Compositions with sugar-like characteristics

Abstract

Disclosed herein is a sweetener composition comprising at least one compound of formula (I) and at least one additional sweetener to provide a "sugar-like" feature. Beneficially, the sweetener composition provides features similar to sucrose, including maximum response, flavor characteristics, time characteristics, adaptation behavior and mouthfeel. The sweetener composition can be included in various foods, beverages and other consumable products to provide a pure sugar-like taste, and can be used as a sweetener or sweetness enhancer in low-sugar foods, beverages and other consumable products.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of U.S. Provisional Patent Application No. 62 / 860,701, filed on June 12, 2019, which is hereby incorporated by reference in its entirety.

[0003] Disclosed herein is a sweetener composition comprising at least one compound of formula (I) and at least one additional sweetener to provide a "sugar-like" feature. Beneficially, the sweetener composition provides features similar to sucrose, including maximum response, flavor characteristics, time characteristics, adaptation behavior and mouthfeel. The sweetener composition can be included in various foods, beverages and other consumable products to provide a pure sugar-like taste, and can be used as a sweetener or sweetness enhancer in low-sugar foods, beverages and other consumable products.

[0004] Sugar and sweeteners are widely used in food, beverages and other consumable products, and play a key role in the choice of consumers and the preference of such products. What is expected is the sweet taste of sugar and / or the flavor caused by sugar. Sucrose imparts a taste preferred by consumers, which is the "gold standard" in terms of the sweet taste onset (appearance time) and sweet taste decay (fading time) of expectation. Although sucrose provides excellent sweet taste characteristics, it is high in calories. Calorie-free or low-calorie sweeteners (both nutritive and non-nutritive) have been introduced to meet the needs of consumers for sweet products providing calorie-free or low-calorie sweet taste.

[0005] The major challenge of replacing sucrose with non-nutritive high-efficiency sweeteners is to achieve a sweet taste characteristic similar to sucrose. In addition, sweeteners may be difficult to be formulated into products such as food and beverages. Sweeteners cannot simply be substituted into products containing sugar. There may be various formulation and processing challenges, including finding the desired sugar taste when using combined sugars and / or sweeteners, and removing any undesirable taste characteristics that they can impart. In taste, no-calorie or low-calorie sweeteners show time characteristics, maximum response, flavor characteristics, mouthfeel and / or adaptation behavior that are different from sugar. Specifically, no-calorie or low-calorie sweeteners show delayed sweet taste onset, long sweet aftertaste, bitterness, metallic taste, astringency, cool taste and / or liquorice-like taste.

[0006] Therefore, there is a continuing need for sweetener compositions that provide "sugar-like" characteristics, including the maximum response of sucrose, flavor characteristics (i.e., lack of detectable off-tastes (e.g., metallic notes, licorice notes, and bitterness)), cooling taste, and adaptation behavior. There is also a mouthfeel aspect that is characteristic of the "sugar-like" taste. There is a clear consumer demand for natural non-caloric and / or low-calorie sweeteners that have the same taste qualities as sucrose.

[0007] There is also a need to develop natural low-calorie or no-calorie sweeteners (also referred to as low-calorie and / or zero-calorie sweeteners) that provide temporal and flavor characteristics similar to sucrose. This need is to replace the detectable off-flavors (e.g., metallic, licorice, and bitter), cooling, and adaptive behavior of high-potency sweeteners while still providing natural non-caloric sweeteners with the same taste qualities as sucrose.

[0008] Additionally, there remains a need to develop sweetening compositions, such as foods, beverages and / or other consumable products, containing low-calorie or no-calorie sweetener compositions that have more sugar-like characteristics than currently available low-calorie or no-calorie sweetener compositions. Summary of the invention

[0009] Sweetener compositions and foods, beverages and / or other consumable products containing the sweetener compositions are disclosed herein. The sweetener compositions described herein have "sugar-like" properties and can be beneficially included in various foods, beverages and / or other consumable products to provide a pure sugar-like taste while providing low-sugar foods, beverages and other consumable products.

[0010] In one embodiment, the sweetener composition comprises: (a) an effective amount of at least one compound of formula (I) to provide at least 1% of the equivalent sucrose sweetness of the sweetener composition:

[0011] Formula (I) or its edible or physiologically acceptable salt or stereoisomeric form, wherein: R1 is hydrogen or C1-C6 alkyl; R2-R5 and R7 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, hydroxyl or trifluoromethyl; and R6 is I, hydrogen, C4-C6 alkyl, C4-C6 alkoxy or hydroxyl; and (b) at least one additional sweetener, the at least one additional sweetener comprising a full-calorie, low-calorie and / or zero-calorie sweetener, wherein the sweetener composition provides a more sugar-like characteristic than a sweetener composition without the compound of formula (I).

[0012] In another embodiment, a consumable food, beverage or other product comprises: one or more sweetener compositions described herein at a concentration of about 5 ppm to about 4000 ppm; at least one additive, bulking agent and / or functional ingredient; and a food, beverage or other consumable composition, wherein the consumable food, beverage or other product has a sweetness equivalent to a sucrose solution having a concentration between 10,000 ppm and 400,000 ppm (1-40 equivalent sucrose sweetness). In some embodiments, the sweetener compound has the following structure:

[0013]

[0014] In another embodiment, a method for enhancing the sugar-like characteristics of a consumable food, beverage, or other product comprises providing a sweet consumable food, beverage, or other product composition; and adding to the product one or more sweetener compositions described herein.

[0015] By various embodiments described herein, various sweetener compositions can be prepared and used that impart desired sweetness levels and "sugar-like" properties (including maximum response, flavor characteristics, adaptation behavior, and mouthfeel). These sweetener compositions can be used as sweeteners in many applications, including but not limited to food products, pharmaceutical compositions, edible gel mixtures and compositions, dental compositions, sweets, condiments, chewing gum, cereal compositions, baked goods, dairy products, table sweeteners, beverage products, fruit preparations and concentrates, seasonings, frozen foods, canned foods, desserts, bars, snacks, sauces, and spreads. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1 The concentration relationship between sucrose and test compound sweeteners using the dose response model as described in Example 1 is shown.

[0017] Figure 2 A rating scale for sweetness intensity on the gLMS scale is shown to assess the different sweetness intensities assessed in Example 1.

[0018] Figure 3 The sweetness intensity scale for blends of test compound sweeteners and Reb M as evaluated in Example 2 is shown.

[0019] Reference will now be made in detail to various embodiments of the present invention, examples of which are shown in the accompanying drawings. In the following description, a large number of specific details are set forth in order to provide a thorough understanding of the present invention. However, unless otherwise indicated or implied from the context, the details are intended to be examples and should not be considered to limit the scope of the present invention in any way. In addition, the features described in conjunction with each or a particular embodiment should not be understood as being unsuitable for use in conjunction with other embodiments disclosed herein, unless such exclusivity is explicitly stated or implied from the context.

[0020] All terms used herein are only used for the purpose of describing specific embodiments and are not intended to be limited in any way or scope. For example, unless the context clearly indicates otherwise, the singular forms "one", "a kind of" and "the" used in this specification and the appended claims may include plural forms. In addition, all units, prefixes and symbols can be expressed in the form accepted by their SI. The numerical ranges listed in this specification include numbers within the limited range. Throughout this disclosure, various aspects are presented in range format. It should be understood that the description of the range format is only for convenience and simplicity, and should not be interpreted as an unchangeable limitation to the scope of the invention. Therefore, the description of the range should be considered to specifically disclose all possible sub-ranges and single numerical values ​​within the range (for example, 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4 and 5).

[0021] In order to make it easier to understand the present invention, some terms are first defined. Unless otherwise defined, all technical terms and scientific terms used herein have the same meaning as those generally understood by those of ordinary skill in the art to which the embodiments of the present invention belong. Many methods and materials similar to, modified or equivalent to those described herein can be used to practice the embodiments without excessive experimentation. When describing and claiming the embodiments, the following terms will be used according to the definitions listed below.

[0022] As used herein, the term "about" refers to variations in the numerically represented quantity that may occur due to, for example, typical measurements and processing procedures; careless errors in such procedures; differences in the manufacture, origin, or purity of ingredients; etc. Whether or not modified by the term "about," the claims include equivalents to the quantities.

[0023] The term "alkoxy" means -OR radical or group, wherein R is an alkyl group as defined above, such as methoxy, ethoxy, propoxy or 2-propoxy, n-butoxy, isobutoxy or tert-butoxy, etc. In certain embodiments, preferred alkoxy groups of the present invention have 1 to 6 carbon atoms. In other embodiments, preferred alkoxy groups of the present invention have three or more carbon atoms, preferably 4 to 6 carbon atoms. Alkoxy groups may be optionally substituted when effective valence permits. Examples of substituted alkoxy groups include trifluoromethoxy, hydroxymethyl, hydroxyethyl, hydroxypropyl and alkoxyalkyl groups, such as methoxymethyl, methoxyethyl, polyoxyethylene, polyoxypropylene and similar groups. Unless otherwise specified as "unsubstituted", the chemical moieties mentioned herein should be understood to include substituted variations.

[0024] The term "alkyl" means a saturated straight or branched hydrocarbon chain having, for example, 1 to 20 carbon atoms. In some embodiments, the alkyl group includes a "C1 to C6 alkyl" group (alternatively referred to as a "low alkyl" group), which includes methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2,3-dimethylbutyl, hexyl, n-hexyl, tert-hexyl, neohexyl, isohexyl, sec-hexyl, etc. In certain embodiments, the preferred alkyl groups of the present invention have 1 to 6 carbon atoms. In certain embodiments, the preferred alkyl groups of the present invention have three or more carbon atoms, preferably 4 to 6 carbon atoms. The alkyl group may be optionally substituted when the effective valence permits. Unless otherwise specified as "unsubstituted", the chemical moieties mentioned herein should be understood to include substituted variations.

[0025] As used herein, the term "Brix" refers to the sugar content in an aqueous solution in terms of sucrose. One Brix is ​​1 gram of sucrose in 100 grams of solution. The Brix of a sweetener compound or composition can be calculated by a sensory evaluation panel using the sweetness relative to sucrose. For example, the sweetener compound of formula (I) is about 100 times the sweetness of sucrose; therefore, the amount of the sweetener compound of formula (I) equivalent to 1 Brix in terms of sucrose is about 100 ppm of the sweetener compound of formula (I). The equivalent sweetness of the sweetener compound expressed in Brix can be similarly calculated using the concentration response determined by the sensory evaluation panel. Approximate relative sweetness values ​​for sweeteners that can be used as sucrose substitutes are listed in Table 1.1 of Alternative Sweeteners, 4th Edition, Lyn O'Brien-Nabors CRC Press (published October 26, 2016), ISBN 9781138198562-CAT#K31388. The contents of this reference are incorporated herein by reference for all purposes.

[0026] As used herein, the term "combination" refers to a mixture of two or more compounds (or other referenced components). The combination may include, but is not limited to, a combination of one or more compounds of formula (I) or their physiologically acceptable salts, derivatives, diastereomers or enantiomers, or one or more additional sweeteners.

[0027] As used herein, and unless otherwise indicated, the term "edible or physiologically acceptable salt" refers to any edible or physiologically acceptable salt, ester, or salt of such an ester of a compound of the invention, which, when ingested, is capable of (directly or indirectly) providing a compound of the invention or a metabolite, residue, or portion thereof characterized by the ability to provide characteristics similar to sucrose (including maximum response, flavor characteristics, temporal characteristics, adaptation behavior, and mouthfeel). In certain embodiments, the preferred edible or physiologically acceptable salt of a compound of formula (I) is a hydrochloride.

[0028] As used herein, the term "enantiomerically pure" means a stereomerically pure composition of a compound having at least one chiral center.

[0029] As used herein, and unless otherwise indicated, the terms "halo" and "halogen" refer to a fluorine, chlorine, bromine or iodine atom. One or more halogens may be present, the same or different.

[0030] As used herein, the term "pharmaceutically acceptable salt" refers to a salt prepared from a pharmaceutically acceptable non-toxic acid or base (including inorganic acid and base and organic acid and base). Suitable pharmaceutically acceptable base addition salts of the compounds provided herein (such as compounds of formula (I), compound 1, compound 2, compound 3, compound 4, compound 5, compound 6, compound 7, compound 8 or compound 9)) include, but are not limited to, metal salts made from aluminum, calcium, lithium, magnesium, potassium, sodium and zinc, or organic salts made from lysine, N, N'-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, ethylenediamine, meglumine (N-methylglucamine) and procaine. Suitable non-toxic acids include, but are not limited to, inorganic and organic acids such as acetic acid, alginic acid, anthranilic acid, benzenesulfonic acid, benzoic acid, camphorsulfonic acid, citric acid, ethylenesulfonic acid, formic acid, fumaric acid, furoic acid, galacturonic acid, gluconic acid, glucuronic acid, glutamic acid, glycolic acid, hydrobromic acid, hydrochloric acid, isethionic acid, lactic acid, maleic acid, malic acid, mandelic acid, methanesulfonic acid, mucic acid, nitric acid, pamoic acid, pantothenic acid, phenylacetic acid, phosphoric acid, propionic acid, salicylic acid, stearic acid, succinic acid, sulfanilic acid, sulfuric acid, tartaric acid, and p-toluenesulfonic acid. Specific non-toxic acids include hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, and methanesulfonic acid. Other non-toxic acids are well known in the art, see, for example, Remington's Pharmaceutical Sciences, 18th edition, Mack Publishing, Easton PA, 1990 or Remington: The Science and Practice of Pharmacy, 19th edition, Mack Publishing, Easton PA, 1995.

[0031] As used herein, the term "ppm" means parts per million and is a relative weight parameter. Parts per million are micrograms per gram, such that a component present at 10 ppm is present at 10 micrograms of the particular component per 1 gram of aggregate mixture.

[0032] As used herein, the term "stereoisomer" or "stereoisomeric form" refers to one stereoisomer of a compound of formula (I) and is substantially free of other stereoisomers of the compound. For example, a stereoisomerically pure compound with one chiral center will be substantially free of the opposite enantiomer of the compound. A stereoisomerically pure compound with two chiral centers will be substantially free of other diastereomers of the compound. A typical stereoisomerically pure compound contains greater than about 80% by weight of one stereoisomer of the compound and less than about 20% by weight of other stereoisomers of the compound, greater than about 90% by weight of one stereoisomer of the compound and less than about 10% by weight of other stereoisomers of the compound, greater than about 95% by weight of one stereoisomer of the compound and less than about 5% by weight of other stereoisomers of the compound, or greater than about 97% by weight of one stereoisomer of the compound and less than about 3% by weight of other stereoisomers of the compound.

[0033] The compound of formula (I) may have a chiral center, and may occur as a racemate, a single enantiomer or a diastereomer and a mixture thereof. All such isomeric forms (including their mixtures) are included in the embodiments disclosed herein. The embodiments disclosed herein encompass the use of stereoisomerically pure forms of such compounds, and use mixtures of those forms. In certain embodiments, a racemic mixture of isomers (each stereoisomer of the compound of about 50% by weight) is adopted in a sweetener composition. These isomers can be synthesized or separated asymmetrically using standard techniques (such as chiral chromatographic columns, chiral separation agents or via the chiral reduction of enzymes). See, e.g., Jacques, J. et al., Enantiomers, Racemates and Resolutions, Wiley Interscience, New York, 1981); Wilen, SH et al., Tetrahedron, Vol. 33, p. 2725, 1977; Eliel, EL, Stereochemistry of Carbon Compounds, McGraw Hill, NY, 1962); and Wilen, SH, Tables of Resolving Agents and Optical Resolutions, p. 268, EL Eliel, ed., Univ. of Notre Dame, Notre Dame, IN, 1972.

[0034] As used herein, a "substantially pure" compound is substantially free of other compounds (i.e., impurities). In certain embodiments, a substantially pure compound contains less than about 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.4%, 0.3%, 0.2%, 0.1%, 0.05% or 0.01% of one or more other compounds based on weight. Detection of other compounds can be achieved by any method apparent to those of ordinary skill in the art, including but not limited to chemical analysis methods, such as, for example, mass spectrometry, spectral analysis, thermal analysis, elemental combustion analysis and / or chromatographic analysis.

[0035] As used herein, the term "substituted" means a group that may be substituted by one or more independent substituents, examples of which include, but are not limited to, halo, alkyl, alkoxy, trifluoromethyl, trifluoromethoxy, hydroxy, alkoxy, cycloalkyloxy, heterocyclooxy, oxy, alkanoyl, alkylcarbonyl, cycloalkyl, aryl, aryloxy, aralkyl, alkanoyloxy, cyano, azido, amino, alkylamino, -S(0)2OH, arylamino, aralkylamino, cycloalkylamino, heterocycloamino, mono- and di-substituted amino (wherein the two substituents on the amino group are selected from alkyl, aryl, aralkyl, alkanoylamino, aroylamino, arylalkanoylamino, substituted alkanoylamino, substituted arylamino, substituted arylalkanoyl) amino, thiol, alkylthio, arylthio, aralkylthio, cycloalkylthio, heterocyclicthio, alkylthiocarbonyl, arylthiocarbonyl, aralkylthiocarbonyl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, oxo, sulfonamido (e.g., -SO2NH2), substituted sulfonamido, nitro, carboxyl, carbamoyl (e.g., -CONH2), substituted carbamoyl (e.g., -CONHalkyl, -CONHRyl, -CONHRalkyl, or an example in which there are two substituents selected from alkyl, aryl or aralkyl on nitrogen), alkoxycarbonyl, aryl, substituted aryl, guanidinyl, and heterocyclic groups such as indolyl, imidazolyl, furanyl, thienyl, thiazolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, and the like.

[0036] As used herein, the phrases "sugar-like features", "sugar-like taste", "sugar-like sweetness", "sugar-containing" and "sugar-like" are synonymous.Sugar-like features include any features similar to sucrose, and include but are not limited to maximum response, flavor characteristics, time characteristics, adaptation behavior, mouthfeel, concentration / response functional behavior, tastants and flavor / sweetness interactions, and temperature effects. These features are aspects in which the taste of sucrose is different from the taste of natural and synthetic high-potency sweeteners. Whether the feature is more sugar-like is determined by a specialized taster or a trained sensory evaluation panel to the evaluation of sugar and a composition comprising at least one natural and / or synthetic high-potency sweetener with and without a sweet taste improvement composition. Such evaluations quantify the similarity of the features of a composition comprising a sweetener composition according to the present invention compared to a composition comprising sugar. Suitable procedures for determining whether a composition has a more sugar-like taste are well known in the art. In addition, the flavor characteristics of a sweetener composition are the quantitative distribution of the relative intensities of all taste attributes in the presented taste attributes. Such distributions are usually plotted as bar graphs or radar plots.

[0037] As used herein, "throwing syrup" or "concentrated syrup" refers to a composition comprising a sweetener composition dissolved in a certain volume of a liquid medium, the volume of which is less than the volume of the liquid medium contained in the finished beverage product. In one embodiment described herein, the throw-in syrup or concentrated syrup comprises a sweetener composition and a liquid medium in a ratio of 1:1 to 120:1. The throw-in syrup is combined with the liquid medium to form a finished beverage product. The throw-in syrup may optionally contain flavorings, colorants and other additives, such as food-grade acids and preservatives. Reducing the volume of the liquid medium in the throw-in syrup allows for reduced storage and shipping costs and extended shelf life. In some embodiments, the throw-in syrup is formulated to provide a finished beverage composition of about 2 times to about 120 times the volume of the liquid medium when diluted, for example, 3 times, 4 times, 5 times, 6 times, 7 times, 8 times, 9 times, 10 times, etc. to 120 times the volume. For example, a carbonated beverage is made in the following manner: first, a concentrated syrup is prepared, and then the syrup is diluted with water at the time and place of preparing the beverage. Such beverages are typically diluted at a 1:5 ratio, meaning one part syrup is mixed with five parts water. The beverages are typically carbonated when bottled or otherwise packaged.

[0038] As used herein, the terms "weight percent," "weight %," "percent by weight," "% by weight," and variations thereof refer to the concentration of a substance, i.e., the weight of the substance divided by the total weight of the composition and multiplied by 100. It should be understood that, as used herein, "percent," "%," and the like are intended to be synonymous with "weight percent," "weight %," and the like.

[0039] These methods and compositions may comprise, consist essentially of, or consist of the components and ingredients described herein and other ingredients. As used herein, "consisting essentially of" means that these methods and compositions may include additional steps, components, or ingredients, but only if the additional steps, components, or ingredients do not materially alter the basic and novel characteristics of the claimed methods and compositions. Sweetener Compositions

[0040] In another embodiment, the sweetener composition comprises: an effective amount of a sweetener compound according to formula (I) to provide at least 1% of the equivalent sucrose sweetness to the sweetener composition; and at least one additional sweetener selected from full calorie, low calorie and / or zero calorie sweeteners. The sweetener composition imparts a more sugar-like characteristic than a composition without a sweetener compound according to formula (I).

[0041] In some embodiments, the sweetener composition is a table sweetener composition. In other embodiments, the sweetener composition is incorporated into a product, such as a food, a beverage (non-alcoholic and alcoholic) or other consumable product. In embodiments where the sweetener composition is a table sweetener or a dietary sweetener composition, the sweetener composition may be a zero-calorie, low-calorie or medium-calorie sweetener composition.

[0042] In some embodiments, the sweetener composition contains: an effective amount of a sweetener compound according to formula (I) to provide at least 1% of the equivalent sucrose sweetness of the sweetener composition; and at least one additional sweetener selected from full-calorie, low-calorie and / or zero-calorie sweeteners, based on the equivalent sucrose sweetness of the compound, the ratio of the sweetener compound to the at least one additional sweetener is about 1:10 to about 9:10, about 2:10 to about 8:10, about 3:10 to about 8:10, about 4:10 to about 8:10, or about 5:10. In other embodiments, the sweetener composition contains a sweetener compound according to formula (I) and at least one additional sweetener in an amount of about 25:75 to about 75:25, or about 50:50.

[0043] Sweetener compounds

[0044] In addition to at least one additional sweetener, the sweetener composition described herein further comprises at least one sweetener compound according to formula (I). Disclosed herein is a sweetener compound of formula (I):

[0045]

[0046] or an edible or physiologically acceptable salt or stereoisomeric form thereof, wherein:

[0047] R1 is hydrogen or C1-C6 alkyl;

[0048] R2-R5 and R7 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, hydroxyl or trifluoromethyl; and

[0049] R6 is I, hydrogen, C4-C6 alkyl, C4-C6 alkoxy or hydroxy.

[0050] In some embodiments, an effective amount of one or more compounds of Formula (I) is included in a sweetener composition described herein to provide at least 1%, at least 5%, at least 10%, at least 15%, or at least 20% equivalent sucrose sweetness.

[0051] In certain embodiments, R1, R2, R3, R5, R6, and R7 of the compounds of Formula (I) described herein are independently hydrogen at each occurrence.

[0052] In certain embodiments, R4 of the compounds of Formula (I) described herein is methyl.

[0053] In certain embodiments, the compound of formula (I) described herein is 2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid.

[0054] In certain embodiments, R1, R2, R3, R4, R6 and R7 of the compounds of formula (I) described herein are independently hydrogen at each occurrence. In certain embodiments, R5 of the compounds of formula (I) described herein is methyl.

[0055] In certain embodiments, the compound of formula (I) described herein is 2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid.

[0056] In certain embodiments, R1, R3, R4, R5, R6 and R7 of the compounds of formula (I) described herein are independently hydrogen at each occurrence. In certain embodiments, R2 of the compounds of formula (I) is methyl.

[0057] In certain embodiments, the compound of formula (I) described herein is 2-amino-3-(2-methyl-1H-indol-3-yl)propanoic acid.

[0058] In certain embodiments, the compound of formula (I) described herein is selected from the compounds in Table 1 or an edible or physiologically acceptable salt or stereoisomeric form thereof. In some embodiments, the compound of formula (I) is selected from compound 4, compound 5, and compound 6. In other embodiments, the compound of formula (I) is selected from compound 4, compound 5, and compound 6, wherein the compound is a D-isomer.

[0059] Table 1. Compounds of formula (I)

[0060]

[0061]

[0062] For the purpose of this disclosure, Table 1 is used to define specific structures associated with specific names. Whenever a specific name is recited in the present disclosure or claims, the chemical structure associated with the specific name shall be the structure identified in Table 1.

[0063] In a specific embodiment, the compound of formula (I) provided herein is selected from: 2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid ("Compound 1"); (R)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid ("Compound 2"); (S)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid ("Compound 3"); 2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid ("Compound 4"); (R)-2-amino-3-(5-methyl-1H -indol-3-yl)propionic acid ("Compound 5"); (S)-2-amino-3-(5-methyl-1H-indol-3-yl)propionic acid ("Compound 6"); 2-amino-3-(2-methyl-1H-indol-3-yl)propionic acid ("Compound 7"); (R)-2-amino-3-(2-methyl-1H-indol-3-yl)propionic acid ("Compound 8"); and (S)-2-amino-3-(2-methyl-1H-indol-3-yl)propionic acid ("Compound 9"); or their edible or physiologically acceptable salts or stereoisomeric forms.

[0064] In some embodiments, the compound of formula (I) is selected from 2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid ("Compound 4"), (R)-2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid ("Compound 5") and (S)-2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid ("Compound 6") or an edible or physiologically acceptable salt or stereoisomeric form thereof.

[0065] Edible or physiologically acceptable salts of compounds provided herein include salts derived from inorganic or organic acids and bases. Examples of such salts include, but are not limited to, those derived from suitable bases, including alkali metals (e.g., sodium and potassium), alkaline earth metals (e.g., magnesium), ammonium and N+(Cr-4 alkyl)4 salts. In one embodiment, the salt is selected from sodium salts, potassium salts, ammonium salts or calcium salts. In another embodiment, the salt is selected from sodium salts, potassium salts or calcium salts. In another embodiment, the salt is a sodium salt, wherein the sodium salt of the compound provided herein can disintegrate or dissolve 300-400 times faster than the free base of the compound of Formula I.

[0066] In certain embodiments, the compounds provided herein (such as compounds of Formula (I), Compound 1, Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, Compound 8, or Compound 9) are isolated (including, for example, if they are derived from a natural source or product, from their naturally occurring environment), synthesized, or physiologically synthesized. In certain embodiments, the compounds are isolated and substantially pure. In certain embodiments, the compounds provided herein are not less than about 80%, not less than about 85%, not less than about 90%, not less than about 95%, not less than about 96%, not less than about 97%, not less than about 98%, not less than about 98.5%, not less than about 99%, not less than about 99.5%, or not less than about 99.8% pure.

[0067] In a specific embodiment, provided herein are compounds (such as compounds of formula (I), compound 1, compound 4, or compound 7) wherein provided herein are racemic ones. In a specific embodiment, provided herein are compounds L-isomers. In a more preferred embodiment, provided herein are compounds D-isomers. In certain embodiments, provided herein are D-isomers of compounds (such as compounds of formula (I), compound 4, compound 5, or compound 6).

[0068] In the case of inconsistency between the structure shown and the name given to the structure, the structure shown will be given more weight. Unless stated to the contrary, the formula with the chemical bond shown only as a solid line rather than a wedge line or a dotted line covers each possible isomer (for example, each enantiomer and diastereomer, or geometric isomer (that is, E, Z)) and a mixture of isomers, such as racemic or non-racemic mixtures. Single stereochemical isomers and compounds provided herein (such as compounds of formula (I), compound 1, compound 2, compound 3, compound 4, compound 5, compound 6, compound 7, compound 8 or compound 9) enantiomers and diastereomeric mixtures are within the scope of the present invention. In addition, unless otherwise indicated, the formula shown herein is also meant to include compounds that are different only in the presence of one or more isotopically enriched atoms. For example, provided herein are compounds of formula (I) with the present invention formula (different is to replace hydrogen with deuterium or tritium or to replace carbon with 13C- or 14C-enriched carbon) within the scope of the present invention.

[0069] Compounds provided herein (such as compounds of formula (I), compound 1, compound 2, compound 3, compound 4, compound 5, compound 6, compound 7, compound 8 or compound 9) may also exist as solvates and hydrates. Therefore, these compounds may crystallize with, for example, one molecule, a plurality of molecules or any portion thereof of a molecule of water of hydration or a mother liquid solvent. Solvates and hydrates of such compounds are included within the scope of the present invention.

[0070] In one embodiment, one or more compounds of formula (I) as described herein are contained in an aqueous solution in an effective amount to impart a maximum sweetness intensity equivalent to a 20%, 25%, 30%, 35% or 40% aqueous sucrose solution by weight. In another embodiment, about 50 mg to 100 mg of one or more compounds of formula (I) as described herein in 100 mg of water is equivalent to 1 Brix. In another embodiment, when added to an unsweetened or sweetened beverage product, one or more compounds of formula (I) as described herein provide a Brix of about 1 to about 12 (based on the amount of the compound provided).

[0071] Additional disclosure of compounds of formula (I) described herein is set forth in PCT Application No. PCT / US18 / 064473, which claims priority to US Application Serial No. 62 / 596,667, both of which are incorporated herein by reference in their entirety.

[0072] Additional sweeteners

[0073] In addition to the sweetener compound according to formula (I), the sweetener composition also comprises at least one additional sweetener. Suitable sweeteners for combining with the sweetener compound include, for example, full calories, low calories and / or zero calories sweeteners. These sweeteners may also be referred to as nutritious sweeteners, partial nutritious sweeteners and non-nutritious sweeteners (i.e., high potency sweeteners (or high intensity sweeteners)). The non-nutritious sweeteners including both natural sweeteners and synthetic sweeteners (i.e., artificial sweeteners) are alternative forms of nutritious sweeteners together with partial nutritious sweeteners, to provide desired taste characteristics and other functional characteristics with significantly lower caloric content. Non-nutritional sweeteners do not contribute to the caloric content of the sweetener composition.

[0074] Exemplary zero-calorie sweeteners (i.e., non-nutritive, natural high-potency sweeteners) include sweeteners that occur in nature, either raw, extracted, purified, or in any other form (e.g., by fermentation, physiological transformation), either alone or in combination, and are characterized by having a sweetness potency greater than sucrose, fructose, or glucose while having lower calories. Non-limiting examples of natural zero-calorie sweeteners include steviol glycosides, including rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside D2 (Reb D2), rebaudioside D4 (Reb D4), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside G (Reb G), rebaudioside H (Reb H), rebaudioside I (Reb I), rebaudioside J (Reb J), rebaudioside K (Reb K), rebaudioside L (Reb L), rebaudioside M2 ​​(Reb M2), rebaudioside M (Reb M, also known as REB X), rebaudioside N (Reb N), rebaudioside O (Reb O), rebaudioside S (Reb S), rebaudioside T (Reb T), rebaudioside U (Reb U), rebaudioside V (RebV), rebaudioside W (Reb W), rebaudioside Z1 (Reb Z1), rebaudioside Z2 (Reb Z2) and enzymatically glucosylated steviol glycosides; amino acids, tryptophan, stevioside, stevioside, dulcoside A, dulcoside B, rubusoside, stevioside, steviol, steviol glycoside, mogroside, mogroside IV, mogroside V, mogroside VI, isomogoside V, grosmomoside, mogroside, simoneoside, monk fruit sweetener, monk fruit, simoneoside, monatin and its salts (monatin SS, RR, RS, SR), curculigo sweet protein, glycyrrhizic acid and its salts, African sweet fruit element, should be sweetened protein, mabintan protein, Brazilian sweet protein (brazzein), cyclamate (hemandulcin), phyllotoxin, sarsaparilla glycoside, phloridzin, trilobtain (trilobtain), baiyun ginsenoside, European polypodium sweet, polyboside A, maple glycoside (pterocaryoside) A, maple glycoside B, soapberry sesquiterpene glycosides, rough suside I, Brazilian licorice sweet (periandrin) I, abrin triterpene glycoside A and cyclocaryoside I. Natural high-potency sweeteners also include modified natural high-potency sweeteners.

[0075] Exemplary amino acid additives include, but are not limited to, aspartic acid, arginine, glycine, glutamic acid, praline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, arabinose, trans-4-hydroxyproline, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid (α-isomer, β-isomer and / or δ-isomer), glutamine, hydroxyproline, taurine, norvaline, sarcosine, and their salt forms, such as sodium or potassium salts or acid salts. The amino acid additives may also be in the D-configuration or the L-configuration. The amino acids may be natural or synthetic. The amino acids may also be modified. A modified amino acid refers to any amino acid (e.g., N-alkyl amino acids, N-acyl amino acids, or N-methyl amino acids) in which at least one atom has been added, removed, substituted, or a combination thereof. As used herein, amino acids also encompass both peptides and polypeptides (eg, dipeptides, tripeptides, tetrapeptides, and pentapeptides), such as glutathione and L-alanyl-L-glutamine.

[0076] Exemplary polyamino acid additives include poly-L-aspartic acid, poly-L-lysine (e.g., poly-L-α-lysine or poly-L-ε-lysine), poly-L-ornithine (e.g., poly-L-α-ornithine or poly-L-ε-ornithine), poly-L-arginine, other polymeric forms of amino acids, and their salt forms (e.g., calcium, potassium, sodium or magnesium salts, such as monosodium L-glutamate). Suitable sugar acid additives include, but are not limited to, aldonic acid, uronic acid, saccharic acid, alginic acid, gluconic acid, glucuronic acid, glucaric acid, galactaric acid, galacturonic acid and their salts (e.g., sodium, potassium, calcium, magnesium or other physiologically acceptable salts), and combinations thereof. Suitable nucleotide additives include, but are not limited to, inosine monophosphate ("IMP"), guanosine monophosphate ("GMP"), adenosine monophosphate ("AMP"), cytosine monophosphate (CMP), uridine monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uridine triphosphate, alkali metal or alkaline earth metal salts thereof, and combinations thereof. The nucleotides described herein may also include nucleotide-related additives such as nucleosides or nucleic acid bases (e.g., guanine, cytosine, adenine, thymine, uracil). Exemplary non-nutritive synthetic high potency sweeteners include those that are not naturally present in nature and are characterized by having a sweetness potency greater than sucrose, fructose, or glucose, but with fewer calories or no calories.

[0077] Additional exemplary synthetic zero-calorie (i.e., high potency) sweeteners include sucralose, acesulfame potassium (acesulfame potassium), aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamates, neotame, advantame, N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-α-aspartyl]-L-phenylalanine-1-methyl ester, N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanine-1-methyl ester, N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-α-aspartyl]-L-phenylalanine-1-methyl ester, salts thereof, etc. Synthetic high potency sweeteners also include modified synthetic high potency sweeteners.

[0078] Low-calorie (i.e., partially nutritive) sweeteners contribute to the caloric content of the composition. In some embodiments, the use of low-calorie sweeteners can provide a "medium-calorie" composition such that when added to a sweet composition (such as, for example, as a beverage product), they impart a desired sweetness and have less than about 60 calories per 8 oz portion. In other embodiments, the use of low-calorie sweeteners can provide a "low-calorie" composition such that when added to a sweet composition (such as, for example, a beverage product), they impart a desired sweetness and have less than 40 calories per 8 oz portion.

[0079] Exemplary low-calorie sweeteners include polyols. As used herein, the term "polyol" refers to a molecule containing more than one hydroxyl group. A polyol can be a diol, triol or tetraol containing 2, 3 and 4 hydroxyl groups, respectively. A polyol can also contain more than 4 hydroxyl groups, such as pentaol, hexaol, heptaol, etc., which contain 5, 6 or 7 hydroxyl groups, respectively. In addition, a polyol can also be a sugar alcohol, a polyol or a polyol in a reduced form of a carbohydrate, wherein the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary hydroxyl group or a secondary hydroxyl group. Examples of polyols include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerine), threitol, dulcitol, palatinose, reduced isomaltooligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, sugar alcohols, or any other carbohydrate that can be reduced and does not adversely affect the taste of the sweetening composition.

[0080] Additional exemplary low-calorie sweeteners include psicose (also known as D-psicose). In some embodiments, psicose includes a mixture of psicose and additional monosaccharides and disaccharides, as measured by the purity level of psicose.

[0081] In some embodiments, full caloric sweeteners may be included as nutritive sweeteners, and typically include carbohydrate sweeteners. Examples of carbohydrate sweeteners include, but are not limited to, sucrose, cane sugar, fructose, glucose, maple syrup, honey, molasses, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, D-psicose, D-tagatose, leucrose, trehalose, galactose, rhamnose, cyclodextrins (e.g., α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, glucosamine, mannosamine, fucose, fucose, glucuronic acid , gluconic acid, glucono-lactone, abacose, galactosamine, xylooligosaccharides (xylotriose, xylobiose, etc.), gentiooligosaccharides (gentiobiose, gentiotriose, gentiotetraose, etc.), galacto-oligosaccharides, sorbose, ketotriose (dihydroxyacetone), trialdose (glyceraldehyde), niger oligosaccharides, fructooligosaccharides (kestose, kestose, etc.), maltotetraose, maltotriol, tetrasaccharides, manno-oligosaccharides, maltooligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, etc.), dextrin, lactulose, melibiose, rhamnose, ribose, isomerized liquid sugars such as high fructose corn / starch syrup (HFCS / HFSS) (e.g., HFCS55, HFCS42 or HFCS90), coupling sugars, soybean oligosaccharides, glucose syrup, and combinations thereof.

[0082] In another embodiment, the additional sweetener is selected from Reb A, Reb B, Reb D, Reb M, Reb J, stevioside, mogroside, erythritol, psicose, HFCS, sucrose, cane sugar, aspartame, acesulfame potassium, sucralose, and any combination of two or more of the foregoing.

[0083] In another embodiment, a sweetener composition comprises a sweetener compound of Formula (I) and Reb A as an additional sweetener ingredient. The relative weight percentages of the sweetener compound of formula (I) and Reb A can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% Reb A, about 90% compound of formula (I) / 10% Reb A, about 85% compound of formula (I) / 15% Reb A, about 80% compound of formula (I) / 20% Reb A, about 75% compound of formula (I) / 25% Reb A, about 70% compound of formula (I) / 30% Reb A, about 65% compound of formula (I) / 35% Reb A, about 60% compound of formula (I) / 40% Reb A, about 55% compound of formula (I) / 45% Reb A, about 50% compound of formula (I) / 50% Reb A, about 45% compound of formula (I) / 55% Reb A, and about 50% compound of formula (I) / 50% Reb A. A, about 40% compound of formula (I) / 60% Reb A, about 35% compound of formula (I) / 65% Reb A, about 30% compound of formula (I) / 70% Reb A, about 25% compound of formula (I) / 75% Reb A, about 20% compound of formula (I) / 80% Reb A, about 15% compound of formula (I) / 85% Reb A, about 10% compound of formula (I) / 90% Reb A, or about 5% compound of formula (I) / 10% Reb A, including the ends of the ranges therein.

[0084] In yet another embodiment, a sweetener composition comprises a sweetener compound of Formula (I) and Reb B as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and Reb B can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% Reb B, about 90% compound of formula (I) / 10% Reb B, about 85% compound of formula (I) / 15% Reb B, about 80% compound of formula (I) / 20% Reb B, about 75% compound of formula (I) / 25% Reb B, about 70% compound of formula (I) / 30% Reb B, about 65% compound of formula (I) / 35% Reb B, about 60% compound of formula (I) / 40% Reb B, about 55% compound of formula (I) / 45% Reb B, about 50% compound of formula (I) / 50% Reb B, about 45% compound of formula (I) / 55% Reb B, about 40% compound of formula (I) / 60% Reb B.

[0013] In some embodiments, the present invention relates to a compound of formula (I) having a concentration of about 1% to about 2% Reb B, about 35% compound of formula (I) / 65% Reb B, about 30% compound of formula (I) / 70% Reb B, about 25% compound of formula (I) / 75% Reb B, about 20% compound of formula (I) / 80% Reb B, about 15% compound of formula (I) / 85% Reb B, about 10% compound of formula (I) / 90% Reb B, or about 5% compound of formula (I) / 10% Reb B, including the ranges therein.

[0085] In yet another embodiment, a sweetener composition comprises a sweetener compound of Formula (I) and Reb D as an additional sweetener ingredient. The relative weight percentages of the sweetener compound of formula (I) and Reb D can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% Reb D, about 90% compound of formula (I) / 10% Reb D, about 85% compound of formula (I) / 15% Reb D, about 80% compound of formula (I) / 20% Reb D, about 75% compound of formula (I) / 25% Reb D, about 70% compound of formula (I) / 30% Reb D, about 65% compound of formula (I) / 35% Reb D, about 60% compound of formula (I) / 40% Reb D, about 55% compound of formula (I) / 45% Reb D, about 50% compound of formula (I) / 50% Reb D, about 45% compound of formula (I) / 55% Reb D, about 40% compound of formula (I) / 60% Reb D. D, about 35% compound of formula (I) / 65% Reb D, about 30% compound of formula (I) / 70% Reb D, about 25% compound of formula (I) / 75% Reb D, about 20% compound of formula (I) / 80% Reb D, about 15% compound of formula (I) / 85% Reb D, about 10% compound of formula (I) / 90% Reb D, or about 5% compound of formula (I) / 10% Reb D, including the ends of the ranges therein.

[0086] In even yet another embodiment, a sweetener composition comprises a sweetener compound of Formula (I) and Reb M as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and Reb M can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% Reb M, about 90% compound of formula (I) / 10% Reb M, about 85% compound of formula (I) / 15% Reb M, about 80% compound of formula (I) / 20% Reb M, about 75% compound of formula (I) / 25% Reb M, about 70% compound of formula (I) / 30% Reb M, about 65% compound of formula (I) / 35% Reb M, about 60% compound of formula (I) / 40% Reb M, about 55% compound of formula (I) / 45% Reb M, about 50% compound of formula (I) / 50% Reb M, about 45% compound of formula (I) / 55% Reb M, about 40% compound of formula (I) / 60% Reb M.

[0013] In some embodiments, the present invention relates to a compound of formula (I) having a concentration of about 1% to about 2% Reb M, about 35% compound of formula (I) / 65% Reb M, about 30% compound of formula (I) / 70% Reb M, about 25% compound of formula (I) / 75% Reb M, about 20% compound of formula (I) / 80% Reb M, about 15% compound of formula (I) / 85% Reb M, about 10% compound of formula (I) / 90% Reb M, or about 5% compound of formula (I) / 10% Reb M, including the ranges therein.

[0087] In another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and stevioside as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and stevioside can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% stevioside, about 90% compound of formula (I) / 10% stevioside, about 85% compound of formula (I) / 15% stevioside, about 80% compound of formula (I) / 20% stevioside, about 75% compound of formula (I) / 25% stevioside, about 70% compound of formula (I) / 30% stevioside, about 65% compound of formula (I) / 35% stevioside, about 60% compound of formula (I) / 40% stevioside, about 55% compound of formula (I) / 45% stevioside. % stevioside, about 50% compound of formula (I) / 50% stevioside, about 45% compound of formula (I) / 55% stevioside, about 40% compound of formula (I) / 60% stevioside, about 35% compound of formula (I) / 65% stevioside, about 30% compound of formula (I) / 70% stevioside, about 25% compound of formula (I) / 75% stevioside, about 20% compound of formula (I) / 80% stevioside, about 15% compound of formula (I) / 85% stevioside, about 10% compound of formula (I) / 90% stevioside, or about 5% compound of formula (I) / 10% stevioside, including the end values ​​of the ranges therein.

[0088] In yet another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and mogroside as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and mogroside can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% mogroside, about 90% compound of formula (I) / 10% mogroside, about 85% compound of formula (I) / 15% mogroside, about 80% compound of formula (I) / 20% mogroside, about 75% compound of formula (I) / 25% mogroside, about 70% compound of formula (I) / 30% mogroside, about 65% compound of formula (I) / 35% mogroside, about 60% compound of formula (I) / 40% mogroside, about 55% compound of formula (I) / 45% mogroside, about 50% compound of formula (I) / 50% mogroside, about 45% compound of formula (I) / 55% mogroside, about 40% compound of formula (I) / 60% mogroside, about 35% compound of formula (I) / 65% mogroside, about 30% compound of formula (I) / 70% mogroside, about 25% compound of formula (I) / 75% mogroside, about 20% compound of formula (I) / 80% mogroside, about 15% compound of formula (I) / 85% mogroside, about 10% compound of formula (I) / 90% mogroside, or about 5% compound of formula (I) / 10% mogroside, including the end values ​​of the ranges therein.

[0089] In another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and psicose as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and psicose can each vary from about 1% to about 99%, such as, for example, about 95% of the compound of formula (I) / 5% psicose, about 90% of the compound of formula (I) / 10% psicose, about 85% of the compound of formula (I) / 15% psicose, about 80% of the compound of formula (I) / 20% psicose, about 75% of the compound of formula (I) / 25% psicose, about 70% of the compound of formula (I) / 30% psicose, about 65% of the compound of formula (I) / 35% psicose, about 60% of the compound of formula (I) / 40% psicose, about 55% of the compound of formula (I) / 45% psicose. picose, about 50% of the compound of formula (I) / 50% picose, about 45% of the compound of formula (I) / 55% picose, about 40% of the compound of formula (I) / 60% picose, about 35% of the compound of formula (I) / 65% picose, about 30% of the compound of formula (I) / 70% picose, about 25% of the compound of formula (I) / 75% picose, about 20% of the compound of formula (I) / 80% picose, about 15% of the compound of formula (I) / 85% picose, about 10% of the compound of formula (I) / 90% picose, or about 5% of the compound of formula (I) / 10% picose, including the end values ​​of the ranges therein.

[0090] In another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and aspartame as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and aspartame can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% aspartame, about 90% compound of formula (I) / 10% aspartame, about 85% compound of formula (I) / 15% aspartame, about 80% compound of formula (I) / 20% aspartame, about 75% compound of formula (I) / 25% aspartame, about 70% compound of formula (I) / 30% aspartame, about 65% compound of formula (I) / 35% aspartame, about 60% compound of formula (I) / 40% aspartame, about 55% compound of formula (I) / 45% aspartame. aspartame, about 50% compound of formula (I) / 50% aspartame, about 45% compound of formula (I) / 55% aspartame, about 40% compound of formula (I) / 60% aspartame, about 35% compound of formula (I) / 65% aspartame, about 30% compound of formula (I) / 70% aspartame, about 25% compound of formula (I) / 75% aspartame, about 20% compound of formula (I) / 80% aspartame, about 15% compound of formula (I) / 85% aspartame, about 10% compound of formula (I) / 90% aspartame, or about 5% compound of formula (I) / 10% aspartame, including the end values ​​of the ranges therein.

[0091] In another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and potassium acesulfame as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and potassium acesulfame can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% potassium acesulfame, about 90% compound of formula (I) / 10% potassium acesulfame, about 85% compound of formula (I) / 15% potassium acesulfame, about 80% compound of formula (I) / 20% potassium acesulfame, about 75% compound of formula (I) / 25% potassium acesulfame, about 70% compound of formula (I) / 30% potassium acesulfame, about 65% compound of formula (I) / 35% potassium acesulfame, about 60% compound of formula (I) / 40% potassium acesulfame, about 55% compound of formula (I) / 45% potassium acesulfame. about 50% of the compound of formula (I) / 50% potassium acesulfamate, about 45% of the compound of formula (I) / 55% potassium acesulfamate, about 40% of the compound of formula (I) / 60% potassium acesulfamate, about 35% of the compound of formula (I) / 65% potassium acesulfamate, about 30% of the compound of formula (I) / 70% potassium acesulfamate, about 25% of the compound of formula (I) / 75% potassium acesulfamate, about 20% of the compound of formula (I) / 80% potassium acesulfamate, about 15% of the compound of formula (I) / 85% potassium acesulfamate, about 10% of the compound of formula (I) / 90% potassium acesulfamate, or about 5% of the compound of formula (I) / 10% potassium acesulfamate, including the end values ​​of the ranges therein.

[0092] In one embodiment, the sweetener composition comprises a sweetener compound of formula (I) and sucralose as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and sucralose can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% sucralose, about 90% compound of formula (I) / 10% sucralose, about 85% compound of formula (I) / 15% sucralose, about 80% compound of formula (I) / 20% sucralose, about 75% compound of formula (I) / 25% sucralose, about 70% compound of formula (I) / 30% sucralose, about 65% compound of formula (I) / 35% sucralose, about 60% compound of formula (I) / 40% sucralose, about 55% compound of formula (I) / 45% Sucralose, about 50% compound of Formula (I) / 50% sucralose, about 45% compound of Formula (I) / 55% sucralose, about 40% compound of Formula (I) / 60% sucralose, about 35% compound of Formula (I) / 65% sucralose, about 30% compound of Formula (I) / 70% sucralose, about 25% compound of Formula (I) / 75% sucralose, about 20% compound of Formula (I) / 80% sucralose, about 15% compound of Formula (I) / 85% sucralose, about 10% compound of Formula (I) / 90% sucralose, or about 5% compound of Formula (I) / 10% sucralose, including the end values ​​of the ranges therein.

[0093] In even another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and erythritol as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and erythritol can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% erythritol, about 90% compound of formula (I) / 10% erythritol, about 85% compound of formula (I) / 15% erythritol, about 80% compound of formula (I) / 20% erythritol, about 75% compound of formula (I) / 25% erythritol, about 70% compound of formula (I) / 30% erythritol, about 65% compound of formula (I) / 35% erythritol, about 60% compound of formula (I) / 40% erythritol, about 55% compound of formula (I) / 45% erythritol. % erythritol, about 50% compound of formula (I) / 50% erythritol, about 45% compound of formula (I) / 55% erythritol, about 40% compound of formula (I) / 60% erythritol, about 35% compound of formula (I) / 65% erythritol, about 30% compound of formula (I) / 70% erythritol, about 25% compound of formula (I) / 75% erythritol, about 20% compound of formula (I) / 80% erythritol, about 15% compound of formula (I) / 85% erythritol, about 10% compound of formula (I) / 90% erythritol, or about 5% compound of formula (I) / 10% erythritol, including the end values ​​of the ranges therein.

[0094] In yet another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and HFCS as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and HFCS can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% HFCS, about 90% compound of formula (I) / 10% HFCS, about 85% compound of formula (I) / 15% HFCS, about 80% compound of formula (I) / 20% HFCS, about 75% compound of formula (I) / 25% HFCS, about 70% compound of formula (I) / 30% HFCS, about 65% compound of formula (I) / 35% HFCS, about 60% compound of formula (I) / 40% HFCS, about 55% compound of formula (I) / 45% HFCS. HFCS, about 50% compound of formula (I) / 50% HFCS, about 45% compound of formula (I) / 55% HFCS, about 40% compound of formula (I) / 60% HFCS, about 35% compound of formula (I) / 65% HFCS, about 30% compound of formula (I) / 70% HFCS, about 25% compound of formula (I) / 75% HFCS, about 20% compound of formula (I) / 80% HFCS, about 15% compound of formula (I) / 85% HFCS, about 10% compound of formula (I) / 90% HFCS, or about 5% compound of formula (I) / 10% HFCS, including the end values ​​of the ranges therein.

[0095] In even another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and sucrose as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and sucrose can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% sucrose, about 90% compound of formula (I) / 10% sucrose, about 85% compound of formula (I) / 15% sucrose, about 80% compound of formula (I) / 20% sucrose, about 75% compound of formula (I) / 25% sucrose, about 70% compound of formula (I) / 30% sucrose, about 65% compound of formula (I) / 35% sucrose, about 60% compound of formula (I) / 40% sucrose, about 55% compound of formula (I) / 45% sucrose. 5% sucrose, about 50% compound of formula (I) / 50% sucrose, about 45% compound of formula (I) / 55% sucrose, about 40% compound of formula (I) / 60% sucrose, about 35% compound of formula (I) / 65% sucrose, about 30% compound of formula (I) / 70% sucrose, about 25% compound of formula (I) / 75% sucrose, about 20% compound of formula (I) / 80% sucrose, about 15% compound of formula (I) / 85% sucrose, about 10% compound of formula (I) / 90% sucrose, or about 5% compound of formula (I) / 10% sucrose, including the end values ​​of the ranges therein.

[0096] In another embodiment, the sweetener composition comprises a sweetener compound of formula (I) and sucrose as an additional sweetener component. The relative weight percentages of the sweetener compound of formula (I) and sucrose can each vary from about 1% to about 99%, such as, for example, about 95% compound of formula (I) / 5% sucrose, about 90% compound of formula (I) / 10% sucrose, about 85% compound of formula (I) / 15% sucrose, about 80% compound of formula (I) / 20% sucrose, about 75% compound of formula (I) / 25% sucrose, about 70% compound of formula (I) / 30% sucrose, about 65% compound of formula (I) / 35% sucrose, about 60% compound of formula (I) / 40% sucrose, about 55% compound of formula (I) / 4 5% cane sugar, about 50% compound of formula (I) / 50% cane sugar, about 45% compound of formula (I) / 55% cane sugar, about 40% compound of formula (I) / 60% cane sugar, about 35% compound of formula (I) / 65% cane sugar, about 30% compound of formula (I) / 70% cane sugar, about 25% compound of formula (I) / 75% cane sugar, about 20% compound of formula (I) / 80% cane sugar, about 15% compound of formula (I) / 85% cane sugar, about 10% compound of formula (I) / 90% cane sugar, or about 5% compound of formula (I) / 10% cane sugar, including the end values ​​of the ranges therein.

[0097] Foods, beverages and / or other consumable products containing one or more sweetener compositions described herein

[0098] One or more sweetener compositions as described herein are suitable for various applications, including but not limited to food, beverage products and / or other consumable products. One of the advantages of sweetener compositions is that they can be easily incorporated into the known processes for making food, beverages and other consumable products without any additional processing steps. For example, sweetener compositions as described herein can be mixed with solvents before or simultaneously with other components of food, beverages or other consumable products at room temperature or under heat (e.g., gradient heat treatment).

[0099] In exemplary embodiments, the sweetener composition can be between about 5 ppm and about 4000 ppm, about 5 ppm and about 50 ppm, about 10 ppm and about 100 ppm, about 20 ppm and about 100 ppm, about 20 ppm and about 200 ppm, about 20 ppm and about 300 ppm, about 20 ppm and about 400 ppm, about 20 ppm and about 500 ppm, about 50 ppm and about 500 ppm, about 100 ppm and about 500 ppm, about 100 ppm and about 700 ppm, about 100 ppm and about 800 ppm, about ppm to about 1500 ppm, about 100 ppm to about 1600 ppm, about 1000 ppm to about 1700 ppm, about 1500 ppm to about 1800 ppm, about 1500 ppm to about 19 ... ppm, about 1500 ppm to about 2000 ppm, about 2000 ppm to about 2100 ppm, about 2100 ppm to about 2200 ppm, about 2200 ppm to about 2300 ppm, about 2300 ppm to about 2400 ppm, about 2400 ppm to about 2500 ppm, about 2500 ppm to about 2600 ppm, about 2600 ppm to about 2700 ppm, about 2700 ppm to about 2800 ppm, about 2800 ppm to about 2900 ppm, about 2900 ppm to about 3000 ppm, An amount between about 3000 ppm and about 3100 ppm, about 3100 ppm and about 3200 ppm, about 3200 ppm and about 3300 ppm, about 3300 ppm and about 3400 ppm, about 3400 ppm and about 3500 ppm, about 3500 ppm and about 3600 ppm, about 3600 ppm and about 3700 ppm, about 3700 ppm and about 3800 ppm, about 3800 ppm and about 3900, or about 3900 ppm and about 4000, or increments between the recited values, is included in the beverage product composition.

[0100] In some embodiments, one or more of the beverage products described herein are mid-calorie, low-calorie, or zero-calorie non-alcoholic beverages and alcoholic beverages.

[0101] In exemplary embodiments, the sweetener composition can be included in the food product composition in an amount between about 0.1% to about 50% by weight, about 0.5% to about 40% by weight, about 1% to about 40% by weight, about 5% to about 35% by weight, about 5% to about 30% by weight, about 10% to about 30% by weight, about 10% to about 25% by weight, about 10% to about 20% by weight, or increments therebetween.

[0102] The disclosed concentration of the sweetener compound of formula (I) in food, beverage and / or other consumable product is beneficial to provide the desired degree of sugar-like characteristics for such food, beverage and / or other consumable product composition, wherein sugar-like characteristics may include maximum response, flavor characteristics, time characteristics, adaptation behavior, mouthfeel, concentration / response functional behavior, tastant and flavor / sweet interaction, and temperature effect. In other embodiments, the sweetener composition suppresses, weakens or eliminates at least one undesirable taste associated with the sweetener, wherein at least one undesirable taste may include delayed sweetness onset, long sweet aftertaste, metallic taste, bitter taste, cooling taste, menthol-like taste or licorice-like taste.

[0103] Exemplary foods, beverages and / or other consumer food product compositions containing sweetener compounds of formula (I) are listed in Table 2 below. When used as a single sweetener, exemplary foods, beverages and / or other consumer food product compositions provide a ppm range of typical concentrations of one or more compounds of Formula I. Concentrations may vary depending on formulation, flavor and target consumer.

[0104]

[0105]

[0106] Examples of food products include, but are not limited to, confections, dressings, chewing gum, frozen foods, desserts, canned foods, soy-based products, sauces, custards, bars, snacks, whipped toppings, mayonnaise, sauces, gravies, spreads, vinegars, ice cream, cereal compositions, baked goods, dairy products such as yogurt, fruit preparations and concentrates, non-dairy products, protein products, snacks, and tabletop sweetener compositions.

[0107] Examples of beverage products include, but are not limited to, ready-to-drink products that are carbonated (e.g., cola or other soft drinks, sparkling beverages, alcoholic beverages, and malt) or non-carbonated (e.g., fruit juices, beverages containing fruit, nectar, vegetable juices, sports drinks, energy drinks, enhanced water, coconut water tea, RTD tea, non-dairy beverages, protein drinks, meal replacement drinks, coffee, cocoa drinks, beverages containing milk, coffee creamers, beverages containing grain extracts, smoothies, and alcoholic beverages), and powdered beverage products (dry mixes) that are combined with a liquid base (such as water, milk, or club soda) and a beverage concentrate (such as a throwaway syrup). Throwaway syrups can be used to prepare any of the beverages described herein by adding an appropriate amount of water or other liquid medium.

[0108] In some embodiments, the beverage products and disposable syrups disclosed herein may include a composition based on juice obtained from a fruit or vegetable. The composition based on juice may be used in any form such as a juice form, a concentrate, an extract, a powder (which can be reconstituted with water or other suitable liquids), etc. Suitable juices include, for example, non-citrus juices, such as apple juice, grape juice, pear juice, peach juice, blackcurrant juice, raspberry juice, gooseberry juice, blackberry juice, blueberry juice, strawberry juice, sugar apple juice, pomegranate juice, guava juice, kiwi juice, mango juice, papaya juice, watermelon juice, cantaloupe juice, cherry juice, cranberry juice, peach juice, apricot juice, plum juice, and pineapple juice; citrus juices, such as orange juice, lemon juice, lime juice, grapefruit juice, and tangerine juice; and vegetable juices, such as carrot juice and tomato juice; or any combination thereof. The beverage products and disposable syrups disclosed herein may include fruit or vegetable liquids containing a certain percentage of solids derived from fruits or vegetables (e.g., pulp, seeds, skin, fiber, etc. and pectin naturally present in fruits or vegetables). In some embodiments, juice-based compositions are fortified with dissolved calcium in the form of calcium carbonate, calcium lactate, calcium oxide, or calcium hydroxide.

[0109] In some embodiments, the beverage products and disposable syrups disclosed herein include a dairy composition, wherein the dairy composition contains dairy protein. Exemplary dairy compositions include any type of dairy product, including cream, whole milk, low-fat milk, skim milk, milk solids, condensed milk, or any combination thereof, particularly a combination of cream and skim milk. The dairy composition typically contains a certain amount of dairy protein, such as whey protein containing β-lactoglobulin, α-lactalbumin, or serum albumin; and the like. In some embodiments, the dairy product may be replaced by a certain amount of non-dairy components, such as soy milk, soy protein, almond milk, coconut milk, or any combination thereof.

[0110] The sweetener compositions described herein may also be used in dental and pharmaceutical compositions.

[0111] Further description of exemplary foods, beverages and / or other consumable products suitable for including one or more sweetener compositions described herein is disclosed in U.S. Patent Application Publication US2013 / 096420, the portions of which that disclose exemplary foods, beverages and / or other consumable compositions that can be sweetened with one or more sweetener compositions described herein are incorporated herein by reference in their entirety.

[0112] When incorporated into foods, beverages, and / or other consumable products, the sweetener composition may be the sole sweetening ingredient or other sugars and / or sweeteners may also be incorporated into the product.

[0113] Sweetener compositions may also be combined with one or more additives (which may or may not be additional sweeteners) in foods, beverages, and / or other consumable products. Examples of additives include, but are not limited to, carbohydrates (also described above in Additional Sweeteners), polyols (also described above in Additional Sweeteners), amino acids and their corresponding salts (also described above in Additional Sweeteners), sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts (including organic acid salts and organic base salts), inorganic salts, bitter compounds, caffeine, flavoring agents and flavoring ingredients, astringent compounds, proteins or protein hydrolyzates, surfactants, emulsifiers, weighing agents, fruit juices, dairy products, cereals and other plant extracts, gums, coloring agents, flavonoids, alcohols, polymers, essential oils, antifungal agents, and combinations thereof.

[0114] The sweetener composition may also be combined with one or more leavening agents in food, beverages, and / or other consumable products (which may or may not be suitable as additives or additional sweeteners). Leavening agents may, for example, be used to promote direct replacement of sugar with the sweetener composition disclosed herein in applications such as baking, cooking, and table use. Examples of leavening agents include, but are not limited to, bulk sweeteners such as sucrose, dextrose, invert sugar maltose, dextrin, maltodextrin, fructose, levulose, and galactose; low-glycemic carbohydrates such as oligofructose, oligogalactose, mannitol, inulin, xylitol, lactitol, erythritol, and maltitol; fibers such as polydextrose, resistant maltodextrin, resistant starch, soluble corn fiber, and cellulose; and aqueous colloids such as pectin, guar gum, carboxymethyl cellulose, locust bean gum, gum arabic, xanthan gum, and alginate. In some embodiments, the leavening agent is selected from maltodextrin, a dextrose-maltodextrin blend, corn syrup solids, sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, mannitol, galactitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, polydextrose, oligofructose, cellulose and cellulose derivatives, or a combination thereof.

[0115] In some embodiments, consumable products (e.g., food, beverages and / or other consumable products) do not include nutritive sweeteners, including sucrose (table sugar), glucose, fructose, corn syrup (including high fructose corn syrup), maltose, lactose, molasses, honey, agave, fruit juice, maple syrup, etc. In other embodiments, the product contains a reduced amount of nutritive sweeteners, because these nutritive sweeteners are advantageously replaced (or reduced in content) by adding a sweetener composition disclosed herein (or a sweetener compound of formula (I)). In exemplary embodiments, the nutritive sweeteners in the composition are reduced by at least about 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%, 10% or 5% in consumable products disclosed herein.

[0116] Sweetener compositions can also be combined with one or more functional ingredients in food, beverages and / or other consumable products. Examples of functional ingredients include, but are not limited to, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydrating agents, probiotics, prebiotics, long-chain aliphatic saturated primary alcohols, phytosterols, and combinations thereof.

[0117] In a particular embodiment, the sweetener composition (or the combination of the sweetener compound according to formula (I) and the reagent described in the present embodiment) is a table sweetener composition. In such embodiments, the sweetener composition (or the combination of the sweetener compound according to formula (I) and the reagent described in the present embodiment) may also include at least one leavening agent, additive, anti-caking agent, functional ingredient, and a combination thereof. The table sweetener composition may be present in the form of a solid, a suspension, or a liquid; including co-crystallized sweetener compositions, condensed sweetener compositions, compacted sweetener compositions, dry sweetener compositions, granular sweetener compositions, spherical sweetener compositions, spray-dried compositions, granular sweetener compositions, liquid suspension compositions, and liquid sweetener compositions with sugar or polyols. Exemplary liquid table sweeteners may include water and optional additives, such as, for example, polyols (e.g., erythritol, sorbitol, propylene glycol, or glycerol), acidulants (e.g., citric acid, malic acid, tartaric acid, phosphoric acid), antimicrobial agents (e.g., benzoic acid or its salts)

[0118] Method for enhancing the sugar-like characteristics of a consumable food, beverage or other product

[0119] In one embodiment, a method is provided for imparting a time characteristic, a flavor characteristic, or both of a sweetening composition or a consumable food, a beverage, or other consumable product that is more sugar-like. The method includes providing a consumable food, a beverage, or other product as a sweetening composition, and adding one or more sweetener compositions as described herein to such products to impart a sugar-like characteristic of such compositions or product desired degrees. Expected features may include maximum response, flavor characteristics, time characteristics, adaptation behavior, mouthfeel, concentration / response functional behavior, tastants, and flavor / sweetness interactions, and temperature effects.

[0120] In another embodiment, one or more methods for enhancing the sugar-like characteristics of consumable foods, beverages, or other products described herein include adding one or more sweetening compositions described herein to such products, wherein such sweetening compositions contain nutritive, non-nutritive, and / or partially nutritive sweeteners as additional sweeteners, and wherein the sweetening compositions provide a beneficial shortened sweetness onset and / or a prolonged decay time closer to sucrose. Since most non-nutritive high potency sweeteners delay the sweetness onset, the sweetener compounds of formula (I) are used in sweetener compositions described herein to significantly shorten the sweetness onset (also referred to as appearance time) compared to individual non-nutritive high potency sweeteners (or at larger concentrations), which is a desired attribute of a sweetening system.

[0121] In another embodiment, one or more methods for enhancing the sugar-like characteristics of consumable foods, beverages or other products described herein include adding one or more sweetening compositions described herein to such products, wherein such sweetening compositions contain nutritious, non-nutritional and / or partially nutritious sweeteners as additional sweeteners, and wherein the sweetening compositions provide the adaptation of beneficial weakening. Known non-nutritional high-efficiency sweeteners can cause adaptation (the magnitude of the sweetness intensity perceived after repeated exposure is reduced). Beneficially, one or more sweetener compositions described herein do not cause any adaptation or reduce the degree of adaptation.

[0122] In yet another embodiment, one or more methods described herein for enhancing the sugar-like characteristics of a consumable food, beverage, or other product described herein comprise adding one or more sweetening compositions described herein to such a product, wherein the sweetener composition inhibits, attenuates, or eliminates at least one undesirable taste associated with other sweetener compositions that do not contain a sweetener compound of formula (I), wherein the at least one undesirable taste may include a delayed sweetness onset, a lingering sweet aftertaste, a metallic taste, a bitter taste, a cooling sensation, a menthol-like taste, or a licorice-like taste.

[0123] In yet another embodiment, one or more methods described herein for enhancing the sugar-like characteristics of consumable food, beverages, or other products comprises adding one or more sweetening compositions described herein to such products, wherein the combination of the sweetener compound of formula (I) and the additional sweetener beneficially has a pure sugar-like taste and is free of undesirable off-flavors, including bitterness, metallic taste, astringency, and / or bitter lingering, while also exhibiting sugar-like temporal characteristics. Example

[0124] Embodiments of the present invention are further defined in the following non-limiting examples. It should be understood that although these examples illustrate certain embodiments of the present invention, they are only given by way of example. Through the above discussion and these examples, those skilled in the art can determine the basic characteristics of the present invention, and without departing from the spirit and scope of the present invention, various changes and modifications can be made to the embodiments of the present invention to make them suitable for various purposes and conditions. Therefore, in addition to those shown and described herein, various modifications of the embodiments of the present invention will be apparent to those skilled in the art from the previous description. Such modifications are also intended to fall within the scope of the appended claims.

[0125] The examples described herein were tested using sweetener compounds of Formula (I), particularly Compound 5. All experiments were performed using the free base of Compound 5 unless otherwise stated.

[0126] Example 1

[0127] Concentration-response testing of test compounds (sweeteners)

[0128] Concentration-response (CR) testing of test compounds was performed by a trained descriptive analysis (DA) panel to compare test compounds with sucrose in an aqueous matrix. Concentration-response curves of natural sweeteners (test compounds) were determined using a universal quantitative scale (gLMS). Trained panelists were asked to rate the sweetness intensity of eight (8) concentrations of sweeteners and sucrose in water at room temperature (RT).

[0129] Concentration-Response

[0130] Figure 1 The concentration relationship between sucrose and test compound sweetener is shown. This relationship was established using the dose response model for sucrose and test compound sweetener (Equation 2: R = Rmin + (C^Hillslope) * (Rmax-Rmin) / (C^HillSlope + EC50^HillSlope)).

[0131] The concentration relationship of the test compound sweetener required to achieve the target equivalent sweetness compared to the concentration of sucrose required to achieve the target equivalent sweetness was linear.

[0132] Study Design and Test Samples: 10 to 12 trained descriptive analysis panelists participated in the experiment. All participants received training during which the panelists familiarized themselves with the rating of sweetness intensity on the gLMS scale. The scale is shown in Figure 4 as a vertical line marked with anchor points describing different intensities. The panelists were instructed to rate the perceived sweetness intensity of each sample by drawing a line on the scale.

[0133] The order of samples was randomized and blinded using a William Latin Square design. The order of presentation of samples within each sweetener group was also randomized. All samples were evaluated using a sip and spit protocol.

[0134] The test showed that the concentration-response curve of the test compound sweetener exhibited a linear relationship within the tested concentration range: 0% to 0.2% (2000 ppm).

[0135] Example 2

[0136] Sensory Results of Sweetener Blends

[0137] The sensory results of blends of sweeteners with Reb M were evaluated by a trained descriptive analysis (DA) panel. Five blend samples were tested by the panel; each sample was designed to target an equivalent sucrose sweetness of 10 degrees Brix. As shown in Table 3, the blends consisted of aqueous solutions of test compound sweeteners and rebaudioside M (Reb M) at different ratios to evaluate sweetness quality and off-flavor characteristics.

[0138]

[0139] Study Design and Test Sample: A validated and trained panel of 10 to 12 descriptive analysis panelists was involved in these experiments.

[0140] During the test, panelists rated the intensity of each attribute on a 15 cm scale. For each attribute, five test samples were tested in triplicate. The order of samples was randomized and blinded using a William Latin Square design. All samples were prepared in reverse osmosis (RO) water and consumed at room temperature and evaluated using an aspiration protocol.

[0141] Each of the five samples was evaluated for sensory attributes corresponding to sweetness quality and off-flavor characteristics. Sweetness intensity, sweetness onset time, sweetness aftertaste, and consistency attributes were evaluated as part of the sweetness quality analysis. Specifically, for sweet aftertaste, two time points, 1 minute and 3 minutes after spitting out, were evaluated. The sweet aftertaste corresponds to the sweetness lingering characteristics common to high potency sweeteners. Figure 3 It is shown that each sample achieved a sweetness intensity of "10" on the 15 cm scale (corresponding to 10 Brix sucrose) without any significant differences in sweetness intensity.

[0142] Sweetness characteristics

[0143] Sweetness characteristics of 5 blend samples were evaluated in which the addition of the test compound sweetener to Reb M proportionally and significantly improved the desirable attributes of sweetness onset, sweet aftertaste, and body. Table 4 lists the LSD mean differences for the sweetness quality evaluations of the blends with Reb M.

[0144] Table 4

[0145]

[0146] AT = appearance time, na = not significant

[0147] Different letter groups indicate significant differences at the 95% confidence level.

[0148] The results in Table 3 indicate that increasing the ratio of the test compound sweetener significantly reduced the sweetness onset, shortened the sweetness lingering, and increased the perceived body in the samples, which are highly desirable attributes for low sugar applications.

[0149] Off-flavor characteristics: All five blend samples were also evaluated for the attributes of bitterness, astringency, metallic, licorice, and bitter aftertaste as part of the off-flavor analysis. Specifically, for bitter aftertaste, two time points were evaluated, 1 minute and 3 minutes after expectoration. When referring to a "bitter" taste herein, it refers to a sample that imparts a bitter taste, activates a subject's perception of bitterness, or is detectable by a bitter taste receptor and / or imparts a subject's perception of bitterness. Table 5 lists the LSD mean differences in the off-flavor evaluations for the five blend samples of Reb M.

[0150] Table 5

[0151]

[0152] Different letter groups indicate differences at the 95% confidence level

[0153] The results in Table 5 indicate that increasing the ratio of the combination of the test compound sweetener and Reb M significantly reduced the bitter taste, bitter aftertaste, metallic off-taste, licorice off-taste, and astringent off-taste.

[0154] The sensory results show that in aqueous solution, the test compound sweetener itself has minimal bitterness, astringency and bitterness retention, and exhibits sucrose-like characteristics. The inclusion of the test compound sweetener in the blend results in significant taste improvements in a variety of attributes. This taste improvement is due to the increased concentration of the test compound sweetener in the blend, where samples with a greater proportion of the test compound sweetener show greater taste improvements. The results confirm that specific aspects of significant taste improvements include sweetness onset time, consistency, sweet aftertaste (retention), bitterness, licorice, astringency, metallic taste and bitter aftertaste. The sweetness quality and off-flavor characteristics of Reb M are significantly improved with the addition of the test compound sweetener. In addition to the taste improvement findings in these blends, these results also confirm that the test compound sweetener is a sweetener that tastes significantly purer than Reb M.

[0155] Example 3

[0156] Sensory Evaluation of Test Compound Sweetener Blends

[0157] The taste characteristics of the test compound sweeteners were evaluated in combination and relative to known sweeteners, namely rebaudioside A (Reb A), high fructose corn syrup (HFCS-55), psicose, erythritol, monk fruit, rebaudioside M (Reb M), and sucralose. The test samples are shown in Table 6, which lists the contents of all samples evaluated in water. All samples were prepared by dissolving the desired concentration of sweetener in reverse osmosis (RO) water. For all evaluations, the samples tasted cool.

[0158]

[0159] The samples were evaluated by a panel of expert tasters (n=6). The samples were tasted in a blinded manner using the aspiration method. The evaluation focused on sweetness characteristics, off-flavor characteristics (described as bitterness, sweetness lingering, sweetness onset, mouthfeel, mouth coating, and metallic taste), and flavor characteristics. Qualitative descriptors for the water samples are provided by the panel for each sample in Table 7.

[0160]

[0161]

[0162] Table 8 Contents of all samples evaluated in tea. All samples were prepared by dissolving the desired concentration of sweetener in commercial unsweetened ready-to-drink (RTD) black tea. For all evaluations, the samples were tasted cold.

[0163]

[0164] Qualitative descriptors for the tea samples were provided by the panel for each sample in Table 9.

[0165]

[0166] Sensory evaluation of samples in water and tea matrices showed that the addition of the test compound sweetener significantly improved the sweetness characteristics of caloric and non-caloric sweeteners by reducing off-flavor attributes. Specifically, bitterness, sweetness onset, sweetness lingering, metallic taste, and mouth coating were reduced. It also enhanced the mouthfeel of the samples. These attributes observed in the blends were relative to the individual sweeteners.

[0167] Example 4

[0168] Evaluation of the taste profile of test compound sweetener blends

[0169] The taste characteristics of the test compound sweetener (Na salt of the compound) were evaluated in combination with a sweetener, i.e., high fructose corn syrup (HFCS-55). These samples were evaluated by 3 tasters in a pH 3.0 buffer. The samples were tasted in a blind manner using the aspiration method. The focus of the evaluation was to obtain an indication of the sweet taste characteristics of the blend when compared to sucrose. The evaluated formulations are shown in Table 10.

[0170]

[0171] Materials and Methods: Potassium sorbate was dissolved in water. The remaining ingredients were added and mixed until completely dissolved. The pH of each sample was recorded and the samples were tasted using the aspiration method. The samples were then compared to each other.

[0172] Results: 1100 ppm of the test compound was fairly clean in taste and provided good upfront sweetness. Poor mouthfeel. The combination of 550 ppm of the test compound + 6.49% HFCS-55 had a similar sweetness to the test compound alone and a slightly stronger mouthfeel. 12.987% HFCS-55 had a similar sweetness and was very clean.

[0173] The results showed that the sweetness of the test compound was quite pure, with good onset and decay, but lacked mouthfeel compared to HFCS-55. The tests confirmed that the test compound together with HFCS provided sugar-like taste characteristics and made the product closer to sucrose.

[0174] Example 5

[0175] Evaluation of the taste profile of test compound sweetener blends

[0176] The taste profile of the test compound sweetener (Na salt of the compound) was evaluated in combination with the sweetener, Reb A (Reb A). 300000 (Reb A 95) was used in combination with the test compound. These samples were evaluated by 3 tasters in pH 3.0 buffer. The samples were tasted in a blinded manner using the aspiration method. The focus of the evaluation was to obtain an indication of the sweetness characteristics of the blend when compared to sucrose. The formulations evaluated are shown in Table 11.

[0177]

[0178] Materials and Methods: Potassium sorbate was dissolved in water. The remaining ingredients were added and mixed until completely dissolved. The pH of each sample was recorded and the samples were tasted using the aspiration method. The samples were then compared to each other.

[0179] Results: 880ppm of the test compound Na salt was fairly clean in taste and provided a similar sweetness. It had a good onset and decay, but had a slight finish at the end. It lacked mouthfeel compared to HFCS-55, but provided some mouthfeel compared to RebA. The combination of 440ppm of the test compound Na salt + 275ppm of Reb A was slightly sweeter than 8SE. The addition of the test compound attenuated the off-flavor common with Reb A. 550ppm of Reb A was much less sweet than 8SE. It had a plastic / floral / metallic taste with a bitter and astringent lingering taste. This was the worst tasting sample in the off-flavor group.

[0180] The results confirm that the sweetness of the test compound Na salt is quite pure with good onset and decay. It provides slightly more mouthfeel than Reb A and can help reduce some of the off-flavors commonly found in Reb A without reducing sweetness. The test compound helps reduce the adaptations commonly found in Reb A.

[0181] Example 6

[0182] Evaluation of the taste profile of test compound sweetener blends

[0183] The taste profile of the test compound sweetener (Na salt of the compound) was evaluated in combination with the sweetener, psicose. Liquid psicose was used in combination with the test compound. These samples were evaluated by 3 tasters in pH 3.0 buffer with different equivalent sweetness (SE) targets (also referred to as equivalent sucrose sweetness (SSE)). The samples were tasted in a blind manner using the aspiration method. The focus of the evaluation was to obtain an indication of the sweetness characteristics of the blend when compared to sucrose. The evaluated formulations are shown in Table 12.

[0184]

[0185] Materials and Methods: Potassium sorbate was dissolved in water. The remaining ingredients were added and mixed until completely dissolved. The pH of each sample was recorded and the samples were tasted using the aspiration method. The samples were then compared to each other.

[0186] Results: At 5 SE, the Na salt of the test compound and The combination of liquid allulose was similar to the HFCS target at 5 SSE in terms of sweetness. It was slightly less sour, but little difference was observed in bitterness, mouthfeel, and aftertaste. The combination of liquid allulose was close to the HFCS target in terms of sweetness. Mouthfeel was slightly weakened, but all other attributes were comparable. At 12.5 SE, the test compound Na salt and The combination of liquid allulose was close to the HFCS target in terms of sweetness. The bitterness was very slightly increased, and the mouthfeel was very slightly reduced, but the aftertaste remained comparable.

[0187] The test confirmed that the Na salt of the test compound Liquid psicose has the ability to replace HFCS over a wide range of equivalent sweetness targets. They provide pure sweetness when paired, and no severe off-flavors. When the equivalent sweetness increases, the mouthfeel difference may be noticeable. The combination of the test compound and psicose provides a "sugar-like" taste characteristic and makes the product closer to sucrose.

[0188] Example 7

[0189] Evaluation of the taste profile of test compound sweetener blends

[0190] The taste characteristics of the test compound sweetener (Na salt of the compound) were evaluated in combination with a sweetener, namely sucralose. These samples were evaluated by 3 tasters in a pH 3.0 buffer at 10 SE. The samples were tasted in a blind manner using the aspiration method. The focus of the evaluation was to obtain an indication of the sweetness characteristics of the blend when compared to sucrose. The evaluated formulations are shown in Table 13.

[0191]

[0192] Materials and Methods: Dissolve potassium sorbate in water. Add remaining ingredients and mix until completely dissolved. Taste samples using the puff method. Samples are then compared to each other and to the HFCS-55 equivalent sweetness target (10 SE).

[0193] Results: The sweetness of the test compound Na salt at 1100ppm was lower than HFCS (10SE), but similar to the sweetness of sucralose at 170ppm. The mouthfeel of the test compound Na salt was slightly reduced, and there was a slight sour taste and a lingering taste. The sweetness of the combination of 550ppm test compound Na salt + 85ppm sucralose was lower than HFCS (10SE). The combination of the two sweeteners and the test compound Na salt at 1100ppm was closer to HFCS in taste quality. Less aftertaste / lingering was observed than sucralose at 170ppm. The sweetness of sucralose itself at 170ppm was lower than HFCS (10SE) and had a delayed sweetness. A significant aftertaste / lingering was detected.

[0194] The test demonstrated that the test compound Na salt with sucralose can help reduce the aftertaste / lasting of sucralose alone at similar equivalent sweetness. The test compound helps reduce the common adaptations of sucralose.

[0195] It should be understood that although the invention has been described in conjunction with specific embodiments of the invention, the foregoing description is intended to illustrate rather than limit the scope of the invention, which is defined by the scope of the appended claims. Other embodiments, advantages and modifications are within the scope of the following claims. The features disclosed in the foregoing description or the following claims or the accompanying drawings are represented in their specific form or in a manner for performing the disclosed functions, or the methods or processes for obtaining the disclosed results may be used alone or in any combination of such features as appropriate, thereby realizing the invention in its various different forms.

Claims

1. A sweetener composition, comprising: At least one compound of formula (I): or its edible or biologically acceptable salt or stereoisomeric form, wherein R1, R2, R3, R4, R6 and R7 are independently hydrogen at each occurrence, and wherein R5 is methyl; wherein the sweetener composition contains a compound of formula (I) in an amount of up to 2.5% by weight; The sweetener composition contains at least one additional sweetener which is psicose.

2. The sweetener composition of claim 1, wherein the compound of formula (I) comprises a racemic mixture of the at least one compound, or wherein the compound of formula (I) is a D-isomer.

3. The sweetener composition according to claim 1, wherein the compound of formula (I) is:

4. The sweetener composition according to claim 1 or 3, wherein the salt is selected from a sodium salt, an ammonium salt or a calcium salt.

5. A consumable product comprising: A sweetener composition according to any one of claims 1 to 4 at a concentration of 5 ppm to 4000 ppm; and at least one additive and / or functional ingredient.

6. A consumable product comprising: A sweetener composition according to any one of claims 1 to 4 at a concentration of 5 ppm to 4000 ppm; and at least one leavening agent and / or functional ingredient.

7. A consumable product according to claim 5 or 6, wherein the consumable product is a beverage product.

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