Methods of modulating and improving vanilla flavors

Abstract

Disclosed herein are small molecule compounds that can be used to modulate vanilla flavors in extracts, foods, beverages, and other articles intended for delivery to the oral cavity.

Description

[0001] METHODS OF MODULATING AND IMPROVING VANILLA FLAVORS

[0002] CROSS-REFERENCE TO RELATED APPLICATION

[0003] This application claims the benefit of U.S. Provisional Application 63 / 600,779, filed November 20, 2023, the contents of which are hereby incorporated in its entirety.

[0004] FIELD OF THE INVENTION

[0005] The invention relates to flavor modulating compounds and their use as an additive for food and drink. The invention provides compositions and methods for improving the flavor qualities of vanilla extracts and flavorings, as well modulating the flavors of other products.

[0006] BACKGROUND

[0007] Vanilla is among the most popular flavors today. It is prevalent in foods, beverages, cosmetics, pharmaceuticals, nutraceuticals, and other products. Nevertheless, it is also one of the most expensive spices, recently reported at $630 / kg. The high price of vanilla is due in part to the time and labor-intensive process needed to obtain it. Historically, vanilla is obtained a hand-pollinated orchid native to Mexico. The plants can take 3 to 4 years to mature, and 8-10 months from flower to bean. The beans are then subjected to a multistep extraction process that can take upon to nine months. Environmental factors can affect the quality of the beans, and the attempts to shorten the extraction process can lead to low quality spices.

[0008] There remains a need improved vanilla flavor products and methods of improving low- quality vanilla products.

[0009] BRIEF DESCRIPTION OF THE FIGURES

[0010] Figure 1 depicts the results of a panel sensory evaluation following addition of compounds according to the disclosure to apple juice.

[0011] Figure 2 depicts the results of a panel sensory evaluation following addition of compounds according to the disclosure to tea.

[0012] Figure 3 depicts the results of a panel sensory evaluation following addition of compounds according to the disclosure to pea milk.

[0013] Figure 4 depicts the results of a panel sensory evaluation following addition of compounds according to the disclosure to a nutritional shake.

[0014] Figure 5 depicts the results of a panel sensory evaluation following addition of compounds according to the disclosure to flavored milk combined with imitation vanilla extract. Figure 6 depicts a representation of a sensory recombination study.

[0015] DETAILED DESCRIPTION

[0016] Before the present methods and systems are disclosed and described, it is to be understood that the methods and systems are not limited to specific synthetic methods, specific components, or to particular compositions. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting.

[0017] As used in the specification and the appended claims, the singular forms “a,” “an” and “the” include plural referents unless the context clearly dictates otherwise. Ranges may be expressed herein as from “about” one particular value, and / or to “about” another particular value. When such a range is expressed, another embodiment includes-1from the one particular value and / or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms another embodiment. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint.

[0018] “Optional” or “optionally” means that the subsequently described event or circumstance may or may not occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.

[0019] Throughout the description and claims of this specification, the word “comprise” and variations of the word, such as “comprising” and “comprises,” means “including but not limited to,” and is not intended to exclude, for example, other additives, components, integers or steps. “Exemplary” means “an example of’ and is not intended to convey an indication of a preferred or ideal embodiment. “Such as” is not used in a restrictive sense, but for explanatory purposes.

[0020] Disclosed are components that can be used to perform the disclosed methods and systems. These and other components are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc. of these components are disclosed that while specific reference of each various individual and collective combinations and permutation of these may not be explicitly disclosed, each is specifically contemplated and described herein, for all methods and systems. This applies to all aspects of this application including, but not limited to, steps in disclosed methods. Thus, if there are a variety of additional steps that can be performed it is understood that each of these additional steps can be performed with any specific embodiment or combination of embodiments of the disclosed methods. The term “alkyl” as used herein is a branched or unbranched hydrocarbon group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and the like. The alkyl group can also be substituted or unsubstituted. Unless stated otherwise, the term “alkyl” contemplates both substituted and unsubstituted alkyl groups. The alkyl group can be substituted with one or more groups including, but not limited to, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol. An alkyl group which contains no double or triple carbon-carbon bonds is designated a saturated alkyl group, whereas an alkyl group having one or more such bonds is designated an unsaturated alkyl group. Unsaturated alkyl groups having a double bond can be designated alkenyl groups, and unsaturated alkyl groups having a triple bond can be designated alkynyl groups. Unless specified to the contrary, the term alkyl embraces both saturated and unsaturated groups.

[0021] The term “cycloalkyl” as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “heterocycloalkyl” is a cycloalkyl group as defined above where at least one of the carbon atoms of the ring is replaced with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, selenium or phosphorus. The cycloalkyl group and heterocycloalkyl group can be substituted or unsubstituted. Unless stated otherwise, the terms “cycloalkyl” and “heterocycloalkyl” contemplate both substituted and unsubstituted cyloalkyl and heterocycloalkyl groups. The cycloalkyl group and heterocycloalkyl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol. A cycloalkyl group which contains no double or triple carbon-carbon bonds is designated a saturated cycloalkyl group, whereas a cycloalkyl group having one or more such bonds (yet is still not aromatic) is designated an unsaturated cycloalkyl group. Unless specified to the contrary, the term cycloalkyl embraces both saturated and unsaturated, non-aromatic, ring systems.

[0022] The term “aryl” as used herein is an aromatic ring composed of carbon atoms. Examples of aryl groups include, but are not limited to, phenyl and naphthyl, etc. The term “heteroaryl” is an aryl group as defined above where at least one of the carbon atoms of the ring is replaced with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, selenium or phosphorus. The aryl group and heteroaryl group can be substituted or unsubstituted. Unless stated otherwise, the terms “aryl” and “heteroaryl” contemplate both substituted and unsubstituted aryl and heteroaryl groups. The aryl group and heteroaryl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol.

[0023] Exemplary heteroaryl and heterocyclyl rings include: benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzoxazolinyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazolinyl, carbazolyl, 4aH carbazolyl, carbolinyl, chromanyl, chromenyL cirrnolinyl, decahydroquinolinyl, 2H,6H~ 1,5,2-dithiazinyl, dihydrofuro[2,3 b]tetrahydrofuran, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, IH-indazolyl, indolenyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isatinoyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3- oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxindolyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, piperidonyl, 4-piperidonyl, piperonyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridooxazole, pyridoimidazole, pyridothiazole, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrazolyl, 6H-l,2,5-thiadiazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4- thiadiazolyl, thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiophenyl, and xanthenyl.

[0024] The terms “alkoxy,” “cycloalkoxy,” “heterocycloalkoxy,” “cycloalkoxy,” “aryloxy,” and “heteroaryloxy” have the aforementioned meanings for alkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl, further providing said group is connected via an oxygen atom.

[0025] As used herein, the term “substituted” is contemplated to include all permissible substituents of organic compounds. In a broad aspect, the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. The permissible substituents can be one or more and the same or different for appropriate organic compounds. For purposes of this disclosure, the heteroatoms, such as nitrogen, can have hydrogen substituents and / or any permissible substituents of organic compounds described herein which satisfy the valencies of the heteroatoms. This disclosure is not intended to be limited in any manner by the permissible substituents of organic compounds. Also, the terms “substitution” or “substituted with” include the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound, e.g., a compound that does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, etc. Unless specifically stated, a substituent that is said to be “substituted” is meant that the substituent can be substituted with one or more of the following: alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol. In a specific example, groups that are said to be substituted are substituted with a protic group, which is a group that can be protonated or deprotonated, depending on the pH.

[0026] Acceptable salts are salts that retain the desired flavor modulating activity of the parent compound and do not impart undesirable toxicological effects. Examples of such salts are acid addition salts formed with inorganic acids, for example, hydrochloric, hydrobromic, sulfuric, phosphoric, and nitric acids and the like; salts formed with organic acids such as acetic, oxalic, tartaric, succinic, maleic, fumaric, gluconic, citric, malic, methanesulfonic, p-toluenesulfonic, napthalenesulfonic, and polygalacturonic acids, and the like; salts formed from elemental anions such as chloride, bromide, and iodide; salts formed from metal hydroxides, for example, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, and magnesium hydroxide; salts formed from metal carbonates, for example, sodium carbonate, potassium carbonate, calcium carbonate, and magnesium carbonate; salts formed from metal bicarbonates, for example, sodium bicarbonate and potassium bicarbonate; salts formed from metal sulfates, for example, sodium sulfate and potassium sulfate; and salts formed from metal nitrates, for example, sodium nitrate and potassium nitrate. Salts may be prepared using procedures well known in the art, for example, by reacting a sufficiently basic compound such as an amine with a suitable acid comprising a physiologically acceptable anion. Alkali metal (for example, sodium, potassium, or lithium) or alkaline earth metal (for example, calcium) salts of carboxylic acids can also be made.

[0027] Unless stated to the contrary, a formula with chemical bonds shown only as solid lines and not as wedges or dashed lines contemplates each possible isomer, e.g., each enantiomer and diastereomer, and a mixture of isomers, such as a racemic or scalemic mixture. Compounds described herein can contain one or more asymmetric centers and, thus, potentially give rise to diastereomers and optical isomers. Unless stated to the contrary, the present invention includes all such possible diastereomers as well as their racemic mixtures, their substantially pure resolved enantiomers, and all possible geometric isomers. Disclosed herein are flavor modulating compounds having the formula: wherein:

[0028] Rais H, OH, Ci-3alkyl, or OCi-3alkyl;

[0029] Rbis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0030] Rcis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0031] Rdis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0032] Reis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0033] R1, R2, R3, and R4are independently selected from H, OH, Ci-3alkyl, or OCi-3alkyl, or a group having the formula:

[0034] In some implementations, the compound has the formula:

[0035] In some implementations,

[0036] R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0037] R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0038] R3is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0039] R4is a group having the formula: preferably, R4is

[0040] In some implementations, R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0041] R3is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0042] R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0043] R1is a group having the formula: preferably, R1is

[0044] In some implementations, R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0045] R3is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0046] R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0047] R2is a group having the formula: preferably, R2is

[0048] In some implementations,

[0049] R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0050] R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0051] R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0052] R3is a group having the formula: preferably, R3is

[0053] In some implementations, R2and R4are H.

[0054] In some implementations, R1is OH or OCi-3alkyl, preferably OH.

[0055] In some implementations, Rcand Rdare independently selected from OH or OCi-3alkyl, preferably Rcand Rdare both OH.

[0056] In some implementations, Ra, Rb, and Reare independently selected from H or Ci-3alkyl, preferably CH3. In some implementations, Ra, Rb, and Reare each H.

[0057] In some implementations the compound is an eriodictyol-7-O-glucoside, e.g.:

[0058]

[0059] Also provided are methods of modifying and improving vanilla flavors using nigerose, an a-1-3- linked di-D-glucose disaccharide.

[0060] The vanilla flavor modulating compounds may be used to improve the quality of vanilla extracts. The vanilla flavor modulating compounds may be used as additives during the vanilla extraction process, for example during the dipping, sweating, drying and / or conditioning steps.

[0061] The vanilla flavor modulating compounds may be used to modulate the aroma and / or somatosensory characteristics of a food or beverage. The compound may be added to a variety of different foods to increase palatability. For instance, the compounds may be added to vegetables, including cruciferous vegetables, yogurts, cranberries and other bitter fruits, cocoa, coffee, wine, or beer. The compounds may be added to fruit juices, for example orange juice, apple juice, grape juice, cranberry juice, grapefruit juice, pomegranate juice, passion fruit juice, dragonfruit juice, guava juice, lemon juice, lime juice, papaya juice, pineapple juice, and combinations thereof. The compounds may be added to teas, for example black teas, green teas, white teas, herbal teas, flower teas, rooibos teas, and combinations thereof. The compounds may be added to milk and milk substitutes (e.g., plant milks), for example pea milk, almond milk, soy milk, coconut milk, oat milk, rice milk, cashew milk, hazelnut milk, and combinations thereof.

[0062] In certain embodiments, the vanilla flavor modulating compounds can be used to mask the taste of anti-oxidants and preservatives, thereby increasing a food’s shelf life without compromising its flavor. The vanilla flavor modulating compounds may be added to the wettable adhesives found in stamps and envelopes. The vanilla flavor modulating compounds may be added to medications, including liquid formulations, chewable formulations, dissolvable formulations, aerosol formulations, dry powder formulations, and spray formulations. By improving palatability, an increased adherence to a treatment regimen can be achieved, especially with pediatric patients. In other embodiments, the vanilla flavor modulating compounds may be combined with dental formulations, including topical anesthetics, adhesives, including denture adhesives, and cleaning products such as toothpastes, mouthwashes, and sealants.

[0063] The vanilla flavor modulating compounds may be added in an amount of at least 0.1 mg / kg, at least 0.5 mg / kg, at least 1 mg / kg, at least 2.5 mg / kg, at least 5 mg / kg, at least 10 mg / kg, at least 20 mg / kg, at least 30 mg / kg, at least 40 mg / kg, at least 50 mg / kg, at least 60 mg / kg, at least 70 mg / kg, at least 80 mg / kg, at least 90 mg / kg, or at least 100 mg / kg, relative to the total weight of the consumable. In some embodiments, the flavor modulating compound can be added in an amount from 0.1-100 mg / kg, from 0.1-50 mg / kg, from 0.1-25 mg / kg, from 0.1-10 mg / kg, from 0.1-5 mg / kg, from 0.1-2.5 mg / kg, from 5-100 mg / kg, from 5-50 mg / kg, from 5-25 mg / kg, from 5-10 mg / kg, from 10-100 mg / kg, from 10-50 mg / kg, from 10-25 mg / kg, from 25- 100 mg / kg, from 25-50 mg / kg, from 50-100 mg / kg, or from 75-100 mg / kg.

[0064] The vanilla flavor modulating compounds disclosed herein may be provided in an aqueous composition to more readily combine them with foods, beverages, and the like. The composition may be buffered, for instance at a pH between 6 and 8, between 6.5 and 8, between 6.5 and 7, between 6.5 and 7.5, between 6.5 and 8, between 7 and 8, or between 7.5 and 8. In other embodiments, the composition may be buffered at an acidic pH, for instance similar to found in citrus juice, vinegar, or yogurt. In some embodiment, the composition may be buffered at a pH between 2 and 8, between 2 and 7, between 2 and 6, between 2 and 5, between 2 and 4, between 3 and 8, between 3 and 7, between 3 and 6, between 3 and 5, between 3 and 4, between 4 and 8, between 4 and 7, between 4 and 6, between 4 and 5, between 5 and 8, between 5 and 7, or between 5 and 6.

[0065] The vanilla flavor modulating compounds may be provided in the composition at a concentration between about 0.1 - 100 mM, between about 0.5 - 100 mM, between about 1 - 100 mM, between about 5 - 100 mM, between about 10 - 100 mM, between about 25 - 100 mM, between about 50 - 100 mM, between about 0.1 - 50 mM, between about 0.1 - 25 mM, between about 0.1 - 10 mM, between about 0.1 - 5 mM, or between about 0.1 - 1 mM. When the aqueous composition contains more than one vanilla flavor modulating flavor modulating compound, the concentration refers to the total concentration of all the compounds.

[0066] The vanilla flavor modulating compounds may be provided in an aqueous composition, wherein the vanilla flavor modulating compound constitute at least 50%, at least 75%, at least 80%, at least 90%, or at least 95% by weight of all non-solvent components. As used herein, non-solvent refers to any compound, when in isolated form is not a liquid at 23 °C. The aqueous composition may include water-soluble organic solvents like lower alcohols, acetone, DMSO, and the like to promote dissolution of the vanilla flavor modulating compounds.

[0067] EXAMPLES

[0068] Example 1 - Vanilla flavor modulation

[0069] A vanilla sample including 2% fat milk, 4% sucrose, and 0.4% of a low-quality vanilla extract. To the sample was added either 4.1 mg / L nigerose or 18.5 mg / mL eriodictyol-7-O-glucoside. Compared to control samples, a panel composed of 122 vanilla enjoy ers rated both samples to have a more complex, desirable vanilla flavor. The sample to which nigerose was added was considered sweeter and less acidic, with higher vanilla intensity and mouthfeel compared with control. The sample to which eriodictyol-7-O-glucoside was added was rated as sweeter and creamier compared with the control, which higher vanilla intensity as well.

[0070] Nigerose was added to McCormick All-Natural Pure Vanilla Extract (4.1 mg / L) and Market Pantry Imitation Vanilla Flavor (18.8 mg / L). The tasting panel considered both commercial extracts to have improved flavor when the nigerose was added.

[0071] Solutions of eriodictyol-7-O-glucoside (78.3 mg / mL) and nigerose (18.1 mg / mL) were prepared using pure water. Both solutions were tasteless when the vanilla flavor modulating compounds when consumed as pure samples.

[0072] Example 2 - consumable product flavor modulation Four experienced panelists evaluated 3 treatment samples versus control [no added compound(s)]

[0073] Treatments (dosage): Nigerose (18.8 mg / L), Eriodictyol-7-O-glucoside (78.3 mg / L), Nigerose (18.8 mg / L) + Eriodictyol-7-O-glucoside (78.3 mg / L)

[0074] Food products tested:

[0075] Sweetened Tea - Golden Peak Zero Sugar

[0076] Apple Juice - Mott’s Light

[0077] Pea milk - Ripple (vanilla)

[0078] Nutritional shake - Ensure (vanilla)

[0079] 2% fat bovine milk, 4% sucrose, 0.4% imitation vanilla extract (Market Pantry)

[0080] Panelists evaluated the degree of difference for each treatment sample when compared to a control (sample without compound) using a 6-point scale (sensory difference from control test), and provided comments about the changes (if any) in sensory perception:

[0081] 1 - Mott’s Light Apple Juice - Figure 1

[0082] Individual compounds very slightly / slightly increased sweetness and decreased sourness, resulting in a small change to the apple character of the juice. When the two compounds were added as a mixture, there was a larger difference (from control) than the sum of the individual samples indicating a synergistic effect. The mixture sample was described as more balanced / natural with a noted decrease in artificial aftertaste, in addition to an increase in sweetness and decrease in sourness.

[0083] 2 - Gold Peak Zero Sugar Tea - Figure 2

[0084] Individual compounds resulted in a very slight / slight change in the flavor profile of the tea product, increasing tea flavor intensity. When the two compounds were added as a mixture, there was a larger difference (from control) than the sum of the individual samples indicating a synergistic effect. The mixture of compounds was described as less artificial with an enhanced tea-like flavor, and a honey-like sweetness.

[0085] 3 - Ripple Milk - Figure 3

[0086] Individual compounds slightly changed flavor perception, increasing sweetness and vanilla intensities and reducing the pea flavor. The mixture of compounds resulted in greater increases in vanilla and sweetness intensities, and a larger reduction in pea flavor. The vanilla character was described as having woody and bourbon notes, and noted to be more balanced and complex. 4 - Ensure Vanilla Shake - Figure 4

[0087] Individual compounds slightly changed flavor perception, very slightly increasing sweetness and the dairy flavor and slightly increasing the vanilla and caramel notes. When the two compounds were added as a mixture, there was a larger difference (from control) than the sum of the individual samples indicating a synergistic effect. The mixture of compounds was described as increases in the vanilla and caramel flavors, and a rounded butterscotch-like flavor.

[0088] 5 - Market Pantry Imitation Vanilla Flavored Milk - Figure 5

[0089] Individual compounds slightly changed flavor perception, very slightly increasing sweetness and slightly increasing the vanilla and caramel notes and decreasing the artificial aftertaste. When the two compounds were added as a mixture, there was a larger difference (from control) than the sum of the individual samples indicating a synergistic effect. The mixture of compounds was described as having a more complex vanilla flavor (vanilla / caramel / bourbon notes) as well as enhanced richness / creaminess. In addition, there was a noted decrease in the artificial character of the vanilla and enhanced sweetness of the sample.

[0090] ADDITIONAL EMBODIMENTS

[0091] 1. A compound for the improvement of vanilla flavors in a composition, having the structure:

[0092] Rais H, OH, Ci-3alkyl, or OCi-3alkyl;

[0093] Rbis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0094] Rcis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0095] Rdis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0096] Reis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0097] R1, R2, R3, and R4are independently selected from H, OH, Ci-3alkyl, or OCi-3alkyl, or a group having the formula: The compound for use according to any preceding embodiment, having the formula:

[0098] R4is a group having the formula: preferably, R4is The compound for use according to embodiment 1 or embodiment 2, wherein R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0099] R3is H, OH, Ci-3alkyl, or OCi-3alkyl; R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0100] R1is a group having the formula: preferably, R1is The compound for use according to embodiment 1 or embodiment 2, wherein

[0101] R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0102] R3is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0103] R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0104] R2is a group having the formula: preferably, R2is The compound for use according to embodiment 1 or embodiment 2, wherein

[0105] R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0106] R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0107] R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0108] R3is a group having the formula: preferably, R3is

[0109] 7. The compound for use according to any preceding embodiment, wherein R2and R4are H.

[0110] 8. The compound for use according to any preceding embodiment, wherein R1is OH or OCi-3alkyl, preferably OH.

[0111] 9. The compound for use according to any preceding embodiment, wherein Rcand Rdare independently selected from OH or OCi-3alkyl, preferably Rcand Rdare both OH. 10. The compound for use according to any preceding embodiment, wherein Ra, Rb, and Reare independently selected from H or Ci-3alkyl, preferably CH3.

[0112] 11. The compound for use according to any preceding embodiment, wherein Ra, Rb, and Reare each H.

[0113] 12. The compound for use according to any preceding embodiment, having the formula:

[0114]

[0115] 13. A compound for use in the modification of a vanilla flavor in a composition, wherein the compound is nigerose.

[0116] 14. The compound for use according to any preceding embodiment, wherein the compound is added to the composition in an amount of at least 0.1 mg / kg, at least 0.5 mg / kg, at least 1 mg / kg, at least 2.5 mg / kg, at least 5 mg / kg, at least 10 mg / kg, at least 20 mg / kg, at least 30 mg / kg, at least 40 mg / kg, at least 50 mg / kg, at least 60 mg / kg, at least 70 mg / kg, at least 80 mg / kg, at least 90 mg / kg, or at least 100 mg / kg, relative to the total weight of the consumable. In some embodiments, the flavor modulating compound can be added in an amount from 0.1-100 mg / kg, from 0.1-50 mg / kg, from 0.1-25 mg / kg, from 0.1-10 mg / kg, from 0.1-5 mg / kg, from 0.1-2.5 mg / kg, from 5-100 mg / kg, from 5-50 mg / kg, from 5-25 mg / kg, from 5-10 mg / kg, from 10-100 mg / kg, from 10-50 mg / kg, from 10-25 mg / kg, from 25-100 mg / kg, from 25-50 mg / kg, from 50-100 mg / kg, or from 75-100 mg / kg.

[0117] 15. The compound for use of any preceding embodiment, wherein the compound is added as an aqueous composition, wherein the compound constitutes at least 50%, at least 75%, at least 80%, at least 90%, or at least 95% by weight of all non-solvent components in the aqueous composition.

[0118] 16. The compound for use of any preceding embodiment, wherein the composition is a vanilla extract, i.e., an artificial vanilla extract or natural vanilla extract. The compound for use of any preceding embodiment, wherein the composition is a food or beverage. The compound for use of any preceding embodiment, wherein the composition is a coffee, sodas, milk, tea, fruit juice, vegetable juice, vegetable, cheese, yogurt, grain, beers, wine, distilled spirit, cocoa, fruit, or vegetable. The compound for use of any preceding embodiment, wherein the composition is a milk product, for example an animal milk or a plant milk. The compound for use of any preceding embodiment, wherein the composition is cow milk, goat milk, sheep milk, almond milk, coconut milk, soy milk, rice milk, hemp milk, oat milk, pea milk, or peanut milk. The compound for use of any preceding embodiment, wherein the composition is a coffee product. The compound for use of any preceding embodiment, wherein the composition is brewed coffee, coffee concentrate, bottled coffee, coffee beans, processed coffee beans (raw, unroasted, roasted, fermented, ground, instant coffee products). The compound for use of any preceding embodiment, wherein the composition is a confection. The compound for use of any preceding embodiment, wherein the composition is ice cream, frozen yogurt, chocolate, frozen desert. A method of modifying the flavor of a composition, comprising adding to the composition a compound having the structure: wherein

[0119] Rais H, OH, Ci-3alkyl, or OCi-3alkyl;

[0120] Rbis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0121] Rcis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0122] Rdis H, OH, Ci-3alkyl, or OCi-3alkyl;

[0123] Reis H, OH, Ci-3alkyl, or OCi-3alkyl; R1, R2, R3, and R4are independently selected from H, OH, Ci-3alkyl, or OCi-3alkyl, or a group having the formula: nigerose, or a combination thereof.

[0124] 26. The method according to any preceding embodiment, wherein the compound has the formula:

[0125] R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0126] R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0127] R3is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0128] R4is a group having the formula: preferably, R4is

[0129] 28. The method according to any preceding embodiment, wherein

[0130] R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0131] R3is H, OH, Ci-3alkyl, or OCi-3alkyl; R4is H, OH, Ci -3 alkyl, or OC 1-3 alkyl; and R1is a group having the formula: preferably, R1is The method according to any preceding embodiment, wherein

[0132] R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0133] R3is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0134] R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and R2is a group having the formula: preferably, R2is The method according to any preceding embodiment, wherein R1is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0135] R2is H, OH, Ci-3alkyl, or OCi-3alkyl;

[0136] R4is H, OH, Ci-3alkyl, or OCi-3alkyl; and

[0137] R3is a group having the formula: preferably, R3is

[0138] 31. The method according to any preceding embodiment, wherein R2and R4are H. 32. The method according to any preceding embodiment, wherein R1is OH or OCi-3alkyl, preferably OH.

[0139] 33. The method according to any preceding embodiment, wherein Rcand Rdare independently selected from OH or OCi-3alkyl, preferably Rcand Rdare both OH.

[0140] 34. The method according to any preceding embodiment, wherein Ra, Rb, and Reare independently selected from H or Ci-3alkyl, preferably CH3.

[0141] 35. The method according to any preceding embodiment, wherein Ra, Rb, and Reare each H.

[0142] 36. The method according to any preceding embodiment, wherein the compound has the formula:

[0143]

[0144] 37. The method of any preceding embodiment, wherein the composition is a vanilla extract, i.e., an artificial vanilla extract or natural vanilla extract.

[0145] 38. The method of any preceding embodiment, wherein the composition is a food or beverage.

[0146] 39. The method of any preceding embodiment, wherein the composition is a coffee, sodas, milk, tea, fruit juice, vegetable juice, vegetable, cheese, yogurt, grain, beers, wine, distilled spirit, cocoa, fruit, or vegetable.

[0147] 40. The method of any preceding embodiment, wherein the composition is a milk product, for example an animal milk or a plant milk.

[0148] 41. The method of any preceding embodiment, wherein the composition is cow milk, goat milk, sheep milk, almond milk, coconut milk, soy milk, rice milk, hemp milk, oat milk, pea milk, or peanut milk.

[0149] 42. The method of any preceding embodiment, wherein the composition is a coffee product.

[0150] 43. The method of any preceding embodiment, wherein the composition is brewed coffee, coffee concentrate, bottled coffee, coffee beans, processed coffee beans (raw, unroasted, roasted, fermented, ground, instant coffee products).

[0151] 44. The method of any preceding embodiment, wherein the composition is a confection. 45. The method of any preceding embodiment, wherein the composition is ice cream, frozen yogurt, chocolate, frozen desert.

[0152] The compositions and methods of the appended claims are not limited in scope by the specific compositions and methods described herein, which are intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims. Various modifications of the compositions and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims. Further, while only certain representative compositions and method steps disclosed herein are specifically described, other combinations of the compositions and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited. Thus, a combination of steps, elements, components, or constituents may be explicitly mentioned herein or less, however, other combinations of steps, elements, components, and constituents are included, even though not explicitly stated. The term “comprising” and variations thereof as used herein is used synonymously with the term “including” and variations thereof and are open, non-limiting terms. Although the terms “comprising” and “including” have been used herein to describe various embodiments, the terms “consisting essentially of’ and “consisting of’ can be used in place of “comprising” and “including” to provide for more specific embodiments of the invention and are also disclosed. Other than in the examples, or where otherwise noted, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood at the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, to be construed in light of the number of significant digits and ordinary rounding approaches.

Claims

CLAIMSWhat is claimed is:

1. A compound for the improvement of vanilla flavors in a composition, having the structure:whereinRais H, OH, Ci-3alkyl, or OCi-3alkyl;Rbis H, OH, Ci-3alkyl, or OCi-3alkyl;Rcis H, OH, Ci-3alkyl, or OCi-3alkyl;Rdis H, OH, Ci-3alkyl, or OCi-3alkyl;Reis H, OH, Ci-3alkyl, or OCi-3alkyl;R1, R2, R3, and R4are independently selected from H, OH, Ci-3alkyl, or OCi-3alkyl, or a group having the formula:

2. The compound for use according to claim 1, having the formula:R2is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl; andR4is a group having the formula:preferably, R4is4. The compound for use according to claim 1 or claim 2, whereinR2is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR1is a group having the formula:preferably, R1is5. The compound for use according to claim 1 or claim 2, whereinR1is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR2is a group having the formula:preferably, R2is6. The compound for use according to claim 1 or claim 2, whereinR1is H, OH, Ci-3alkyl, or OCi-3alkyl;R2is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR3is a group having the formula:preferably, R3is7. The compound for use according to any of claims 1-6, wherein R2and R4are H.

8. The compound for use according to any of claims 1-7, wherein R1is OH or OCi-3alkyl, preferably OH.

9. The compound for use according to any of claims 1-8, wherein Rcand Rdare independently selected from OH or OCi-3alkyl, preferably Rcand Rdare both OH.

10. The compound for use according to any of claims 1-9, wherein Ra, Rb, and Reare independently selected from H or Ci-3alkyl, preferably CH3.

11. The compound for use according to any of claims 1-10, wherein Ra, Rb, and Reare each H.

12. The compound for use according to any of claims 1-11, having the formula:

13. A compound for use in the modification of a vanilla flavor in a composition, wherein the compound is nigerose.

14. The compound for use according to any of claims 1-13, wherein the compound is added to the composition in an amount of at least 0.1 mg / kg, at least 0.5 mg / kg, at least 1 mg / kg, at least 2.5 mg / kg, at least 5 mg / kg, at least 10 mg / kg, at least 20 mg / kg, at least 30 mg / kg, at least 40 mg / kg, at least 50 mg / kg, at least 60 mg / kg, at least 70 mg / kg, at least 80 mg / kg, at least 90 mg / kg, or at least 100 mg / kg, relative to the total weight of theconsumable, or in an amount from 0.1-100 mg / kg, from 0.1-50 mg / kg, from 0.1-25 mg / kg, from 0.1-10 mg / kg, from 0.1-5 mg / kg, from 0.1-2.5 mg / kg, from 5-100 mg / kg, from 5-50 mg / kg, from 5-25 mg / kg, from 5-10 mg / kg, from 10-100 mg / kg, from 10-50 mg / kg, from 10-25 mg / kg, from 25-100 mg / kg, from 25-50 mg / kg, from 50-100 mg / kg, or from 75-100 mg / kg.

15. The compound for use of any of claims 1-14, wherein the compound is added as an aqueous composition, wherein the compound constitutes at least 50%, at least 75%, at least 80%, at least 90%, or at least 95% by weight of all non-solvent components in the aqueous composition.

16. The compound for use of any of claims 1-15, wherein the composition is a vanilla extract, i.e., an artificial vanilla extract or natural vanilla extract.

17. The compound for use of any of claims 1-15, wherein the composition is a food or beverage.

18. The compound for use of any of claims 1-15, wherein the composition is a coffee, sodas, milk, tea, fruit juice, vegetable juice, vegetable, cheese, yogurt, grain, beers, wine, distilled spirit, cocoa, fruit, or vegetable.

19. The compound for use of any of claims 1-15, wherein the composition is a milk product, for example an animal milk or a plant milk.

20. The compound for use of any of claims 1-15, wherein the composition is cow milk, goat milk, sheep milk, almond milk, coconut milk, soy milk, rice milk, hemp milk, oat milk, pea milk, or peanut milk.

21. The compound for use of any of claims 1-15, wherein the composition is a coffee product.

22. The compound for use of any of claims 1-15, wherein the composition is brewed coffee, coffee concentrate, bottled coffee, coffee beans, processed coffee beans (raw, unroasted, roasted, fermented, ground, instant coffee products).

23. The compound for use of any of claims 1-15, wherein the composition is a confection.

24. The compound for use of any of claims 1-15, wherein the composition is ice cream, frozen yogurt, chocolate, frozen desert.

25. A method of modifying the flavor of a composition, comprising adding to the composition a compound having the structure:whereinRais H, OH, Ci-3alkyl, or OCi-3alkyl;Rbis H, OH, Ci-3alkyl, or OCi-3alkyl;Rcis H, OH, Ci-3alkyl, or OCi-3alkyl;Rdis H, OH, Ci-3alkyl, or OCi-3alkyl;Reis H, OH, Ci-3alkyl, or OCi-3alkyl;R1, R2, R3, and R4are independently selected from H, OH, Ci-3alkyl, or OCi-3alkyl, or a group having the formula:nigerose, or a combination thereof.

26. The method according to claim 25, wherein the compound has the formula:R4is a group having the formula:preferably, R4is28. The method according to claim 25 or 26, whereinR2is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR1is a group having the formula:preferably, R1is29. The method according to claim 25 or 26, whereinR1is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR2is a group having the formula:preferably, R2is30. The method according to claim 25 or 26, wherein R1is H, OH, Ci-3alkyl, or OCi-3alkyl;R2is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR3is a group having the formula:preferably, R3is31. The method according to any of claims 25-30, wherein R2and R4are H.

32. The method according to any of claims 25-31, wherein R1is OH or OCi-3alkyl, preferably OH.

33. The method according to any of claims 25-32, wherein Rcand Rdare independently selected from OH or OCi-3alkyl, preferably Rcand Rdare both OH.

34. The method according to any of claims 25-33, wherein Ra, Rb, and Reare independently selected from H or Ci-3alkyl, preferably CH3.

35. The method according to any of claims 25-34, wherein Ra, Rb, and Reare each H.

36. The method according to any of claims 25-35, wherein the compound has the formula:

37. The method of any of claims 25-36, wherein the composition is a vanilla extract, i.e., an artificial vanilla extract or natural vanilla extract.

38. The method of any of claims 25-36, wherein the composition is a food or beverage.

39. The method of any of claims 25-36, wherein the composition is a coffee, sodas, milk, tea, fruit juice, vegetable juice, vegetable, cheese, yogurt, grain, beers, wine, distilled spirit, cocoa, fruit, or vegetable.

40. The method of any of claims 25-36, wherein the composition is a milk product, for example an animal milk or a plant milk.

41. The method of any of claims 25-36, wherein the composition is cow milk, goat milk, sheep milk, almond milk, coconut milk, soy milk, rice milk, hemp milk, oat milk, pea milk, or peanut milk.

42. The method of any of claims 25-36, wherein the composition is a coffee product.

43. The method of any of claims 25-36, wherein the composition is brewed coffee, coffee concentrate, bottled coffee, coffee beans, processed coffee beans (raw, unroasted, roasted, fermented, ground, instant coffee products).

44. The method of any of claims 25-36, wherein the composition is a confection.

45. The method of any of claim2 25-36, wherein the composition is ice cream, frozen yogurt, chocolate, frozen desert.

46. A composition, comprising nigerose and at least one compound having the structure:whereinRais H, OH, Ci-3alkyl, or OCi-3alkyl;Rbis H, OH, Ci-3alkyl, or OCi-3alkyl;Reis H, OH, Ci-3alkyl, or OCi-3alkyl;R1, R2, R3, and R4are independently selected from H, OH, Ci-3alkyl, or OCi-3alkyl, or a group having the formula:

47. The composition according to claim 46, wherein the compound has the formula:

48. The composition according to claim 46 or 47, whereinR1is H, OH, Ci-3alkyl, or OCi-3alkyl;R2is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl; andR4is a group having the formula:preferably, R4is49. The composition according to claim 46 or 47, whereinR2is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR1is a group having the formula:preferably, R1is50. The composition according to claim 46 or 47, whereinR1is H, OH, Ci-3alkyl, or OCi-3alkyl;R3is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR2is a group having the formula:preferably, R2is51. The composition according to claim 46 or 47, whereinR1is H, OH, Ci-3alkyl, or OCi-3alkyl;R2is H, OH, Ci-3alkyl, or OCi-3alkyl;R4is H, OH, Ci-3alkyl, or OCi-3alkyl; andR3is a group having the formula:preferably, R3is52. The composition according to any of claims 46-51, wherein R2and R4are H.

53. The composition according to any of claims 46-52, wherein R1is OH or OCi-3alkyl, preferably OH.

54. The composition according to any of claims 46-53, wherein Rcand Rdare independently selected from OH or OCi-3alkyl, preferably Rcand Rdare both OH.

55. The composition according to any of claims 46-54, wherein Ra, Rb, and Reare independently selected from H or Ci-3alkyl, preferably CH3.

56. The composition according to any of claims 46-55, wherein Ra, Rb, and Reare each H.

57. The composition according to any of claims 46-56, wherein the compound has the formula:

58. The composition according to any of claims 46-57, wherein the nigerose and the at least one compound are present in the composition in an amount of 0.1-100 mg / kg, from 0.1- 50 mg / kg, from 0.1-25 mg / kg, from 0.1-10 mg / kg, from 0.1-5 mg / kg, from 0.1-2.5 mg / kg, from 5-100 mg / kg, from 5-50 mg / kg, from 5-25 mg / kg, from 5-10 mg / kg, from 10-100 mg / kg, from 10-50 mg / kg, from 10-25 mg / kg, from 25-100 mg / kg, from 25-50 mg / kg, from 50-100 mg / kg, or from 75-100 mg / kg.

59. The composition according to any of claims 46-57, wherein the nigerose and the at least one compound are present in the composition in a weight ratio from 10: 1 to 1 : 10, from 10:1 to 5:1, from 10:1 to 1:1, from 5:1 to 1:1, from 5:1 to 2.5:1, from 2.5:1 to 1:1, from 2.5:1-1:1.25, from 1:1 to 1:2.5, from 1:1 to 1:5, from 1:2.5 to 1:5, from 1:1 to 1:10, or from 1:5 to 1:10.

60. The composition according to any of claims 46-59, wherein the composition further comprises water.

61. The composition according to any of claims 46-60, wherein the composition comprises water in an amount from 50-99 wt.%, from 50-90 wt.%, from 50-75 wt.%, from 25-75 wt.%, from 25-50 wt.%, from 80-90 wt.%, from 90-95 wt.%, from 95-99 wt.%, or from 85-95% wt.%, relative to the total weight of the composition.

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