Flavanone compounds and their use as flavor modifiers

Abstract

The present disclosure relates generally to certain flavanone compounds and the use of such compounds to modify the flavor or taste of ingestible compositions. These flavanone compounds include 8-methylnaringenin (5, 7, 4 '-trihydroxy-8-methylflavanone), 5, 3'-dihydroxy-7, 4 '-dimethoxyflavanone, 5-hydroxy-7, 3', 4 '-trimethoxyflavanone, 5, 4'-dihydroxy-7, 3 '-dimethoxyflavanone, or any combination thereof. In some embodiments, the use of these flavanone compounds includes use to enhance sweetness, use to reduce off-taste of high intensity sweeteners, use to enhance salty taste, use to enhance umami or rich taste, or any combination thereof. In certain embodiments, these compounds are used in combination with other natural taste modifiers (e.g., flavonoids or dihydrochalcones). In certain forms, the present disclosure provides ingestible compositions comprising such flavanone compounds. In some related forms, the ingestible composition is a variety of flavored products or is included in a variety of flavored products, such as a food product, a beverage product, a pharmaceutical product, an oral care product, or an animal feed product.

Description

Technical Field

[0001] This disclosure generally relates to certain flavanone compounds and the use of such compounds to modify the flavor or taste of ingestible compositions. These flavanone compounds include 8-methylnaringenin (5,7,4'-trihydroxy-8-methylflavanone), 5,3'-dihydroxy-7,4'-dimethoxyflavanone, 5-hydroxy-7,3',4'-trimethoxyflavanone, 5,4'-dihydroxy-7,3'-dimethoxyflavanone, or any combination thereof. In some embodiments, the use of these flavanone compounds includes enhancing sweetness, reducing the off-flavor of high-intensity sweeteners, enhancing saltiness, enhancing umami or kokumi, or any combination thereof. In some embodiments, these compounds are used in combination with other natural flavor modifiers, such as flavonoids or dihydrochalcones. In some forms, this disclosure provides ingestible compositions comprising such flavanone compounds. In some related forms, the ingestible composition is a variety of flavored products or is contained in a variety of flavored products, such as food products, beverage products, pharmaceutical products, oral care products or animal feed products. Background Technology

[0002] The taste system provides sensory information about the chemical composition of the external world. Taste transduction is one of the more complex forms of chemically triggered sensation in animals. Taste signals can be found throughout the animal kingdom, from simple metazoans to the most complex vertebrates. Mammals are believed to have five basic forms of taste: sweet, bitter, sour, salty, and umami.

[0003] Sweetness is the most commonly perceived taste when consuming foods high in sugar. Mammals generally perceive sweetness as a pleasant sensation, unless in excess. Caloric sweeteners, such as sucrose and fructose, are typical examples of sweet substances. Although many caloric and low-calorie alternatives exist, these caloric sweeteners remain the primary means by which edible products are perceived as sweet.

[0004] Metabolic disorders and related diseases, such as obesity, diabetes, and cardiovascular disease, are major public health problems worldwide. Their prevalence is growing at an alarming rate in almost every developed country. Caloric sweeteners are a key factor contributing to this trend, as they are included in a wide variety of packaged food and beverage products to make them more palatable to consumers. In many cases, caloric or low-caloric alternatives can be used in food and beverages to replace sucrose or fructose. Even so, these compounds impart a different sweetness than caloric sweeteners, and many consumers fail to perceive them as suitable substitutes. Moreover, such compounds can be difficult to incorporate into certain products. In some cases, they can be used as partial substitutes for caloric sweeteners, but their very presence can cause many consumers to perceive unpleasant off-flavors, including astringency, bitterness, metallic taste, and licorice-like notes. Therefore, the adoption of low-caloric sweeteners faces certain challenges.

[0005] Sweetness enhancement offers an alternative approach to overcome some of the adoption challenges faced by low-calorie sweeteners. These compounds can be used in combination with sucrose or fructose to enhance their sweetness, allowing for the use of lower amounts of these calorie sweeteners in a variety of food or beverage products. However, in addition to enhancing the perceived sweetness of the primary sweetener, these compounds still alter the perceived taste of the sweetener. Consequently, many consumers find consuming these sweetened products less enjoyable compared to unenhanced alternatives with higher calories. Therefore, there is an ongoing need to discover compounds that can enhance the sweetness of calorie sweeteners without altering their perceived taste in a way that diminishes the pleasure consumers experience when consuming or drinking products containing these sweeteners. Summary of the Invention

[0006] This disclosure relates to the discovery that certain flavanones and related compounds impart and / or enhance sweetness in a more natural way, and in some cases can also be used to mask bitterness, enhance mouthfeel, or mask astringency.

[0007] In a first embodiment, the present disclosure provides a flavor-modifying compound that is 5,7,4'-trihydroxy-8-methylflavanone, 5,3'-dihydroxy-7,4'-dimethoxyflavanone, 5-hydroxy-7,3',4'-trimethoxyflavanone, 5,4'-dihydroxy-7,3'-dimethoxyflavanone, or any combination thereof.

[0008] In a second embodiment, this disclosure provides the use of the flavor-modifying compound of the first embodiment for modifying the flavor of an ingestible composition. In some related embodiments, this disclosure provides a method for modifying the flavor of an ingestible composition, the method comprising introducing the flavor-modifying compound of the first embodiment into the ingestible composition. In some embodiments, the ingestible composition comprises one or more sweeteners, such as high-intensity sweeteners. In some embodiments, the ingestible composition comprises one or more flavonoids or dihydrochalcones. In some embodiments, modifying the flavor of an ingestible composition refers to enhancing the sweetness of the ingestible composition. In some embodiments, modifying the flavor of an ingestible composition refers to reducing off-flavors of the ingestible composition, such as the off-flavors of high-intensity sweeteners. In some such embodiments, off-flavors include bitterness, astringency, lingering aftertaste, or any combination thereof. In one embodiment, modifying the flavor of an ingestible composition refers to enhancing the saltiness of the ingestible composition. In some embodiments, modifying the flavor of an ingestible composition refers to enhancing the umami flavor of the ingestible composition. In some embodiments, modifying the flavor of an ingestible composition refers to enhancing the richness of the ingestible composition.

[0009] In a third embodiment, this disclosure provides an ingestible composition comprising one or more flavor-modifying compounds of the first embodiment. In some embodiments, the ingestible composition comprises one or more sweeteners, such as high-intensity sweeteners. In some embodiments, the ingestible composition comprises one or more bitterness enhancers. In some embodiments, the ingestible composition comprises sodium chloride or potassium chloride. In some embodiments, the ingestible composition comprises one or more umami enhancers, such as glutamate (including glutamate and monosodium glutamate), aspartate (including aspartic acid), arginine, purine ribonucleotides (including guanosine monophosphate, inosine monophosphate, or combinations thereof), yeast extracts, fermentation products, or extracts thereof.

[0010] In a fourth embodiment, this disclosure provides a flavored product comprising an ingestible composition of the third embodiment. In some embodiments, the flavored product is a food or beverage product. In some embodiments, the flavored product is an oral care product or a pharmaceutical product. In some embodiments, the flavored product is an animal feed product, such as pet food.

[0011] Further forms and embodiments thereof are set forth in the following detailed description, figures, abstract and claims. Attached Figure Description

[0012] The following figures are provided to illustrate various embodiments of the compositions and methods disclosed herein. The figures are provided for illustrative purposes only and are not intended to describe any preferred compositions or methods, nor are they intended as a source of any limitation on the scope of the claimed invention.

[0013] Figure 1 The chemical formulas representing the flavor-modifying compounds disclosed herein are shown, with non-specific stereochemical properties shown on the carbon atoms marked with asterisks. Detailed Implementation

[0014] The following detailed description illustrates the various forms and implementations provided herein. This description is intended for reading by a person skilled in the art. Therefore, information familiar to such a person may not be included.

[0015] definition

[0016] Unless otherwise specified herein, the following terms and phrases have the meanings indicated below. This disclosure may employ other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings that those skilled in the art would have in the context of this disclosure. In some cases, a term or phrase may be defined in a singular or plural form. In such cases, it should be understood that any term in its singular form may include its plural form, and vice versa, unless the contrary is explicitly stated.

[0017] "Sweeteners" are compounds that induce a detectable sweet taste in subjects or salts that are acceptable in their intake, such as compounds that activate T1R2 and T1R3 taste receptors in vivo or in vitro.

[0018] "Bitterness enhancers (or bitterness enhancers)" are compounds that induce a detectable bitter taste in subjects or salts that are acceptable to their intake, such as compounds that activate one or more T2R taste receptors in vivo or in vitro.

[0019] As used herein, the singular forms “an,” “a,” and “the” include plural indicators unless the context clearly indicates otherwise. For example, reference to “an substituent” covers a single substituent as well as two or more substituents, and so on.

[0020] As used herein, the words “for example,” “such as,” “like,” or “including” are intended to introduce examples that further illustrate a more general subject. Unless otherwise expressly stated, such examples are provided only to aid in understanding the embodiments shown in this disclosure and are not intended to be limiting in any way. These phrases also do not indicate any kind of preference for the disclosed embodiments.

[0021] As used herein, “include,” “contain,” “with,” and “comprised of” refer to an open group, meaning that the group may include other members besides those explicitly stated. For example, the phrase “includes A” means that A must be present, but other members may also be present. The terms “include,” “have,” and “composed of,” and their grammatical variations, have the same meaning. Conversely, “consist of,” “formed by,” or “constituting as” refer to a closed group. For example, the phrase “composed of A” means that only A exists.

[0022] As used herein, "optionally" means that the events described below may or may not occur. In some embodiments, the optional event does not occur. In other embodiments, the optional event does occur once or more.

[0023] As used herein, “or” will be given its broadest reasonable interpretation and is not limited to the “either / or” construction. Therefore, the phrase “containing A or B” means that A may exist while B does not, or B may exist while A does not, or both A and B may exist. Furthermore, for example, if A defines a class that can have multiple members (e.g., A1 and A2), then one or more members of that class may exist simultaneously.

[0024] Chemical structures are typically displayed using a "skeleton" format, therefore carbon atoms are not explicitly shown, and hydrogen atoms bonded to carbon atoms are completely omitted. For example, the structure... This represents butane (i.e., n-butane). Furthermore, aromatic groups such as benzene contribute by exhibiting a resonance structure.

[0025] To represent. For example, structure. It represents toluene.

[0026] As used herein, according to any embodiment described herein, the term "flavor-modifying compound" means 5,7,4'-trihydroxy-8-methylflavanone, 5,3'-dihydroxy-7,4'-dimethoxyflavanone, or any salt thereof.

[0027] Other terms are defined in other parts of this specification, even if not included in this subsection.

[0028] Flavor-modifying compounds

[0029] In some forms, this disclosure provides a flavor-modifying compound, namely 5,7,4'-trihydroxy-8-methylflavanone, 5,3'-dihydroxy-7,4'-dimethoxyflavanone, or any salt thereof.

[0030] In some embodiments, the flavor-modifying compound is 5,7,4'-trihydroxy-8-methylflavanone, whose chemical structure is shown below:

[0031] Or its salt.

[0032] In some embodiments, the flavor-modifying compound is 5,7,4'-trihydroxy-8-methylflavanone. In some embodiments, the flavor-modifying compound is a salt of 5,7,4'-trihydroxy-8-methylflavanone, such as a sodium salt, potassium salt, calcium salt, magnesium salt, etc. The above structure has a stereocenter at the carbon atom adjacent to the asterisk. In some embodiments, 5,7,4'-trihydroxy-8-methylflavanone is the S enantiomer. Hereinafter, the S enantiomer is also referred to as "compound 101". In other embodiments, 5,7,4'-trihydroxy-8-methylflavanone is the R enantiomer. In some embodiments, 5,7,4'-trihydroxy-8-methylflavanone is a racemic mixture comprising both the S enantiomer and the R enantiomer. In some embodiments, the mixture may be enriched with either of the two enantiomers. For example, in some embodiments, the weight ratio of the S enantiomer to the R enantiomer in the racemic mixture ranges from 1:1 to 1000:1, or 1:1 to 500:1, or 1:1 to 100:1, or 1:1 to 50:1, or 1:1 to 10:1.

[0033] In one embodiment, the flavor-modifying compound is 5,3'-dihydroxy-7,4'-dimethoxyflavanone, whose chemical structure is shown below:

[0034] Or its salt.

[0035] In some embodiments, the flavor-modifying compound is 5,3'-dihydroxy-7,4'-dimethoxyflavanone. In some embodiments, the flavor-modifying compound is a salt of 5,3'-dihydroxy-7,4'-dimethoxyflavanone, such as a sodium salt, potassium salt, calcium salt, magnesium salt, etc. The above structure has a stereocenter at the carbon atom adjacent to the asterisk. In some embodiments, 5,3'-dihydroxy-7,4'-dimethoxyflavanone is the S enantiomer. Hereinafter, the S enantiomer is also referred to as "compound 102". In other embodiments, 5,3'-dihydroxy-7,4'-dimethoxyflavanone is the R enantiomer. In some embodiments, 5,3'-dihydroxy-7,4'-dimethoxyflavanone is a racemic mixture comprising both the S enantiomer and the R enantiomer. In some embodiments, the mixture may be enriched with either of the two enantiomers. For example, in some embodiments, the weight ratio of the S enantiomer to the R enantiomer in the racemic mixture ranges from 1:1 to 1000:1, or 1:1 to 500:1, or 1:1 to 100:1, or 1:1 to 50:1, or 1:1 to 10:1.

[0036] In one embodiment, the flavor-modifying compound is 5,3'-dihydroxy-7,4'-dimethoxyflavanone, whose chemical structure is shown below:

[0037] Or its salt.

[0038] In some embodiments, the flavor-modifying compound is 5-hydroxy-7,3',4'-trimethoxyflavanone. In some embodiments, the flavor-modifying compound is a salt of 5-hydroxy-7,3',4'-trimethoxyflavanone, such as a sodium salt, potassium salt, calcium salt, magnesium salt, etc. The above structure has a stereocenter at the carbon atom adjacent to the asterisk. In some embodiments, 5-hydroxy-7,3',4'-trimethoxyflavanone is the S enantiomer. Hereinafter, the S enantiomer is also referred to as "compound 103". In other embodiments, 5-hydroxy-7,3',4'-trimethoxyflavanone is the R enantiomer. In some embodiments, 5-hydroxy-7,3',4'-trimethoxyflavanone is a racemic mixture comprising both the S enantiomer and the R enantiomer. In some embodiments, the mixture may be enriched with either of the two enantiomers. For example, in some embodiments, the weight ratio of the S enantiomer to the R enantiomer in the racemic mixture ranges from 1:1 to 1000:1, or 1:1 to 500:1, or 1:1 to 100:1, or 1:1 to 50:1, or 1:1 to 10:1.

[0039] In one embodiment, the flavor-modifying compound is 5,3'-dihydroxy-7,4'-dimethoxyflavanone, whose chemical structure is shown below:

[0040] Or its salt.

[0041] In some embodiments, the flavor-modifying compound is 5,4'-dihydroxy-7,3'-dimethoxyflavanone. In some embodiments, the flavor-modifying compound is a salt of 5,4'-dihydroxy-7,3'-dimethoxyflavanone, such as a sodium salt, potassium salt, calcium salt, magnesium salt, etc. The above structure has a stereocenter at the carbon atom adjacent to the asterisk. In some embodiments, 5,4'-dihydroxy-7,3'-dimethoxyflavanone is the S enantiomer. Hereinafter, the S enantiomer is also referred to as "compound 104". In other embodiments, 5,4'-dihydroxy-7,3'-dimethoxyflavanone is the R enantiomer. In some embodiments, 5,4'-dihydroxy-7,3'-dimethoxyflavanone is a racemic mixture comprising both the S enantiomer and the R enantiomer. In some embodiments, the mixture may be enriched with either of the two enantiomers. For example, in some embodiments, the weight ratio of the S enantiomer to the R enantiomer in the racemic mixture ranges from 1:1 to 1000:1, or 1:1 to 500:1, or 1:1 to 100:1, or 1:1 to 50:1, or 1:1 to 10:1.

[0042] The isolation of individual isomers or the selective synthesis of individual isomers is accomplished by applying various methods well known to those skilled in the art. Unless otherwise stated (e.g., in cases where the stereochemistry clearly demonstrates a chiral center), all such isomers and mixtures thereof are included within the scope of the compounds disclosed herein. Furthermore, the compounds disclosed herein may exist in one or more crystalline or amorphous forms. Unless otherwise stated, all such forms are included within the scope of the compounds disclosed herein, including any polymorphic forms. Additionally, some of the compounds disclosed herein can form solvates with water (i.e., hydrates) or common organic solvents. Unless otherwise stated, these solvates are included within the scope of the compounds disclosed herein.

[0043] Those skilled in the art will recognize that some of the structures described herein may be resonance forms or tautomers of compounds, which can be reasonably represented by other chemical structures, even kinetically; and that such structures may represent only a small fraction of such sample compounds. Such compounds are considered to be within the range of structures shown, although such resonance forms or tautomers are not shown herein.

[0044] Isotopes may be present in the described compounds. Each chemical element represented in the compound structure may include any isotope of that element. For example, in the compound structure, a hydrogen atom may be explicitly stated or understood to be present in the compound. Wherever a hydrogen atom may be present in the compound, it may be any isotope of hydrogen, including but not limited to hydrogen-1 (protium) and hydrogen-2 (deuterium). Therefore, the compounds mentioned herein encompass all possible isotopic forms unless the context clearly indicates otherwise.

[0045] In some embodiments, the flavor-modifying compounds disclosed herein are capable of forming acidic and / or basic salts due to the presence of phenolic, amino, and / or carboxyl groups or similar groups. Edible acid addition salts can be formed from inorganic and organic acids. Inorganic acids from which salts can be derived include, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, etc. Organic acids from which salts can be derived include, for example, acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, etc. Edible salts can be formed from inorganic and organic bases. Inorganic bases from which salts can be derived include, for example, bases containing sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum, etc.; particularly preferred are ammonium, potassium, sodium, calcium, and magnesium salts. In some embodiments, treatment of the compound disclosed herein with an inorganic base causes the compound to lose unstable hydrogen, thereby yielding a compound containing an inorganic cation such as Li. + Na + K + Mg 2+ and Ca 2+ The salt can be in the form of salts. Organic bases from which salts can be derived include, for example, primary, secondary, and tertiary amines, substituted amines (including naturally occurring substituted amines), cyclic amines, basic ion exchange resins, etc., particularly isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, and ethanolamine. In some embodiments, the salt is an edible salt, which is a salt suitable for inclusion in ingestible compositions such as food or beverage products. In some embodiments, the edible salt is a sodium or potassium salt.

[0046] Uses and methods

[0047] In some forms, this disclosure provides the use of the flavor-modifying compounds of the foregoing forms and embodiments thereof for modifying the flavor of an ingestible composition. In some related forms, this disclosure provides a method for modifying the flavor of an ingestible composition, the method comprising introducing a flavor-modifying compound of the foregoing forms or any embodiment thereof into the ingestible composition.

[0048] The term "modifying the flavor of an ingestible composition" refers to any modification of the taste, aroma, or other physical sensation of an ingestible composition, such as texture, juiciness, mouthcoating, etc. In some embodiments, modifying the flavor of an ingestible composition includes enhancing its sweetness. In some embodiments, modifying the flavor of an ingestible composition includes reducing off-flavors, such as the off-flavors of high-intensity sweeteners. In some such embodiments, off-flavors include bitterness, astringency, lingering aftertaste, or any combination thereof. In some embodiments, modifying the flavor of an ingestible composition includes enhancing its saltiness. In some embodiments, modifying the flavor of an ingestible composition includes enhancing its umami flavor. In some embodiments, modifying the flavor of an ingestible composition includes enhancing its richness.

[0049] As will be described in further detail in the following subsection, the ingestible composition may contain a variety of flavor enhancers, such as sweet flavor enhancers, bitter flavor enhancers, umami flavor enhancers, and strong flavor enhancers. In some embodiments, the flavor-modifying compound in the aforementioned form or any embodiment thereof is used in combination with such flavor enhancers. In some such embodiments, the use of such flavor-modifying compounds can reduce the amount of such flavor enhancers in the ingestible composition without materially affecting its flavor, compared to a similar ingestible composition containing sufficient amounts of flavor enhancers but not containing such flavor-modifying compounds. For example, in some embodiments, enhancing the sweetness of the ingestible composition includes reducing the amount of sweeteners in the ingestible composition, such as reducing carbohydrate sweeteners (e.g., sucrose, fructose, glucose, allulose, erythritol, etc.) or high-intensity sweeteners (e.g., aspartame, acesulfame potassium, neotame, cyclamates, saccharin, steviol glycosides such as rebaudioside A, rebaudioside D, and rebaudioside M, and mogrosides such as mogroside V, symmonoside I, isomogroside V, and mogroside IV). E Isomogroside IV, mogroside III E The dosage of 1,6-α isomers of 1,1-oxomogroside V or symmenidine I. The ingestible composition may also contain one or more other flavor-modifying compounds, such as various flavonoids or dihydrochalcones.

[0050] The foregoing uses and methods relate to ingestible compositions. In addition to the features of ingestible compositions described above, ingestible compositions may also contain any or a combination of features described below.

[0051] Ingestible Compositions

[0052] In some forms, this disclosure provides an ingestible composition comprising a flavor-modifying compound according to the embodiments described above. When introduced into or used in an ingestible composition, the flavor-modifying compound is used or introduced into the ingestible composition in the range of 0.01 ppm to 1000 ppm, or 0.01 ppm to 900 ppm, or 0.01 ppm to 800 ppm, or 0.01 ppm to 700 ppm, or 0.01 ppm to 600 ppm, or 0.1 ppm to 500 ppm, or 0.1 ppm to 400 ppm, or 0.1 ppm to 300 ppm, or 0.1 ppm to 200 ppm, or 1 ppm to 100 ppm, or 1 ppm to 80 ppm, or 1 ppm to 60 ppm, or 1 ppm to 50 ppm, or 1 ppm to 40 ppm.

[0053] In some embodiments, the ingestible composition comprises one or more bitterness enhancers. In some embodiments, the bitterness enhancer is a high-intensity sweetener, such as acesulfame potassium, aspartame, neotame, cyclohexylsulfamic acid salt, saccharin, sucralose, steviol glycosides (e.g., rebaudioside A, rebaudioside B, rebaudioside M, rebaudioside D, or rebaudioside E), and mogrosides (e.g., mogroside III, mogroside IV, mogroside V, symmonoside I, isomogroside V, mogroside IV). E Isomogroside IV, mogroside III E (1,6-α isomers of 11-oxomogroside V or symmenidine I). Therefore, flavor-modifying compounds are suitable for use in low-sugar or zero-sugar products to reduce the bitterness imparted by low-calorie or zero-calorie sweeteners.

[0054] In some implementations, the bitterness enhancer is a potassium salt, such as potassium chloride, which is commonly used as a partial or complete substitute for sodium chloride in certain low-sodium or zero-sodium foods. Therefore, flavor-modifying compounds may be suitable for use in such products to reduce the bitterness imparted by the potassium salt.

[0055] In some embodiments, the bitterness enhancer is a non-animal protein, such as plant protein, algae protein, or fungal protein. In some embodiments, the ingestible composition comprises a plant protein. Non-limiting examples of plant proteins include pea protein, soy protein, almond protein, cashew protein, low-erucic acid canola protein, chickpea protein, broad bean protein, sunflower seed protein, wheat protein, oat protein, barley protein, and potato protein. Such non-animal proteins are commonly used as partial or complete substitutes for animal proteins in dairy and meat analogues. Therefore, flavor-modifying compounds are suitable for use in such products to reduce the bitterness imparted by non-animal proteins. By blocking the bitterness of such proteins, flavor-modifying compounds can reduce the perceived grain and green notes experienced by consumers.

[0056] In some implementations, bitterness enhancers include caffeine, quinine, green tea, catechins, polyphenols (e.g., polyphenol antioxidants), tannins, Robusta green coffee bean extract, green coffee bean extract, menthol, etc. These compounds are commonly found in various natural food products such as tea and coffee, as well as packaged food products such as instant tea, instant coffee, and packaged beverages. When one or more of these bitterness enhancers are present, flavor-modifying compounds are suitable for blocking the bitterness of these compounds and improving the consumer's perceived taste of the product.

[0057] In some embodiments, the bitterness enhancer is a pharmaceutical compound. Non-limiting examples of pharmaceutical compounds having a bitter taste include atropine, brinzolamide, chloramphenicol, chloroquine, clindamycin, dexamethasone, digoxin, diltiazem, diphenhydramine, docusate, dazolamide, doxepin, doxylamine, enalapril, erythromycin, esomeprazole, famotidine, gabapentin, ginkgolide A, guaifenesin, L-histidine, lomefloxacin, methylprednisolone, ofloxacin, oleuropein, oxifenebromide, pirenzepine, prednisone, ranitidine, tramidil, trimethoprim, and cetirizine. When one or more of these pharmaceutical compounds are used in oral pharmaceutical formulations, flavor-modifying compounds are suitable for blocking the bitterness of these compounds and improving the consumer's perceived taste of the pharmaceutical product.

[0058] In some implementations, bitterness enhancers are oral care ingredients. Many oral care ingredients impart a bitter taste, which must be masked or blocked to improve consumer acceptance of the product. Non-limiting examples of such oral care ingredients include menthol, menthol analogs, peppermint extract, sodium bicarbonate, potassium persulfate, cetylpyridine chloride, lauramide propyl betaine, cocamidopropyl betaine, arginine, hydrogen peroxide, chlorhexidine gluconate, potassium nitrate, pentasodium triphosphate, tetrasodium pyrophosphate, stannous fluoride, thymol, methyl salicylate, eucalyptol, thymol, pentamethasone, and any combination thereof. When one or more of these oral care compounds are used in an oral care product, flavor-modifying compounds are suitable for blocking the bitterness of these compounds and improving the consumer's perceived taste of the oral care product.

[0059] In some implementations, bitterness enhancers are bittering agents found in citrus fruits, such as limonin, nomilin, or naringin. Many citrus-containing formulations impart a bitter off-flavor, which must be masked or blocked to improve consumer acceptance of the product. In some cases, this bitter off-flavor may be caused by citrus greening disease, which causes citrus fruits to turn green before they are fully ripe. When one or more of these citrus bittering agents are present in the product, flavor-modifying compounds are suitable for blocking the bitterness of these compounds and improving the consumer's perceived taste of the citrus product.

[0060] In one embodiment, the ingestible composition comprises one or more flavanones. In some embodiments, such flavanones synergize with flavor-modifying compounds disclosed herein to reduce bitterness, enhance the perception of sweetness, or reduce sourness. In some embodiments, the flavanone is sennaol, hesperidin, hesperidin, sennaol, naringenin, or any combination thereof. In some other embodiments, the flavanone is sennaol. In some other embodiments, the flavanone is sennaol. Such flavanones can be present in the ingestible composition at any suitable concentration, for example, in the range of 0.01 ppm to 1000 ppm, or 0.01 ppm to 900 ppm, or 0.01 ppm to 800 ppm, or 0.01 ppm to 700 ppm, or 0.01 ppm to 600 ppm, or 0.1 ppm to 500 ppm, or 0.1 ppm to 400 ppm, or 0.1 ppm to 300 ppm, or 0.1 ppm to 200 ppm, or 1 ppm to 100 ppm, or 1 ppm to 80 ppm, or 1 ppm to 60 ppm, or 1 ppm to 50 ppm, or 1 ppm to 40 ppm.

[0061] In some embodiments, the ingestible composition comprises one or a combination of sweeteners. In some embodiments, the sweetener is a common sugar sweetener, such as sucrose, fructose, glucose, or a sweetener composition comprising natural sugars such as corn syrup (including high-fructose corn syrup) or other syrups or sweetener concentrates derived from natural fruit and vegetable sources. In some embodiments, the sweetener is sucrose, fructose, or a combination thereof. In some embodiments, the sweetener is sucrose. In some other embodiments, the sweetener is selected from rare natural sugars, including D-allose, D-allulose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, D-malinobiose, and D-leucobionic acid. In some embodiments, the sweetener is selected from semi-synthetic "sugar alcohol" sweeteners, such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, etc. In some embodiments, the sweetener is selected from artificial sweeteners, such as aspartame, saccharin, acesulfame potassium, cyclohexanesulfonate, sucralose, and alitane. In some embodiments, the sweetener is selected from the group consisting of: cyclamic acid, mogroside, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, allulose, neotame and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomaltitol, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysate (HSH), steviol, rebaudioside A, other sweet steviol glycosides, chemically modified steviol glycosides (such as glucosylated steviol glycosides), other mogrosides, chemically modified mogrosides (such as glucosylated mogrosides), carrelame, and other guanidine sweeteners. In some embodiments, the sweetener is a combination of two or more sweeteners described in this paragraph. In some embodiments, the sweetener may be a combination of two, three, four, or five sweeteners disclosed herein. In some embodiments, the sweetener may be sugar. In some embodiments, the sweetener may be a combination of one or more sugars with other natural and artificial sweeteners. In some embodiments, the sweetener is sugar. In some embodiments, the sugar is cane sugar. In some embodiments, the sugar is beet sugar. In some embodiments, the sugar may be sucrose, fructose, glucose, or a combination thereof. In some embodiments, the sugar may be sucrose. In some embodiments, the sugar may be a combination of fructose and glucose.

[0062] Sweeteners may also include, for example, sweetener compositions containing one or more natural or synthetic carbohydrates, such as corn syrup, high-fructose corn syrup, high-maltose corn syrup, glucose syrup, sucralose syrup, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysate (HSH), or other syrups or sweetener concentrates derived from natural fruit and vegetable sources, or semi-synthetic "sugar alcohol" sweeteners, such as polyols. In some embodiments, non-limiting examples of polyols include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomaltitol, propylene glycol, glycerol, threitol, galactitol, palaginose, reduced isomaltose oligosaccharides, reduced xylose oligosaccharides, reduced gentian oligosaccharides, reduced maltose syrup, reduced glucose syrup, isomaltulose, maltodextrin, etc., as well as sugar alcohols or any other carbohydrates or combinations thereof that can be reduced without adversely affecting taste.

[0063] Sweeteners can be natural or synthetic, including but not limited to agave inulin, agave nectar, agave syrup, amazake, brazzein, brown rice syrup, coconut crystals, coconut sugar, coconut syrup, date sugar, fructan (also known as inulin fiber, fructooligosaccharides, or oligofructose), green stevia, stevia (Steviarebaudiana), rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M and other steviosides, steviosides, stevioside extracts, honey, Jerusalem artichoke (Jerusalem africanum) Artichoke syrup, licorice root, monk fruit (fruit, powder, or extract), lucuma (fruit, powder, or extract), maple sap (including sap extracted from, for example, sugar maple (Acer saccharum), black maple (Acer nigrum), American red maple (Acer rubrum), silver maple (Acersaccharinum), Norway maple (Acer platanoides), ash-leaved maple (Acer negundo), large-leaved maple (Acer macrophyllum), coarse-toothed maple (Acer grandidentatum), Rocky mountain maple (Acer glabrum), and maple (Acermono), maple syrup, maple sugar, walnut sap (including sap extracted from, for example, white walnut (Juglans cinerea), black walnut (Juglans nigra), ghost walnut (Juglans ailatifolia), and walnut (Juglans regia), birch sap (including sap extracted from, for example, paper birch (Betula)). Sap extracted from various trees including papyrifera, Canadian yellow birch (Betula alleghaniensis), mountain birch (Betula lenta), river birch (Betula nigra), grey birch (Betula populifolia), and weeping birch (Betula pendula), sycamore sap (e.g., sap extracted from Platanus occidentalis), ironwood sap (e.g., sap extracted from Ostryavirginiana), unrefined cane sugar (mascobado), molasses (e.g., blackstrap molasses), molasses sugar, monalose, monellin, and cane sugar.Sugar (also known as natural sugar, unrefined sucrose, or sucrose), palm sugar, panocha, piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, tapioca syrup (also known as tapioca starch syrup), thaumatin, yacon. root), malt syrup, barley malt syrup, barley malt powder, beet sugar, cane sugar, crystallized fruit juice crystals, caramel, carob syrup, castor oil, hydrogenated starch hydrosol, hydrolyzed canned fruit juice, hydrolyzed starch, invert sugar, anethole, arabinogalactan, concentrated grape juice, syrup, P-4000, acesulfame potassium (also known as acetylsupan potassium or ace-K), aclame (also known as aclame), advans, aspartame, baiyunosdie, neotame, benzamide derivatives, bernadame, aspartame alias (canderel), carrelame and other guanidine sweeteners, plant fiber, corn sugar, conjugated sugars, curculigosin, cyclamates, cyclocaryoside I I) Demerara sugar, beta-glucan, dextrin, diastatic maltmalt), dulcin, sucrol, valzin, dulcioside A, dulcioside B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucin, gluconic acid, gluconolactone, glucosamine, glucuronic acid, glycerol, glycyphillin, glycyrrhizin, glycyrrhetinic acid monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, Gynostemma pentaphyllum, hernandulcin, isomerized liquid sugar, jallab, chicory root dietary fiber, kynurenine derivatives (including N'-formyl-kynurenine, N'-acetyl-kynurenine) Amino acid, 6-chloro-kynurenine), galactitol, litesse, ligicane, lycasin, N-(4-cyanophenyl)-N-(2,3-methylenedioxybenzyl)guanidinacetic acid, guanidine, farernum syrup, areca nut protein I, areca nut protein II, maltol, crystalline maltitol, maltodextrin, maltotriol, mannosamine, miraculin, mizuame, mogrosides (including, for example, mogroside IV, mogroside V and neomogroside), mukurozioside, nanosugars. sugar), naringin dihydrochalcone, neohesperidin dihydrochalcone, nib sugar, black oligosaccharides, norbu, almond syrup, osladin, pekmez, pentadin, periandrin I, perillartine, petphyllum, phenylalanine, phloisosideside I, phlorodizin, phyllodulcin, polyglycitol syrup, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refined syrup, rub syrup, rubusoside, selligueain A) Shugr, sermonoside I, monk fruit (Siraitia grosvenorii), soybean oligosaccharides, Splenda, SRIoximeV, steviol glycosides, steviol disaccharides, steviol glycosides, strogins 1, 2 and 4, sucronic acid, sucrononate, sugars, sodium suosan, phloridzin, super aspartame, tetrasaccharides, threitol, treacle, trilobtain, tryptophan and its derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanilla sugar, heptenetropeol, beet syrup, aspartame-acesulfame, assugrin, and any combination or blend of two or more of them.

[0064] Additional sweeteners include combinations of any two or more of the aforementioned sweeteners. In some embodiments, the sweetener may comprise a combination of two, three, four, or five sweeteners disclosed herein. In some embodiments, the sweetener may be a sugar. In some embodiments, the sweetener may be a combination of one or more sugars with other natural and artificial sweeteners. In some embodiments, the sweetener is a caloric sweetener, such as sucrose, fructose, xylitol, erythritol, or combinations thereof. In some embodiments, the ingestible composition is free of (or in some embodiments substantially free of) stevia-derived sweeteners, such as steviol glycosides, glucosylated steviol glycosides, or rebaudioside.

[0065] In some embodiments, the sweetener is sucrose. In other embodiments, the sweetener is steviol glycoside.

[0066] In some embodiments, the ingestible composition contains an acidifying agent, such as an organic acid. Non-limiting examples of such organic acids include acetic acid, malonic acid, citric acid, lactic acid, etc.

[0067] In one embodiment, the ingestible composition comprises certain savory flavor enhancers (umami or rich flavor enhancers) or flavor-enhancing compounds. Such flavor enhancers include, but are not limited to, N-(heptane-4-yl)-benzo[d][1,3]m-dioxane-5-carboxamide, N... 1 -(2,4-Dimethoxybenzyl)-N 2-(2-(pyridin-2-yl)ethyl)-oxalamide, alkylamides, glutamates (e.g., monosodium glutamate (MSG)), arginine salts, purine ribonucleotides (e.g., inosine monophosphate (IMP), adenosine monophosphate (AMP), guanosine monophosphate (GMP), and their sodium salts), amino acids (e.g., L-threonine), yeast extracts, and alcohols (alcohols). Other such flavoring ingredients include, but are not limited to, yeast extracts, fermented food products, cheese, garlic or its extracts, γ-glutamyl-containing peptides, γ-glutamyl-containing oligopeptides (e.g., γ-glutamyl-containing tripeptides), cinnamic acid amides or their derivatives such as (E)-N-(4-cinnamamidobutyl)-4-hydroxy-2-methylbut-2-enamide, nucleotides, oligonucleotides, plant extracts, food extracts, sorbitan, avocadoene, or any combination thereof. In some embodiments, the ingestible composition contains a salty flavor enhancer, such as sodium chloride or potassium chloride.

[0068] Ingestible compositions may contain any additional ingredients or combinations of ingredients commonly used in food and beverage products, including but not limited to:

[0069] Acids, including, for example, citric acid, phosphoric acid, ascorbic acid, sodium bisulfate, lactic acid, or tartaric acid;

[0070] Bitter components include, for example, caffeine, quinine, green tea, catechins, polyphenols, Robusta coffee bean extract, coffee bean extract, potassium chloride, menthol, or proteins (such as proteins and protein isolates derived from plants, algae, or fungi).

[0071] Coloring agents, including, for example, caramel color, red #40, yellow #5, yellow #6, blue #1, red #3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, beta-carotene, curcumin, or titanium dioxide;

[0072] Preservatives, including, for example, sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfite, sorbic acid, or benzoic acid;

[0073] Antioxidants, including, for example, ascorbic acid, calcium disodium EDTA, α-tocopherol, mixed tocopherols, rosemary extract, grape seed extract, resveratrol, or sodium hexametaphosphate;

[0074] Vitamins or functional ingredients, including, for example, resveratrol, Co-Q10, omega-3 fatty acids, theanine, choline chloride (citocoline), cellulose, inulin (chicory root), taurine, ginseng extract, guarana extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D-glucuronide, inositol, bioflavonoids, echinacea, ginkgo biloba, yerba mate, flaxseed oil, Garcinia cambogia peel extract, white tea extract, ribose, milk thistle (milk) Thistle extract, grape seed extract, pyridoxine hydrochloride (vitamin B6), cyanocobalamin (vitamin B12), nicotinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, copper sulfate, folic acid, ferric pyrophosphate, iron, magnesium lactate, magnesium carbonate, magnesium sulfate, monopotassium phosphate, monosodium phosphate, phosphorus, potassium iodide, potassium phosphate, riboflavin, sodium sulfate, sodium gluconate, sodium polyphosphate, sodium bicarbonate, thiamine mononitrate, vitamin D3, vitamin A palmitate, zinc gluconate, zinc lactate or zinc sulfate;

[0075] Clouding agents include, for example, ester gum, brominated vegetable oil (BVO), or sucrose isobutyrate acetate (SAIB).

[0076] Buffer solutions, including, for example, sodium citrate, potassium citrate, or salts;

[0077] Flavors (food flavorings), including, for example, propylene glycol, ethanol, glycerin, gum arabic, maltodextrin, modified corn starch, dextrose, natural flavorings, natural flavorings with other natural flavorings (WONF), natural and artificial flavorings, artificial flavorings, silica, magnesium carbonate or tricalcium phosphate; or

[0078] Starch and stabilizers, including, for example, pectin, xanthan gum, carboxymethyl cellulose (CMC), polysorbate 60, polysorbate 80, medium-chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum arabic (acacia gum), inulin, or carrageenan.

[0079] The ingestible composition may have any suitable pH value. In some embodiments, amide compounds enhance the sweetness of the sweetener over a wide range of pH values, such as from lower to neutral pH values. Lower and neutral pH values ​​include, but are not limited to, 1.5 to 9.0, or 2.5 to 8.5; 3.0 to 8.0; 3.5 to 7.5, and 4.0 to 7 pH values. In some embodiments, the compounds disclosed and described herein, alone or in combination, can enhance the perceived sweetness of a fixed concentration of sweetener at low to neutral pH values ​​in taste tests at compound concentrations of 50 μM, 40 μM, 30 μM, 20 μM, or 10 μM. In some embodiments, the enhancement factor of the compounds disclosed and described herein, alone or in combination, at lower pH values ​​is substantially similar to the enhancement factor of the compounds at neutral pH values. This consistent sweetness enhancement property over a wide pH range allows the compounds disclosed and described herein, alone or in combination, to be widely used in a variety of foods and beverages.

[0080] In some embodiments, the ingestible composition includes flavorings. Any suitable flavoring can be used. In some embodiments, the flavoring comprises synthetic flavoring oils and flavoring aromatic substances or oils, oleoresins, and extracts derived from plants, leaves, flowers, fruits, etc., and combinations thereof. Non-limiting examples of flavoring oils include spearmint oil, cinnamon oil, deer hoof oil (methyl salicylate), peppermint oil, peppermint oil, clove oil, laurel oil, fennel oil, eucalyptus oil, thyme oil, cedarwood leaf oil, nutmeg oil, allspice, sage oil, nutmeg (mace), bitter almond oil, and cassia seed oil. Non-limiting examples of other flavors include natural and synthetic fruit flavorings such as vanilla and citrus oils including lemon, orange, lime, grapefruit, yazu, and sudachi, as well as fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, plum, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya, etc. Other potential flavorings include milk flavorings, butter flavorings, cheese flavorings, cream flavorings, and yogurt flavorings; vanilla flavorings; tea or coffee flavorings, such as green tea flavorings, oolong tea flavorings, tea flavorings, cocoa flavorings, chocolate flavorings, and coffee flavorings; mint flavorings, such as peppermint flavorings, spearmint flavorings, and Japanese mint flavorings; and spice flavorings, such as asafoetida flavorings, Indian anise flavorings, star anise flavorings, angelica flavorings, fennel flavorings, allspice flavorings, cinnamon flavorings, chamomile flavorings, mustard flavorings, cardamom flavorings, coriander flavorings, fennel flavorings, clove flavorings, pepper flavorings, coriander flavorings, and sassafras flavorings. Flavoring agents include: savory flavoring agents, Sichuan pepper flavoring agents, perilla flavoring agents, juniper berry flavoring agents, ginger flavoring agents, star anise flavoring agents, horseradish flavoring agents, thyme flavoring agents, tarragon flavoring agents, dill flavoring agents, bell pepper flavoring agents, nutmeg flavoring agents, basil flavoring agents, marjoram flavoring agents, rosemary flavoring agents, bay leaf flavoring agents, and wasabi (Japanese horseradish) flavoring agents; alcoholic flavoring agents, such as red wine flavoring agents, whiskey flavoring agents, brandy flavoring agents, rum flavoring agents, gin flavoring agents, and liqueur flavoring agents; floral flavoring agents; and vegetable flavoring agents, such as onion flavoring agents, garlic flavoring agents, cabbage flavoring agents, carrot flavoring agents, celery flavoring agents, mushroom flavoring agents, and tomato flavoring agents. These flavoring agents can be used in liquid or solid form and can be used alone or in combination.In dairy or dairy-like products, the most commonly used flavoring agents are agents that impart flavors such as vanilla, French vanilla, chocolate, banana, lemon, hazelnut, coconut, almond, strawberry, mocha, coffee, tea, chai, cinnamon, caramel, cream, brown sugar, toffee, pecan, pecan butter, toffee, Irish cream, white chocolate, raspberry, pumpkin pie spice, spearmint, or any combination thereof.

[0081] In some embodiments, the ingestible composition comprises vanillin or a vanillin analogue, which imparts a vanilla flavor to the flavoring agent. In some other embodiments, the ingestible composition comprises one or more lactones, which impart a creamy flavor to the flavoring agent.

[0082] In some embodiments, the ingestible composition comprises a yeast extract, such as yeast lysate. Such extracts can be obtained from any suitable yeast strain, wherein such extracts are suitable for human consumption. Non-limiting examples of such yeasts include: yeasts of the genus *Saccharomyces*, such as *Saccharomyces cerevisiae* or *Saccharomyces pastorianus*; yeasts of the genus *Candida*, such as *Candida utilis*; yeasts of the genus *Kluyveromyces*, such as *Kluyveromyces lactis* or *Kluyveromyces marxianus*; yeasts of the genus *Pichia*, such as *Pichia pastoris*; yeasts of the genus *Debaryomyces*, such as *Debaryomyces hansenii*; and yeasts of the genus *Zygosaccharomyces*, such as *Zygosaccharomyces mellis*. In some embodiments, the yeast is collected after brewing beer, sake, etc. In some implementations, the yeast is yeast that has been dried after collection (dry yeast).

[0083] Such extracts can be produced by any suitable means. Generally, yeast extracts or lysates are prepared by extracting the contents of yeast cells from cell wall material. In many cases, digestive enzymes in the cells (or other enzymes added to the composition) break down proteins and polynucleotides in yeast into amino acids, oligopeptides (e.g., 2 to 10 peptides), nucleotides, oligonucleotides (2 to 10 nucleotides), and mixtures thereof. Yeast lysates can be prepared by lysing yeast. For example, in some embodiments, cultured yeast is broken down or lysed by enzymatic hydrolysis, autodigestion, alkaline extraction, hot water extraction, acid hydrolysis, ultrasonic disruption, homogenization, freeze-thaw, etc. (two or more of these may be used in combination) to obtain yeast lysates. Yeast can be cultured using conventional methods. In some embodiments, cultured yeast is heat-treated and then treated with a lysin to obtain enzyme lysates. The heat treatment conditions are, for example, 80°C to 90°C for 5 to 30 minutes. As the lysin used for enzymatic hydrolysis, various enzymes can be used as long as they can lyse the yeast cell wall. The reaction conditions can be set to be optimal or suitable for the lysin used, and specific examples may include a temperature of 50°C to 60°C and a pH of 7.0 to 8.0. There are no particular limitations on the reaction time; for example, it can be 3 to 5 hours.

[0084] Compositions containing yeast lysates can be obtained from a variety of commercial sources. For example, in some embodiments, the yeast lysates are provided by a flavoring additive marketed under the name MODUMAX (DSM Food Specialties BV, Delft, Netherlands).

[0085] In some embodiments, the ingestible composition comprises a sweetener. Any suitable sweetener may be used in the ingestible compositions disclosed herein, including synthetic sweeteners, natural sweeteners, or any combination thereof. Examples of suitable synthetic sweeteners include, but are not limited to, N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methylpropyl-2-yl)isonicotinamide, or any edible-acceptable salt thereof, 3-hydroxybenzoic acid, or any compound listed in U.S. Patent Nos. 8,541,421, 8,815,956, 9,834,544, 8,592,592, 8,877,922, 9,000,054, and 9,000,051, and U.S. Patent Application Publication No. 2017 / 0119032. Suitable examples of natural sweeteners include, but are not limited to, hesperidin dihydrochalcone, hesperidin dihydrochalcone-4'-O' glucoside, neohesperidin dihydrochalcone, brazzein, hesperidin, folate, naringenin, naringenin, phloretin, glucosylated steviol glycoside, (2R,3R)-3-acetoxy-5,7,4'-trihydroxyflavanone, and (2R,3R)-3-acetoxy-5,7,3'-trihydroxy-4'-methoxyflavanone. Ketones, raspberry glycosides, thaumatin, monellin, miraculin, glycyrrhizin and their edible salts (e.g., monoammonium salts), naringin dihydrochalcone, myricetin, nobiletin, polymethoxyflavones, mixed methoxy and hydroxyflavones, quercetin, certain amino acids, etc. As used herein, the term "glucosylated steviol glycosides" refers to the product of enzymatic glucosylation of natural steviol glycoside compounds. Glucosylation typically occurs via glycosidic bonds, such as α-1,2, α-1,4, α-1,6, β-1,2, β-1,4, and β-1,6 bonds.

[0086] In some embodiments of any of the foregoing embodiments, the ingestible composition comprises 3-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2,2-dimethyl-N-propyl-propionamide, N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]-thiadiazin-5-yl)oxy)-2-methyl-propyl-2-yl)isonicotinamide, or an edible salt thereof. In some embodiments, the ingestible composition comprises N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-propyl-2-yl)isonicotinamide, or an edible salt thereof. In some embodiments, the ingestible composition comprises N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-propyl-2-yl)isonicotinamide.

[0087] In some embodiments, the ingestible composition comprises one or more umami-enhancing compounds. Such umami-enhancing compounds include, but are not limited to, compounds of natural origin or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 8,735,081, 8,124,121, and 8,968,708. In some embodiments, the umami-enhancing compound is (2R,4R)-1,2,4-trihydroxy-heptadec-16-ene, (2R,4R)-1,2,4-trihydroxy-heptadec-16-yne, or a mixture thereof. In some embodiments, the umami-enhancing compound is (3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol diacetate. In some embodiments, the umami-enhancing compound is N-(heptane-4-yl)benzo-[d][1,3]m-dioxane-5-carboxamide.

[0088] In some other embodiments, the ingestible composition comprises one or more cooling-enhancing compounds. Such cooling-enhancing compounds include, but are not limited to, compounds of natural origin, such as menthol or analogues thereof, or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 9,394,287 and 10,421,727. Non-limiting examples include N-ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, 2-(4-fluorophenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide, 2-(2-hydroxy-4-methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide, and 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)acetamide. 2-((2,3-dihydro-1H-indene-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiazo-5-ylmethyl)-acetamide, 2-((5-methoxybenzofuran-2-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiazo-2-ylmethyl)-acetamide, (E / Z)-2-methyl-2-butenal, (E / Z)-2-isopropyl-5-methyl-2-hexenal, phlorizin, naringenin, hesperidin, hesperidin dihydrochalcone, naringin dihydrochalcone and any combination thereof.

[0089] In some other embodiments, the ingestible composition comprises one or more bitterness-blocking or bitterness-masking compounds. Such bitterness-blocking or bitterness-masking compounds include, but are not limited to, compounds of natural origin or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 8,076,491, 8,445,692, and 9,247,759. Non-limiting examples include 3-(1-((3,5-dimethylisoxazol-4-yl)-methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)-imidazoline-2,4-dione, 4-(2,2,3-trimethylcyclopentyl)butyric acid, 3β-hydroxydihydrosaponin lactone, 3β-hydroxypelenolide, probenecid, sakuranetin, 6-methoxysakuranetin, jaceosidin, 4'-fluoro-6-methoxyflavone, 6,3'-dimethoxyflavone, 6-methoxyflavone, γ-aminobutyric acid, Nα,Nα-bis(carboxymethyl)-L-lysine Acids, (+ / -)abscisic acid, sodium gluconate, monosodium glutamate, sodium acetate, serotonin, 7-O-methylserotonin, serotonin, 2,4,dihydrobenzoic acid, neodiosmin, 1-carboxymethyl-5-hydroxy-2-hydroxymethylpyridinium, flavan-3-spiro-C-glycoside, poly-γ-glutamic acid, α,α-trehalose, taurine, (2)-gingerdione, 2,4,-dihydroxybenzoic acid, L-theanine, enterodiol, lariciresinol, enterolactone, matairesinol, and any combination thereof.

[0090] In some other embodiments, the ingestible composition comprises one or more acid-modifying compounds.

[0091] In some other embodiments, the ingestible composition comprises one or more taste-modifying compounds. Such taste-modifying compounds include, but are not limited to, tannins, cellulose materials, bamboo powder, etc.

[0092] In some other embodiments, the ingestible composition comprises one or more flavor-masking compounds. Such flavor-masking compounds include, but are not limited to, cellulose materials, materials extracted from fungi, materials extracted from plants, citric acid, carbonic acid (or carbonates), etc.

[0093] Flavored products

[0094] In some forms, this disclosure provides flavored products comprising any ingestible composition of the foregoing forms. In some embodiments, the flavored product is a beverage product, such as soda water, flavored water, tea, etc. In some other embodiments, the flavored product is a food product, such as yogurt. In some embodiments, the flavored product is an oral care product, such as toothpaste, mouthwash, dental floss, whitening agent, etc.

[0095] In embodiments where the flavored product is a beverage, the beverage may be selected from enhanced sparkling beverages, cola, lemon-lime sparkling beverages, orange sparkling beverages, grape sparkling beverages, strawberry sparkling beverages, pineapple sparkling beverages, ginger ale, root beer, fruit juice, fruit-flavored fruit juice, fruit juice beverages, honey beverages, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, fortified water beverages, vitamin-fortified water, near-water beverages, coconut water, tea beverages, coffee, cocoa beverages, beverages containing milk ingredients, beverages containing cereal extracts, and smoothies. In some embodiments, the beverage may be a soft drink.

[0096] In some embodiments of any form and implementation of flavored products described herein, the flavored product is a non-naturally occurring product, such as a packaged food or beverage product.

[0097] Other non-limiting examples of food and beverage products or formulations include sweet coatings, frostings, or icings of such products, or any entity comprising: soups, dry processed foods, beverages, ready-to-eat foods, canned or pickled foods, frozen processed foods, chilled processed foods, snack foods, baked goods, confectionery, dairy products, ice cream, meal replacements, pasta and noodles, and sauces, seasonings, condiments, baby food and / or spreads.

[0098] Generally, soups refer to canned / marinated, dehydrated, instant, refrigerated, UHT, and frozen soups. For the purposes of this definition, soup is a food made from meat, poultry, fish, vegetables, grains, fruits, and other ingredients, cooked in a liquid that may contain some or all of these ingredients in visible pieces. It may be clear (as broth) or thick (as chowder), smooth, mushy, or chunky, ready-to-eat, semi-concentrated, or concentrated, and can be served hot or cold as a first course or main course, or as a snack (sip) between meals. Soup can be used as an ingredient in the preparation of other dietary components, ranging from broths (consommés) to sauces (cream- or cheese-based soups).

[0099] Dehydrated and cooked food products generally refer to: (i) cooking aids, such as powdered, granular, paste-like, concentrated liquid products, including bouillon, broth, and broth-like products in compressed blocks, tablets, or powdered or granular form, sold separately as finished products or as ingredients in products, seasonings, and formulation mixtures (regardless of technology); (ii) dietary solution products, such as dehydrated soups and freeze-dried soups, including dehydrated soup mixtures, dehydrated instant soups, dehydrated ready-to-eat soups, dehydrated or self-heating preparations of ready-made dishes, meals, and single-serving main courses, including pasta, potatoes, and rice; and (iii) dietary garnish products, such as seasonings, marinades, salad dressings, salad toppings, dips, mixes, batter mixtures, storage-stable sauces, barbecue sauces, liquid formulation mixtures, concentrates, sauces or gravy mixtures, including salad formulation mixtures, sold as finished products or as ingredients in products, whether dehydrated, liquid, or frozen.

[0100] The beverage category generally refers to beverages, beverage mixtures, and concentrates, including but not limited to carbonated and non-carbonated beverages, alcoholic and non-alcoholic beverages, ready-to-drink beverages, liquid concentrates used to prepare beverages (such as soda water), and dry powder beverage precursor mixtures. The beverage category also includes alcoholic beverages, soft drinks, sports drinks, isotonic beverages, and hot beverages. Alcoholic beverages include, but are not limited to, beer, cider / pear liqueur, FABs, wine, and spirits. Soft drinks include, but are not limited to, carbonated beverages, such as cola and non-cola carbonated beverages; fruit juices, such as fruit juice, honey drinks, fruit juice beverages, and fruit-flavored beverages; bottled water, including soda water, spring water, and purified / catering water; functional beverages, which can be carbonated or non-carbonated, including sports drinks, energy drinks, or elixir beverages; and concentrates, such as ready-to-drink liquid and powder concentrates. Whether hot or cold, beverages include, but are not limited to, coffee or iced coffee, such as fresh, instant and blended coffee; tea or iced tea, such as black tea, green tea, white tea, oolong tea and flavored tea; and other beverages, including flavored, malt-based or plant-based powders, granules, blocks or tablets mixed with milk or water.

[0101] Snacks generally refer to any simple, informal meal, including but not limited to sweet and savory (salty, spicy, and other non-sweet) snacks and snack bars. Examples of snacks include, but are not limited to, fruit desserts, potato chips / crisps, extruded snacks, tortillas / cornflakes, popcorn, pretzels, nuts, and other sweet and savory snacks. Examples of snack bars include, but are not limited to, granola / cereal bars, breakfast bars, energy bars, fruit bars, and other snack bars.

[0102] Baked goods generally refer to any edible product whose preparation involves exposure to heat or excessive sunlight. Examples of baked goods include, but are not limited to, bread, buns, biscuits, muffins, cereals, toaster pastries, cakes, waffles, tortillas, soft biscuits, pies, bagels, egg tarts, quiche, cakes, any baked goods, and any combination thereof.

[0103] Ice cream generally refers to frozen desserts containing cream, sugar, and flavorings. Examples of ice cream include, but are not limited to: instant ice cream; family-sized ice cream; frozen yogurt and artisanal ice cream; and ice cream based on soy, oats, legumes (such as red beans and mung beans), and rice.

[0104] Confectionery generally refers to sweet-tasting edible products. Examples of confectionery include, but are not limited to, hard candy, gelatin, chocolate, sugar candy, chewing gum, and any combination of these products.

[0105] Meal replacement foods generally refer to any food designed to replace a regular diet, especially for those concerned about health or fitness. Examples of meal replacements include, but are not limited to, weight loss products and recovery products.

[0106] Ready-to-eat foods generally refer to any food that can be consumed as a meal without extensive preparation or processing. Ready-to-eat foods include products for which manufacturers have added recipe "skills," thus offering high levels of convenience, completeness, and readiness. Examples of ready-to-eat foods include, but are not limited to, canned / marinated, frozen, dried, and refrigerated ready-to-eat foods; dinner mixes; frozen pizzas; refrigerated pizzas; and pre-made salads.

[0107] Pasta and noodles include any pasta and / or noodles, including but not limited to canned, dried, and chilled / fresh pasta; as well as plain, instant, chilled, frozen, and snack noodles.

[0108] Canned / pickled foods include, but are not limited to, canned / pickled meat and meat products, fish / seafood, vegetables, tomatoes, beans, fruits, ready-to-eat foods, soups, pasta and other canned / pickled foods.

[0109] Frozen processed foods include, but are not limited to, frozen processed red meat, processed poultry, processed fish / seafood, processed vegetables, meat substitutes, processed potatoes, baked goods, desserts, ready-to-eat foods, pizzas, soups, noodles and other frozen foods.

[0110] Dry processed foods include, but are not limited to, rice, dessert mixes, dry ready-to-eat foods, dehydrated soups, instant soups, dried pasta, plain pasta, and instant noodles. Refrigerated processed foods include, but are not limited to, refrigerated processed meats, processed fish / seafood products, lunch boxes, fresh-cut fruit, ready-to-eat foods, pizzas, pre-made salads, soups, fresh pasta, and noodles.

[0111] Sauces, condiments and seasonings include, but are not limited to, tomato sauce and puree, broth / soup cubes, herbs and spices, monosodium glutamate (MSG), table sauces, soy sauces, pasta sauces, wet / cooking sauces, dry / powder mixtures, ketchup, mayonnaise, mustard, salad dressings, balsamic vinegar, dips, marinades, and other sauces, condiments and seasonings.

[0112] Infant food includes, but is not limited to, milk- or soy-based formula foods; as well as prepared, dried, and other infant foods.

[0113] Spreads include, but are not limited to, jams and preserves, honey, chocolate sauce, nut spreads, and yeast spreads.

[0114] Dairy products generally refer to edible products derived from the milk of mammals. Examples of dairy products include, but are not limited to, dairy drinks, cheese, yogurt and fermented milk beverages, and other dairy products.

[0115] The following are further examples of flavored products, particularly food and beverage products or formulations. Exemplary ingestible compositions include one or more candies, chocolates, chocolate chips, countlines, selflines / softlines, boxed varieties, standard boxed varieties, twist-wrapped miniature chocolates, flavored chocolates, toy-shaped chocolates, sandwich cookies, other chocolate confectionery, mints, standard mints, strong mints, hard candy, soft lozenges, gums, jellies and chewables, toffee, caramel and nougat, medicated candies, lollipops, licorice, other confectionery, bread, packaged / industrial bread, bulk / artificial bread, pastries, cakes, packaged / industrial cakes, bulk / artificial cakes, biscuits, and chocolate coatings. Cookies, sandwich cookies, tart biscuits, savory biscuits and crackers, bread substitutes, breakfast cereals, instant cereals, family breakfast cereals, flakes, muesli, other cereals, children's breakfast cereals, hot cereals, ice cream, ready-to-eat ice cream, single serving dairy ice cream, single serving water ice cream, multi-pack dairy ice cream, multi-pack water ice cream, family pack ice cream, family pack dairy ice cream, ice cream desserts, bulk ice cream, family pack water ice cream, frozen yogurt, artisanal ice cream, dairy products, milk, fresh / pasteurized milk, whole milk fresh / pasteurized milk, semi-skimmed fresh / pasteurized milk, extended shelf life / UHT milk, whole milk extended shelf life / UHT milk Semi-skimmed / UHT milk with extended shelf life, non-fat / UHT milk with extended shelf life, goat milk, condensed milk / unsalted condensed milk, plain condensed milk / unsalted condensed milk, flavored, functional and other condensed milk, flavored milk beverages, dairy-only flavored milk beverages, flavored milk beverages with fruit juice, soy milk, yogurt beverages, fermented milk beverages, coffee creamer, milk powder, flavored milk powder beverages, cream, cheese, processed cheese, spreadable cheese, processed cheese that is difficult to spread, unprocessed cheese, spreadable unprocessed cheese, hard cheese, packaged hard cheese, unpackaged hard cheese, yogurt, plain / natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, drinking yogurt, regular drinking yogurt, probiotic drinking yogurt, frozen and shelf-stable snacks, dairy-based snacks, dairy-based snacks... Bean desserts, frozen snacks, fresh cheese and quark cheese, plain fresh cheese and quark cheese, flavored fresh cheese and quark cheese, savory fresh cheese and quark cheese, sweet and savory snacks, fruit snacks, potato chips / fries, puffed snacks, tortilla chips / corn chips, popcorn, pretzels, nuts, other sweet and delicious snacks, snack bars, granola, breakfast bars, energy bars, fruit bars, other snack bars, meal replacements, weight loss products, recovery drinks, ready-to-eat foods, canned ready-to-eat foods, frozen ready-to-eat foods, dried ready-to-eat foods, frozen ready-to-eat meals, dinner mixes, frozen pizzas, chilled pizzas, soups, canned soups, dehydrated soups, instant soups, cold soups, hot soups, frozen soups, pasta, canned pasta, dried pasta.Frozen / fresh pasta, noodles, plain noodles, instant noodles, cup / bowl instant noodles, bagged instant noodles, frozen noodles, snack noodles, canned foods, canned meat and meat products, canned fish / seafood, canned vegetables, canned tomatoes, canned beans, canned fruit, canned ready-to-eat foods, canned soups, canned pasta, other canned foods, frozen foods, frozen processed red meat, frozen processed poultry, frozen processed fish / seafood, frozen processed vegetables, frozen meat substitutes, frozen potatoes, oven-baked potato chips, other oven-baked potato products, non-oven frozen potatoes, frozen baked foods, frozen desserts, frozen ready-to-eat foods, frozen pizzas, frozen soups, frozen noodles, other frozen foods, dried foods, dessert mixtures, dried ready-to-eat foods, dehydrated soups, instant soups, dried pasta, plain noodles, instant noodles, cup / bowl instant noodles, bagged instant noodles, refrigerated foods, refrigerated processed meats, refrigerated fish / seafood products, refrigerated processed fish, refrigerated coated fish Refrigerated smoked fish, refrigerated lunch packs, refrigerated ready-to-eat foods, refrigerated pizzas, refrigerated soups, refrigerated / fresh pasta, refrigerated noodles, oils and fats, olive oil, vegetable and seed oils, cooking fats, butter, margarine, spread oils and fats, functional spread oils and fats, sauces, seasonings and condiments, tomato paste and puree, broth / soup cubes, soup cubes, gravy granules, liquid soup bases and ingredients, herbs and spices, fermented sauces, soy sauces, pasta sauces, wet sauces, dry sauces / powder mixtures, tomato sauce, mayonnaise, regular mayonnaise, mustard, salad dressing, regular salad dressing, low-fat salad dressing, balsamic vinegar sauce, dips, marinades, other sauces, seasonings and condiments, baby food, formula milk powder, standard formula milk powder, growing-up formula milk powder, toddler formula milk powder, hypoallergenic formula, prepared baby food, dried baby food, other baby food, spreads, jams and preserves, honey, chocolate spread, nut spreads and yeast spreads. Exemplary ingestible compositions also include confectionery, baked goods, ice cream, dairy products, sweet and delicious snacks, snack bars, meal replacement products, ready-to-eat foods, soups, pasta, noodles, canned foods, frozen foods, dried foods, refrigerated foods, oils and fats, baby foods, or spreads, or mixtures thereof. Exemplary ingestible compositions also include breakfast cereals, sweetened beverages, or solid or liquid concentrate compositions for preparing beverages, ideally enabling the reduction of the concentration of previously known sugar sweeteners or artificial sweeteners.

[0116] Some embodiments provide chewable compositions that can be swallowed or not. In some embodiments, the chewable composition may be gum, chewing gum, saccharified gum, sugar-free gum, functional gum, bubble gum, which individually or in combination comprises compounds disclosed and described herein.

[0117] Typically, one or more of the compounds of the present invention are added to an ingestible composition in the presence of a sweetener, such as a sweet receptor modulator, a sweet receptor ligand modulator, a sweet flavor modulator, a sweet flavor enhancer, or a therapeutically effective amount, thereby giving the sweet flavor-modified ingestible composition an increased sweetness compared to an ingestible composition prepared without the compounds of the present invention, as generally determined by a human or animal, or, in the case of formulation testing, by a majority of a panel of at least eight human taste testers using procedures well known in the art.

[0118] In some embodiments, the compounds disclosed and described herein, alone or in combination, modulate the sweetness or other taste properties of other natural or synthetic sweeteners and the ingestible compositions thus prepared. In one embodiment, the compounds disclosed and described herein may be used or provided alone or in combination with their ligand-enhancing concentrations. For example, the amounts of the compounds disclosed and described herein, alone or in combination, may be from 0.001 ppm to 100 ppm, or a narrower alternative range of 0.1 ppm to 50 ppm, 0.01 ppm to 40 ppm, 0.05 ppm to 30 ppm, 0.01 ppm to 25 ppm, 0.1 ppm to 30 ppm, or 0.1 ppm to 25 ppm, or 1 ppm to 30 ppm, or 1 ppm to 25 ppm.

[0119] In some embodiments, the ingestible compositions disclosed herein may be provided, alone or in combination, as flavoring concentrate formulations, for example, suitable for subsequent processing to produce ready-to-use (i.e., ready-to-eat) products. A “flavoring concentrate formulation” refers to a formulation that should be reconstituted with one or more diluting media to become an ingestible composition. The term “ingestible composition” is used herein interchangeably with “ingestible composition,” which means any substance that can be ingested orally, whether alone or in combination with another substance, whether intended for consumption or not. In one embodiment, an ingestible composition includes a composition that can be directly consumed by a human or animal. Flavoring concentrate formulations are typically used by mixing with or diluting with one or more diluting media, such as any edible or ingestible ingredient or product, to impart or alter one or more flavorings to the diluting media. Such a process of use is generally referred to as reconstitution. Reconstitution can be carried out in a home or industrial setting. For example, a consumer may reconstitute frozen fruit juice concentrate in the kitchen with water or other aqueous media to obtain an ingestible fruit juice beverage. In another example, soft drink syrup concentrates can be reconstituted by manufacturers on a large industrial scale using water or other aqueous media to produce ready-to-use soft drinks. Because flavor concentrate formulations have a higher concentration of flavorings or seasonings than ready-to-use compositions, they are generally not suitable for direct consumption without reconstitution. There are many advantages to using and producing flavor concentrate formulations. For example, one advantage is reduced weight and volume during transportation, as flavor concentrate formulations can be reconstituted at the time of use by adding a suitable solvent, solid or liquid.

[0120] The flavor product according to any one of the foregoing embodiments may further include, in some embodiments, one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperidin, naringin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness, compounds that enhance saltiness, compounds that enhance cooling effects, or any combination thereof.

[0121] In some embodiments of any form and implementation of a sweetener or flavoring concentrate described herein, the sweetener or flavoring concentrate is a non-naturally occurring product, such as a composition specifically manufactured for the production of flavored products, such as food or beverage products.

[0122] In one embodiment, the flavor concentrate formulation comprises i) compounds disclosed and described herein, alone or in combination; ii) a carrier; and iii) optionally at least one adjuvant. The term "carrier" refers to a generally inert auxiliary substance, such as a solvent, binder, or other inert medium, used in combination with the compounds of the present invention and one or more optional adjuvants to form a formulation. For example, water or starch can be a carrier for the flavor concentrate formulation. In some embodiments, the carrier is the same as the dilution medium used to reconstitute the flavor concentrate formulation; in other embodiments, the carrier is different from the dilution medium. As used herein, the term "carrier" includes, but is not limited to, an ingestible carrier.

[0123] The term "adjuvant" refers to an additive that complements, stabilizes, maintains, or enhances the intended function or efficacy of an active ingredient, such as the compounds of the present invention. In one embodiment, at least one adjuvant comprises one or more flavoring agents. Flavoring agents may have any flavor known to those skilled in the art or to consumers, such as chocolate, coffee, tea, mocha, French vanilla, peanut butter, Indian milk tea, or combinations thereof. In another embodiment, at least one adjuvant comprises one or more sweeteners. The one or more sweeteners may be any sweetener described in this application. In yet another embodiment, the at least one adjuvant comprises one or more ingredients selected from the group consisting of: emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts are described in U.S. Patent No. 6,468,576, the entire contents of which are incorporated herein by reference for all purposes.

[0124] In one embodiment, the flavor concentrate formulation of the present invention may be in the form of liquids, solids, foam materials, pastes, gels, emulsions, and combinations thereof, including solutions and suspensions, such as liquids containing a certain amount of solid contents. In one embodiment, the flavor concentrate formulation is in the form of a liquid, including both water-based and non-water-based formulations. In some embodiments, the flavor concentrate formulation of the present invention may be carbonized or non-carbonated.

[0125] Flavor concentrate formulations may further include a freezing point lowering agent, a nucleating agent, or both as at least one adjuvant. A freezing point lowering agent is an ingestible compound or reagent that lowers the freezing point of a liquid or solvent to which the compound or reagent is added. That is, the freezing point of a liquid or solution containing a freezing point lowering agent is lower than the freezing point of a liquid or solvent without a freezing point lowering agent. In addition to lowering the initial freezing point, freezing point lowering agents can also lower the water activity of the flavor concentrate formulation. Examples of freezing point lowering agents include, but are not limited to, carbohydrates, oils, ethanol, polyols such as glycerol, and combinations thereof. A nucleating agent refers to an ingestible compound or reagent capable of promoting nucleation. The presence of a nucleating agent in a flavor concentrate formulation can improve the texture of slush and help maintain the physical properties and performance of slush at freezing temperatures by increasing the number of desired ice crystal centers. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

[0126] In one embodiment, the flavor concentrate formulation is formulated to have a low water activity to extend shelf life. Water activity is the ratio of the vapor pressure of water in a formulation to the vapor pressure of pure water at the same temperature. In one embodiment, the water activity of the flavor concentrate formulation is less than about 0.85. In another embodiment, the water activity of the flavor concentrate formulation is less than about 0.80. In yet another embodiment, the water activity of the flavor concentrate formulation is less than about 0.75.

[0127] In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least twice the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least five times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least ten times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least 15 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least 20 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least 30 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least 40 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least 50 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is at least 60 times the concentration of the compound in the ready-to-use composition. In one embodiment, the concentration of the compound in the flavor concentrate formulation is up to 100 times that in the ready-to-use composition.

[0128] In some embodiments, flavoring agents can be used in many different physical forms well known in the art to provide an initial flavor burst and / or a prolonged flavor sensation. These physical forms are not limited to this, and include free forms such as spray-dried, powdered, beaded, encapsulated, and mixtures thereof.

[0129] In some embodiments, the ingestible composition comprises a flavor-modifying compound according to any of the embodiments described above, as well as a building agent. Suitable building agents include, but are not limited to, maltodextrin (10DE, 18DE, or 5DE), corn syrup solids (20 or 36DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomaltitol, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and mixtures thereof. Furthermore, sugar (sucrose) or other caloric sweeteners (e.g., crystalline fructose, other carbohydrates, or sugar alcohols) can be used as building agents because they provide good uniformity of content without adding significant calories.

[0130] In one embodiment, at least one extender may be the extender described in U.S. Patent No. 8,993,027.

[0131] In one embodiment, at least one extender may be the extender described in U.S. Patent No. 6,607,771.

[0132] In one embodiment, at least one extender may be the extender described in U.S. Patent No. 6,932,982.

[0133] In some embodiments, the tabletop sweetener composition may further comprise at least one anti-caking agent. As used herein, the phrases "anti-caking agent" and "flow agent" refer to any composition that prevents, reduces, inhibits, or suppresses the attachment, binding, or contact of at least one sweetener with another sweetener molecule. Alternatively, an anti-caking agent may refer to any composition that contributes to uniformity of content and uniform dissolution. Non-limiting examples of anti-caking agents include cream of tartar, calcium silicate, silica, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pennsylvania), and tricalcium phosphate. In one embodiment, the anti-caking agent is present in the tabletop sweetener composition in an amount of about 0.001% to about 3% by weight of the tabletop sweetener composition.

[0134] In some embodiments, the sweetener composition of any of the foregoing forms and embodiments thereof is encapsulated using typical methods for encapsulating flavoring or fragrance compounds. Non-limiting examples of such technologies are described in U.S. Patent Application Publications 2016 / 0235102, 2019 / 0082727, 2018 / 0369777, 2018 / 0103667, 2016 / 0346752, 2015 / 0164117, 2014 / 0056836, 2012 / 0027866, 2010 / 0172945, and 2007 / 0128234, and U.S. Patents 7,488,503, 6,416,799, 5,897,897, 5,786,017, 5,603,971, 4,689,235, 4,610,890, 3,704,137, 3,041,180, and 2,809,895. All prior patent publications and patents are incorporated herein by reference, as if their entire contents were set forth herein.

[0135] Non-animal protein materials and products made from them

[0136] Products designed to replace or substitute for meat or dairy products typically rely on a variety of non-animal-based materials, such as starches and proteins derived from plants, algae, fungi, or combinations thereof, to mimic the texture and flavor of meat or dairy. Non-limiting examples of non-animal-based proteins include plant proteins such as pea protein, soy protein, almond protein, cashew protein, low-erucic acid canola (rapeseed) protein, chickpea protein, broad bean protein, sunflower protein, wheat protein, oat protein, barley protein, potato protein, and combinations thereof. Due to the compositional differences between such plant-based materials and animal-derived materials, such as the lack of glutamate-containing proteins and glutathione, these products may lack the umami or rich flavor that consumers traditionally associate with meat or dairy, or may have a bitterness that animal proteins lack.

[0137] Therefore, in some forms, this disclosure provides a flavored product comprising a plant-based material (e.g., plant-based starch, plant-based protein, or a combination thereof) and a zinc salt according to any of the illustrated embodiments. In some further embodiments, the flavored product may include any of the features described above for the combination of features of an ingestible composition containing a zinc salt. In some embodiments, the flavored product is a beverage, such as soy milk, almond milk, rice milk, oat milk, protein drinks, meal replacement drinks, or other similar products. In some other embodiments, the flavored product is a meat substitute product, such as a plant-based chicken product (e.g., plant-based chicken nuggets), a plant-based beef product (e.g., a plant-based burger), etc. In some other embodiments, the flavored product is a protein powder, a dietary substitute powder, a plant-based creamer for coffee or tea, etc. In some additional embodiments, any such product contains additional ingredients and has additional features, such as those commonly used in the preparation and / or manufacture of such products. For example, according to known techniques in the relevant art, flavor-modifying compounds may be combined with other flavoring agents and taste modifiers, or even encapsulated in certain materials. The appropriate concentration of the flavor-modifying compound is as described above.

[0138] In some embodiments, the flavored product comprises one or more plant-based proteins that impart bitterness, which is at least partially reduced by using flavor-modifying compounds in the product. Such plant-based proteins include, but are not limited to, pea protein, soy protein, almond protein, cashew protein, low-erucic acid rapeseed protein, chickpea protein, broad bean protein, sunflower protein, wheat protein, oat protein, barley protein, potato protein, and combinations thereof.

[0139] In some further embodiments similar to the above embodiments, algal or fungal proteins or starches are used alternatively. In some embodiments, these flavored products also contain fibers to provide texture to the product. Suitable fibers include, but are not limited to, psyllium fiber, pea fiber, potato fiber, gelling polysaccharides, soluble corn fiber (glucan and / or maltodextrin), citrus fiber, and combinations thereof. In such products, flavor-modifying compounds can be introduced in any suitable manner. In some embodiments, flavor-modifying compounds are incorporated together with other flavor-enhancing ingredients into flavored emulsions, such as water-in-oil emulsions.

[0140] Non-meat protein materials and products made from them

[0141] Certain non-meat animal proteins, such as milk proteins and proteins from bone broth, are commonly used in food products and are also sold as the main ingredient in some protein powders. These proteins may impart a bitter taste that consumers may not want. This is particularly true for protein isolates, such as whey protein, collagen, casein, etc. Therefore, this disclosure provides ingestible compositions comprising non-meat animal proteins and flavor-modifying compounds. According to embodiments set forth in the preceding sections of this disclosure, the flavor-modifying compositions may be present in any suitable combination. In some embodiments, the non-meat animal protein is a bone protein, such as collagen derived from animal bones, such as those from cows, pigs, donkeys, horses, chickens, ducks, goats, geese, rabbits, lambs, sheep, buffalo, ostriches, camels, etc. In some embodiments, the non-meat animal protein is a milk protein, such as whey protein, casein, or any combination thereof. The milk may be from any suitable animal, such as cows, donkeys, horses, sheep, buffalo, camels, etc.

[0142] Flavor-modifying compositions can also be included in certain food or beverage products, including animal milk or materials derived from animal milk. Such products include cheese, cheese spreads, yogurt, kefir, milk, processed dairy products, cottage cheese, sour cream, butter, etc.

[0143] Uses in oral care products

[0144] Oral care products typically contain ingredients that impart astringency or bitterness. These ingredients include menthol, menthol analogues, peppermint extract, sodium bicarbonate, potassium persulfate (alkali metal persulfate), hexadecylpyridine chloride, lauramide propyl betaine, cocamidopropyl betaine, arginine, hydrogen peroxide, chlorhexidine gluconate, potassium nitrate, pentasodium triphosphate, tetrasodium pyrophosphate, stannous fluoride, thymol, methyl salicylate, eucalyptol, or any combination thereof. Suitable oral care products include toothpaste, mouthwash, whitening agents, and dental floss. These oral care products may contain flavor-modifying compounds to block or mask the bitterness of such compounds.

[0145] Example

[0146] To further illustrate the invention, the following embodiments are included. These embodiments should not be construed as specifically limiting the invention. Variations of these embodiments within the scope of the claims are within the capabilities of those skilled in the art and are considered to fall within the scope of the invention described and claimed herein. The reader will recognize that those skilled in the art, upon mastering this disclosure, can prepare and use the invention without exhaustive examples.

[0147] Example 1 – Preparation of compounds 102 and 103

[0148] Hesperidin (10.0 g, 33.1 mmol) was dissolved in 500 mL of analytical grade acetone, and then anhydrous potassium carbonate (4.57 g, 33.1 mmol, 1 equivalent) was added. The mixture was refluxed and stirred for 1.5 hours, followed by slow dropwise addition of iodomethane (2.86 mL, 40 mmol, 1.2 equivalent). The mixture was refluxed for 17 hours, and the anhydrous potassium carbonate was removed by filtration. The acetone was evaporated to obtain a yellow powdery crude product, which was separated by silica gel column chromatography (petroleum ether / ethyl acetate = 2:1, v / v) to obtain a solid product. Then, 1.7 g of the solid product was dissolved in 25 mL of acetonitrile (ACN). The solution was injected into a Gilson preparative HPLC system equipped with a Phenomenex Luna PFP (2) column (150 × 21.20 mm, 5 µm). The elution gradient was from 55% ACN to 70% ACN over 10 minutes. The injection volume was 500 µL, and the UV detection wavelengths were 285 nm and 320 nm. Compounds 102 and 103 were obtained as pale white powders. The chemical structures of compounds 102 and 103 were determined by NMR analysis.

[0149] Example 2 – Preparation of Compound 104

[0150] 410 mg (1.36 mmol) of succinyl acetone was dissolved in 30 mL of analytical grade acetone, followed by the addition of anhydrous potassium carbonate (500 mg, 3.62 mmol), and then iodomethane (529 mg, 3.72 mmol, 2.6 equivalents) was slowly added dropwise. The mixture was heated under reflux for 17 hours, filtered to remove the anhydrous potassium carbonate, and the acetone was evaporated to obtain a yellow powdery crude product. 400 mg of the crude product was dissolved in 10 mL of acetonitrile (ACN). This solution was injected into a Gilson preparative HPLC system equipped with a Phenomenex Luna C18 (2) column (150 mm × 21.20 mm, 5 µm). The elution gradient was from 50% ACN to 70% ACN over 10 minutes. The injection volume was 300 µL, and the UV detection wavelengths were 285 nm and 320 nm. The obtained compound 104 was a pale white powder. The chemical structure of compound 104 was determined by NMR analysis.

[0151] Example 3 – Sensory Testing

[0152] Compounds 101 and 102 underwent human sensory testing. A panel of 20 trained members evaluated several sets of three samples (a reference sample containing the flavoring agent, one test sample containing the same concentration of the flavoring agent and 10 ppm of compound 101, and another test sample containing the same concentration of the flavoring agent and 1 ppm of compound 102). Members were asked to rate the samples on a scale of -5 to 5 based on one or more sensory characteristics (e.g., sweetness, licorice flavor, sweet aftertaste, sourness, saltiness, and umami), where -5 indicates a strong masking effect relative to the reference sample, 5 indicates a strong enhancing effect relative to the reference sample, and 0 indicates the strength of the reference sample (water). All solutions were aqueous solutions. The average evaluation results are shown in Table 1.

[0153] Table 1

[0154]

[0155] *SG95 refers to a stevia leaf extract containing at least 95% by weight of steviol glycosides.

[0156] Example 4 – Sensory Testing

[0157] Compounds 103 and 104 underwent human sensory testing. A panel of 20 trained members evaluated several sets of three samples (a reference sample containing the flavoring agent, one test sample containing the same concentration of the flavoring agent and 1 ppm of compound 103, and another test sample containing the same concentration of the flavoring agent and 1 ppm of compound 102). Members were asked to rate the samples on a scale of -5 to 5 based on one or more sensory characteristics (e.g., sweetness, saltiness, and umami), where -5 indicates a strong masking effect relative to the reference sample, 5 indicates a strong enhancing effect relative to the reference sample, and 0 indicates the strength of the reference sample (water). All solutions were aqueous solutions. Average evaluation results are shown in Table 2.

[0158] Table 2

[0159] .

Claims

1. A flavor-modifying compound for modifying the flavor of an ingestible composition, wherein the flavor-modifying compound is 5,7,4'-trihydroxy-8-methylflavanone, 5,3'-dihydroxy-7,4'-dimethoxyflavanone, 5-hydroxy-7,3',4'-trimethoxyflavanone, 5,4'-dihydroxy-7,3'-dimethoxyflavanone, a salt of any of the above compounds, or any combination thereof.

2. The use according to claim 1, wherein modifying the flavor of the ingestible composition includes enhancing the sweetness of the ingestible composition.

3. The use according to claim 1, wherein modifying the flavor of the ingestible composition includes enhancing the umami flavor of the ingestible composition.

4. The use according to claim 1, wherein modifying the flavor of the ingestible composition includes enhancing the saltiness of the ingestible composition.

5. The use according to claim 1, wherein modifying the flavor of the ingestible composition includes reducing the off-flavor of the ingestible composition.

6. The use according to claim 5, wherein the ingestible composition comprises a high-intensity sweetener, and odor reduction comprises reducing the licorice flavor or reducing the residual sweetness of the high-intensity sweetener.

7. The use according to any one of claims 1 to 6, wherein the flavor-modifying compound is 5,7,4'-trihydroxy-8-methylflavanone.

8. The use according to any one of claims 1 to 6, wherein the flavor-modifying compound is 5,3'-dihydroxy-7,4'-dimethoxyflavanone.

9. The use according to any one of claims 1 to 6, wherein the flavor-modifying compound is 5-hydroxy-7,3',4'-trimethoxyflavanone.

10. The use according to any one of claims 1 to 6, wherein the flavor-modifying compound is 5,4'-dihydroxy-7,3'-dimethoxyflavanone.

11. The use according to any one of claims 1 to 10, wherein the concentration of the flavor-modifying compound used in the ingestible composition ranges from 0.01 ppm to 1000 ppm.

12. The use according to any one of claims 6 to 9, wherein the ingestible composition comprises one or more bitterness enhancers.

13. A method of modifying the flavor of an ingestible composition, the method comprising introducing a flavor-modifying compound into the ingestible composition, wherein the flavor-modifying compound is 5,7,4'-trihydroxy-8-methylflavanone, 5,3'-dihydroxy-7,4'-dimethoxyflavanone, 5-hydroxy-7,3',4'-trimethoxyflavanone, 5,4'-dihydroxy-7,3'-dimethoxyflavanone, a salt of any of the above compounds, or any combination thereof.

14. An ingestible composition comprising: (a) an extender or carrier; and (b) a flavor-modifying compound, wherein the flavor-modifying compound is 5,7,4'-trihydroxy-8-methylflavanone, 5,3'-dihydroxy-7,4'-dimethoxyflavanone, 5-hydroxy-7,3',4'-trimethoxyflavanone, 5,4'-dihydroxy-7,3'-dimethoxyflavanone, a salt of any of the above compounds, or any combination thereof.

15. A flavored product comprising the ingestible composition of claim 14.

16. The flavored product according to claim 15, wherein the product is a beverage product, a food product, an oral care product, or a pharmaceutical product.

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