Composition containing aromadendrin 3-acetate

Aromadendrin 3-acetate combined with sweetness and taste modifiers addresses the undesirable profiles of high-intensity sweeteners, enhancing sweetness and mouthfeel in consumables.

JP2025528262APending Publication Date: 2025-08-26GIVAUDAN SA
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Patent Information

Application Number
JP2025511823
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Priority Date
2022-08-23
Filing Date
2023-08-18
Publication Date
2025-08-26

AI Technical Summary

Technical Problem

High-intensity sweeteners exhibit undesirable temporal and flavor profiles, including slower onset, longer duration, and off-tastes such as bitterness, metallic taste, and lingering sweetness, which undermine the sugar-like sweetness in consumables.

Method used

Combining aromadendrin 3-acetate with sweetness and taste modifiers like steviol glycosides, mogrosides, dihydrochalcones, and chlorogenic acid to create flavor compositions that enhance sweetness perception, reduce off-tastes, and improve mouthfeel.

Benefits of technology

The combination provides a more sugar-like temporal and flavor profile, reduces sweetness linger, enhances sweetness impact, and alleviates bitter and licorice tastes, resulting in improved taste quality and mouthfeel.

✦ Generated by Eureka AI based on patent content.

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Abstract

A flavor composition is provided, comprising aromadendrin 3-acetate and at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins, and combinations thereof.
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Description

[Technical Field]

[0001] Technical Field The present disclosure relates to compositions and methods of using aromadendrin 3-acetate in combination with sweetness modifiers and / or taste modifiers in flavor compositions and consumables to improve the taste quality and / or mouthfeel of sweet tastants.

[0002] background Compounds are widely used to modify the taste of consumable products, i.e., products that are taken orally, either by ingestion or expectoration, such as foods, beverages, confectionery, and oral care products. While they do not themselves add flavor to the consumable product, they provide desirable collateral benefits, such as enhancing mouthfeel and / or sweetness, or mask undesirable characteristics of other ingredients, such as the distinctive taste and texture that can be perceived as unappealing in products containing sugar substitutes.

[0003] In the case of sugar substitutes, the taste they impart may exhibit different temporal profiles, flavor profiles, or adaptive behaviors compared to the sugars they replace in whole or in part. For example, the sweetness of natural and synthetic high-intensity sweeteners (HISs) generally has a slower onset and longer duration than the sweetness produced by sugar (a sweet, short-chain, soluble carbohydrate including glucose, fructose, sucrose, maltose, and lactose) or high-fructose corn syrup (HFCS), a known sugar substitute, which can alter the balance of the taste of edible compositions containing them. This can create an unbalanced temporal taste profile. In addition to the difference in temporal profile, high-intensity sweeteners generally exhibit a lower maximum response than sugar; off-tastes include bitterness, metallic taste, cooling sensation, astringency, licorice-like taste, and / or sweetness, which diminish with repeated tasting.

[0004] However, all high-intensity sweeteners have an undesirable aftertaste in the form of off-tastes, such as a licorice-like aftertaste and / or a lingering sweetness. In the specific case of Reb A, this takes the form of a combination of an undesirable lingering sweetness and a licorice-like aftertaste. This aftertaste undermines the desired sugar-like sweetness. Therefore, effectively masking undesirable or off-tastes in edible compositions is key to consumer acceptance of many edible compositions.

[0005] Thus, there remains a need to provide flavor compositions for improving the taste quality and / or mouthfeel of sweet tastants. Summary of the Invention

[0006] overview In one exemplary embodiment, the flavor composition comprises aromadendrin 3-acetate (“ADA”); and at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins, and combinations thereof.

[0007] In another exemplary embodiment, the flavor composition comprises aromadendrin 3-acetate and at least one taste modifier selected from the group consisting of chlorogenic acid, choline chloride, N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof.

[0008] In another exemplary embodiment, the flavor composition comprises aromadendrin 3-acetate, at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins, and combinations thereof; and at least one taste modifier selected from the group consisting of chlorogenic acid, choline chloride, N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof.

[0009] In yet another exemplary embodiment, a method is disclosed of imparting a more sugar-like temporal profile, flavor profile, and / or taste profile to a consumable by adding a flavor composition disclosed herein to the consumable, thereby providing a consumable with a more sugar-like temporal profile, flavor profile, and / or taste profile.

[0010] In another aspect, the more sugar-like temporal profile is a reduced sweetness linger compared to a consumable without the flavor compositions disclosed herein.

[0011] In a further aspect, the more sugar-like flavor profile is an improved mouthfeel (e.g., increased body or fullness) compared to a consumable product to which the flavor compositions disclosed herein are not added.

[0012] In yet another exemplary embodiment, a consumable product is provided. The consumable product includes at least one sweetener and a flavor composition according to the present disclosure, the flavor composition including aromadendrin 3-acetate. The at least one sweetener is present in a sweetening amount.

[0013] Particular embodiments of any aspect of the present disclosure may provide one or more of the following advantages. - increased sweetness in the composition; - enhanced sweetness in compositions including at least one sweetener; - A reduction in the amount of caloric sweetener required to obtain the desired sweetness; - improving one or more sweetness characteristics to make the sweetness more similar to that of sugar (sucrose); - Prolonged sweetness relief (e.g., a reduction in the time sweetness lingers and / or a more rapid decrease in sweetness intensity); - Reduction of bitter and / or licorice and / or metallic taste; - Alleviation of the sensory perception of dryness and / or astringency in the mouth; - Improved sweetness impact (e.g., increased maximum sweetness intensity and / or reduced duration of sweetness detection) (e.g., reduced lingering sweetness).

[0014] These and other features, aspects and advantages of particular embodiments will become apparent to those of ordinary skill in the art from reading this disclosure.

[0015] Detailed Description The following text sets forth a broad description of many different aspects of the present disclosure. This description is to be construed as illustrative only and does not describe every possible embodiment, as describing every possible embodiment would be impractical, if not impossible. It will be understood that any feature, characteristic, element, composition, component, product, step, or method described herein can be omitted, and any other feature, characteristic, element, composition, component, product, step, or method described herein can be combined with or substituted, in whole or in part, for any other feature, characteristic, element, composition, component, product, step. Numerous alternative embodiments can be implemented using either current technology or technology developed after the filing date of this patent and still fall within the scope of the claims. All publications and patents cited herein are incorporated herein by reference.

[0016] The present disclosure relates to the surprising discovery that the combination of a flavor composition comprising aromadendrin 3-acetate with a sweetness modifier and / or taste modifier improves the taste quality and / or mouthfeel of the sweet tastant.

[0017] According to certain exemplary embodiments, the flavor composition may include aromadendrin 3-acetate in combination with at least one sweetness modifier.

[0018] Aromadendrin 3-acetate is also known as 2R,3R-3-acetoxy-5,7,4'-trihydroxyflavanone (CAS No. 62458-55-3). Its chemical structure (I) is given below: [ka]

[0019] In some embodiments, aromadendrin 3-acetate exists as a mixture of any two or more, any three or more, or all four of the stereoisomers encompassed by the structure, i.e., (2R,3R), (2R,3S), (2S,3R), and (2S,3S). In other embodiments, aromadendrin 3-acetate exists in a substantially pure form of one of the four stereoisomers, i.e., in a purity of 95% or greater, or 97% or greater, 98% or greater, or 99% or greater.

[0020] In another embodiment, the flavor composition may include aromadendrin 3-acetate in combination with glucosylated aromadendrin 3-acetate.

[0021] According to certain exemplary embodiments, the flavor composition may include aromadendrin 3-acetate in combination with a sweetness modifier and / or a taste modifier. According to certain embodiments, the amount of aromadendrin 3-acetate present in the flavor composition may be from about 100 ppm to about 70,000 ppm, or in other embodiments, from about 100 ppm to about 50,000 ppm, such as from about 100 ppm to about 30,000 ppm, from about 100 ppm to about 25,000 ppm, from about 100 ppm to about 20,000 ppm, from about 100 ppm to about 15,000 ppm, from about 100 ppm to about 10,000 ppm, and from about 500 ppm to about 10,000 ppm.

[0022] According to certain exemplary embodiments, the flavor composition may include aromadendrin 3-acetate in combination with glucosylated aromadendrin 3-acetate. According to certain embodiments, the amount of glucosylated aromadendrin 3-acetate present in the flavor composition may be from about 100 ppm to about 70,000 ppm, or in other embodiments, from about 100 ppm to about 50,000 ppm, such as from about 100 ppm to about 30,000 ppm, from about 100 ppm to about 25,000 ppm, from about 100 ppm to about 20,000 ppm, from about 100 ppm to about 15,000 ppm, from about 100 ppm to about 10,000 ppm, and from about 500 ppm to about 10,000 ppm.

[0023] The sweetness modifier may comprise one or more of a wide variety of compounds. According to certain exemplary embodiments, the sweetness modifier is selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, and combinations thereof. The term "sweetness modifier," as used herein, refers to a compound that modifies, enhances, amplifies, or intensifies the sweetness perception of a consumable when the compound is present in the consumable at a concentration below the compound's sweetness perception threshold, i.e., a concentration that does not contribute to noticeable sweetness in the absence of additional sweetener(s).

[0024] According to certain embodiments, the amount of sweetness modifier present in the flavor composition may be at a concentration of from about 1,000 ppm to about 200,000 ppm, in another embodiment from about 2,000 ppm to about 100,000 ppm, and in another embodiment from about 5,000 ppm to about 100,000 ppm.

[0025] The term "sweet taste perception threshold concentration" as used herein is the lowest known concentration of a compound that can be perceived as sweet by the human palate. In one embodiment, the sweet taste modifier is a steviol glycoside(s). Examples of steviol glycosides include, for example, stevioside (CAS: 57817-89-7), rebaudioside A (CAS: 58543-16-1), rebaudioside B (CAS: 58543-17-2), rebaudioside C (CAS: 63550-99-2), rebaudioside D (CAS: 63279-13-0), rebaudioside E (CAS: 63279-14-1), rebaudioside F (CAS: 438045-89-7), rebaudioside G (CAS: 127345-21-5), rebaudioside H, and rebaudioside I (CAS: Rebaudioside A (CAS: 64432-06-0), Dulcoside B (CAS: 63550-99-2), and Rubusoside (CAS: 64849-39-4).

[0026] In another embodiment, the steviol glycoside can be a glucosylated steviol glycoside. The glucosylated steviol glycoside included in the composition can be selected from any one or more steviol glycosides that can be subjected to a glucosylation reaction to add one or more glucose units to the molecule. By way of example, and not limitation, glucosylated steviol glycosides included in the sweet taste modifying composition include glucosylated stevioside, glucosylated rebaudioside A, glucosylated rebaudioside B, glucosylated rebaudioside C, glucosylated rebaudioside D, glucosylated rebaudioside E, glucosylated rebaudioside F ... Glucosylated rebaudioside G, Glucosylated rebaudioside H, Glucosylated rebaudioside I, Glucosylated rebaudioside J, Glucosylated rebaudioside K, Glucosylated rebaudioside L, Glucosylated rebaudioside M, Glucosylated rebaudioside N, Glucosylated rebaudioside O, Glucosylated Dulcoside A, Glucosylated Dulcoside B, Glucosylated Rubusoside, any other glucosylated steviol glycosides from an extract of Stevia rebaudiana, and mixtures thereof.

[0027] The glucosylated steviol glycosides may have different degrees of glucosylation. The glucosylated steviol glycosides of the composition may therefore comprise a blend of the same type of glucosylated steviol glycosides, but with different or varying degrees of glucosylation. The glucosylated steviol glycosides of the composition may also comprise a blend of one or more different types of glucosylated steviol glycosides, each having the same degree of glucosylation. The glucosylated steviol glycosides of the composition may further comprise a blend of one or more different types of glucosylated steviol glycosides, each type having a different or varying degree of glucosylation.

[0028] The glucosylated steviol glycoside can comprise a blend of at least one glucosylated steviol glycoside and at least one residual steviol glycoside, where residual steviol glycoside refers to unreacted, non-glucosylated steviol glycoside. The remaining steviol glycosides can include residual stevioside, residual rebaudioside A, residual rebaudioside B, residual rebaudioside C, residual rebaudioside D, residual rebaudioside E, residual rebaudioside F, residual rebaudioside G, residual rebaudioside H, residual rebaudioside I, residual rebaudioside J, residual rebaudioside K, residual rebaudioside L, residual rebaudioside M, residual rebaudioside N, residual rebaudioside O, residual dulcoside A, residual dulcoside B, residual rubusoside, any other residual steviol glycosides from an extract of Stevia rebaudiana, and mixtures thereof. A blend of at least one glucosylated steviol glycoside and at least one remaining steviol glycoside may contain between about 1 percent and 15 percent of the at least one remaining steviol glycoside. According to certain embodiments, a blend of at least one glucosylated steviol glycoside and at least one remaining steviol glycoside may contain between about 1 percent and 10 percent, or between about 1 percent and about 8 percent, or between about 1 percent and about 6 percent, or between about 1 percent and about 4 percent, or between about 1 percent and about 2 percent of the at least one remaining steviol glycoside.

[0029] Glucosylated steviol glycosides can be prepared by preparing a reaction mixture of one or more steviol glycosides, a source of glucose units to be added to the steviol glycoside molecule, an enzyme that catalyzes the glucosylation reaction, and a suitable solvent. According to a specific embodiment, glucosylated steviol glycosides are prepared by preparing a reaction mixture of one or more steviol glycosides, starch as a source of glucose units to be added to the steviol glycoside molecule, CGTase (cyclodextrin glucanotransferase) that catalyzes the glucosylation reaction, and water as a solvent. The glucosylation reaction is carried out on the reaction mixture, and the resulting product is purified and dried. As an example, glucosylated steviol glycosides can be prepared according to the disclosure of Japanese Patent Application Laid-Open No. 2001-120218, which is incorporated by reference. Alpha-glycosylsteviol glycosides (alpha-GS) are prepared by alpha-addition of glucose to a Stevia extract containing at least 1.5 times the amount of RebA as stevioside using cyclodextrin glucosyltransferase.

[0030] In another embodiment, the sweetness modifier may be one or more mogroside(s). Mogrosides are a group of triterpene glycosides obtained from the fruit of Siraitia grosvenorii, also known as Monk Fruit, Longevity Fruit, and Swingle Fruit. Mogrosides make up approximately 1% of the flesh of the fresh fruit. Through extraction, powdered extracts containing up to 80% mogrosides can be obtained. Examples of mogrosides are, for example, grosvenolin II, grosvenolin I, 11-O-mogroside II(I), 11-O-mogroside II(II), 11-O-mogroside II(III), mogroside II(I), mogroside II(II), mogroside II(III), 11-dehydroxy-mogroside III, 11-O-mogroside III, mogroside III(I), mogroside III(II), mogroside IIIe, mogroside IIIx, mogroside IV(I) (siamenoside), ... Mogroside IV(II), mogroside IV(III), mogroside IV(IV), deoxymogroside V(I), deoxymogroside V(II), 11-O-mogroside V(I), mogroside V isomer, mogroside V, isomogroside V, isomogroside VI, 7-O-mogroside V, 11-O-mogroside VI, 11-epi-mogroside, mogroside VI(I), mogroside VI(II), mogroside VI(III) (neomogroside), and mogroside VI(IV). The mogroside(s) may be obtained or obtainable, for example, from a monk fruit extract.

[0031] In another embodiment, the sweetness modifier can be one or more dihydrochalcones. Examples of dihydrochalcones include, for example, trilobatin (1-[4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone (also known as p-phlorizin, phloretin, phloretin 4'-glucoside, phloretin-4'-glucoside, prunin dihydrochalcone, or p-phlorizin); HDG or hesperitin dihydrochalcone (4''-beta-D-glucoside (also known as 1-[4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone);

[0023] Naringin dihydrochalcone (NarDHC, also known as 1-[4-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone); and Neohesperidin dihydrochalcone (NHDC, E959).

[0032] Trilobatin is a natural dihydrochalcone-type sweetener occurring in the Chinese sweet tea plant, Lithocarpus polystachyus, whose leaves have been consumed as sweet tea in southern China for centuries. HDG is present in the peel / fruit of Citrus sinensis L. (Rutaceae), commonly known as sweet orange, and C. reticulata, commonly known as tangerine or mandarin. HDG can be synthesized by reducing hesperidin in dilute alkali to produce hesperidin dihydrochalcone, followed by partial hydrolysis with acid or dissolved or immobilized enzymes to form HDG, as described, for example, in U.S. Pat. No. 3,429,873.

[0033] In another embodiment, the sweetness modifier can be a sweet protein, such as brazzein. Brazzein is a sweet protein extracted from the fruit of the West African vine Pentadiplandra brazzeana (Baillon). It was first isolated in 1994 by the University of Wisconsin-Madison. Brazzein is found in the extracellular region of the fleshy tissue surrounding the seeds. Like other sweet proteins found in plants, it is extremely sweet (500 to 2,000 times sweeter than sucrose) compared to commonly used sweeteners. Other sweet proteins may include thaumatin, monellin, curculin, mabinlin, miraculin, and pentadin.

[0034] Other additional sweetness modifiers include glycyphyllin, mukurodioside IIb, (+)-hernandulcin, 4β-hydroxyhernandulcin, baionoside, phlomisoside I, bryodulcoside, bryoside bryonoside, abrusoside AE, cyclocarioside A, cyclocarioside I, albiziasaponin AE, glycyrrhizin, aboglycyrrhizin, periandrin IV, pterocaryosides A and B, osladin, polypodosides A and B, telosmosides A8-18, phyllodulcin, and huanchioside. E, neostilbin, monatin, 3-acetoxy-5,7-dihydroxy-4'-methoxyflavanone, 4'-trihydroxyflavanone, (2R,3R)-dihydroquercetin 3-O-acetate, dihydroquercetin 3-O-acetate 4'-methyl ether, hesepertin, neoculin, or a combination thereof.

[0035] According to certain exemplary embodiments, the flavor composition may include aromadendrin 3-acetate in combination with at least one taste modifier.

[0036] The taste modifier may comprise one or more of a wide variety of compounds. According to certain exemplary embodiments, the at least one taste modifier may be selected from the group consisting of chlorogenic acid, choline chloride, N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof. For purposes of this specification, the term "taste modifier" refers to one or more components that improve the sweetness profile of a reduced-sugar sweetened composition or sweetened consumable to which it is added.

[0037] According to a specific embodiment, the amount of the specific taste modifier selected from chlorogenic acid or choline chloride and combinations thereof present in the flavor composition can be about 500 ppm to about 100,000 ppm, about 1,000 ppm to about 50,000 ppm, and about 5,000 ppm to about 30,000 ppm in another embodiment. According to another embodiment, the amount of the specific taste modifier selected from N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide and combinations thereof present in the flavor composition can be about 0.1 ppm to about 1,000 ppm, about 0.5 ppm to about 500 ppm, and about 1 ppm to about 100 ppm in another embodiment.

[0038] According to another exemplary embodiment, the taste-modifying agent of the composition comprises one or more chlorogenic acids. The term chlorogenic acids refers to quinic acid conjugates, which include one or more compounds of the ester family formed between cis- and trans-cinnamic acids (e.g., caffeic acid, ferulic acid, p-coumaric acid, sinapic acid) and quinic acid. Quinic acid conjugates are represented by the following formula: [ka]

[0039] Here, certain exemplary quinic acid conjugates are defined by the substitution of the R groups as shown in the table below: [Table 1]

[0040] The use of chlorogenic acid as a taste modifier is described in more detail in WO2002 / 100192 A1, which is incorporated herein by reference in its entirety.

[0041] According to other exemplary embodiments, the taste-modifying agent of the composition may include choline chloride as described in WO2011 / 073187 A1, which is incorporated by reference.

[0042] According to other exemplary embodiments, the taste modifier of the composition comprises one or more carboxylic acid-amino acid conjugates and derivatives thereof of the following formula: [ka] wherein R1 is an alkyl residue having 6 to 30 carbon atoms or an alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and m is 0 or 1. Edible derivatives may include edible salts, including those typically used in the food and beverage industry, including, but not limited to, chloride, sulfate, phosphate, gluconate, sodium salt, citrate, carbonate, acetate, and lactate. These carboxylic acid-amino acid conjugates are described in more detail in WO 2013 / 148991 A1, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates may include C18:2-Beta Ala and C18:2-GABA.

[0043] According to other exemplary embodiments, the taste modifier of the composition comprises one or more carboxylic acid-amino acid conjugates and derivatives thereof of the following formula: [ka] wherein R1 is an alkyl residue having 6 to 30 carbon atoms or an alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and m is 0 or 1. Edible derivatives may include edible salts, including those typically used in the food and beverage industry, including, but not limited to, chloride, sulfate, phosphate, gluconate, sodium salt, citrate, carbonate, acetate, and lactate. These carboxylic acid-amino acid conjugates are described in more detail in WO 2013 / 149022 A1, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates may include N-geranoyl-Pro, N-palmitenoyl-Pro, N-stearoyl-Pro, N-oleoyl-Pro, N-linoleoyl-Pro, and N-linolenoyl-Pro.

[0044] According to other exemplary embodiments, the taste modifier of the composition comprises one or more carboxylic acid-amino acid conjugates and derivatives thereof of the following formula: [ka] wherein R1 is an alkyl residue having 6 to 30 carbon atoms or an alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and m is 0 or 1. Edible derivatives may include edible salts, including those typically used in the food and beverage industry, including, but not limited to, chloride, sulfate, phosphate, gluconate, sodium salt, citrate, carbonate, acetate, and lactate. These carboxylic acid-amino acid conjugates are described in more detail in WO 2013 / 149019 A1, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates may include N-geranoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met, N-oleoyl-Met, N-linoleoyl-Met, and N-linolenoyl-Met.

[0045] According to other exemplary embodiments, the taste modifier of the composition comprises one or more carboxylic acid-amino acid conjugates and derivatives thereof of the following formula: [ka] wherein R1 is an alkyl residue containing 2 to 18 carbon atoms or an alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, and R1, together with the carbonyl group to which it is attached, is the residue of a carboxylic acid. These carboxylic acid-amino acid conjugates are described in more detail in U.S. Pat. No. 10,385,015, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates include (2S)-2-acetamido-4-(methylsulfinyl)butanoic acid; (2S)-2-hexanamido-4-(methylsulfinyl)butanoic acid; (2S)-2-decanamido-4-(methylsulfinyl)butanoic acid; (2S)-2-((Z)-dodec-5-enamido)-4-(methylsulfinyl)butanoic acid; (2S)-2-dodecanamido-4-(methylsulfinyl)butanoic acid; (2S)-4-(methylsulfinyl)-2-tetradecanamidobutanoic acid; (2S)-4-(methyl (2S)-4-(methylsulfinyl)-2-pentadecanamidobutanoic acid; (2S)-4-(methylsulfinyl)-2-palmitamidobutanoic acid; (2S)-2-heptadecanamido-4-(methylsulfinyl)butanoic acid; (2S)-4-(methylsulfinyl)-2-((9Z,12Z)-octadeca-9,12-dieamido)butanoic acid; (2S)-4-(methylsulfinyl)-2-oleamidobutanoic acid; and (2S)-4-(methylsulfinyl)-2-stearamidobutanoic acid.

[0046] In one aspect, the present invention provides the use of a compound or an edible salt thereof according to the formula: [ka] where R1 is an alkyl residue containing 6 to 20 carbon atoms or an alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is the residue of a carboxylic acid, and NR2R3 (where R3 is H or together with R2 and the N atom to which they are attached is a 5-membered ring) is the residue of an amino acid, especially a proteinogenic amino acid, ornithine, gamma-aminobutyric acid, or beta-alanine, or a 1-aminocycloalkylcarboxylic acid. These carboxylic acid-amino acid conjugates are described in more detail in WO2013 / 148965 A1, which is incorporated herein by reference.

[0047] Edible salts include those typically used in the food and beverage industry, including chloride, sulfate, phosphate, gluconate, sodium salt, citrate, carbonate, acetate, and lactate. Proteinogenic amino acids include alanine (Ala), cysteine ​​(Cys), aspartic acid (Asp), phenylalanine (Phe), glutamic acid (Glu), histidine (His), isoleucine (Ile), lysine (Lys), leucine (Leu), methionine (Met), asparagine (Asn), glutamine (Gln), arginine (Arg), serine (Ser), theronine (Thr), valine (Val), tryptophan (Trp), tyrosine (Tyr), proline (Pro), or glycine (Gly). Examples of carboxylic acid-amino acid conjugates include N-oleoylvaline, N-oleoylserine, and N-oleoylaspartic acid.

[0048] According to another exemplary embodiment, the taste-modifying agent of the composition comprises glucosylated aromadendrin 3-acetate ("ADA"). The glucosylated aromadendrin 3-acetate may have different degrees of glucosylation. In one embodiment, the glucosylated aromadendrin 3-acetate of the composition may comprise a blend of the same type of glucosylated aromadendrin 3-acetate but with different or varying degrees of glucosylation. For example, the glycosylated ADA may be β-G-ADA, or may comprise any one of 7-β-glycosylated ADA, 4'-β-glycosylated ADA, or 7,4'-β-glycosylated ADA, where n is an integer between 1 and 15. In another embodiment, the glycosylated ADA can be α-G-ADA, and can include any one of 7-α-glycosylated ADA, 4'-α-glycosylated ADA, or 7,4'-α-glycosylated ADA, where n is an integer from 1 to 15.

[0049] The flavor compositions described herein can modify and / or adjust the taste of at least one sweetener, which can be any known sweetener, such as a natural sweetener, a natural high-sweetener, or an artificial sweetener.

[0050] At least one sweetener is present in a sweetening amount. As used herein, "sweetening amount" refers to the amount of a compound present in a consumable, e.g., a beverage, necessary to provide a detectable sweetness.

[0051] As used herein, the phrase "natural high-intensity sweetener" refers to any sweetener that is naturally found in nature and that characteristically has a sweeter taste than sucrose, fructose, or glucose, but has fewer calories. Natural high-intensity sweeteners can be provided as pure compounds or, alternatively, as part of an extract. As used herein, the phrase "synthetic sweetener" refers to any composition that is not naturally found in nature and that characteristically has a sweeter taste than sucrose, fructose, or glucose, but has fewer calories.

[0052] In other embodiments, the at least one sweetener is a carbohydrate sweetener. Suitable carbohydrate sweeteners include, but are not limited to, sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedopertulose, octolose, fucose, rhamnose, turanose, cellobiose, sialose, and combinations thereof. In other embodiments, the at least one sweetener does not include a carbohydrate sweetener.

[0053] In another embodiment, the additional sweetener is a rare sugar selected from sorbose, lyxose, ribulose, xylose, xylulose, D-allose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, turanose, D-allulose (D-psicose), rhamnose, and combinations thereof. Other sweeteners include siamenoside I, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, tamatin, hemandulcin, phyllodulcin, glycyphyllin, trilobatin, bayunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukuroziosid, phlomisoside I, periandrin I, abrusoside A, Steviolbioside and cyclocaryoside I, sucralose, acesulfame potassium, acesulfamic acid and its salts, aspartame, alitame, saccharin and its salts, hesperidin dihydrochalcone glucoside, neohesperidin dihydrochalcone, cyclamic acid, cyclamic acid and its salts, neotame, advantame, glucosylated steviol glycosides (GSG), and combinations thereof.

[0054] In another embodiment, the additional sweetening agent is a sugar alcohol selected from allulose, erythritol, xylitol, maltitol, mannitol, isomalt, sorbitol, inositol, lactitol, and combinations thereof.

[0055] In one embodiment, the sweetener is a caloric sweetener or a mixture of caloric sweeteners, hi another embodiment, the caloric sweetener is selected from sucrose, fructose, glucose, high fructose corn / starch syrup, beet sugar, cane sugar, and combinations thereof.

[0056] In other embodiments, the sweetening agent comprises at least one steviol glycoside or mogroside, wherein the at least one steviol glycoside or mogroside is present in a sweetening amount.

[0057] product In accordance with the present disclosure, aromadendrin 3-acetate may be added to a sweetened consumable (i.e., a consumable that includes at least one sweetening agent) or may be provided as part of a flavor composition for the consumable.

[0058] In one embodiment, aromadendrin 3-acetate is present in the flavor composition in an amount such that when the flavor composition is added to a sweetened consumable, the sucrose equivalent of the consumable is increased compared to the consumable in the absence of aromadendrin 3-acetate.

[0059] When added to a consumable product, aromadendrin 3-acetate and / or glycosylated aromadendrin 3-acetate are present in an amount effective to modify the sweetness or mouthfeel of the sweetener without imparting an off-taste. According to certain embodiments, the amount of aromadendrin 3-acetate present in the consumable product can be from about 0.05 ppm to about 70 ppm, and in other embodiments, from about 0.05 ppm to about 50 ppm, e.g., from about 0.05 ppm to about 30 ppm, from about 0.05 ppm to about 25 ppm, from about 0.05 ppm to about 20 ppm, from about 0.05 ppm to about 15 ppm, from about 0.05 ppm to about 10 ppm, from about 0.1 ppm to about 10 ppm, and from about 0.5 ppm to about 10 ppm.

[0060] In another embodiment, the flavor composition may include aromadendrin 3-acetate in combination with an aroma component, a sweetness modifier, and / or a taste modifier to improve the taste quality and / or mouthfeel of a sweet tastant. According to certain embodiments, the amount of sweetness modifier present in the consumable may be from about 1 ppm to about 200 ppm, from about 2 ppm to about 100 ppm in another embodiment, and from about 5 ppm to about 50 ppm in another embodiment. According to certain embodiments, the amount of a specific taste modifier selected from chlorogenic acid or choline chloride and combinations thereof present in the consumable may be from about 0.5 ppm to about 100 ppm, from about 1 ppm to about 50 ppm in another embodiment, and from about 5 ppm to about 30 ppm in another embodiment. According to another embodiment, the amount of a particular taste modifier selected from N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof present in the consumable may be at a concentration of from about 0.0001 ppm to about 1 ppm, in another embodiment, from about 0.0005 ppm to about 0.5 ppm, and in another embodiment, from about 0.001 ppm to about 0.1 ppm.

[0061] In one embodiment, at least one sweetener described herein is added to the consumable at a concentration of from about 50 ppm to about 600 ppm, e.g., from about 50 ppm to about 500 ppm, from about 50 ppm to about 400 ppm, from about 50 ppm to about 300 ppm, from about 50 ppm to about 200 ppm, from about 50 ppm to about 100 ppm, from about 100 ppm to about 600 ppm, from about 100 ppm to about 500 ppm, from about 100 ppm to about 400 ppm, from about 100 ppm to about 300 ppm, In another embodiment, for full sugar and low sugar applications, at least one sweetener may be present in the consumable at a concentration of up to 1,000 ppm.

[0062] When expressed as "ppm," the concentration is in parts per million by weight based on the total weight of the consumable. When ranges of values ​​are set forth in this disclosure, it should be understood that it is intended that any and all values ​​within the range, including the endpoints, be considered disclosed. The inventors recognize and understand that any and all values ​​within a range should be considered specific, and it should be understood that the inventors own the entire range and all values ​​within the range.

[0063] The flavor composition may contain one or more food-grade excipient(s). Excipients suitable for flavor compositions are well known in the art and include, for example, without limitation, solvents (including water, alcohol, ethanol, oils, fats, vegetable oils, and miglyol), binders, diluents, disintegrants, lubricants, flavoring agents, colorants, preservatives, antioxidants, emulsifiers, stabilizers, flavor enhancers, sweeteners, anti-caking agents, etc. Examples of such carriers or diluents for flavors can be found, for example, in "Perfume and Flavor Materials of Natural Origin", S. Arctander, Ed., Elizabeth, NJ, 1960; "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; "Flavorings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", J.M. Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0064] The flavor composition may have any suitable form, for example liquid or solid, wet or dry, or bound to or coated on a carrier / particle, encapsulated, or as a powder.

[0065] In this disclosure, the term "about" when used in connection with a value is inclusive of the stated value and has a meaning dictated by the context. For example, it encompasses at least the degree of error associated with measuring the specific value. Those skilled in the art will understand that the term "about" is used herein to mean that an amount of "about" the recited value will produce a desired degree of efficacy in the compositions and / or methods of the present disclosure. Those skilled in the art will further understand that the boundaries of "about" for percentage, amount, or quantity values ​​of any component in an embodiment can be determined by varying the values, determining the effectiveness of the composition or method for each value, and determining the range of values ​​that will produce a composition or method with the desired degree of efficacy according to the present disclosure.

[0066] A consumable product may include a base. As used herein, the term "base" refers to all ingredients necessary for a consumable product, excluding flavor compositions. These may vary in both nature and proportion depending on the nature and use of the consumable or additive, but they are all well known in the art and may be used in art-recognized proportions. Therefore, the formulation of such a base for any conceivable purpose is within the ordinary skill of the art. For example, a beverage base according to the present disclosure may include about 5% sucrose and about 0.05% citric acid in water.

[0067] By way of example only, and not limitation, suitable bases may include anti-caking agents, anti-foaming agents, antioxidants, binders, colorants, diluents, disintegrants, emulsifiers, encapsulating agents or formulations, enzymes, fats, flavor enhancers, flavoring agents, gums, polysaccharides, preservatives, proteins, solubilizers, solvents, stabilizers, sugar derivatives, surfactants, sweeteners, vitamins, waxes, etc. Solvents that may be used are known to those skilled in the art and include, by way of example, water, ethanol, ethylene glycol, propylene glycol, glycerin, and triacetin. Encapsulating agents and gums include maltodextrin, gum arabic, alginates, gelatin, modified starch, other polysaccharides, and proteins.

[0068] Examples of excipients, carriers, diluents or solvents for flavor compounds can be found, for example, in "Perfume and Flavor Materials of Natural Origin", S. Arctander, Ed., Elizabeth, NJ, 1960; "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; "Flavorings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", JM Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0069] Non-limiting examples of suitable flavor-providing ingredients include natural flavors, artificial flavors, spices, seasonings, etc. These include synthetic flavor oils, flavoring aromas and / or oils, oleoresins, essences, distillates, and combinations thereof.

[0070] Supplementary ingredients may be present to provide other benefits, such as enhanced stability, ease of incorporation into consumables or additives, and enhanced nutritional value. Non-limiting examples of such supplementary ingredients include stabilizers, emulsifiers, preservatives, gums, starches, dextrins, vitamins and minerals, functional ingredients, salts, antioxidants, and polyunsaturated fatty acids. Specific examples are emulsifiers and carriers useful in spray-drying processes. Non-limiting examples of these are modified starches such as CAPSUL™ and maltodextrin.

[0071] The additive may be a single component or a blend of components, or may be encapsulated in any suitable encapsulating agent. The additive may be prepared by any suitable method, such as spray drying, extrusion, and fluidized bed drying.

[0072] In accordance with the present disclosure, the term "consumable" refers to a product intended for consumption by a subject, typically via the oral cavity (although consumption can also occur via parenteral means, such as inhalation), for at least one purpose of enjoyment, nutrition, or health and wellness benefit. Consumables can exist in any form, including, but not limited to, liquids, solids, semisolids, tablets, capsules, lozenges, strips, powders, gels, gums, pastes, slurries, solutions, suspensions, syrups, aerosols, and sprays. The term also refers to, for example, dietary and nutritional, and health and wellness supplements. Consumables include compositions that are discarded after being placed in the oral cavity for a period of time but are not swallowed. They can be placed in the mouth before consumption or can be held in the mouth for a period of time before being discarded.

[0073] In its broadest sense, consumables include, but are not limited to, food products of all kinds, confectionery products, baked goods, sweet products, savory products, fermented products, dairy products, non-dairy products, beverages, nutritional products, and pharmaceutical products.

[0074] Non-limiting examples of consumables include wet / liquid soups, including frozen soups, regardless of concentration or container. For purposes of this definition, soup(s) means a food product cooked in a liquid and prepared from meat, poultry, fish, vegetables, grains, fruit, and other ingredients, including any or all visible pieces of these ingredients.It can be clear (broth) or thick (chowder), smooth, pureed or chunky, instant, semi-condensed or concentrated, hot or cold, and served as the first or main course of a meal or as a snack between meals (sipped like a beverage). Soups can be used as an ingredient to prepare other meal components and can range from broths (consomme) to sauces (cream or cheese-based soups); dehydrated and prepared foods, including cooking aid products such as powders, granules, pastes, concentrated liquid products (including compressed cubes, tablets, or concentrated bouillons, bouillons, and bouillon-like products in powdered or granular form, sold individually (regardless of technology) as finished products or as ingredients in products, sauces, and recipe mixes); meal solution products, such as dehydrated and freeze-dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated cooking soups, ready-to-eat dishes, meals, and single-served entrees (pasta, dips, etc.). dehydrated or ambient preparations of foods (potato, and rice dishes); meal garnish products, such as condiments, marinades, salad dressings, salad toppings, dips, breadcrumbs, batter mixes, shelf-stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes (including salad recipe mixes), whether dehydrated, liquid, or frozen, sold as a finished product or as an ingredient in a product; beverages, including beverage mixes and concentrates, including, but not limited to: alcoholic and non-alcoholic ready-to-drink beverages and dry powdered beverages, carbonated and non-carbonated beverages, such as soda, fruit or vegetable juices, alcoholic and non-alcoholic beverages, teas, such as green tea and black tea, and wines, such as red wine; confectionery products, such as cakes, cookies, pies, candy, chewing gum, gelatin, ice cream, sorbet, puddings, jams, jellies, salad dressings and other condiments, cereals, and other breakfast foods, canned fruit and fruit sauces, and the like.

[0075] Methods are provided for enhancing the sweetness of a consumable and / or adjusting one or more taste characteristics of a sweetener to make the taste of the consumable more similar to a sucrose-sweetened consumable.

[0076] The present disclosure is further described with reference to the following non-limiting examples.

[0077] example The following examples are given for illustrative purposes only and should not be construed as limiting the invention, many variations of which are possible without departing from the spirit and scope of the disclosure.

[0078] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

[0079] example A beverage base (5% sucrose and 0.05% citric acid in water) was prepared. The base did not contain aromadendrin 3-acetate ("ADA"). A control was prepared by combining the base with ADA. The controls in Examples 15 and 16 were prepared by combining the base with ADA and G-ADA. According to the following examples, different combinations of base with ADA, sweetness modifiers and / or taste modifiers were prepared, and the sensory perception of sweetness characteristics and mouthfeel was evaluated by trained flavorists.

[0080] Example 1 (control) [Table 2]

[0081] Example 2 (Control + 30 ppm Reb A) [Table 3]

[0082] Example 3 (control + 30 ppm mogrosides)

Table 4

[0083] Example 4 (Control + 30 ppm Steviol Glycoside Mixture)

Table 5

[0084] Example 5 (Control + 20 ppm Reb M)

Table 6

[0085] Example 6 (Control + 60 ppm Steviol Glycoside Mixture)

Table 7

[0086] Example 7 (Control + 10 ppm Siamenoside I)

Table 8

[0087] Example 8 (Control + 10 ppm HDG)

Table 9

[0088] Example 9 (Control + 5 ppm Brazzein)

Table 10

[0089] Example 10 (Control + 10 ppm chlorogenic acid)

Table 11

[0090] Example 11 (Control + 20 ppm Choline Chloride)

Table 12

[0091] Example 12 (4% sucrose in nonfat yogurt, 30 ppm Reb A)

Table 13

[0092] Example 13 (30 ppm Reb A in pea protein drink)

Table 14

[0093]

Table 15

[0094] Example 14 (Control + 0.1 ppm Thaumatin) Table 16

[0095] Example 15 (Control) Table 17

[0096] Example 16 (Control + 30 ppm Reb A) Table 18

[0097] For Examples 15 and 16, β-glycosylation of ADA was performed using a natural enzyme. This enzyme transfers a glucose unit from a glucose donor to ADA. The enzyme used to facilitate this transfer is produced by bacterial fermentation. In one example, the enzyme can be UGT (UDP-glucuronosyltransferase) or CGTase (cyclomaltodextrin glucanotransferase). The steps of β-glycosylation of ADA are as follows: a) Dissolve UDPG (uridine diphosphate glucose) in Tri-HCl buffer (pH 7-8); b) adding the compound ADA having a purity between 75% and 99% to the UDPG buffer mixture; c) The molar ratio of UDPG to ADA was optimized between 35:65 and 65:35; d) YIJC1 (UGT) is added to the mixture and incubated at 45°C for a desired reaction time to glycosylate ADA with a glucose molecule derived from UDPG; e) adding methanol to the reaction mixture to inactivate the enzyme, and then applying the resulting solution to HP20 resin for purification, and the concentrated glycosylated ADA (G-ADA) is further concentrated and dried using a conventional vacuum evaporator; and f) Glycosylated ADA (β-G-ADA) includes any one of 7-β-glycosylated ADA, 4'-β-glycosylated ADA, or 7,4'-β-glycosylated ADA (see below), where n is an integer from 1 to 15.

[0098] [ka]

[0099] In another embodiment, alpha glycosylation of ADA can be produced. The steps for alpha glycosylation of ADA are as follows: a) Dissolve soluble potato starch in RO water; b) adding the compound ADA having a purity between 75% and 99% to the starch solution; c) The molar ratio of soluble potato starch to ADA was optimized between 35:65 and 65:35; d) CGTase (cyclomaltodextrin glucanotransferase) enzyme is added to the mixture and incubated at 60°C for the desired reaction time to glycosylate ADA with glucose molecules derived from starch; e) heating the reaction mixture at 100°C for 15 minutes to inactivate the CGTase, and then applying the resulting solution to HP20 resin for purification, and the concentrated glycosylated ADA (G-ADA) is further concentrated and dried using a conventional vacuum evaporator; and f) α-glycosylated ADA (α-G-ADA) includes any one of 7-α-glycosylated ADA, 4'-α-glycosylated ADA, or 7,4'-α-glycosylated ADA (see below), where n is an integer from 1 to 15.

[0100] [ka]

[0101] The above example compositions were taste tested by an experienced flavorist, and the combinations were compared with the base. As can be seen, the combination of ADA with sweetness modifier(s) was found to have a sweeter and / or more sugary mouthfeel and / or less lingering sweetness and / or less licorice-like taste. The combination of ADA with taste modifier(s) was also found to have a more sugary mouthfeel and / or less lingering sweetness and / or less licorice-like taste and / or less bitterness and / or less astringency.

[0102] The dimensions and values ​​disclosed herein should not be understood as being strictly limited to the exact numerical values ​​recited. Instead, unless otherwise specified, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "approximately 40 mm."

[0103] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

Claims

1. A flavor composition comprising: a. aromadendrin 3-acetate; and b. At least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins, and combinations thereof.

2. Steviol glycosides include rebaudioside M, rebaudioside D, rebaudioside A, rebaudioside N, rebaudioside O, rebaudioside E, steviolmonoside, steviolbioside, rubusoside, dulcoside B, dulcoside A, rebaudioside B, rebaudioside G, stevioside, rebaudioside C, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, 2. The flavor composition of claim 1, wherein the steviol glycoside is selected from the group consisting of rebaudioside K, rebaudioside J, rebaudioside M2, rebaudioside D2, rebaudioside S, rebaudioside T, rebaudioside U, rebaudioside V, rebaudioside W, rebaudioside Z1, rebaudioside Z2, rebaudioside IX, enzymatically glucosylated steviol glycosides, and combinations thereof.

3. Mogrosides include grosvenolin II, grosvenolin I, 11-O-mogroside II(I), 11-O-mogroside II(II), 11-O-mogroside II(III), mogroside II(I), mogroside II(II), mogroside II(III), 11-dehydroxy-mogroside III, 11-O-mogroside III, mogroside III(I), mogroside III(II), mogroside IIIe, mogroside IIIx, mogroside IV(I) (siamenoside), mogroside IV(II), mogroside IV(II) 11-O-mogroside V(I), mogroside IV(IV), deoxymogroside V(I), deoxymogroside V(II), 11-O-mogroside V(I), mogroside V isomers, mogroside V, iso-mogroside V, iso-mogroside VI, 7-O-mogroside V, 11-O-mogroside VI, 11-epi-mogroside, mogroside VI(I), mogroside VI(II), mogroside VI(III) (neomogroside), mogroside VI(IV), and combinations thereof.

4. 2. The flavor composition of claim 1, wherein the dihydrochalcone is selected from the group consisting of phloretin, HDG, trilobatin, naringin dihydrochalcone, neohesperidin dihydrochalcone, and combinations thereof.

5. 10. The flavor composition of claim 1, further comprising glucosylated aromadendrin 3-acetate.

6. 10. The flavor composition of claim 1, wherein aromadendrin 3-acetate is present in the flavor composition at a concentration of 100 ppm to 70,000 ppm.

7. A flavor composition comprising: a. aromadendrin 3-acetate; and b. At least one taste-modifying agent selected from the group consisting of chlorogenic acid, choline chloride, N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof.

8. A flavor composition comprising: a. Aromadendrin 3-acetate; and b. Brazzein.

9. Consumables including: a. at least one sweetening agent, and b. a flavor composition comprising aromadendrin 3-acetate; and at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins, and combinations thereof; wherein at least one sweetener is present in a sweetening amount.

10. 10. The consumable of claim 9, wherein the at least one sweetening agent is selected from the group consisting of sucrose, fructose, glucose, xylose, arabinose, rhamnose, tagatose, allulose, trehalose, isomaltulose, steviol glycosides, mogrosides, stevia, trilobatin, rubusoside, aspartame, advantame, agave syrup, acesulfame potassium (Acek), high fructose corn syrup, neotame, saccharin, sucralose, high fructose corn syrup, starch syrup, monk fruit extract, neohesperidin dihydrochalcone, naringin dihydrochalcone, HDG, sugar alcohols, cellobiose, psicose, cyclamate, tamatin, molasses, rice syrup, and combinations thereof.

11. 10. The consumable of claim 9, wherein the at least one sweetness modifier is present in a concentration of from 1 ppm to 200 ppm.

12. 10. The consumable product of claim 9, wherein the consumable product is a beverage.

13. 10. The consumable product of claim 9, further comprising glucosylated aromadendrin 3-acetate.

14. 10. The consumable of claim 9, wherein the amount of aromadendrin 3-acetate present in the consumable is at a concentration of 0.05 ppm to 70 ppm.

15. Consumables including: a. at least one sweetening agent, and b. a flavor composition comprising aromadendrin 3-acetate; and at least one sweetness modifier selected from the group consisting of chlorogenic acid, choline chloride, N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof; wherein at least one sweetener is present in a sweetening amount.

16. 16. The consumable of claim 15, wherein the at least one sweetening agent is selected from the group consisting of sucrose, fructose, glucose, xylose, arabinose, rhamnose, tagatose, allulose, trehalose, isomaltulose, steviol glycosides, mogrosides, stevia, trilobatin, rubusoside, aspartame, advantame, agave syrup, acesulfame potassium (AceK), high fructose corn syrup, neotame, saccharin, sucralose, high fructose corn syrup, starch syrup, monk fruit extract, neohesperidin dihydrochalcone, naringin dihydrochalcone, HDG, sugar alcohols, cellobiose, psicose, cyclamate, tamatin, molasses, rice syrup, and combinations thereof.

17. 16. The consumable of claim 15, wherein the at least one sweetness modifier is present in a concentration of from 1 ppm to 200 ppm.

18. 16. The consumable product of claim 15, wherein the consumable product is a beverage.

19. 16. The consumable product of claim 15, further comprising glucosylated aromadendrin 3-acetate.

20. 16. The consumable of claim 15, wherein the amount of aromadendrin 3-acetate present in the consumable is at a concentration of 0.05 ppm to 70 ppm.

Citation Information

Patent Citations

  • Flavonoid-containing powder composition

    JP2019004906A

  • Novel flavonoids o-a-glucosylated on the b cycle, method for the production thereof and uses

    US20170107242A1

  • Flavanone derivatives and their use as sweetness enhancers

    WO2021043842A1