Compositions comprising mogroside

Abstract

A fragrance composition is provided. The composition comprises mogroside selected from the group consisting of symbioside I, 1,6-α isomers of symbioside I, and combinations thereof, and aromatic components selected from the group consisting of 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof.

Description

Technical Field

[0001] This disclosure relates to compositions and methods that use mogrosides, such as symmenidine I, in combination with aromatic ingredients, sweeteners, and / or flavor modifiers in flavor compositions and consumer products to improve the taste quality and / or mouthfeel of sweet substances.

[0002] background

[0003] Compounds used to alter the taste of consumer products (i.e., products taken orally for ingestion or vomiting, such as food, beverages, confectionery, oral care products, etc.) are widely used. They do not add flavor to consumer products on their own, but they provide desired auxiliary benefits, such as enhanced mouthfeel and / or sweetness, or mask undesirable characteristics of other ingredients, such as the distinctive taste and texture of products containing sugar substitutes that are perceived as unappealing.

[0004] In the case of sugar substitutes, the flavors they impart can exhibit different temporal characteristics, flavor properties, or adaptation behaviors compared to the sugars they wholly or partially replace. For example, the sweetness of natural and synthetic high-intensity sweeteners (HIS) typically takes longer to develop and lasts longer than that of sugars (sweet, short-chain, soluble carbohydrates, including glucose, fructose, sucrose, maltose, and lactose) or high-fructose corn syrup (HFCS), often referred to as sugar substitutes, and this can alter the flavor balance of edible compositions containing them. This can result in unbalanced temporal flavor characteristics. In addition to differences in temporal characteristics, high-intensity sweeteners generally exhibit a lower maximum response than sugars; off-flavors, including bitterness, metallic taste, coolness, astringency, licorice-like taste, and / or sweetness, diminish with repeated tasting.

[0005] However, all high-intensity sweeteners have an undesirable aftertaste, 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 diminishes the desired sugary sweetness and thus effectively masks undesirable flavors or off-flavors in edible compositions, which is key to consumer acceptance of many edible compositions.

[0006] Therefore, it remains necessary to provide flavor compositions in order to improve the taste quality and / or mouthfeel of sweet substances.

[0007] Overview

[0008] In one illustrative embodiment, the fragrance composition comprises mogroside and an aromatic component, wherein the mogroside is selected from the group consisting of symbioside I, the 1,6-a isomer of symbioside I, and combinations thereof, and the aromatic component is selected from the group consisting of 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof.

[0009] In another illustrative embodiment, the flavor composition comprises mogroside, an aromatic component, and a sweetener, wherein the mogroside is selected from the group consisting of symbioside I, its 1,6-a isomer, and combinations thereof; the aromatic component is selected from the group consisting of 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof; and the sweetener is selected from the group consisting of steviol glycoside, hesperidin, trilobatin, phloretin, thaumatin, neohesperidin dihydrochalcone, and combinations thereof.

[0010] In yet another illustrative embodiment, the consumer product comprises at least one sweetener; and a flavor composition comprising mogroside, an aromatic component, and a sweetener modifier, wherein the mogroside is selected from the group consisting of symbioside I, 1,6-α isomers of symbioside I, and combinations thereof; the aromatic component is selected from the group consisting of 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof; and the sweetener is selected from the group consisting of steviol glycosides, hesperidin, trifolin, phloretin, thomatose, neohesperidin dihydrochalcone, and combinations thereof. The at least one sweetener is present in a sweetened amount.

[0011] In yet another illustrative embodiment, a method is disclosed to impart more sugar-like temporal, flavor, and / or taste characteristics to a consumer product by adding the flavor composition disclosed in this application to the consumer product, thereby providing a consumer product having more sugar-like temporal, flavor, and / or taste characteristics.

[0012] In another embodiment, the more sugar-like temporal characteristic is a reduced sweetness retention compared to consumer products without the flavor compositions disclosed in this application.

[0013] In another embodiment, the more sugar-like flavor characteristic is an improved mouthfeel (e.g., increased body or fullness) compared to consumer products without the flavor compositions disclosed in this application.

[0014] In yet another illustrative embodiment, a consumer product is provided. The consumer product comprises at least one sweetener and a flavor composition according to the present disclosure, the flavor composition containing mogroside selected from the group consisting of symbioside I, its 1,6-α isomer, and combinations thereof. The at least one sweetener is present in a sweetening amount.

[0015] Certain embodiments of any aspect of this disclosure may provide one or more of the following advantages:

[0016] - Increased sweetness in the composition;

[0017] - Enhanced sweetness in a composition containing at least one sweetener;

[0018] - The amount of caloric sweetener required to achieve the desired sweetness is reduced;

[0019] - One or more sweetness characteristics are improved to make the sweetness more similar to sugar (sucrose);

[0020] - Prolong the sweetness reduction (e.g., reduce the length of time the sweetness is retained and / or reduce the intensity of the sweetness more quickly);

[0021] - The bitterness and / or licorice and / or metallic taste is weakened;

[0022] - The sensory perception of dryness and / or astringency is weakened;

[0023] - Improved sweetness impact (e.g., increasing the maximum intensity of sweetness and / or reducing the duration of sweetness perception) (e.g., reducing the duration of sweetness).

[0024] These and other features, aspects, and advantages of the particular embodiments will become apparent to those skilled in the art upon reading this disclosure.

[0025] Detailed description

[0026] The following text provides a broad description of many different embodiments of this disclosure. This specification is to be interpreted as exemplary only and does not describe every possible embodiment, as it would be impractical to describe every possible embodiment if not impossible. It will be understood that any feature, characteristic, component, composition, ingredient, product, step, or method described in this application may be deleted, combined with, or substituted for any other feature, characteristic, component, composition, ingredient, product, step, or method described in this application. Many alternative embodiments may be implemented using current technology or technology developed after the filing date of this patent, which will still fall within the scope of the claims of this application. All publications and patents referenced in this specification are incorporated herein by reference.

[0027] This disclosure relates to the unexpected discovery that flavor compositions comprising symbioside I and / or its 1,6-a isomer in combination with aromatic components, sweeteners and / or flavor modifiers improve the taste quality and / or mouthfeel of sweet substances.

[0028] The chemical formula of symbioside I is C 54 H 92 O 24 Its molecular weight is 1125.29. The chemical structure of symmenidine I is given below.

[0029]

[0030] Ciprofloxacin I was originally derived from the Siamese monk fruit (Siraitia grosvenorii). Siraitia siamensis (Kasai, R. et al., Agric. Biol. Chem. 1989, 53, 3347-3349), after which from monk fruit ( Siraitia grosvenorii mogrosides isolated from *Siraitia grosvenorii* (Matsumoto, K. et al., Chem. Pharm. Bull. 1990, 38, 2030-2032). Cimanin I, used according to this disclosure, can be prepared by any suitable means, including but not limited to synthesis, biosynthesis, or extraction. In other embodiments, cimanin I is extracted from the fruit.

[0031] According to certain illustrative embodiments, the fragrance composition may comprise symbioside I, 1,6-a isomers of symbioside I, and combinations thereof in combination with aromatic components.

[0032] The aromatic component may comprise one or more of a wide variety of compounds. According to certain illustrative embodiments, the aromatic component is selected from 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof. As used herein, the term "fragrance component" refers to a compound that, as understood by those skilled in the art to which this disclosure pertains, may influence or modify, in a positive manner or in a manner that makes the perception and taste of the composition pleasant, and is not merely a odorous compound.

[0033] According to some embodiments, the amount of symbioside I present in the fragrance composition may be from about 2,000 ppm to about 200,000 ppm, and in another embodiment, from about 3,000 ppm to about 100,000 ppm. In yet another embodiment, the amount of symbioside I present in the fragrance composition may be from about 5,000 ppm to about 50,000 ppm.

[0034] According to some embodiments, the amount of aromatic components present in the fragrance composition may be from about 10 ppm to about 100,000 ppm, in another embodiment from about 20 ppm to about 20,000 ppm, and in yet another embodiment from about 50 ppm to about 10,000 ppm. In yet another embodiment, the amount of aromatic components present in the fragrance composition may be from about 10 ppm to about 5,000 ppm.

[0035] According to certain illustrative embodiments, the flavor composition may comprise symbioside I, its 1,6-a isomer, or combinations thereof, in combination with aromatic components and sweeteners.

[0036] The sweetness improver may comprise one or more of a wide variety of compounds. According to certain illustrative embodiments, the sweetness improver is selected from the group consisting of steviol glycosides, hesperidin, trifolin, phloretin, sematriene, neohesperidin dihydrochalcone, and combinations thereof. As used herein, the term "sweetness improver" refers to a compound that, when present in a consumer product at a concentration at or below the sweetness recognition threshold of the compound (i.e., a concentration at which the compound does not contribute any noticeable sweetness in the absence of other sweeteners), improves, enhances, amplifies, or strengthens the perceived sweetness of the consumer product.

[0037] According to some embodiments, the amount of the sweetener present in the flavor composition may be from about 1,000 ppm to about 500,000 ppm, in another embodiment from about 2,000 ppm to about 200,000 ppm, in another embodiment from about 5,000 ppm to about 100,000 ppm, and in another embodiment from about 10,000 ppm to about 50,000 ppm. In another embodiment, the amount of the sweetener present in the flavor composition may be from about 1,000 to about 50,000 ppm.

[0038] As used in this application, the term "sweetness recognition threshold concentration" is the lowest known concentration of a compound that can be perceived as sweet by human sense of taste.

[0039] In one embodiment, the sweetener is steviol glycoside. Examples of steviol glycosides include, for example, steviol glycoside (CAS: 57817-89-7), ribavirin A (CAS: 58543-16-1), ribavirin B (CAS: 58543-17-2), ribavirin C (CAS: 63550-99-2), ribavirin D (CAS: 63279-13-0), ribavirin E (CAS: 63279-14-1), ribavirin F (CAS: 438045-89-7), ribavirin G (CAS: 127345-21-5), ribavirin H, and ribavirin I (CAS: 122061). 6-34-1), Rebaudisin J, Rebaudisin K, Rebaudisin L, Rebaudisin M (CAS: 1220616-44-3), Rebaudisin N (CAS: 1220616-46-5), Rebaudisin O (CAS: 1220616-48-7), Dulcoside A (CAS: 64432-06-0), Dulcoside B (CAS: 63550-99-2), Rubusoside (CAS: 64849-39-4), and Naringin Dihydrochalcone (CAS: 18916-17-1).

[0040] In another embodiment, the steviol glycoside may be a glucosylated steviol glycoside. The glucosylated steviol glycoside included in the composition may be selected from any one or more steviol glycosides capable of having one or more glucose units added to the molecule via a glucosylation reaction. As an example and not a limitation, the glucosylated steviol glycosides included in the sweetening modified composition may be selected from glucosylated steviol glycoside, glucosylated riboflavin A, glucosylated riboflavin B, glucosylated riboflavin C, glucosylated riboflavin D, glucosylated riboflavin E, glucosylated riboflavin F, glucosylated riboflavin G, glucosylated riboflavin H, glucosylated riboflavin I, glucosylated riboflavin J, glucosylated riboflavin K, glucosylated riboflavin L, glucosylated riboflavin M, glucosylated riboflavin N, glucosylated riboflavin O, glucosylated dulcitin A, glucosylated dulcitin B, glucosylated stevia glycoside, and stevia ( Stevia rebaudiana Any other glucosylated steviol glycosides obtained from the extract, and mixtures thereof.

[0041] Glucosylated steviol glycosides can have varying degrees of glucosylation. Therefore, the glucosylated steviol glycosides of the composition may comprise blends of the same type but with different or varying degrees of glucosylation of glucosylated steviol glycosides. The glucosylated steviol glycosides of the composition may also comprise blends of one or more different types of glucosylated steviol glycosides having the same degree of glucosylation. The glucosylated steviol glycosides of the composition may further comprise blends of one or more different types of glucosylated steviol glycosides, wherein each type has different or varying degrees of glucosylation.

[0042] Glucosylated steviol glycosides may comprise blends of at least one glucosylated steviol glycoside and at least one residual steviol glycoside. Residual steviol glycosides refer to unreacted steviol glycosides that have not been glucosylated. Residual steviol glycosides may comprise residual steviol glycosides, residual ribobadiol glycoside A, residual ribobadiol glycoside B, residual ribobadiol glycoside C, residual ribobadiol glycoside D, residual ribobadiol glycoside E, residual ribobadiol glycoside F, residual ribobadiol glycoside G, residual ribobadiol glycoside H, residual ribobadiol glycoside I, residual ribobadiol glycoside J, residual ribobadiol glycoside K, residual ribobadiol glycoside L, residual ribobadiol glycoside M, residual ribobadiol glycoside N, residual ribobadiol glycoside O, residual dulcitol glycoside A, residual dulcitol glycoside B, residual stevia glycoside, any other residual steviol glycosides obtained from stevia extract, and mixtures thereof. The blend of the at least one glucosylated steviol glycoside and the at least one residual steviol glycoside may contain about 1% and 15% of the at least one residual steviol glycoside. According to certain embodiments, the blend of the at least one glucosylated steviol glycoside and the at least one residual steviol glycoside may contain about 1% to 10%, or about 1% to about 8%, or about 1% to about 6%, or about 1% to about 4%, or about 1% to about 2% of the at least one residual steviol glycoside.

[0043] Glucosylsteviosides can be prepared by a reaction mixture of one or more steviol glycosides, a glucose unit source added to the steviol glycoside molecule, an enzyme catalyzing the glucosylation reaction, and a suitable solvent. According to some embodiments, glucosylsteviosides are prepared by a reaction mixture of one or more steviol glycosides, starch as the glucose unit source added to the steviol glycoside molecule, a CGT enzyme (cyclodextrin-glucan-transferase) catalyzing 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. For example, glucosylsteviosides can be prepared according to the disclosure in JP 2001-120218 A (which is incorporated herein by reference). α-Glucosylsteviosides (α-GS) are prepared by α-addition of glucose to a stevia extract containing at least 1.5 times the Reb A of the steviol glycoside.

[0044] In another embodiment, the sweetener may be one or more dihydrochalcones. Examples of dihydrochalcones include, for example, leucoside (l-[4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-l-propanone, also known as p-phlorizin, phloretin 4'-glucoside, phloretin-4'-glucoside, cherry dihydrochalcone, or p-phlorizin); naringin dihydrochalcone (NarDHC, also known as l-[4-[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-l-propanone); and neohesperidin dihydrochalcone (NHDC, E959).

[0045] Trifolin is a natural dihydrochalcone sweetener found in the Chinese sweet tea plant, *Cephalotaxus fortunei* (also known as *Cephalotaxus fortunei*). Lithocarpus polystachyus Its leaves have been consumed as sweet tea in southern China for centuries.

[0046] In another embodiment, examples of additional sweetness modifiers include, for example, stevia, Rubus extract, glyphiline, mukurozioside Iib, (+)-hernandulcin, 4β-hydroxystevia, baiyunoside, fromisoside I, bryonychoid, bryroside abrusosides AE, cyclocarioside A, cyclocarioside I, albiziasaponins AE, glycyrrhizic acid, arabinoglycyrrhizic acid, periandrines IV, pterocariosides A and B, osladine, polypodosides A and B, telosmosis A8-18, telosmosis, 3-hanguine acetoxy-5,7-dihydroxy-4'-methoxyflavone, (2R,3R)-dihydroquercetin 3-O-acetate, dihydroquercetin-4'-methyl ether, Selligueain A, Cinnamtannin B-1 and Cinnamtannin D-1, extensumside C-1, Millettiasaponin A, Derrisaponin A, hematoxylin and high Gaudichaudioside A, Huangqioside E, Neotoastilbin, Aspalathin, Nothofagin, Curculin, Mabinline, Monelin, Neoculin, Pentadine, Soma, or combinations thereof.

[0047] According to certain illustrative embodiments, the flavor composition may comprise symbioside I, the 1,6-a isomer of symbioside I, and combinations thereof in combination with sweeteners and flavor enhancers.

[0048] Flavor improvers may comprise one or more of a wide variety of compounds. According to certain illustrative embodiments, flavor improvers may be selected from the group consisting of: chlorogenic acid, choline chloride, betaine, naringin, naringenin, γ-aminobutyric acid, glycyrrhizic acid, N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof. For the purposes of this specification, the term "flavor improver" refers to one or more components that improve the sweetness characteristics of a reduced-sugar sweetened composition or a sweetened consumer product to which a flavor improver has been added.

[0049] According to some embodiments, the amount of certain flavor modifiers selected from chlorogenic acid or choline chloride and combinations thereof present in the flavor composition may be from about 100 ppm to about 200,000 ppm, in another embodiment from about 500 ppm to about 100,000 ppm, in another embodiment from about 1,000 ppm to about 50,000 ppm, and in another embodiment from about 2,000 ppm to about 20,000 ppm. According to other embodiments, the amount of certain flavor modifiers selected from N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide and combinations thereof present in the flavor composition may be from about 0.05 ppm to about 10,000 ppm, in another embodiment from 0.2 ppm to about 5,000 ppm, in another embodiment from about 1 ppm to about 2,000 ppm, and in another embodiment from about 5 ppm to about 1,000 ppm.

[0050] According to other illustrative embodiments, the flavor modifier of the composition comprises one or more chlorogenic acid compounds. The term chlorogenic acid refers to a quinic acid conjugate comprising one or more compounds from the ester family formed between cis-cinnamic acid and trans-cinnamic acid (e.g., caffeic acid, ferulic acid, p-coumaric acid, sinapic acid) and quinic acid. Quinic acid conjugates are represented by the following formula:

[0051]

[0052] Some of the illustrative quinic acid conjugates are defined by substitution of the R group as shown in the table below:

[0053]

[0054] The use of chlorogenic acid as a flavor modifier is described more fully in WO 2002 / 100192 A1, which is incorporated herein by reference in its entirety.

[0055] According to other illustrative embodiments, the flavor modifier of the composition may contain choline chloride as described in WO 2011 / 073187 A1, which is incorporated herein by reference in its entirety.

[0056] According to other illustrative embodiments, the flavor improver of the composition comprises one or more carboxylic acid-amino acid conjugates and their derivatives of the following formula:

[0057]

[0058] R1 is an alkyl residue having 6-30 carbon atoms, or an olefin residue having 9-25 carbon atoms and 1-6 double bonds. R1, together with the carbonyl group it is attached to, is a carboxylic acid residue, and m is 0 or 1. Edible derivatives may contain edible salts, including those commonly used in the food and beverage industry, including but not limited to chlorides, sulfates, phosphates, gluconates, sodium salts, citrates, carbonates, acetates, and lactates. These carboxylic acid-amino acid conjugates are described more fully in WO 2013 / 148991 A1, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates may include C18:2-β Ala and C18:2-gaba.

[0059] According to other illustrative embodiments, the flavor improver of the composition comprises one or more carboxylic acid-amino acid conjugates and their derivatives of the following formula:

[0060]

[0061] R1 is an alkyl residue having 6-30 carbon atoms, or an olefin residue having 9-25 carbon atoms and 1-6 double bonds. R1, together with the carbonyl group to which it is attached, is a carboxylic acid residue, and m is 0 or 1. Edible derivatives may contain edible salts, including those commonly used in the food and beverage industry, including but not limited to chlorides, sulfates, phosphates, gluconates, sodium salts, citrates, carbonates, acetates, and lactates. These carboxylic acid-amino acid conjugates are described more fully in WO 2013 / 149022 A1, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates may include N-geranoyl-Pro, N-palmitoyl-Pro, N-stearoyl-Pro, N-oleoyl-Pro, N-linoleoyl-Pro, and N-linolenic acid-Pro.

[0062] According to other illustrative embodiments, the flavor improver of the composition comprises one or more carboxylic acid-amino acid conjugates and their derivatives of the following formula:

[0063]

[0064] R1 is an alkyl residue having 6-30 carbon atoms, or an olefin residue having 9-25 carbon atoms and 1-6 double bonds. R1, together with the carbonyl group to which it is attached, is a carboxylic acid residue, and m is 0 or 1. Edible derivatives may contain edible salts, including those commonly used in the food and beverage industry, including but not limited to chlorides, sulfates, phosphates, gluconates, sodium salts, citrates, carbonates, acetates, and lactates. These carboxylic acid-amino acid conjugates are described more fully in W 02013 / 149019 A1, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates may include N-geraniol-Met, N-palmitoyl-Met, N-stearoyl-Met, N-oleoyl-Met, N-linoleoyl-Met, and N-linolenic acid-Met.

[0065] According to other illustrative embodiments, the flavor improver of the composition comprises one or more carboxylic acid-amino acid conjugates and their derivatives of the following formula:

[0066]

[0067] R1 is an alkyl residue containing 2-18 carbon atoms, or an olefin residue containing 9-25 carbon atoms and 1-6 double bonds, wherein R1, together with the carbonyl group to which it is attached, is a carboxylic acid residue. These carboxylic acid-amino acid conjugates are described more fully in US 10,385,015, which is incorporated herein by reference. Examples of carboxylic acid-amino acid conjugates may include sulfoxide compounds selected from the group consisting of: (2S)-2-acetamido-4-(methylsulfinyl)butyric acid; (2S)-2-hexanoylamino-4-(methylsulfinyl)butyric acid; (2S)-2-decanoylamino-4-(methylsulfinyl)butyric acid; (2S)-2-((Z)-dodecano-5-enoylamino)-4-(methylsulfinyl)butyric acid; (2S)-2-dodecanoylamino-4-(methylsulfinyl)butyric acid; (2S)-4-(methylsulfinyl) -2-Tetradecanoylaminobutyric acid; (2S)-4-(methylsulfinyl)-2-pentadecanoylaminobutyric acid; (2S)-4-(methylsulfinyl)-2-palmitoylaminobutyric acid; (2S)-2-heptadecanoylamino-4-(methylsulfinyl)butyric acid; (2S)-4-(methylsulfinyl)-2-((9Z,12Z)-octadecano-9,12-dienoylamino)butyric acid; (2S)-4-(methylsulfinyl)-2-oleoylaminobutyric acid; and (2S)-4-(methylsulfinyl)-2-stearoylaminobutyric acid.

[0068] In one aspect, the present invention provides the use of a compound or an edible salt thereof according to the following formula.

[0069]

[0070] R1 is an alkyl residue containing 6-20 carbon atoms, or an olefin residue containing 9-25 carbon atoms and 1-6 double bonds. R1, together with its attached carbonyl group, is a carboxylic acid residue, NR2R3, where R3 is H or, together with R2 and its attached N-atom, a 5-membered ring, and is an amino acid residue, particularly a proteogenic amino acid, ornithine, γ-aminobutyric acid, or β-alanine, or a 1-aminocycloalkylcarboxylic acid residue. These carboxylic acid-amino acid conjugates are described more fully in WO 2013 / 148965, which is incorporated herein by reference.

[0071] Edible salts include salts commonly used in the food and beverage industry, and include chlorides, sulfates, phosphates, gluconates, sodium, citrates, carbonates, acetates, and lactates. Proteogenic amino acids are 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 (Gin), arginine (Arg), serine (Ser), threonine (Thr), valine (Vai), tryptophan (Trp), tyrosine (Tyr), proline (Pro), or glycine (Gly). Examples of carboxylic acid-amino acid conjugates may include N-oleoylvaline, N-oleoylserine, and N-oleoylaspartic acid.

[0072] The flavor composition described in this application can improve and / or modulate the flavor of at least one sweetener. The at least one sweetener can be any known sweetener, such as a natural sweetener, a natural high-potency sweetener, or a synthetic sweetener.

[0073] The at least one sweetener is present in a sweetening amount. As used in this application, "sweetening amount" refers to the amount of compound required to provide a detectable sweetness when present in a consumer product (e.g., a beverage).

[0074] As used in this application, the phrase "natural high-potency sweetener" refers to any sweetener that is naturally occurring in nature and is characterized by having a sweetening potency greater than that of sucrose, fructose, or glucose, but with fewer calories. Natural high-potency sweeteners may be provided as pure compounds or, alternatively, as part of an extract. As used in this application, the phrase "synthetic sweetener" refers to any component that is not naturally occurring in nature and is characterized by having a sweetening potency greater than that of sucrose, fructose, or glucose, but with fewer calories.

[0075] In other embodiments, the at least one sweetener is a carbohydrate. Suitable carbohydrate sweeteners are selected from, but are not limited to, the group consisting of: sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythritol, arabinose, lysolose, ribose, xylose, ribulose, xylitolose, allose, azoose, galactose, glucose, gulose, idole, mannose, tarose, fructose, allulose, sorbitol, tagatose, mannoheptulose, sedoheltulose, octose, fucose, rhamnose, pinosulfan, cellobiose, sialose, and combinations thereof. In other embodiments, the at least one sweetener does not contain a carbohydrate sweetener.

[0076] In another embodiment, the additional sweetener is a rare sugar selected from sorbitol, lysoose, ribulose, xylose, xylulose, D-allose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, menobiose, and combinations thereof. Other sweeteners include symmancoside I, monatine and its salts (monatine SS, RR, RS, SR), curculigoside, glycyrrhizic acid and its salts, sematine, monosodium glutamate, areca oleracea, tamatin, hemandulcin, fosetyl-aluminum, glycyrrhizin, trifolin, kosmoside, osiladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, and phloroglucinol. lomisoside I, periandrin I, abrusoside A, steviol disaccharide and cyclocarioside I, sugar alcohols such as erythritol, sucralose, acetylsupanic acid, acetylsupanic acid and its salts, aspartame, alitran, saccharin and its salts, hesperidin dihydrochalcone glucoside, neohesperidin dihydrochalcone, cyclolazone, cyclolazone and its salts, neotame, adventitia, glucosylstevioside (GSGs), and combinations thereof.

[0077] In one embodiment, the sweetener is a caloric sweetener or a mixture of caloric sweeteners. In another embodiment, the caloric sweetener is selected from sucrose, fructose, glucose, high-fructose corn / starch syrup, beet sugar, cane sugar, and combinations thereof.

[0078] In other embodiments, the sweetener comprises at least one steviol glycoside or mogroside, wherein the at least one steviol glycoside or mogroside is present in a sweetening amount.

[0079] Product

[0080] According to this disclosure, symbioside I and / or its 1,6-a isomer can be added to sweetened consumer products (i.e., consumer products having at least one sweetener), or they can be provided as part of the flavor composition of the consumer product.

[0081] In one embodiment, symbioside I and / or its 1,6-a isomer are present in the flavor composition in an amount such that when the flavor composition is added to a sweetened consumer product, the sucrose equivalent of the consumer product increases compared to a consumer product that does not contain symbioside I and / or its 1,6-a isomer.

[0082] When added to consumer products, the amount of symbioside I and / or its 1,6-a isomer that effectively alters the sweetness or mouthfeel of the sweetener without exhibiting any off-flavor comprises symbioside I and / or its 1,6-a isomer. According to some embodiments, the amount of symbioside I and / or its 1,6-a isomer present in the consumer product may be a concentration of about 2 ppm to about 50 ppm, and in another embodiment, about 2 ppm to about 40 ppm, for example, about 2 ppm to about 30 ppm, about 2 ppm to about 25 ppm, about 2 ppm to about 20 ppm, about 2 ppm to about 15 ppm, or about 2 ppm to about 10 ppm.

[0083] In another embodiment, the flavor composition may comprise symbioside I and / or its 1,6-a isomer in combination with the aromatic component, sweetener, and / or taste modifier to improve the taste quality and / or mouthfeel of the sweet substance. According to some embodiments, the amount of the aroma component present in the consumer product may be from about 0.01 ppm to about 100 ppm, in another embodiment from 0.02 ppm to about 50 ppm, and in yet another embodiment from about 0.1 ppm to about 10 ppm. According to some embodiments, the amount of the sweetener present in the consumer product may be from about 1 ppm to about 200 ppm, in another embodiment from 2 ppm to about 100 ppm, and in yet another embodiment from about 5 ppm to about 50 ppm. According to some embodiments, the amount of certain sweeteners selected from chlorogenic acid, choline chloride, and combinations thereof present in the consumer product may be from about 0.1 ppm to about 100 ppm, in another embodiment from 0.5 ppm to about 50 ppm, and in yet another embodiment from about 1 ppm to about 30 ppm. According to other embodiments, the amount of certain flavor modifiers selected from N-oleoylproline, N-oleoylvaline, N-oleoylserine, N-oleoylaspartic acid, N-acylated methionine sulfoxide, and combinations thereof present in the consumer product may be from a concentration of about 0.0001 ppm to about 5 ppm, from 0.0005 ppm to about 2 ppm in another embodiment, and from about 0.001 ppm to about 1 ppm in yet another embodiment.

[0084] In one embodiment, at least one sweetener described in this application is present in concentrations of about 50 ppm to about 100,000 ppm, for example, about 50 ppm to about 80,000 ppm, about 50 ppm to about 60,000 ppm, about 50 ppm to about 40,000 ppm, about 50 ppm to about 30,000 ppm, about 50 ppm to about 20,000 ppm, about 100 ppm to about 80,000 ppm, about 100 ppm to about 60,000 ppm, about 100 ppm to about 40,000 ppm, about 100 ppm to about 30,000 ppm, about 100 ppm to about 20,000 ppm, about 200 ppm to about 60,000 ppm, about 200 ppm to about 50,000 ppm, about 200 ppm to about 40,000 ppm, about 200 ppm to about 30,000 ppm. The sweetener is present in the consumer product at concentrations of about 300 ppm to about 60,000 ppm, about 300 ppm to about 50,000 ppm, about 300 ppm to about 40,000 ppm, about 400 ppm to about 60,000 ppm, about 400 ppm to about 50,000 ppm, and about 500 ppm to about 60,000 ppm. In another embodiment, for full and reduced-sugar applications, the at least one sweetener may be present in the consumer product at a concentration of up to 200,000 ppm.

[0085] When expressed as "ppm", the concentration is parts per million by weight based on the total weight of the consumer product. It should be understood that when a range of values ​​is described in this disclosure, it is intended that any and every value within that range, including the endpoints, be considered disclosed. It should be understood that the inventor recognizes and understands that any and all values ​​within the range should be considered explicitly stated, and that the inventor owns the entire range and all values ​​within that range.

[0086] The flavor composition may also contain one or more food-grade excipients. Suitable excipients for use in flavor compositions are known in the art and include, for example, but not limited to, solvents (including water, alcohols, ethanol, oils, fats, vegetable oils and triglycerides of caprylic / capric acid), 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 flavoring agents can be found, for example, in "Perfume and Flavor Materials of Natural Origin", S. Arctander, Ed., Elizabeth, NJ, 1960; in "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in "Flavourings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998; and in "CTFA Cosmetic Ingredient Handbook", JM Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0087] Fragrance compositions can be in any suitable form, such as liquid or solid, wet or dry, or in encapsulated form bound to or coated onto a carrier / particle, or as a powder.

[0088] In this disclosure, the term “about” used in conjunction with a value includes the stated value and has a meaning indicated by the context. For example, it includes at least the degree of error associated with the measurement of a particular value. Those skilled in the art will understand that the term “about” used herein to refer to the amount of “about” the value produces the desired degree of effectiveness in the compositions and / or methods of this disclosure. Those skilled in the art will further understand that, according to this disclosure, the range and limits of values ​​relating to percentages, amounts, or quantities of any component in the embodiments can be determined by varying the value, determining the effectiveness of the composition or method for each value, and determining the range of values ​​of the composition or method that produce the desired degree of effectiveness.

[0089] Consumer products may include base ingredients. As used in this application, the term "base ingredient" refers to all the ingredients required for a consumer product, except for the flavor composition. These will naturally vary in nature and proportion depending on the nature and use of the consumer product or additive, but they are all well known in the art and can be used in proportions recognized in the art. Therefore, the formulation of such base ingredients for each conceivable purpose is within the ordinary skill of the art. For example, a base ingredient for a beverage according to this disclosure may contain 5% sucrose and 0.05% citric acid in water.

[0090] Without limitation, and by way of illustration only, suitable base materials may include anti-caking agents, defoamers, antioxidants, binders, colorants, diluents, disintegrants, emulsifiers, encapsulating agents or formulations, enzymes, fats, flavor enhancers, tasters, 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, for example, water, ethanol, ethylene glycol, propylene glycol, glycerol, and triacetin. Encapsulating agents and gums include maltodextrin, gum arabic, alginate, gelatin, modified starch, other polysaccharides, and proteins.

[0091] Examples of excipients, carriers, diluents, or solvents used for fragrance 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; "Flavourings", 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.

[0092] Non-limiting examples of suitable flavoring ingredients include natural spices, artificial spices, flavorings, seasonings, etc. These include synthetic flavoring oils and flavoring aromatics and / or oils, oleoresins, fragrances and distillates, and combinations thereof.

[0093] Co-ingredients may be present to provide additional benefits, such as enhanced stability, ease of incorporation into consumer products or additives, and enhanced nutritional value. Non-limiting typical examples of such co-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 that can be used in spray drying processes. Non-limiting examples of these substances are modified starches, such as CAPLTM. TM And maltodextrin.

[0094] Additives can be single components or blends of components, or they can be encapsulated in any suitable sealant. Additives can be prepared by any suitable method, such as spray drying, extrusion, and fluidized bed drying.

[0095] According to this disclosure, the term "consumer product" means a product intended for consumption by a subject via the mouth (although consumption may occur via non-oral routes such as inhalation) for at least one of the following purposes: enjoyment, nutrition, or health and wellness benefits. Consumer products can exist in any form, including but not limited to liquids, solids, semi-solids, 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 supplements and health and wellness supplements. Consumer products include compositions that remain in the mouth for a period of time before being discarded but are not swallowed. It may be placed in the mouth before consumption, or it may remain in the mouth for a period of time before being discarded.

[0096] Broadly speaking, consumer products include, but are not limited to, all kinds of food, confectionery products, baked goods, sweetened products, sausage products, fermented products, dairy products, non-dairy products, beverages, nutritional products, and pharmaceuticals.

[0097] Non-limiting examples of consumer products include: wet / liquid soups, regardless of concentration or container, including frozen soups. For the purposes of this definition, soup means a food prepared from meat, poultry, fish, vegetables, grains, fruits, and other ingredients, cooked in a liquid that may include some or all of these ingredients. It can be clear (as broth) or thick (as chowder), smooth, pureed or coarse, ready-to-eat, semi-concentrated or concentrated, and can be served hot or cold, as a first course or main course of a meal or as a snack between meals (sipped like a beverage). Soup can be used as an ingredient in the preparation of other dietary components and can range from broth (clear soup) to sauces (cream or cheese-based soups); dehydrated and cooked foods, including cooking aids such as powders, granules, pastes, concentrated liquid products, including concentrated broths, broths, and broth-like products in compressed cubes, tablets, or powder or granule form, sold separately as finished products or as ingredients in products, sauces, and formulation mixtures (regardless of technology); dietary solution products such as dehydrated and freeze-dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready-to-cook soups, dehydrated or environmentally prepared preparations of ready-made dishes, and dietary solutions. Food and single-serving main dishes, including pasta, potato and rice dishes; dietary garnishes, such as: condiments, marinades, salad dressings, salad toppings, dips, breadcrumbs, batter mixtures, shelf-stable spreads, barbecue sauces, liquid formulation mixtures, concentrates, sauces or sauce mixtures, including formulation mixtures for salads, sold as finished products or as ingredients within products, whether dehydrated, liquid or frozen; beverages, including beverage mixtures and concentrates, including but not limited to alcoholic and non-alcoholic ready-to-drink beverages and powdered beverages, carbonated and non-carbonated beverages such as soda water, fruit or vegetable juices, alcoholic and non-alcoholic beverages, teas such as green tea and black tea, wines such as red wine; confectionery products, such as cakes, cookies, pies, candies, chewing gum, gelatin, ice cream, sorbets, puddings, jams, jellies, salad dressings and other condiments, cereals and other breakfast foods, canned fruit and fruit jams, etc.

[0098] Methods are provided to enhance the sweetness of consumer products and / or modulate one or more flavor properties of sweeteners to make the consumer products taste more like sucrose-sweetened consumer products.

[0099] The invention is further described with reference to the following non-limiting embodiments.

[0100] Example

[0101] The following embodiments are provided for illustrative purposes only and should not be construed as limiting the invention, as many variations of the invention are possible without departing from the spirit and scope of this disclosure.

[0102] While specific embodiments of the invention have been shown and described, it will be apparent 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. Therefore, the appended claims are intended to cover all such changes and modifications that fall within the scope of the invention.

[0103] A total of eight base ingredients for beverages were prepared, some containing and some not containing symmenidine I. These base ingredients were combined with various combinations of sweeteners (Table 1), flavor modifiers (Table 2), and / or aromatic components (Table 3), and the sensory perception of sweetness characteristics and mouthfeel was evaluated by experienced flavor technicians. Each attribute was described by an intensity rating on a scale of 1-10, where 1 is low intensity and 10 is high intensity.

[0104] Base material 1 (water containing 5% sucrose and 0.05% citric acid)

[0105] Base Material 1+ (water containing 5% sucrose, 0.05% citric acid, and 10 ppm symbioside I)

[0106] Base 2 (water containing 7% sucrose, 0.1% citric acid, and 0.1% lemon-lime flavoring)

[0107] Base 2+ (water containing 7% sucrose, 0.1% citric acid, 0.1% lemon-lime flavoring, and 10 ppm symbioside I)

[0108] Base ingredient 3 (yogurt containing 4% sucrose and 0.08% strawberry flavoring)

[0109] Base Material 3+ (yogurt containing 4% sucrose, 0.08% strawberry flavoring, and 10 ppm symmancoside I)

[0110] Base 4 (soy milk containing 4% sucrose and 0.2% vanilla flavoring)

[0111] Base 4+ (soy milk containing 4% sucrose, 0.2% vanilla flavoring, and 10 ppm symbioside I)

[0112]

[0113]

[0114]

[0115] Example 1

[0116] The following compositions (Base 1 / Base 1 + sweeteners from Table 1) (Ingredients 1-10) were taste-tested by experienced flavor technicians and compared with a control of Base 1 without symmenidine I.

[0117]

[0118]

[0119] Overall, the combination of symmenidine I and sweeteners was found to be slightly sweeter, with more initial sweetness, a more sucrose-like taste, and less astringency and bitterness.

[0120] Example 2

[0121] The following composition (base 1 / base 1 plus flavor modifier from Table 2) (Ingredient AI) was taste-tested by experienced flavor technicians and compared with a control of base 1 without symmenidine I.

[0122]

[0123]

[0124] Overall, the combination of symmenidine I and the flavor modifier was found to be slightly sweeter, more like sucrose, and less bitter.

[0125] Example 3

[0126] The following composition (base 1 / base 1 plus aromatic components from Table 3) (component ae) was taste-tested by experienced fragrance technicians and compared with a control base 1 without symmenidine I.

[0127]

[0128] Overall, the combination of symmenoside I with flavor components was found to be slightly sweeter, with less astringency and a more sucrose-like taste.

[0129] Example 4

[0130] The following compositions (base 2 / base 2+ plus sweeteners, flavor enhancers and aromatics from Tables 1-3) were taste-tested by experienced flavor technicians and compared with a base 2 control that does not contain symmenidine I.

[0131]

[0132] The composition in Table 7, namely symmenidine I plus sweeteners, flavor modifiers and aromatic components, was found to be slightly sweeter, slightly less bitter, and more like sucrose.

[0133] Example 5

[0134] The following compositions (base 3 / base 3 plus sweeteners, flavor modifiers and aromatics from Tables 1-3 / base 3 plus sweeteners, flavor modifiers and aromatics from Tables 1-3) were taste-tested by experienced flavor technicians and compared with a control base 3 without symmenidine I.

[0135]

[0136] The composition in Table 8, namely symmonoside I plus sweeteners, flavor enhancers and aromatic components, was found to have a more sucrose-like taste and a stronger strawberry aroma.

[0137] Example 6

[0138] The following compositions (base 4 / base 4 plus sweetness modifiers and flavor modifiers from Tables 1-2 / base 4 + plus sweetness modifiers and flavor modifiers from Tables 1-2) were taste-tested by experienced flavor technicians and compared with a control of base 4 without symmenidine I.

[0139]

[0140] The combination in Table 9, namely symmenidine I plus sweeteners and flavor enhancers, was found to have a weaker bitterness, a weaker astringency, a sustained sweetness, a stronger vanilla aroma, and a slightly more sucrose-like taste.

[0141] The dimensions and values ​​disclosed in this application should not be construed as strictly limited to the exact numerical values ​​listed. Rather, unless otherwise stated, each such dimension is intended to mean both the listed value and the range of functionally equivalent values ​​around that value. For example, a dimension intended to be disclosed as “40 mm” means approximately 40 mm.

[0142] While specific embodiments of the invention have been shown and described, it will be apparent 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. Therefore, it is intended that all such changes and modifications falling within the scope of the invention be covered in the appended claims.

Claims

1. A fragrance composition comprising: a. Mogrosides, selected from the group consisting of symbioside I, its 1,6-α isomers, and combinations thereof; and b. Aromatic components, selected from the group consisting of 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof.

2. The flavor composition of claim 1, wherein the mogroside is present at a concentration of 2,000 ppm to 200,000 ppm.

3. The fragrance composition of claim 1, wherein the aromatic component is present at a concentration of 10 ppm to 100,000 ppm.

4. A consumer product comprising the fragrance composition of claim 1.

5. A fragrance composition comprising: a. Monk fruit glycoside, selected from the group consisting of symbioside I, its 1,6-α isomer and combinations thereof; b. Aromatic components selected from the group consisting of 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof; and c. Sweetness improvers, selected from the group consisting of steviol glycosides, hesperidin, trifolin, phloretin, sematriene, neohesperidin dihydrochalcone, and combinations thereof.

6. The fragrance composition of claim 5, wherein the steviol glycoside is selected from the group consisting of: ribordiin M, ribordiin D, ribordiin A, ribordiin N, ribordiin O, ribordiin E, steviol monosaccharide glycoside, steviol B glycoside, stevioside, dulcitin B, dulcitin A, ribordiin B, ribordiin G, steviol glycoside, ribordiin C, ribordiin F, ribordiin I, ribordiin H, ribordiin L, ribordiin K, ribordiin J, ribordiin M2, ribordiin D2, ribordiin S, ribordiin T, ribordiin U, ribordiin V, ribordiin W, ribordiin Z1, ribordiin Z2, ribordiin IX, enzymatically glucosylated steviol glycoside, and combinations thereof.

7. The flavor composition of claim 5, wherein the sweetness modifier is present at a concentration of 1,000 ppm to 500,000 ppm.

8. A consumer product comprising the fragrance composition of claim 5.

9. Consumer goods, including: a. at least one sweetener; and b. A flavor composition comprising mogroside selected from the group consisting of symbioside I, 1,6-α isomers of symbioside I, and combinations thereof; aromatic components selected from the group consisting of 4-hydroxy-2H-furan-5-one, ethylfuranone, maltol, vanillin, benzaldehyde, and combinations thereof; and a sweetener selected from the group consisting of steviol glycosides, hesperidin, trifolin, phloretin, sematriene, neohesperidin dihydrochalcone, and combinations thereof; The at least one sweetener is present in a sweetening amount.

10. The consumer product of claim 9, wherein the at least one sweetener is selected from the group consisting of: sucrose, fructose, glucose, xylose, arabinose, rhamnose, tagatose, allulose, trehalose, isomaltulose, steviol glycosides, mogrosides, stevia, trifolin, stevia glycosides, aspartame, advans, agave syrup, acetylsupan potassium (AceK), high fructose corn syrup, neotame, saccharin, sucralose, high fructose corn syrup, starch syrup, mogroside extract, neohesperidin dihydrochalcone, naringin dihydrochalcone, sugar alcohol cellobiose, allulose, cyclolatate, sematrandini, molasses, rice syrup, and combinations thereof.

11. The consumer product of claim 9, wherein the mogroside is present at a concentration of 2 ppm to 50 ppm.

12. The consumer product of claim 9, wherein the sweetener is present at a concentration of 1 ppm to 200 ppm.

13. The consumer product of claim 9, wherein the aromatic component is present at a concentration of 0.01 ppm to 100 ppm.

14. The consumer product of claim 9, wherein the consumer product is a beverage.

15. The consumer product of claim 9, wherein the consumer product is yogurt.

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