WO2017156432A1 - Esters de glycosides de stéviol - Google Patents

Esters de glycosides de stéviol Download PDF

Info

Publication number
WO2017156432A1
WO2017156432A1 PCT/US2017/021866 US2017021866W WO2017156432A1 WO 2017156432 A1 WO2017156432 A1 WO 2017156432A1 US 2017021866 W US2017021866 W US 2017021866W WO 2017156432 A1 WO2017156432 A1 WO 2017156432A1
Authority
WO
WIPO (PCT)
Prior art keywords
rebaudioside
compound
formula
syrup
acid
Prior art date
Application number
PCT/US2017/021866
Other languages
English (en)
Inventor
Deshou JIANG
Dennis Sawchuk
Original Assignee
Chromocell Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chromocell Corporation filed Critical Chromocell Corporation
Publication of WO2017156432A1 publication Critical patent/WO2017156432A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients

Definitions

  • This disclosure relates to certain esters of steviol glycosides which are suitable for use as sweeteners, for example, by incorporation into edible compositions.
  • Steviol glycosides are sweet-tasting compounds extracted from the stevia plant (Stevia rebaudiana Bertoni). Typically, these compounds are found to include stevioside (4-13% dry weight), steviolbioside (trace), the rebaudiosides, including rebaudioside A (1- 6%), rebaudioside B (trace), rebaudioside C (1-2%), rebaudioside D (trace), rebaudioside E (trace), dulcoside A (0.4-0.7%) and rebaudioside M (trace). Many steviol glycosides are potent, non-nutritive sweeteners. Steviol glycosides comprise a diterpene core (Formula I) substituted at Rl and R2 with various combinations of hydrogen, glucose, rhamnose, and xylose.
  • Formula I diterpene core substituted at Rl and R2 with various combinations of hydrogen, glucose, rhamnose, and xylose.
  • Rl may be hydrogen, l-beta-D-glucopyranosyl,or 2-(l-beta-D- glucopyranosyl)— 1-beta-D-glucopyranosyl, or 2-(l-beta-D-xylopyranosyl)-3-(l-beta-D- glucopyranosyl)-l-beta-D-glucopyranosyl and R2 may be hydrogen, 1-beta-D- glucopyranosyl, 2-(l-beta-D-glucopyranosyl)-l-beta-D-glucopyranosyl, 2,3-bis( 1-beta-D- glucopyranosyl)-!
  • Rebaudioside M is more potent, has higher sweetness intensity, and very slight licorice or bitter aftertaste relative to other steviol glycosides.
  • the food and beverage industry has become interested in steviol glycosides in the pursuit of alternative sweeteners.
  • steviol glycoside derivatives with enhanced sensory properties have now been discovered. These derivatives are mono or di -esters of steviol glycosides. These compounds are useful as sweeteners, and can be included as such in edible compositions such as food products, beverage products, pharmaceutical preparations and consumer goods.
  • Rl to R20 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate and at least eighteen R groups are hydroxyl groups.
  • Rl to R17 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least fifteen R groups are hydroxyl groups.
  • Rl to R14 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least twelve R groups are hydroxyl groups.
  • Rl to Rl 1 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least nine R groups are hydroxyl groups.
  • a compound of Formula II, Formula III, Formula IV, Formula V or any of compounds 1-9 or a combination of the foregoing compounds wherein the compound is isolated and purified.
  • a beverage product comprising:
  • the beverage product is selected from the group consisting of carbonated beverages, non-carbonated beverages, fountain beverages, frozen carbonated beverages, powdered concentrates, beverage concentrates, fruit juices, fruit juice-flavored drinks, fruit-flavored drinks, sports drinks, energy drinks, fortified/enhanced water drinks, soy drinks, vegetable drinks, grain-based drinks, malt beverages, fermented drinks, yogurt drinks, kefir, coffee beverages, tea beverages, dairy beverages, and mixtures of any of them.
  • the beverage product further comprises a sweetener selected from the group consisting of a steviol glycoside, Stevia rebaudiana extracts, Lo Han Guo, Lo Han Guo juice concentrate or extract, Lo Han Guo powder, mogroside V, thaumatin, monellin, brazzein, monatin, erythritol, tagatose, sucrose, liquid sucrose, fructose, liquid fructose, glucose, liquid glucose, high fructose corn syrup, high fructose starch syrup, invert sugar, medium invert sugar, maple syrup, maple sugar, honey, chicory syrup, Agave syrup, brown sugar molasses, cane molasses, sugar beet molasses, sorghum syrup, sorbitol, mannitol, maltitol, xylitol, glycyrrhizin, malitol, maltose, lactose, xylose, arab
  • rebaudioside E rebaudioside F
  • rebaudioside I rebaudioside H
  • rebaudioside L rebaudioside K
  • rebaudioside J rebaudioside N
  • rebaudioside O rebaudioside M
  • dulcoside A rubusoside
  • glycosylated steviol glycosides mogrosides, isomogroside, mogroside IV, siamenoside, monatin and its salts (monatin SS, RR, RS, SR)
  • curculin glycyrrhizic acid and its salts, mabinlin, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, pe
  • the beverage product is a beverage concentrate.
  • a food product comprising a food component, and a compound selected from the group consisting of a compound of Formula II, Formula III, Formula IV, Formula V, any of compounds 1-9 or a combination thereof.
  • the food product is selected from the group consisting of oatmeal, cereal, baked goods, cookies, crackers, cakes, brownies, breads, snack foods, potato chips, tortilla chips, popcorn, snack bars, rice cakes, confections edible gels, jams and jellies, spreads, ketchup, dairy products, frozen dairy products, ice-cream,
  • gelatins/puddings gelatins/puddings, ice-creams, pudding, and grain-based food products.
  • the food product comprises a compound selected from the group consisting of any of Compounds 1-9 or a combination thereof.
  • the food product comprises a compound selected from the group consisting of any of Compounds 1-9 or a combination thereof and further comprises a sweetener selected from the group consisting of a steviol glycoside, Stevia rebaudiana extracts, Lo Han Guo, Lo Han Guo juice concentrate or extract, Lo Han Guo powder, mogroside V, thaumatin, monellin, brazzein, monatin, erythritol, tagatose, sucrose, liquid sucrose, fructose, liquid fructose, glucose, liquid glucose, high fructose corn syrup, high fructose starch syrup, invert sugar, medium invert sugar, maple syrup, maple sugar, honey, chicory syrup, Agave syrup, brown sugar molasses, cane molasses, sugar beet molasses, sorghum syrup, sorbitol, mannitol, maltitol, xylitol, glycyrrh
  • dihydrochalcone sucralose, polydextrose, rebaudioside A, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M, dulcoside A, rubusoside, stevia leaf extract, stevioside, glycosylated steviol glycosides, mogrosides, isomogroside, mogroside IV, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, mabinlin, hernandulcin, phyllodulcin, glycyphyllin, phloridzin,
  • Rl to R20 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate and at least eighteen R groups are hydroxyl groups.
  • a sweetener comprising a compound of Formula III:
  • Rl to R17 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least fifteen R groups are hydroxyl groups.
  • a sweetener comprising a compound of Formula IV:
  • Rl to R14 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least twelve R groups are hydroxyl groups.
  • a sweetener comprising a compound of Formula V:
  • Rl to Rl 1 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least nine R groups are hydroxyl groups.
  • the sweetener according to the disclosure may comprise a filler, bulking agent, or an anticaking agent or any combination thereof.
  • the sweetener as disclosed herein is any one of Compounds 1- 9 or a combination thereof.
  • a method for preparing a compound of Formula II, III, IV, or V comprising mixing an aqueous solution of any of stevioside, RebA, RebM, or RebD with formic acid, acetic acid, propionic acid, butyric acid, valeric acid, tartaric acid, malic acid, malonic acid, oxalic acid or pyruvic acid and heating the solution to a temperature within the range of 30°C to 90°C for a period of time greater than one day.
  • the solution can be heated to a temperature of at least 30, 35, 40, 45, 50, 5, 60, 65, 70, 75, 80, 85, 90, or 95°C for a period of time greater than 1, 2, 3, 4, 5, 6, 7, 8 ,9 or 10 days.
  • the compounds of Formulas II-V may be isolated and purified.
  • isolated and purified means that the purity of the steviol glycoside ester is at least above 80%.
  • Figure 1 is an ESI mass spectrum of rebaudioside M formate, Compound 1.
  • Figure 2 is an ESI mass spectrum of rebaudioside M- formate, Compound 2.
  • Figure 3 is an ESI mass spectrum of stevioside acetate, Compounds 5-9.
  • any numerical range recited herein includes all values from the lower value to the upper value. For example, if a concentration range is stated as 1 % to 50%, it is intended that values such as 2% to 40%, 10% to 30%, or 1 % to 3%, etc., are expressly enumerated in this specification. These are only examples of what is specifically intended, and all possible combinations of numerical values between and including the lowest value and the highest value enumerated are to be considered to be expressly stated in this application.
  • sweet or “sweet taste” or “sweetness” as used herein refers to the perception or gustatory sensation resulting following the detection of a sweet tastant.
  • sweet tastant refers to a compound that can be activated or that can be detected by a sweet taste receptor and/or confers the perception of a sweet taste in a subject.
  • a "sweet tastant” or “sweetener” also refers to a multiplicity of compounds that combine to activate or be detected by a sweet taste receptor and/or confer the perception of a sweet taste in a subject.
  • Sweet tastants may include substances which also possess a bitter taste. Examples of such substances include steviol glycosides, compounds of
  • bitter or “bitter taste” or “bitterness” as used herein refers to the perception or gustatory sensation resulting following the detection of a bitter tastant.
  • bitter tastant refers to a compound that activated or that can be detected by a bitter taste receptor and/or confers the perception of a bitter taste in a subject.
  • a “bitter tastant” also refers to a multiplicity of compounds that combine or activate or be detected by a bitter taste receptor and/or confer the perception of a bitter taste in a subject.
  • bitter tastants may include substances which also possess or primarily possess a bitter taste.
  • Examples of such substances include steviol glycosides, compounds of Formula II, III, IV, V, any one of compounds 1-9 or any combination thereof.
  • Rl to R20 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate. At least eighteen R groups are hydroxyl groups.
  • the compound of Formula II may be isolated and purified. As used herein, "isolated and purified" means that the purity of the steviol glycoside ester is at least above 80%.
  • Rl to R17 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least fifteen R groups are hydroxyl groups.
  • the compound of Formula III may be isolated and purified. As used herein, "isolated and purified" means that the purity of the steviol glycoside ester is at least above 80%.
  • Rl to R14 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate; and at least twelve R groups are hydroxyl groups.
  • the compound of Formula IV may be isolated and purified. As used herein, "isolated and purified" means that the purity of the steviol glycoside ester is at least above 80%.
  • Rl to Rl 1 represent hydroxyl, formate, acetate, propionate, butyrate, valerate, citrate, hydrogen tartrate, malate, hydrogen malonate, hydrogen oxalate, pyruvate. At least nine R groups are hydroxyl groups.
  • the compound of Formula V may be isolated and purified. As used herein, "isolated and purified" means that the purity of the steviol glycoside ester is at least above 80%.
  • each of the steviol glycoside esters of Formula II, Formula III, Formula IV, Formula V or compounds 1-9 disclosed herein may be prepared by treating a suitable steviol glycoside, e.g. the corresponding steviol glycoside, with acid and heat according to the method set forth herein.
  • a suitable steviol glycoside e.g. the corresponding steviol glycoside
  • Reb M may be heated in aqueous solution with different organic acids to a temperature within the range of about 30°C to about 90°C (e.g., within the range of about 40°C to about 50°C, such as 43°C with different organic acids for a sufficient period of time (e.g., greater than 24 hours, such as from one days to about 12 weeks) to produce a compound of Formula II and compounds 1-2.
  • rebaudioside A may be heated in aqueous solution to a temperature within the range of about 30°C to about 90°C (e.g., within the range of about 40°C to about 50°C, such as 43°C) with different organic acids (for a sufficient period of time (e.g., greater than two days, such as from two days to about 11 weeks) to produce a compound of Formula IV or compounds 3-4.
  • a sufficient period of time e.g., greater than two days, such as from two days to about 11 weeks
  • Reb D may be heated in aqueous solution to a temperature within the range of about 30°C to about 90°C (e.g., within the range of about 40°C to about 50°C, such as 43 °C) with different organic acids for a sufficient period of time (e.g., greater than two days, such as from two days to about 11 weeks) to produce a compound of Formula III.
  • a sufficient period of time e.g., greater than two days, such as from two days to about 11 weeks
  • Stevioside may be heated in aqueous solution to a temperature within the range of about 30°C to about 90°C (e.g., within the range of about 40°C to about 50°C, such as 43 °C) with different organic acids for a sufficient period of time (e.g., greater than two days, such as from two days to about 11 weeks) to produce a compound of Formula V or compounds 5-9.
  • a sufficient period of time e.g., greater than two days, such as from two days to about 11 weeks
  • Other synthesis methods may be employed, for example enzymatic esterifi cation.
  • Steviol glycoside esters may be isolated and purified, e.g., by chromatography, recrystallization, etc.
  • Exemplary acids suitable for use in preparing steviol glycoside esters as described and claimed herein are organic acids such as formic acid, citric acid, malic acid, lactic acid, ascorbic acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, tartaric acid, malonic acid, oxalic acid or pyruvic acid etc.
  • One or more acids, and optionally the corresponding acid salt are included in the reaction mixture in an amount sufficient to render the reaction mixture strongly acidic (e.g., to achieve a pH value within the range of about pH 1.0 - 4.0, such as about pH 2.0 - 2.5).
  • Enzymatic esterification may also be employed.
  • steviol glycoside esters comprising at least one compound of Formula II, III, IV, V or any of Compounds 1-9, may be used as a potent non- nutritive sweetener.
  • Sweeteners are edible compositions suitable for consumption and for use in foods and beverages.
  • a "non-nutritive sweetener" is one which does not provide significant caloric content in typical usage amounts, e.g., one which imparts less than 5 calories per 8 oz. serving of beverage to achieve the sweetness equivalent of 10 Brix of sugar.
  • a "potent sweetener” means a sweetener which is at least twice as sweet as sugar (sucrose), that is, a sweetener which on a weight basis requires no more than half the weight of sugar to achieve an equivalent sweetness.
  • a potent sweetener may require less than one-half the weight of sugar to achieve an equivalent sweetness in a beverage sweetened to a level of 10 Brix with sugar.
  • a sweetener may comprise at least one compound of Formula II, III, IV, V or any of Compounds 1-9 or combinations of the foregoing and optionally a filler, a bulking agent such as dextrose, maltodextrin, erythritol, tagatose, or erythritol and tagatose blend, polydextrose, and/or an anti-caking agent.
  • a bulking agent such as dextrose, maltodextrin, erythritol, tagatose, or erythritol and tagatose blend, polydextrose, and/or an anti-caking agent.
  • the amount of bulking agent used is typically the smallest amount that provides for accurate delivery.
  • edible compositions means a food or beverage or an ingredient of a food or beverage for human or animal consumption. Edible compositions may be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, lozenges, powders, gels, gums, pastes, slurries, syrups, aerosols and sprays.
  • edible compositions include food and beverage products, pharmaceutical compositions, and consumer products. The term edible composition also refers to, for example, dietary and nutritional supplements.
  • edible compositions also include compositions that are placed within the oral cavity but not swallowed, including dental products, such as toothpaste, dental treatments, fillings, packing materials, molds and polishes.
  • one or more of the steviol glycoside esters disclosed here may be present as a non-nutritive sweetener in a beverage product.
  • Exemplary beverage products comprise an aqueous liquid and a compound of Formula II, III, IV, V any of Compounds 1-9 or a combination of the foregoing and include beverages such as, for example, ready to drink liquid formulations, beverage concentrates and the like.
  • Beverages include, e.g., carbonated and non-carbonated soft drinks, fountain beverages, frozen ready-to-drink beverages, frozen carbonated beverages, liquid concentrates, powdered concentrates, coffee beverages, tea beverages, dairy beverages, flavored waters, enhanced waters, fruit juice, fruit juice-flavored drinks, fruit-flavored drinks, sports drinks, soy drinks, vegetable drinks, grain-based drinks ( e.g. malt beverages), fermented drinks (e.g., yogurt and kefir), alcoholic beverages, and mixtures of any of them.
  • Exemplary fruit juice sources include citrus fruit, e.g. orange, grapefruit, lemon and lime, berry, e.g.
  • beverage concentrates contemplated are prepared with an initial volume of water to which the additional ingredients are added.
  • Full strength beverage compositions can be formed from the beverage concentrate by adding further volumes of water to the concentrate.
  • full strength beverages can be prepared from the concentrates by combining approximately 1 part concentrate with between approximately 3 to approximately 7 parts water.
  • the full strength beverage is prepared by combining 1 part concentrate with 5 parts water.
  • the additional water used to form the full strength beverages is carbonated water.
  • a full strength beverage is directly prepared without the formation of a concentrate and subsequent dilution.
  • one or more of the steviol glycoside esters disclosed here may be present as a non-nutritive sweetener in a pharmaceutical preparation (e.g. a prescription or over the counter drug). It should be understood that pharmaceutical preparations in accordance with this disclosure may have any of numerous different specific formulations or constituents.
  • one or more of the steviol glycoside mono or di- esters disclosed here may be present as a non-nutritive sweetener in a food product.
  • Food products comprise at least one food component, i.e., any edible material suitable for human or animal consumption, whether or not fully or partially digestible.
  • food components include proteins, carbohydrates, fats, vitamins, minerals, etc.
  • Food products comprising a compound of Formula II, III, IV, V, any of Compounds 1-9 or a combination of the foregoing disclosed here include, e.g., oatmeal, cereals, baked goods (e.g., cookies, crackers, cakes, brownies, breads, etc.), snack foods (e.g., potato chips, tortilla chips, popcorn, snack bars, rice cakes, etc.), and other grain-based food products as well chewing gums, confections (including chocolate, etc.), edible gels, jams and jellies, spreads, ketchup, dairy products, frozen dairy products, gelatins/puddings, and ice-creams (including but not limited to impulse ice cream, take-home ice cream, frozen yogurt, gelato, sorbet, sherbet and soy, oat, bean and rice-based ice cream). All variations, alternatives, options, etc., discussed elsewhere in this disclosure apply to food embodiments of the disclosure.
  • food or beverage products in accordance with this disclosure may have any of numerous different specific formulations or constitutions.
  • the formulation of a food or beverage product in accordance with this disclosure can vary to a certain extent, depending upon such factors as the product's intended market segment, its desired nutritional characteristics, flavor profile and the like. For example, it will generally be an option to add further ingredients to the formulation of a particular food or beverage embodiment. Additional (i.e., more and/or other) sweeteners may be added.
  • Acidulants flavorings, colorings, electrolytes, minerals, non-mineral nutritional supplements, fruit juices or other fruit products, tastants, masking agents and the like, flavor enhancers, buffering agents, aroma, thickeners, emulsifiers, edible particulates, anti-foaming agents, preservatives, carbonation, and mixtures thereof typically can be added to any such formulations to vary the taste, mouthfeel, nutritional characteristics, functionality, etc. of the food or beverage product.
  • non-mineral nutritional supplement ingredients are known to those of ordinary skill in the art and include, for example, antioxidants and vitamins, including Vitamins A, D, E (tocopherol), C (ascorbic acid), B (thiamine), B2 (riboflavin), 86, 812, and K, niacin, folic acid, biotin, and combinations thereof.
  • the optional non-mineral nutritional supplements are typically present in amounts generally accepted under good manufacturing practices. Exemplary amounts are between about 1 % and about 100% RDV (recommended daily value), where such RDV are established.
  • the non-mineral nutritional supplement ingredient(s) are present in an amount of from about 5% to about 20% RDV, where established. Additional and alternative suitable ingredients will be recognized by those skilled in the art given the benefit of this disclosure.
  • Certain exemplary embodiments of carbonated beverages disclosed here are cola flavored carbonated beverages, which characteristically comprise carbonated water, a compound of Formula II, kola nut extract and/or other cola flavoring, caramel coloring, an acidulant (e.g. phosphoric acid), and optionally other ingredients such as other sweeteners.
  • Certain other exemplary embodiments of carbonated beverages disclosed here are citrus flavored (e.g., lemon-lime, grapefruit, lemon, lime, orange, etc.) carbonated beverages, which characteristically comprise carbonated water, a compound of Formula II, III, IV, V, any of Compounds 1-9 or a combination thereof, citrus flavoring, an acidulant (e.g.
  • a beverage concentrate comprising water, a compound of Formula II, III, IV, V any of Compounds 1-9 or a combination thereof, cola flavoring, caramel coloring, and acidulant (e.g., phosphoric acid), and optionally other ingredients such as other sweeteners.
  • a beverage concentrate is provided comprising water, a compound of Formula II, III, IV, V any of Compounds 1-9 or a combination thereof, citrus flavoring, an acidulant (e.g., citric acid), and optionally other ingredients such as coloring agents and /or other sweeteners.
  • flavor means any food-grade material that may be added to the present compositions to provide a desired flavor to foodstuff, including beverages.
  • Additional flavors useful in the present disclosure include, for example, cream, hazelnut, vanilla, chocolate, cinnamon, pecan, lemon, lime, raspberry, peach, mango, vanillin, butter, butterscotch, tea, orange, tangerine, caramel, strawberry, banana, grape, plum, cherry, blueberry, pineapple, elderberry, watermelon, bubblegum, cantaloupe, guava, kiwi, papaya, coconut, mint, spearmint, derivatives, and combinations thereof.
  • Aromas useful in the present disclosure include, but are not limited to , for example, essential oils (citrus oil) , expressed oils (orange oil), distilled oils (rose oil), extracts (fruits), anethole (liquorice, anise seed, ouzo, fennel), anisole (anise seed), benzaldehyde (marzipan, almond), benzyl alcohol (marzipan, almond), camphor (cinnamon camphora), cinnamaldehyde (cinnamon), citral (citronella oil, lemon oil), d-limonene (orange), ethyl butanoate (pineapple), eugenol (clove oil), furaneol (strawberry), furfural (caramel), linalool
  • the aroma may be present in any amount in the composition.
  • the aroma can be present in an amount from 2 to 10-times the detectable amount.
  • the term "detectable amount” is the amount of the aroma component required to produce a scent detectable in the food and beverage products.
  • additional/other sweeteners may be included, for example, nutritive sweeteners or non-nutritive sweeteners.
  • nutritive sweeteners include sucrose, liquid sucrose, fructose, liquid fructose, glucose, liquid glucose, glucose- fructose syrup from natural sources such as apple, chicory, agave, honey, etc., e.g., high fructose com syrup, chicory syrup, Agave syrup, invert sugar, medium invert sugar, maple syrup, maple sugar, honey, brown sugar molasses, e.g., cane molasses and sugar beet molasses, sorghum syrup, an mixtures of any of them.
  • Such sweeteners are present in at least certain exemplary embodiments in an amount of from about 0.1 % to about 20% by weight of the finished food or beverage product, such as from about 6% to about 16% by weight, depending upon the desired level of sweetness for the finished food or beverage product.
  • Nutritive sweeteners may be present in beverage concentrate embodiments up to about 60% by weight of the beverage concentrate.
  • sweeteners include, but are not limited to at least 0.1, 0.5, 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0, 11.0, 12.0, 13.0, 14.0, 15.0, 16.0, 17.0, 18.0, 19.0, 20.0, 21.0, 22.0, 23.0, 24.0, 25.0, 26.0, 27, 28.0, 29.0, 30.0, 31.0, 32.0, 33.0, 34, 35.0, 36.0, 37.0, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59 or 60.0 wt%.
  • Non-limiting examples of potent non-nutritive natural sweeteners that may be included in food and beverage products include rebaudioside A, rebaudioside M, stevioside, other steviol glycosides, Stevia rebaudiana extracts, Lo Han Guo (LHG), e.g., LHG juice concentrate or extract or LHG powder, thaumatin, monellin, brazzein, monatin, and mixtures of any of them.
  • LHG if used, may have for example, mogroside V content of from about 2 to about 99%.
  • a food or beverage product is provided which comprises a mixture of a compound of Formula II and LHG having a mogroside V content of at least 30%.
  • the LHG in the mixture has a mogroside V content of about 45%, plus or minus 5%.
  • Useful amounts of non-nutritive natural sweeteners that may be included in food and beverage products include, but are not limited to at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 2, 25 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96,
  • a mixture comprising LHG and a compound of Formula II- V provides at least 10% of the sweetness in a food or beverage product. In certain exemplary embodiments, the mixture provides about 1/3 to about 2/3 of the sweetness.
  • Useful examples of sweetness provided by the compounds of the disclosure combined with one or more non-nutritive natural sweeteners include, but are not limited to at least 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, or 80 %.
  • non-nutritive sweeteners include sorbitol, mannitol, xylitol, glycyrrhizin, maltitol, maltose, lactose, xylose, arabinose, isomalt, lactitol, trehalulose, ribose, fructo-oligosaccharides, and mixtures of any of them.
  • the sweetener component can include erythritol, tagatose, an erythritol and tagatose blend, or
  • a food or beverage product which comprises a compound of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof and either erythritol, tagatose, or a blend of erythritol and tagatose.
  • a sweetener may comprise at least one compound of Formula II, III, IV, V any of Compounds 1-9 or combinations thereof and optionally a filler, a bulking agent such as dextrose, maltodextrin, erythritol, tagatose, or erythritol and tagatose blend, polydextrose, and/or an anti -caking agent.
  • a bulking agent such as dextrose, maltodextrin, erythritol, tagatose, or erythritol and tagatose blend, polydextrose, and/or an anti -caking agent.
  • a compound of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof provide sweetness when present at a concentration between about 0.001 ppm and about 1000 ppm.
  • a compound of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof provide sweetness when present at a concentration between about 0.005 ppm to about 500 ppm; about 0.01 ppm to 25 about 100 ppm; about 0.05 ppm to about 50 ppm; about 0.1 ppm to about 5 ppm; about 0 .1 ppm to about 10 ppm; about 0.
  • a compound of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof provides a sweetness of at least 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5 fold, compared to a control sample not comprising any one of the compounds according to Formula II, III, IV ,V, or any one of compounds 1-9 or combinations thereof, wherein the concentration of a sweetener, such as for example RebM or Stevioside, in the control sample is the same as the concentration of compound of Formula II, III, IV, V or any one of compounds 1-9 or combinations thereof in the test sample.
  • a sweetener such as for example RebM or Stevioside
  • a compound of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof provides a sweetness of at least 2.5 fold sweetness, when present at a concentration between about 100 about 1000 ppm, compared to a control sample not comprising any of the compounds of the disclosure, wherein the concentration of the sweetener in the control sample is the same as the concentration of compound of Formula II, III, IV, V or any of compounds 1-6 or combinations thereof in the test sample.
  • a compound of Formula II, III, IV, V or any of compounds 1- 9 or combinations thereof provides a sweetness of at least 2.7 fold, when present at a concentration of at least about 500 ppm, compared to a control sample not comprising any of the compounds of the disclosure, wherein the concentration of the sweetener in the control sample is the same as the concentration of compound of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof in the test sample.
  • combinations thereof provide no difference in the perception of bitterness, when compared to a control sample not comprising any one of compounds of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof, wherein the amount of sweetener (e.g. RebM or Stevioside) in the control is the same as the amount of any one of compounds of Formula II, III, IV, V or any of compounds 1-9 or combinations thereof.
  • sweetener e.g. RebM or Stevioside
  • An in vivo sweet responsive assay means an assay where an assessment of increased perception of sweetness can be ascribed.
  • Such an assay may be, for
  • Non-human a human sensory descriptive analysis panel, a human sensory discriminative panel, and/or an expert flavorist assessment.
  • a human sensory descriptive analysis panel for example, but not limited to, a human sensory descriptive analysis panel, a human sensory discriminative panel, and/or an expert flavorist assessment.
  • assessments of sweet response include, but are not limited to, operant conditioned animal studies of sweetness taste perception and/or lick rate/amount bottle
  • An in vitro sweet responsive assay refers to an assay where an assessment of increased sweet response or interaction can be ascribed.
  • An example of such an assay may be, but is not limited to, in vitro receptor binding assays, in vitro
  • enhancement of a sweet taste receptor activation will affect a physiological process or condition.
  • sweet taste receptor activation physiological processes and conditions affected by the enhancement of sweet taste receptor activation include sweet taste, effects on the gastrointestinal tract,
  • appetite appetite, nutrition, nutrient absorption, satiety, hunger, diabetes, obesity, blood
  • sweetness perception is assessed using 2AFC method with HTT protocol.
  • bitterness perception is assessed using 2AFC method with HTT protocol.
  • Non-limiting examples of potent non-nutritive artificial sweeteners that may be included in food and beverage products include peptide based sweeteners, e.g., aspartame, neotame, and alitame, and non-peptide based sweeteners, e.g., sodium saccharin, calcium saccharin, acesulfame (including but not limited to acesulfame potassium), cyclamate (including but not limited to sodium cyclamate and/or calcium cyclamate), neohesperidin dihydrochalcone, sucralose, and mixtures of any of them.
  • peptide based sweeteners e.g., aspartame, neotame, and alitame
  • non-peptide based sweeteners e.g., sodium saccharin, calcium saccharin, acesulfame (including but not limited to acesulfame potassium), cyclamate (including but not limited to sodium
  • Potent non-nutritive sweeteners typically are employed at a level of milligrams per ounce of food or beverage according to their sweetening power, any applicable regulatory provisions of the country where the food or beverage is to be marketed, the desired level of sweetness of the food or beverage, etc. Mixtures of any of the above nutritive and non-nutritive sweeteners are included within the scope of the disclosure. It will be within the ability of those skilled in the art, given the benefit of this disclosure, to select suitable additional or alternative sweeteners for use in various embodiments of the food and beverage products disclosed here.
  • sucrose and liquid sucrose would typically be substantially
  • food and beverage products disclosed here may be preserved by pasteurization.
  • the pasteurization process may include, for example, ultra-high temperature (UHT) treatment and/or high temperature-short time (HTST) treatment.
  • UHT treatment includes subjecting the food or beverage product to high temperatures, such as by direct steam injection or steam infusion, or by indirect heating in a heat exchanger.
  • the product can be cooled as required by the particular product composition/configuration and/or the package filling application.
  • the food or beverage product is subjected to heating to about 85°C to about 121 °C for a short period of time, for example, about 1 to 60 seconds, then cooled quickly to about 2.2°C +/- 2.8°C) for refrigerated products, to ambient temperature for shelf stable or refrigerated products, and to about 85°C +/- 5.5°C for hot-fill applications for shelf-stable products.
  • temperatures used to heat the food and beverage products of the disclosure include, but are not limited to at least 80, 85, 90, 95, 100, 105, 110, 115, 120, or 121 °C for a period of time of at least 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 544, 55, 56, 57, 58, 59, or 60 seconds.
  • the pasteurization process is typically conducted in a closed system, so as not to expose the food or beverage product to atmosphere or other possible sources of contamination.
  • pasteurization or sterilization techniques may also be useful, such as, for example, aseptic packaging, tunnel pasteurization, or retort processing.
  • tunnel pasteurization methods typically use lower temperatures for a longer time, e.g., about 71 °C for 10-15 minutes, and retort methods typically use, e.g., about 121 °C for 3-5 minutes at elevated pressure, i.e., at pressure above 1 atmosphere.
  • multiple pasteurization processes may be carried out in series or parallel, as necessitated by the food or beverage product or ingredients.
  • Reb M formate (Compounds 1 and 2) synthesis: 0.5gram Reb M and 5ml formic acid were dissolved in 45ml water. The solution was heated at 40°C for three days. The reaction mixture was freeze-dried and then subjected to a CI 8 column eluting with a solvent system of 35% acetonitrile and 65% water. Four Reb M formates were isolated in each fraction, which included Compounds 1 and 2. The ESI mass spectra of Compounds 1 and 2 are shown in Figures 1 and 2, respectively.
  • aqueous solutions were prepared by adding appropriate levels of citric acid and sodium citrate to water to achieve a target pH of 4.0.
  • Sensory Methodology Assessment of sweetness perception using 2AFC method with HTT protocol. The method was performed as a double blinded and randomized test where taste panelists (n >15) simultaneously evaluate a pair of samples. In the methodology, panelists were presented simultaneously with a pair of samples (test and control) on contralateral sides of the tongue. After a presentation of the samples for 15 seconds, panelists selected the sample that is sweeter, or in a separate test, more bitter. Each evaluation comprises of a pair of samples; test (aqueous-solubilized compound) and control (Rebaudioside M). Each pair is compared for sweetness in one assessment and for bitterness in another, separate assessment using the methodology.
  • Panelists perceive a compound of Formula II @ 500ppm to be significantly sweeter than control sample of Rebaudioside M @ 500ppm.
  • Stevioside acetate (Compounds 5, 6, 7, 8 and 9) synthesis: 500mg Stevioside and 20ml acetic acid were heated under 75°C for couple minutes until the solution became clear. Then the solution was heated under 45 °C for two days. The reaction mixture was freeze-dried to give around 503mg dry white powder. The powder gave a mixture of compound 5, 6, 7, 8 and 9 and was tested without further separation. Alternatively, compounds 5, 6, 7, 8 and 9 can be separated using a C18 column The ESI mass spectra of Compounds 5, 6, 7, 8 and 9 are shown in Figures 3.
  • aqueous solutions were prepared by adding appropriate levels of citric acid and sodium citrate to water to achieve a target pH of 4.0.
  • HTT half tongue test
  • Sample delivery is via a looped carrier to ensure samples are not mixed with each other in the mouth and that the samples are not absorbed by the test material. Panelists are asked to identify the sweeter sample through a 2 Alternative
  • the 2AFC test used for compound evaluation is a double blinded and randomized test where taste panelists (n >12) evaluate a pair of samples at a time - one sample contains the

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • General Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)

Abstract

La présente invention concerne des compositions comestibles comprenant des formules et des composés d'esters de glycosides de stéviol, ou des combinaisons de ceux-ci, qui sont appropriés pour être utilisés comme édulcorants, par exemple, par l'incorporation dans des compositions comestibles. L'invention concerne également des procédés de préparation de composés d'esters de glycosides de stéviol.
PCT/US2017/021866 2016-03-10 2017-03-10 Esters de glycosides de stéviol WO2017156432A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662306378P 2016-03-10 2016-03-10
US62/306,378 2016-03-10

Publications (1)

Publication Number Publication Date
WO2017156432A1 true WO2017156432A1 (fr) 2017-09-14

Family

ID=59789731

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2017/021866 WO2017156432A1 (fr) 2016-03-10 2017-03-10 Esters de glycosides de stéviol

Country Status (1)

Country Link
WO (1) WO2017156432A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109085276A (zh) * 2018-07-20 2018-12-25 安徽科技学院 一种甜叶菊糖液的提取方法
CN109156795A (zh) * 2018-07-03 2019-01-08 山东香驰健源生物科技有限公司 用于茶饮的调味糖浆及其制备方法
CN113072601A (zh) * 2021-03-30 2021-07-06 固安君德同创生物工程有限公司 一种功能性寡糖糖苷酯的制备方法及其应用
US20210251269A1 (en) * 2018-06-13 2021-08-19 The Coca-Cola Company Beverages Comprising Highly Soluble Steviol Glycoside Blend and Glucosylated Steviol Glycosides
CN114901081A (zh) * 2020-10-13 2022-08-12 弗门尼舍有限公司 丙二酰基甜菊醇糖苷及其可食用用途
CN115666269A (zh) * 2020-04-20 2023-01-31 嘉吉公司 增加甜菊醇糖苷的产率
US11920167B2 (en) 2017-02-03 2024-03-05 Tate & Lyle Solutions Usa Llc Engineered glycosyltransferases and steviol glycoside glucosylation methods

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080226795A1 (en) * 2007-03-14 2008-09-18 Concentrate Manufacturing Company Of Ireland Non-nutritive sweetened beverages with glycerine
US20100189861A1 (en) * 2005-10-11 2010-07-29 Purecircle Sdn Bhd Sweetner and use

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100189861A1 (en) * 2005-10-11 2010-07-29 Purecircle Sdn Bhd Sweetner and use
US20080226795A1 (en) * 2007-03-14 2008-09-18 Concentrate Manufacturing Company Of Ireland Non-nutritive sweetened beverages with glycerine

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CATHARINO, R. R. ET AL.: "On-line monitoring of stevioside sweetener hydrolysis to steviol in acidic aqueous solutions", FOOD CHEMISTRY, vol. 133, no. 4, 2012, pages 1632 - 1635, XP055420826 *
COLOMBO, G. ET AL.: "Remote control of enzyme selectivity: the case of stevioside and steviolbioside", TETRAHEDRON, vol. 60, no. 3, 2004, pages 741 - 746, XP004482890 *
UPRETI, M. ET AL.: "Synthetic study on the relationship between structure and sweet taste properties of steviol glycosides", MOLECULES, vol. 17, no. 4, 2012, pages 4186 - 4196, XP055420823 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11920167B2 (en) 2017-02-03 2024-03-05 Tate & Lyle Solutions Usa Llc Engineered glycosyltransferases and steviol glycoside glucosylation methods
US20210251269A1 (en) * 2018-06-13 2021-08-19 The Coca-Cola Company Beverages Comprising Highly Soluble Steviol Glycoside Blend and Glucosylated Steviol Glycosides
CN109156795A (zh) * 2018-07-03 2019-01-08 山东香驰健源生物科技有限公司 用于茶饮的调味糖浆及其制备方法
CN109085276A (zh) * 2018-07-20 2018-12-25 安徽科技学院 一种甜叶菊糖液的提取方法
CN115666269A (zh) * 2020-04-20 2023-01-31 嘉吉公司 增加甜菊醇糖苷的产率
CN114901081A (zh) * 2020-10-13 2022-08-12 弗门尼舍有限公司 丙二酰基甜菊醇糖苷及其可食用用途
CN113072601A (zh) * 2021-03-30 2021-07-06 固安君德同创生物工程有限公司 一种功能性寡糖糖苷酯的制备方法及其应用

Similar Documents

Publication Publication Date Title
JP6510617B2 (ja) レバウジオシド甘味料組成物及び該レバウジオシド甘味料組成を用いて甘味を付与された食品製品
JP6727886B2 (ja) レバウディオサイドｂを含有するステビアブレンド
EP2866585B1 (fr) Compositions pour masquer le goût, compositions édulcorantes et compositions alimentaires comprenant les mêmes
EP1959755B1 (fr) Composition d'edulcorant tres puissant avec substance reductrice de proteine c reactive et compositions sucrees avec celle-ci
EP1965668B1 (fr) Composition d'edulcorants tres puissants avec de la vitamine et compositions adoucies avec cette composition
US9101161B2 (en) High-potency sweetener composition with phytoestrogen and compositions sweetened therewith
TWI657746B (zh) 含有甜葉菊苷ｅ之可食用產品及使用其製備和強化可食用產品之甜味的方法
EP1962616B1 (fr) Composition d'edulcorant tres puissant avec glucosamine et compositions sucrees avec celle-ci
EP2526778B2 (fr) Compositions édulcorantes naturelles présentant un meilleur profil temporel et/ou un profil de parfum, procédés pour leur préparation et leurs utilisations
WO2017156432A1 (fr) Esters de glycosides de stéviol
EP2753188B1 (fr) Édulcorants de rebaudioside d et boisson gazeuse à base de cola edulcorée avec le rebaudioside d
US20130136839A1 (en) Taste-Masking Compositions, Sweetener Compositions and Consumable Product Compositions Containing the Same
JP6353364B2 (ja) 組成物
WO2013079187A9 (fr) Compositions de masquage de goût, compositions d'édulcorant et compositions de produit consommable les contenant
WO2016103183A1 (fr) Compositions modifiant le goût
CN112601461B (zh) 作为甜度增强剂的多甲氧基黄酮
WO2016103182A1 (fr) Compositions modifiant le goût
EP4440334A1 (fr) Procédé de purification de flavonoïdes polyméthoxylés et compositions obtenues à partir de celui-ci
EP4274426A1 (fr) Composés et procédés pour améliorer la sucrosité d'édulcorants
WO2016103184A1 (fr) Compositions de modification du goût

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17764210

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 17764210

Country of ref document: EP

Kind code of ref document: A1