protein shell |
| CN103404854A (en) | 2013-08-02 | 2013-11-27 | 合肥工业大学 | Preparation method of phytosterol ester microcapsules |
| US9642825B2 (en) | 2014-02-27 | 2017-05-09 | 4141 Holdings, Llc | Bio-available N-acetyl creatine species and compositions thereof |
| CN104432095A (en) | 2014-12-08 | 2015-03-25 | 江南大学 | Creatine instant powder and preparation method thereof |
| CN105285159B (en) | 2015-10-20 | 2020-08-18 | 东北农业大学 | Preparation method of high-oil-content soybean powder grease |
-
2018
- 2018-10-18 EP EP18869052.3A patent/EP3697231A4/en active Pending
- 2018-10-18 KR KR1020207014149A patent/KR20200145824A/en not_active Ceased
- 2018-10-18 AU AU2018351158A patent/AU2018351158A1/en not_active Abandoned
- 2018-10-18 CA CA3079527A patent/CA3079527A1/en active Pending
- 2018-10-18 MX MX2020003970A patent/MX2020003970A/en unknown
- 2018-10-18 US US16/164,762 patent/US12568993B2/en active Active
- 2018-10-18 BR BR112020007883-2A patent/BR112020007883A2/en active Search and Examination
- 2018-10-18 CN CN201880068339.1A patent/CN111246748A/en active Pending
- 2018-10-18 JP JP2020542706A patent/JP7321167B2/en active Active
- 2018-10-18 WO PCT/US2018/056591 patent/WO2019079651A1/en not_active Ceased
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734401A (en) * | 1986-03-17 | 1988-03-29 | W. R. Grace & Co. | Process for spray drying amino acid compositions |
| US5968544A (en) | 1996-05-31 | 1999-10-19 | The Howard Foundation | Compositions containing creatine |
| US5929051A (en) * | 1998-05-13 | 1999-07-27 | Carrington Laboratories, Inc. | Aloe pectins |
| US6114379A (en) | 1999-07-07 | 2000-09-05 | Albion Laboratories, Inc. | Bioavailable chelates of creatine and essential metals |
| WO2003026439A1 (en) | 2001-09-25 | 2003-04-03 | Vitalstate Canada Ltd. | A starch-based delivery system for creatine |
| US7432073B2 (en) * | 2002-10-31 | 2008-10-07 | Kirin Beverage Corporation | Method for detecting guaiacol producing bacteria |
| US20060151899A1 (en) * | 2003-08-06 | 2006-07-13 | Akira Kato | Process for producing drug ultramicroparticle and apparatus therefor |
| US20080020995A1 (en) | 2004-12-17 | 2008-01-24 | Martin Purpura | Use of Cyclodextrin Complexes Containing Lipoic Acid |
| US20140066512A1 (en) | 2011-05-03 | 2014-03-06 | Patentnav Ireland Ltd | Oral compositions comprising creatine |
Non-Patent Citations (2)
| Title |
|---|
| "Aseptic Drink Packages", MINTEL, 24 May 2001 (2001-05-24) |
| See also references of EP3697231A4 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020058297A (en) * | 2018-10-11 | 2020-04-16 | 横浜油脂工業株式会社 | Creatine-containing water-dispersible powdery composition and method for producing the same |
| JP7089278B2 (en) | 2018-10-11 | 2022-06-22 | 横浜油脂工業株式会社 | Creatine-containing water-dispersible powdery composition and its production method |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20200145824A (en) | 2020-12-30 |
| EP3697231A4 (en) | 2021-08-04 |
| EP3697231A1 (en) | 2020-08-26 |
| US12568993B2 (en) | 2026-03-10 |
| CA3079527A1 (en) | 2019-04-25 |
| US20190230960A1 (en) | 2019-08-01 |
| CN111246748A (en) | 2020-06-05 |
| BR112020007883A2 (en) | 2020-11-03 |
| JP2021500404A (en) | 2021-01-07 |
| MX2020003970A (en) | 2020-10-19 |
| AU2018351158A1 (en) | 2020-05-28 |
| JP7321167B2 (en) | 2023-08-04 |
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