Steviol Glycoside Solubility Enhancer

Abstract

The steviol glycoside solubility enhancer may comprise a monocaffeoylquina (MCQ) component comprising at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof, and a dicaffeoylquina (DCQ) component comprising at least one compound selected from the group consisting of 1,3-dicaffeoylquina acid, 1,4-dicaffeoylquina acid, 1,5-dicaffeoylquina acid, 3,4-dicaffeoylquina acid, 3,5-dicaffeoylquina acid, 4,5-dicaffeoylquina acid, and salts thereof. In one preferred implementation, the MCQ and DCQ components together comprise more than 50% (by weight) of the steviol glycoside solubility enhancer, preferably more than 60%, 70%, 80%, 90%, or 95% (by weight).

Description

[Technical field]

[0001] (CROSS REFERENCE TO RELATED APPLICATIONS) This application is a joint venture between U.S. Patent Application No. 62 / 830,450, filed April 6, 2019, and entitled "Steviol Glycoside Solubility Enhancers," U.S. Patent Application No. 62 / 832,062, filed April 10, 2019, and entitled "Steviol Glycoside Solubility Enhancers," U.S. Patent Application No. 16 / 373,206, filed April 2, 2019, and entitled "Steviol Glycoside Solubility Enhancers," which was published on July 25, 2019 as U.S. Patent Application Publication No. 2019 / 0223481, and entitled "Steviol Glycoside Solubility Enhancers," International Application No. PCT / US2018 / 054691, filed October 5, 2018, and entitled "Steviol Glycoside Solubility Enhancers," and International Application No. PCT / US2017 / 054692, filed October 6, 2017, and entitled "Steviol Glycoside Solubility Enhancers," This application claims the benefit of U.S. Provisional Patent Application No. 62 / 569,279, entitled "Polysaccharide Glycoside Solubility Enhancers," the entirety of each of which is incorporated herein by reference.

[0002] FIELD OF THEINVENTION The present disclosure relates to solubilized steviol glycoside solutions having one or more steviol glycoside compounds and a steviol glycoside solubility enhancer, and methods of making and using these solutions. The disclosure also relates to sweetener compositions and slow syrups for preparing sweetened compositions, including foods, beverages, dental products, pharmaceuticals, dietary supplements, and the like. [Background technology]

[0003] Sugars such as sucrose, fructose, and glucose are utilized to provide a pleasant taste to beverages, foods, medicines, and oral hygiene / beauty products. Sucrose, in particular, imparts a taste that is favored by consumers. Sucrose provides excellent sweetness characteristics, but is caloric. Non-caloric or lower caloric sweeteners have been introduced to meet consumer demand, and these types of sweeteners with desirable taste characteristics are in demand.

[0004] Stevia is a genus of about 240 species of herbs and shrubs in the sunflower family (Asteraceae), native to the subtropical and tropical regions of western North America and South America. Stevia rebaudiana, commonly known as sweetleaf, sweet leaf, sugarleaf, or simply stevia, is widely cultivated for its sweet-tasting leaves. Stevia-based sweeteners can be obtained by extracting one or more sweet compounds from the leaves. Many of these compounds are steviol glycoside compounds, which are glycosides of steviol, a diterpene compound. These diterpene glycosides are about 150 to 450 times sweeter than sugar.

[0005] Examples of steviol glycoside compounds are described in WO 2013 / 096420 (see, e.g., the listing in Figure 1) and Ohta et.al., "Characterization of Novel Steviol Glycosides from Leaves of Stevia rebaudiana Morita," J. Appl. Glycosi., 57, 199-209 (2010) (see, e.g., Table 4 on p. 204). Structurally, diterpene glycosides are characterized by a single base, steviol, and differ by the carbohydrate residues present at the C13 and C19 positions, as presented in Figures 2a-k. See also PCT Patent Publication WO 2013 / 096420.

[0006] Typically, the four major steviol glycoside compounds found in stevia leaves are, on a dry weight basis, dulcoside A (0.3%), rebaudioside C (0.6-1.0%), rebaudioside A (3.8%), and stevioside (9.1%). Other glycosides identified in stevia extracts include one or more of rebaudioside B, D, E, F, G, H, I, J, K, L, M, N, O, steviolbioside, and rubusoside.

[0007] The major steviol glycoside Reb A is commonly used as a sweetener in beverage applications, but has an off-taste problem. More recently, certain minor steviol glycoside compounds with better taste characteristics have been attracting attention. For example, Rebaudioside M has a higher sweetness and is more potent than other steviol glycoside compounds (see, for example, Prakash, I., et al. (2013) Nat. Prod. Commun., 8: 1523-1526, and International Publication No. 2013 / 096420). Rebaudioside D is about 200-220 times sweeter than sucrose, and in sensory evaluation, the sweetness has a slow onset and is very refreshing (see, for example, Prakash, I., et al. (2012) Int. J. Mol. Sci., 13: 15126-15136).

[0008] Rebaudiosides can be difficult to use because they have less than desirable water solubility properties. For example, Reb D has been reported to be difficult to use in food products due to its low water solubility at room temperature. For example, to achieve complete dissolution at a concentration of 0.8%, Reb D needs to be heated to near boiling water temperature for 2 hours. Only a maximum of 300-450 ppm can be solubilized in water at 23°C (see, for example, US Patent Application Publication No. 2013 / 0251881). As another example, Rebaudioside M obtained from Stevia rebaudiana has low water solubility and dissolution quality in beverage formulations (see, for example, US Patent Application Publication No. 2014 / 0171519). Summary of the Invention [Problem to be solved by the invention]

[0009] The present disclosure generally relates to solubilized steviol glycoside compositions, such as aqueous solutions having one or more steviol glycoside compounds and one or more steviol glycoside solubility enhancer compounds. The present disclosure also relates to the use of the solubilized steviol glycoside compositions as sweetener compositions that can be used to prepare sweetened compositions, including foods, beverages, and other similar products. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The present disclosure generally relates to steviol glycoside solubility enhancers. For example, some aspects of the disclosure are directed to compositions, such as sweetener compositions, beverages, or food products, that include a steviol glycoside and a steviol glycoside solubility enhancer to enhance the solubility of the steviol glycoside.

[0011] Further purification can be performed if it is desired to provide the steviol glycosides and steviol glycoside solubility enhancer in concentrated or purified form, or if the steviol glycoside solubility enhancer compounds are separated from the steviol glycoside compounds or from each other. Such concentration or purification of the steviol glycoside compounds and steviol glycoside solubility enhancer compounds can be performed on the liquid fermentation medium, or the fermentation medium can then be dried prior to purification. For example, lyophilization can be used to dry the fermentation medium to form a dry composition (e.g., powder or flakes) comprising one or more of the steviol glycoside compounds and steviol glycoside solubility enhancer compounds that can be subsequently processed.

[0012] As used herein, the term "steviol glycosides" generally refers to the total content of steviol glycoside compounds. The weight of steviol glycosides is determined on a dry (anhydrous) basis. Unless otherwise stated herein, the "amount" of steviol glycosides refers to the weight percentage (% weight) of the total content of steviol glycoside compounds.

[0013] As discussed herein, the sweetener composition includes steviol glycosides and steviol glycoside solubility enhancers, as well as other compounds. Steviol glycoside compounds generally have the formula: [ka] where steviol (R1 and R2 = H) is the aglycone backbone, and R1 and R2 can each be hydrogen or one or more sugar moieties. These sugar moieties are most commonly glucose, rhamnose, or xylose, although steviol glycoside compounds containing fructose and deoxyglucose sugar moieties have been reported.

[0014] Exemplary steviol glycoside compounds that may be useful in the solutions described herein include Rebaudioside A (Reb A) (CAS No. 58543-16-1), Rebaudioside B (Reb B) (CAS No. 58543-17-2), Rebaudioside C (Reb C) (CAS No. 63550-99-2), Rebaudioside D (Reb D) (CAS No. 63279-13-0), Rebaudioside E (Reb E) (CAS No. 63279-14-1), Rebaudioside F (Reb F) (CAS No. 438045-89-7), Rebaudioside M (Reb M) (CAS No. 1220616-44-3), rubusoside (CAS No. 63849-39-4), dulcoside A (CAS No. 64432-06-0), rebaudioside I (Reb I) (MassBank Record:FU000332), rebaudioside Q (Reb Q), rebaudioside O (Reb O), rebaudioside N (Reb N) (CAS No. 1220616-46-5), 1,2-stevioside (CAS No. 57817-89-7), 1,3-stevioside (Reb G), steviol-1,2-bioside (MassBank Record:FU000332). Record:FU000299), steviol-1,3-bioside, steviol-13-O-glucoside (13-SMG), steviol-19-O-glucoside (19-SMG), and steviol glycoside compounds having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more sugar additions (e.g., glucose, rhamnose, and / or xylose), and isomers thereof. See, e.g., Steviol Glycosides Chemical and Technical Assessment 82nd JECFA, 2016, revised by Jeff Moore, Food Agric.Org.

[0015] Exemplary steviol glycoside compounds may include Rebaudioside M, Rebaudioside D, Rebaudioside A, Rebaudioside B, Rebaudioside J, Rebaudioside N, and / or Rebaudioside O. In some embodiments, one or more of the steviol glycoside compounds are produced by enzymatic modification or by fermentation by an engineered microorganism. For example, Rebaudioside D and M may be produced by an engineered organism and then isolated to produce steviol glycosides with primarily Rebaudioside D and Rebaudioside M as the major steviol glycoside species. In some embodiments, one or more of the steviol glycoside compounds are isolated from Stevia rebaudiana.

[0016] In some embodiments, the steviol glycosides may contain Rebaudioside D and Rebaudioside M in an amount greater than other steviol glycoside compounds. For example, Rebaudioside M and / or Rebaudioside D may be present in the steviol glycosides in a total amount of about 75 weight percent ("% (wt)" or "wt %) or greater, about 80% (wt) or greater, preferably about 90% (wt) or greater, about 92.5% (wt) or greater, or 95% (wt) or greater of the total amount of steviol glycoside compounds in the composition. Rebaudioside M may be the predominant steviol glycoside compound in the composition, e.g., in an amount ranging from about 45% (wt) to about 70% (wt), about 50% (wt) to about 65% (wt), or about 52.5% (wt) to about 62.5% (wt) of the total amount of steviol glycoside compounds in the composition. Rebaudioside D may be in an amount less than Rebaudioside M, such as in an amount ranging from about 25% (wt) to about 50% (wt), about 30% (wt) to about 45% (wt), or about 32.5% (wt) to about 42.5% (wt) of the total amount of steviol glycoside compounds in the composition.

[0017] The steviol glycosides may optionally include minor amounts of steviol glycoside compounds other than Rebaudioside D and Rebaudioside M. For example, the steviol glycosides may include one or more of Rebaudioside A, Rebaudioside B, or stevioside in an amount of about 1% (by weight) or less, about 0.5% (by weight) or less, or about 0.25% (by weight) or less of the total amount of steviol glycoside compounds in the composition.

[0018] Advantageously, it has been found that certain steviol glycoside solubility enhancer compounds can improve the solubility of steviol glycosides in aqueous solutions, and thus compositions with higher concentrations of steviol glycosides can be prepared. As used herein, "immediate solubility" refers to the solubility of a steviol glycoside compound or a mixture of steviol glycoside compounds that is vigorously mixed with water at room temperature (25°C). As used herein, "equilibrium solubility" refers to the solubility of a steviol glycoside compound or a mixture of steviol glycoside compounds that is vigorously mixed with deionized water at 80°C for 15 minutes, cooled to room temperature (25°C), and then observed for at least 4 days. A clear solution that does not contain precipitate is considered soluble. Unless otherwise indicated herein, the term "solubility" refers to "equilibrium solubility".

[0019] In the absence of a solubility enhancing compound, Rebaudioside D has a very low immediate solubility in water (less than 0.08% at room temperature). When heated to 80° C. for 15 minutes, Rebaudioside D has an equilibrium solubility of 0.08% at room temperature for at least 4 days. Rebaudioside M has a higher solubility than Rebaudioside D. The immediate solubility of Rebaudioside M is about 0.13% and its equilibrium solubility is about 0.2% at room temperature.

[0020] The presence of a steviol glycoside solubility enhancer can improve the solubility of steviol glycosides by 1, 2, 3, 4, 5, 10, 15, 20, 50, 100, 200, or 250 times or more.

[0021] In some embodiments, a steviol glycoside solubility enhancer may be concentrated in a composition. The term "enriched" refers to an increase in the amount of one or more steviol glycoside solubility enhancer compounds relative to one or more other compounds present in the composition. A composition that is enriched for one or more steviol glycoside solubility enhancer compounds may improve the solubility of steviol glycosides in combination with steviol glycosides.

[0022] In yet other embodiments, one or more steviol glycoside solubility enhancer compounds are purified from stevia extracts to provide compositions comprising steviol glycoside solubility enhancers that are essentially free of other components found in stevia leaves, such as those listed in Tables 2 through 6. Such purified compositions may be combined with steviol glycosides to increase the aqueous solubility of steviol glycosides to form compositions having higher steviol glycoside concentrations.

[0023] Thus, another aspect of the present disclosure provides a method of enhancing the solubility of a steviol glycoside in an aqueous composition, the method comprising providing an aqueous composition comprising a steviol glycoside solubility enhancer and a steviol glycoside, e.g., rebaudioside A, rebaudioside B, rebaudioside M, rebaudioside D, rebaudioside I, rebaudioside J, rebaudioside Q, rebaudioside N, rebaudioside O, or stevioside, or any combination thereof. For example, the steviol glycoside can be added to a composition having the steviol glycoside solubility enhancer, the steviol glycoside and the steviol glycoside solubility enhancer may be mixed, or the steviol glycoside solubility enhancer can be added to a composition having the steviol glycoside.

[0024] As used herein, a sweetener composition (also called a sweetening composition) refers to a composition comprising steviol glycosides and a steviol glycoside solubility enhancer. Thus, one or more steviol glycoside compounds, such as Reb B, Reb M, and / or Reb D, may be present in the composition in greater amounts, such as greater than about 75%, greater than about 80%, greater than about 85%, greater than about 90%, greater than about 95%, or greater than about 99% of the total amount of steviol glycosides in the composition. In practice, it may be useful to include at least 0.5% of other steviol glycosides to avoid excessive processing costs.

[0025] In one aspect, the steviol glycoside solubility enhancer is present in the sweetener composition in a molar ratio of steviol glycosides to steviol glycoside solubility enhancer of about 1:1, 1:0.9, 1:0.8, 1:0.7, 1:0.6, 1:0.5, 1:0.4, 1:0.3, 1:0.2, or 1:0.1. In one aspect, the steviol glycoside solubility enhancer is present in the sweetener composition in a molar ratio of steviol glycosides to steviol glycoside solubility enhancer of about 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, or 1:10.

[0026] The sweetener composition may optionally contain another sweetener, an additive, a liquid carrier, or a combination thereof. The sweetener composition is used to sweeten other compositions (sweetenable compositions), such as foods, beverages, pharmaceuticals, oral hygiene compositions, dietary supplements, etc.

[0027] As used herein, "sweetable composition" means a substance that contacts the oral cavity of a human or animal, including substances that are placed in the oral cavity but are later expectorated (such as mouthwash rinses) and substances that are drunk, eaten, swallowed, or digested and are suitable for consumption by humans or animals when used within normally acceptable limits. A sweetener composition is a precursor composition to a sweetened composition, which is converted to a sweetened composition by combining the sweetener composition with at least one sweetening composition and optionally one or more other sweetener compositions and / or other ingredients.

[0028] As used herein, "sweetened composition" refers to a substance derived from ingredients including at least one sweetener composition and at least one sweetener composition. In some embodiments, the sweetened composition itself may be used as a sweetening composition to further sweeten the sweetener composition. In some embodiments, the sweetened composition may be used as a sweetener composition to be further sweetened with one or more additional sweetening compositions. For example, a beverage that does not contain a sweetener component is one type of sweetener composition. A sweetened beverage can be provided by adding a sweetener composition to an unsweetened beverage. A sweetened beverage is one type of sweetened composition.

[0029] In some preparations, steviol glycosides provide the sole sweetening component in the sweetened composition.

[0030] In some embodiments, the sweetening composition comprises steviol glycosides in an amount effective to provide a sweetness intensity equivalent to a particular amount of sucrose. The amount of sucrose in a reference solution may be described in degrees Brix (°Bx). One degree Brix is ​​1 gram of sucrose in 100 grams of solution, expressing the strength of the solution as a weight percentage (% w / w). For example, the sweetener composition contains steviol glycosides in an amount effective to provide a sweetness equivalent to about 0.50 to 14 degrees Brix of sugar, e.g., about 5 to about 11 degrees Brix, about 4 to about 7 degrees Brix, or about 5 degrees Brix, when present in the sweetened composition.

[0031] The amount of steviol glycosides in the sweetener composition may vary. Steviol glycosides can be present in the sweetener composition in any amount that imparts the desired sweetness when the sweetener composition is incorporated into a sweetened composition. For example, Reb M and / or Reb D are present in the sweetener composition in an amount effective to provide a total steviol glycoside concentration, when present in the sweetened composition, of from about 1 ppm to about 10,000 ppm (1% by weight) to about 100,000 ppm (10% by weight), and in another embodiment, steviol glycosides are present in the sweetener composition in an amount effective to provide a steviol glycoside concentration of from about 10 ppm to about 1,000 ppm, more specifically, in the range of from about 10 ppm to about 800 ppm, from about 50 ppm to about 800 ppm, from about 50 ppm to about 600 ppm, or from about 200 ppm to about 500 ppm.

[0032] In one aspect, a steviol glycoside compound other than Reb D, Reb M, Reb G, Reb O, Reb N, and / or Reb E, or other than Reb D, Reb M, Reb B, and / or Reb A, or other than Reb D and / or Reb M, is present in the sweetened composition at about 0.05-70% by weight of the total content of the sweetener composition, e.g., about 0.1-50, 0.5-70, 1-50, 1-35, 2-25, 3-20, 5-15, 0.1-15, 0.5-10, 1-5%, etc. In one aspect, steviol glycoside compounds other than Reb D, Reb M, Reb G, Reb O, Reb N, and / or Reb E, or other than Reb D, Reb M, Reb B, and / or Reb A, or other than Reb D and / or Reb M are present in the sweetened composition in a weight ratio of the sum of all other glycosides of 1:1 to 1:20, 1:1.5 to 1:15, 1:2 to 1:10, 1:2.5 to 1:7.5, or 1:3 to 1:5.

[0033] Unless expressly stated otherwise, ppm is by weight.

[0034] In some embodiments, the sweetener composition having steviol glycosides and a steviol glycoside solubility enhancer also contains one or more additional non-steviol glycoside sweetener compounds. The non-steviol glycoside sweetener compounds can be any type of sweetener, such as sweeteners obtained from plants or plant products, or physically or chemically modified sweeteners obtained from plants, or synthetic sweeteners.

[0035] For example, exemplary non-steviol glycoside sweeteners include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, tagatose, trehalose, galactose, rhamnose, cyclodextrins (e.g., a-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, and arylose. sugar, 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, fuculose, glucuronic acid, gluconic acid, gluconolactone, abequose, galactosamine, xylooligosaccharides, Sugars (xylotriose, xylobiose, etc.), gentiooligosaccharides (gentiobiose, gentiotriose, gentiotetraose, etc.), galactooligosaccharides, sorbose, ketotriose (dehydroxyacetone), aldotriose (glyceraldehyde), nigerooligosaccharides, fructooligosaccharides (kestose, nystose, etc.), maltotetraose, maltotriose, tetrasaccharides, mannanoligosaccharides, maltooligosaccharides (malto Examples of suitable sugars include maltose, maltotriose, maltotetraose, maltopentaose, maltohexaose, and maltoheptaose, dextrins, lactulose, melibiose, raffinose, 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. Where applicable, D or L configurations can be used.

[0036] The steviol glycosides and the carbohydrate sweetener can be present in any weight ratio, such as, for example, about 1:100, such as, for example, from about 1:14,000 to about 100:1. The carbohydrate is present in the sweetener composition in an amount effective to provide a concentration of from about 100 ppm to about 140,000 ppm when present in a sweetened composition, such as, for example, a beverage.

[0037] In another embodiment, the sweetener composition comprising steviol glycosides and a steviol glycoside solubility enhancer further comprises one or more synthetic sweeteners. In one embodiment, the synthetic sweeteners have a higher sweetening potency than sucrose, fructose, and / or glucose, yet have fewer calories than sucrose, fructose, and / or glucose. Exemplary synthetic non-steviol glycoside sweeteners include sucralose, acesulfame potassium, acesulfamic acid and salts thereof, aspartame, alitame, saccharin and salts thereof, neohesperidin dihydrochalcone, cyclamate, cyclamic acid and salts thereof, neotame, advantame, and combinations thereof. In embodiments where the sweetener composition comprises steviol glycosides and a synthetic sweetener, the synthetic sweetener may be present in an amount effective to provide a concentration of from about 0.3 ppm to about 3,500 ppm when present in a sweetened composition, such as, for example, a beverage.

[0038] The sweetener composition can be customized to provide a desired calorie content. For example, the sweetener composition can be "full calorie" such that when added to a sweetened composition (e.g., a beverage, etc.) it provides a desired sweetness and has about 120 calories per 8 ounce serving. Alternatively, the sweetener composition can be "medium calorie" such that when added to a sweetened composition (e.g., a beverage, etc.) it provides a desired sweetness and has less than about 60 calories per 8 ounce serving. In other embodiments, the sweetener composition can be "low calorie" such that when added to a sweetened composition (e.g., a beverage, etc.) it provides a desired sweetness and has less than 40 calories per 8 ounce serving. In yet other embodiments, the sweetener composition can be "zero calorie" such that when added to a sweetened composition (e.g., a beverage, etc.) it provides a desired sweetness and has less than 5 calories per 8 ounce serving. The non-calorie composition is "non-nutritive." In some aspects, low calorie compositions may also be referred to as "non-nutritional."

[0039] The weight ratio of the total amount of sweetener composition used to sweeten the sweetened composition can vary over a wide range, in many embodiments, this weight ratio is in the range of 1:10,000 to 10:1.

[0040] Sweetener compositions having steviol glycosides and steviol glycoside solubility enhancers can be incorporated into any known foodstuff (referred to herein as a "sweetenable composition") or other compositions intended for ingestion and / or contact with the oral cavity of a human or animal, such as pharmaceutical compositions, edible gel mixes and compositions, dental and oral hygiene compositions, foods (confections, condiments, chewing gum, cereal compositions, baked goods, prepared foods, culinary adjuvants, dairy products, and tabletop sweetener compositions), beverages, and other beverage products (e.g., beverage mixes, beverage concentrates, etc.).

[0041] In one embodiment, the sweetened composition is derived from a raw material comprising a sweetenable composition and a composition having steviol glycosides and a steviol glycoside solubility enhancer. In another embodiment, the sweetened composition is derived from a raw material comprising a sweetener composition comprising steviol glycosides and a steviol glycoside solubility enhancer. The sweetened composition may optionally include one or more additives, liquid carriers, binders, sweeteners, functional ingredients, other adjuvants, and combinations thereof.

[0042] Suitable "bulking agents" include, but are not limited to, maltodextrin (10DE, 18DE, or 5DE), corn syrup solids (20 or 36DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose, and cellulose derivatives, and the like, and mixtures thereof. In addition, according to yet another embodiment, granulated sugar (sucrose) or other caloric sweeteners such as crystalline fructose, other carbohydrates, or sugar alcohols can be used as bulking agents by providing good content uniformity without adding significant calories.

[0043] The tabletop sweetener composition may be packaged in any form known in the art. Non-limiting forms include, but are not limited to, powder form, granular form, packet, tablet, sachet, pellet, cube, solid, and liquid. The amount of steviol glycosides in the dry blend tabletop sweetener formulation may vary. In certain embodiments, the dry blend tabletop sweetener formulation may contain steviol glycosides in an amount of about 1% (by weight) to about 10% (by weight) of the tabletop sweetener composition.

[0044] The tabletop sweetener composition may also be embodied in a liquid form, in which a sweetener composition comprising steviol glycosides and comprising a steviol glycoside solubility enhancer is combined with a liquid carrier. Suitable non-limiting examples of carrier agents for liquid tabletop functional sweeteners include water, alcohol, polyols, glycerin-based or citric acid-based sweeteners dissolved in water, and mixtures thereof.

[0045] In one embodiment, the sweetened composition is a beverage product that includes steviol glycosides and includes a steviol glycoside solubility enhancer. As used herein, a "beverage product" is a ready-to-drink beverage, a beverage concentrate, a beverage syrup, a frozen beverage, or a powdered beverage. Suitable ready-to-drink beverages include carbonated and non-carbonated beverages. Carbonated beverages include, but are not limited to, high-effervescent soft drinks, cola, lemon-lime flavored sparkling soft drinks, orange flavored sparkling soft drinks, grape flavored sparkling soft drinks, strawberry flavored sparkling soft drinks, pineapple flavored sparkling soft drinks, ginger ale, soft drinks, and root beer. Non-carbonated beverages include, but are not limited to, fruit juice, fruit juice-flavored juice, juice drinks, nectar, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, fortified water drinks, fortified water drinks with vitamins, mostly water beverages (e.g., water with added natural or synthetic flavorings), coconut water, tea-type beverages (e.g., black tea, green tea, black tea, oolong tea), coffee, cocoa beverages, dairy-containing beverages (e.g., dairy beverages, dairy coffee, cafe au lait, milk tea, fruit milk beverages), beverages containing cereal extracts, smoothies, and combinations thereof.

[0046] Beverage concentrates and beverage syrups can be prepared with an initial volume of a liquid matrix (e.g., water) and the desired beverage ingredients. A full strength beverage is then prepared by adding an additional volume of water. Powdered beverages are prepared by dry mixing all of the beverage ingredients in the absence of a liquid matrix. A full strength beverage is then prepared by adding the entire volume of water.

[0047] The beverage may be non-alcoholic. A non-alcoholic beverage contains less than 0.5% (by weight), preferably less than 0.2% (by weight), less than 0.1% (by weight), or less than 0.05% (by weight) of ethanol. More broadly, a non-alcoholic beverage may contain less than 0.5% (by weight), preferably less than 0.2% (by weight), less than 0.1% (by weight), or less than 0.05% (by weight) of C1-C4 alcohols (e.g., methanol, ethanol, propanol, butanol, etc.). Many non-alcoholic beverages are alcohol-free, i.e., do not contain ethanol or do not contain C1-C4 alcohols. However, non-alcoholic beverages may contain other alcohols, for example sugar alcohols such as erythritol, isomalt, xylitol, glycerol, sorbitol, mannitol, maltitol, lactitol, and inositol. A commercially useful ready-to-drink beverage or beverage concentrate is ethanol-free and contains water, a steviol glycoside solubility enhancer, and a sugar alcohol. Such commercially useful beverages may also contain steviol glycosides.

[0048] In one embodiment, the beverage contains steviol glycosides and a steviol glycoside solubility enhancer. Any sweetener composition comprising steviol glycosides and a steviol glycoside solubility enhancer as detailed herein may be used in the beverage. In another embodiment, a method of preparing a beverage comprises combining a liquid matrix, a steviol glycoside, and a steviol glycoside solubility enhancer. The method may further comprise the addition of one or more sweeteners, additives, and / or functional ingredients. In yet another embodiment, a method of preparing a beverage comprises combining a liquid matrix with a sweetener composition comprising steviol glycosides and a steviol glycoside solubility enhancer.

[0049] In another embodiment, the beverage contains a sweetener composition containing steviol glycosides, and the steviol glycosides are present in the beverage in an amount ranging from about 1 ppm to about 10,000 ppm, for example, from about 25 ppm to about 800 ppm. In another embodiment, the steviol glycosides are present in the beverage in an amount ranging from about 100 ppm to about 600 ppm. In yet another embodiment, the steviol glycosides are present in the beverage in an amount ranging from about 100 ppm to about 200 ppm, from about 100 ppm to about 300 ppm, from about 100 ppm to about 400 ppm, or from about 100 ppm to about 500 ppm. In yet another embodiment, the steviol glycosides are present in the beverage in an amount ranging from about 300 ppm to about 700 ppm, for example, from about 400 ppm to about 600 ppm. In certain embodiments, steviol glycosides are present in the beverage in an amount of about 500 ppm.

[0050] In one embodiment, the composition is a beverage, and the steviol content in the beverage is about 50-1500 ppm, or 100-1200 ppm, 200-1000 ppm, 300-900 ppm, 350-800 ppm, 400-600 ppm, or 450-550 ppm. In one embodiment, steviol glycoside compounds other than Reb D, Reb M, Reb B and / or Reb A, or other than Reb D and / or Reb B, and optionally other than Reb G, Reb J, Reb O, Reb N, and / or Reb E, are present in the beverage at at least about 1 ppm to about 600 ppm, e.g., about 50 ppm to about 500 ppm, including at least 1, 5, 10, 20, 30, 40, 50, 125, 150, 150, 175, or 200 ppm. In one aspect, steviol glycoside compounds other than Reb D, Reb M, Reb B and / or Reb A, or other than Reb D and / or Reb B, and optionally Reb G, Reb O, Reb N, and / or Reb E, are present in the beverage at about 1-600 ppm 10-400, 50-200, 75-150, 5-200, 10-100, 20-90, or 30-80 ppm. In one aspect, steviol glycoside compounds other than Reb D, Reb M, Reb B and / or Reb A, are present in the beverage at about 1-600 ppm 10-400, 50-200, 75-150, 5-200, 10-100, 20-90, or 30-80 ppm. Exemplary Natural Sources of Steviol Glycoside Solubility Enhancers

[0051] Steviol glycoside solubility enhancers may be synthetically prepared or isolated from organisms including, but not limited to, plants, such as plant leaves and stems. The following table provides plant genera that are examples of plants likely to contain compounds within the scope of the steviol glycoside solubility enhancers of the present disclosure, for example, Formula (I), including, for example, caffeic acid, chlorogenic acid, cynarin, and / or structurally related compounds that may aid in the solubility of steviol glycosides. [Table 1-1] [Table 1-2]

[0052] In some embodiments, the steviol glycoside solubility enhancer may be isolated from a plant source, such as those listed in Table 1. Examples of commercially useful plant sources from which the steviol glycoside solubility enhancer may be isolated include the yerba mate plant (Ilex paraguariensis), stevia, coffee, tea, chicory, and globe artichoke. Some plant sources may produce steviol glycoside solubility enhancers that are enriched for one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid, which can increase the solubility of the steviol glycoside composition. For example, a steviol glycoside solubility enhancer isolated from a yerba mate plant may be enriched for dicaffeoylquinic acid, which can increase the solubility of the steviol glycoside composition. In other aspects, a steviol glycoside solubility enhancer isolated from a yerba mate plant that is enriched for dicaffeoylquinic acid may contain 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, 60% or more, 70% or more, or 80% or more, or 90% or more of one or more combinations of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquina, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid, and salts thereof.

[0053] Steviol glycoside solubility enhancers can be isolated in various ways. Some suitable processes are disclosed in detail in U.S. Provisional Patent Application No. 62 / 676,722, filed May 25, 2018, and entitled "Methods for Making Yerba Mate Extract Composition." For example, steviol glycoside solubility enhancers can be isolated from plant sources that contain one or more of monocaffeoylquinic acid, dicaffeoylquinic acid, and salts thereof. For example, yerba mate biomass and stevia biomass can be used to prepare steviol glycoside solubility enhancers. In one exemplary process, steviol glycoside solubility enhancers are prepared from commercially obtained ground yerba mate biomass. Briefly, yerba mate biomass is suspended in 50% (v / v) ethanol / water and shaken for at least 1 hour, and the resulting mixture is filtered to obtain an initial extract. The initial extract is diluted with water to 35% (v / v) ethanol and refiltered. The refiltered permeate is then applied to an AMBERLITE® FPA 53 resin column equilibrated with 35% (v / v) ethanol / water and the column permeate is discarded. The column is washed with 35% (v / v) ethanol / water and the column permeate is discarded. The column is then eluted with 10% (w / v) FCC grade sodium chloride in 50% (v / v) ethanol / water and the eluate is retained. Nitrogen gas is blown over the surface of the eluate at room temperature to remove the ethanol and reduce the eluate to 1 / 3 of its original volume. The reduced volume eluate is then filtered through a 0.2 μm polyethersulfone filter and then decolorized by passing through a 3 kDa molecular weight cutoff membrane. The decolorized permeate is retained and desalted by passing through a nanofiltration membrane. The desalted permeate is then lyophilized to obtain the steviol glycoside solubility enhancer. The process is also suitable for obtaining steviol glycoside solubility enhancers from Stevia biomass and can be adapted to obtain steviol glycoside solubility enhancers from other plant sources.

[0054] Some compounds may adversely affect the flavor or aroma of an aqueous solution or modified steviol glycoside solution. Certain steviol glycoside solubility enhancers, such as those prepared from plant extracts, do not contain one or more of the compounds shown in Table 2, or any combination thereof, above the preferred content levels of the present disclosure. All preferred content levels are listed as weight percentages on a dry weight basis. Certain commercially desirable solid (dry) steviol glycoside solubility enhancers do not contain any of the compounds listed in Table 2 above the preferred content levels. For those listed compounds that are acids, the compounds may exist in the acid form and / or salt form. [Table 2-1] [Table 2-2]

[0055] Preferably, such solid (dry) steviol glycoside solubility enhancers contain less than 50% (wt), e.g., less than 40% (wt), less than 30% (wt), or less than 25% (wt), more preferably less than 20% (wt), less than 15% (wt), less than 10% (wt), less than 5% (wt), less than 4% (wt), less than 3% (wt), less than 2% (wt), less than 1% (wt), less than 0.5% (wt), less than 0.25% (wt), less than 0.10% (wt), or 0% (wt) of steviol glycoside compounds. In selected implementations, such solid (dry) compositions having steviol glycoside solubility enhancers are substantially free of steviol glycoside compounds. In particular, when the steviol glycoside solubility enhancer is derived from stevia, e.g., stevia leaf, reducing the amount of steviol glycoside compounds in the steviol glycoside solubility enhancer allows for more precise selection of steviol glycosides to achieve the desired flavor profile during use.

[0056] In one aspect, a solid (dry) sweetener composition, which may be a powder, has steviol glycosides and steviol glycoside solubility enhancers that do not contain one or more of the following compounds, or any combination thereof, in excess of the preferred content levels of the present disclosure. All preferred content levels are listed as percentages by weight, on a dry weight basis. For those listed compounds that are acids, the compounds may exist in the acid form and / or salt form. [Table 3-1] [Table 3-2]

[0057] In one embodiment, the liquid sweetener concentrate has steviol glycosides and steviol glycoside solubility enhancers that do not contain one or more of the following compounds, or any combination thereof, in excess of the preferred content levels of the present disclosure. These preferred content levels are listed as a percentage by weight of the liquid sweetener concentrate. For those listed compounds that are acids, the compounds may be present in the acid form and / or salt form, taking into account that the compounds may be dissociated in the liquid sweetener concentrate. [Table 4-1] [Table 4-2]

[0058] In one aspect, beverages having steviol glycosides and steviol glycoside solubility enhancers do not contain one or more of the following compounds, or any combination thereof, at the weight percent cutoffs of the present disclosure. All preferred content levels are listed as a weight percentage of the total liquid sweetener concentrate. For those listed compounds that are acids, the compounds may be present in the acid form and / or salt form, taking into account that the compounds may dissociate in the beverage. [Table 5-1] [Table 5-2] Solubility Enhancer

[0059] Examples of solubility enhancers include: caffeic acid, esters of caffeic acid, esters of caffeic acid and quinic acid, mono-caffeoylquinic acids, i.e., esters of caffeic acid and quinic acid containing a single caffeic acid moiety, e.g., chlorogenic acid, cryptochlorogenic acid, or neochlorogenic acid (the structures of each are provided herein), esters of caffeic acid and quinic acid containing two or more caffeic acid moieties, such as dicaffeoylquinic acids, i.e., esters of caffeic acid and quinic acid containing two caffeic acid moieties, e.g., 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, or 4,5-dicaffeoylquinic acid (the structures of each are provided herein), Ferulic acid, esters of ferulic acid, esters of ferulic acid and quinic acid, monoferuloyl quinic acid, i.e. esters of ferulic acid and quinic acid containing a single ferulic acid moiety, for example 3-O-feruloyl quinic acid, 4-O-feruloyl quinic acid, 5-O-feruloyl quinic acid, esters of ferulic acid and quinic acid containing two or more ferulic acid moieties, such as diferuloyl quinic acid, i.e. esters of ferulic acid and quinic acid containing two ferulic acid moieties, for example 1,3-diferuloyl quinic acid, 1,4-diferuloyl quinic acid, 1,5-diferuloyl quinic acid, 3,4-diferuloyl quinic acid, 3,5-diferuloyl quinic acid and 4,5-diferuloyl quinic acid, Quinic acid, esters of quinic acid, Tartaric acid, tartaric acid derivatives, esters of tartaric acid, esters of tartaric acid derivatives, 3-(3,4-dihydroxyphenyl)lactic acid, 3-(3,4-dihydroxyphenyl)lactic acid derivatives, esters of 3-(3,4-dihydroxyphenyl)lactic acid, esters of 3-(3,4-dihydroxyphenyl)lactic acid derivatives, p-Coumaric acid, esters of p-coumaric acid, esters of p-coumaric acid and quinic acid, esters of p-coumaric acid and quinic acid containing a single p-coumaric acid moiety, esters of p-coumaric acid and quinic acid containing two or more p-coumaric acid moieties, and Sinapic acid, esters of sinapic acid, esters of sinapic acid and quinic acid, esters of sinapic acid and quinic acid containing a single sinapic acid moiety, esters of sinapic acid and quinic acid containing two or more sinapic acid moieties.

[0060] The steviol glycoside solubility enhancer may be in its acid form or in its salt form, for example, as a quaternary ammonium salt, sodium salt, potassium salt, lithium salt, magnesium salt, or calcium salt, or a combination of such salts. In the aqueous solution, the steviol glycoside solubility enhancer may be dissociated or undissociated, for example, some or all of the potassium salt of the acid steviol glycoside solubility enhancer compound may be dissociated into a potassium cation and anion.

[0061] In some embodiments, the solubility enhancer compound comprises one or more compounds selected from the group consisting of 3-O-coumaroylquinic acid, 4-O-coumaroylquinic acid, 5-O-coumaroylquinic acid, 1,3-dicumaroylquinic acid, 1,4-dicumaroylquinic acid, 1,5-dicumaroylquinic acid, 3,4-dicumaroylquinic acid, 3,5-dicumaroylquinic acid, 4,5-dicumaroylquinic acid.

[0062] Caffeic acid has the following structure: [ka]

[0063] Ferulic acid has the following structure: [ka]

[0064] P-Coumaric acid has the following structure: [ka]

[0065] Sinapic acid has the following structure: [ka]

[0066] Quinic acid has the following structure: [ka]

[0067] 3-(3,4-dihydroxyphenyl)lactic acid has the following structure: [ka]

[0068] Tartaric acid has the following structure: [ka] It can be in the D and L forms.

[0069] Examples of esters of various acids contemplated herein include esters of caffeic acid and tartaric acid, including chicoric acid, which has the following structure: [ka] It has two caffeic acid molecules linked to a tartaric acid core, caffeic acid has the following structure: [ka] It has one caffeic acid molecule linked to a tartaric acid core.

[0070] Examples of esters of various acids contemplated herein also include esters of caffeic acid and 3-(3,4-dihydroxyphenyl)lactic acid, including, for example, rosmarinic acid, which has the following structure: [ka]

[0071] Examples of esters of various acids contemplated herein include esters of caffeic acid and quinic acid, including mono-caffeoylquinic acid (e.g., chlorogenic acid, neochlorogenic acid, and cryptochlorogenic acid), and dicaffeoylquinic acid (e.g., 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid), and salts thereof. [ka] [ka] [ka] [ka] 4,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 3,4-dicaffeoylquinic acid are most prevalent in the compositions contemplated herein and are most prevalent in large amounts in stevia, yerba mate, globe artichoke, and green coffee.

[0072] Each of the caffeic acid, monocaffeoylquinic acid, dicaffeoylquinic acid, and other solubility enhancer compounds may be considered a weak acid, and each may exist in at least one of its conjugate acid form, its conjugate base form (e.g., its salt form), and a mixed conjugate acid-conjugate base form, with a fraction (e.g., a molar fraction) of the compound being in the conjugate acid form and another fraction being in the conjugate base form. The fraction of the conjugate acid form of the caffeic acid, monocaffeoylquinic acid, dicaffeoylquinic acid, and other solubility enhancer compounds relative to the conjugate base form depends on various factors, including the pKa of each compound and the pH of the composition.

[0073] Examples of salts of caffeic acid, monocaffeoylquinic acid, dicaffeoylquinic acid, and other steviol glycoside solubility enhancer compounds include, but are not limited to, quaternary ammonium, sodium, potassium, lithium, magnesium, and calcium salts thereof, or combinations of such salts.

[0074] In some embodiments, the solubility enhancer may be enriched in one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid. The term "enriched" refers to an increase in the amount of one of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid relative to one or more other compounds present in the solubility enhancer. A solubility enhancer that is enriched in one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid may increase the solubility of a steviol composition.

[0075] In some embodiments, a solubility enhancer enriched in one or more dicaffeoylquinic acids may increase the solubility of a steviol glycoside composition. A solubility enhancer enriched in dicaffeoylquinic acids may contain 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, 60% or more, 70% or more, 80% or more, or 90% or more dicaffeoylquinic acids. In other aspects, the solubility enhancer that is enriched for dicaffeoylquinic acid may comprise 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, 60% or more, 70% or more, or 80% or more, or 90% or more of a combination of one or more of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquina, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid, and salts thereof.

[0076] In some embodiments, the amount of solubility enhancer effective to increase the solubility of steviol glycosides comprises one or more dicaffeoylquinic acids, including at least 10%, at least 15%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, or at least 50%, at least 60%, at least 70%, at least 80%, or at least 90% dicaffeoylquinic acids. In other aspects, the solubility enhancer that is enriched for dicaffeoylquinic acid may comprise 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, 60% or more, 70% or more, or 80% or more, or 90% or more of a combination of one or more of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquina, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid, and salts thereof. Monocaffeoylquinic acid and dicaffeoylquina components

[0077] Certain preferred steviol glycoside solubility enhancers specifically include a dicaffeoylquinic (DCQ) component and, optionally, a monocaffeoylquinic (MCQ) component. The DCQ component comprises at least one, preferably at least two, or at least three dicaffeoylquinic acids, or salts thereof. In one embodiment, the DCQ component comprises at least one compound selected from the group consisting of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and salts thereof. The MCQ component comprises at least one, preferably at least two, or at least three monocaffeoylquinic acids, or salts thereof. In one embodiment, the MCQ ingredient comprises at least one compound selected from the group consisting of chlorogenic acid, cryptochlorogenic acid, neochlorogenic acid, and salts thereof.

[0078] The DCQ and MCQ components (if present) together can comprise more than 50% (by weight) of the steviol glycoside solubility enhancer. Desirably, the DCQ and MCQ components (if present) together comprise more than 60%, more than 70%, more than 80%, more than 90%, more than 95%, or more than 98% (by weight) of the steviol glycoside solubility enhancer.

[0079] Steviol glycoside solubility enhancers may include solubility enhancer compounds in addition to MCQ and DCQ components. One useful steviol glycoside solubility enhancer includes an MCQ component, a DCQ component, and one or more compounds selected from the group consisting of caffeic acid, ferulic acid, p-coumaric acid, sinapic acid, quinic acid, 3-(3,4-dihydroxyphenyl)lactic acid, tartaric acid, chicoric acid, caftaric acid, monoferuloyl quinic acid, diferuloyl quinic acid, monocoumaroyl quinic acid, dicumaroyl quinic acid, and salts thereof. In certain embodiments, such steviol glycoside solubility enhancers include an MCQ component, a DCQ component, and one or more compounds selected from the group consisting of caffeic acid, monoferuloyl quinic acid, diferuloyl quinic acid, and salts thereof.

[0080] One useful steviol glycoside solubility enhancer comprises an MCQ component, a DCQ component, and less than 0.3% (by weight) of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, or malic acid, or less than 0.05% (by weight) of pyruvate, pyruvic acid, fumarate, fumaric acid, tartrate, tartaric acid, sorbate, sorbic acid, acetate, or acetic acid, or less than about 0.05% (by weight) of chlorophyll. In one aspect, the steviol glycoside solubility enhancer is free of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, and malic acid, or free of pyruvate, pyruvic acid, fumarate, fumaric acid, tartrate, tartaric acid, sorbate, sorbic acid, acetate, and acetic acid, or free of chlorophyll.

[0081] Surprisingly, the weight ratio of the DCQ component to the MCQ component can materially affect the effectiveness of the steviol glycoside solubility enhancer on a weight basis. Specifically, a higher weight ratio of the DCQ component to the MCQ component generally is more effective at keeping the steviol glycoside compounds in solution. This is particularly surprising, since, all other things being equal, the total number of molecules in a given weight of steviol glycoside solubility enhancer decreases as the weight ratio increases (there are more molecules in a gram of monocaffeoylquinic acid than in a gram of dicaffeoylquinic acid because monocaffeoylquinic acid has a lower molecular weight than dicaffeoylquinic acid).

[0082] The weight ratio of the DCQ component to the MCQ component (i.e., the weight of the DCQ component divided by the weight of the MCQ component) can be at least 0.2, at least 0.33, or at least 0.5. Preferably, this ratio is at least 1, at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, or at least 10. In certain embodiments, this ratio is 20 or less or 10 or less, e.g., 1-20, preferably 1-10, 2-10, 3-10, 4-10, or 5-10. Depending on the plant source, increasingly higher ratios of DCQ component to MCQ component may increase processing costs to obtain the solubility enhancer without adversely affecting commercially relevant uses, e.g., in beverages having less than 1,000 ppm steviol.

[0083] Certain commercially useful steviol glycoside solubility enhancers have a weight ratio of DCQ component to MCQ component of 0.33 to 5. Such compositions have been found to produce non-alcoholic beverages with particularly desirable sensory properties. Thus, in some embodiments, the weight ratio of DCQ component to MCQ component in the steviol glycoside solubility enhancer is 0.33 to 5, 0.5 to 5, 1 to 5, 1.5 to 5, 2 to 5, 3 to 5, 0.5 to 4, 1 to 4, 1.5 to 4, 0.5 to 3, 1 to 3, or 1.5 to 3.

[0084] One suitable steviol glycoside solubility enhancer has a weight ratio of DCQ component to MCQ component of at least 1, preferably at least 2, at least 3, or at least 4, and the DCQ component and the MCQ component together comprise more than 70% (by weight) of the steviol glycoside solubility enhancer, e.g., more than 80% (by weight), or more than 90% (by weight).

[0085] The effectiveness of the steviol glycoside solubility enhancer can be measured by using the following standardized solubility test: The steviol glycoside solubility enhancer and steviol glycosides containing 89% (by weight) rebaudioside M and 8.2% (by weight) rebaudioside D (based on the weight of the total steviol glycoside content) are added to distilled water. The steviol glycoside solubility enhancer is added at a concentration of 35.7 grams per liter of water (3.57% (wt / vol)) and the steviol glycosides are added at a concentration of 50 grams per liter of water (5% (wt / vol)). The water is then heated to 80°C for 10 minutes with periodic mixing to form a solution. The solution is cooled to 22°C and then stored at 22°C. The solution is then periodically visually inspected for precipitates indicating that the steviol glycosides have come out of solution. The storage period is recorded, i.e., the time of storage at 22° C. that the steviol glycosides remain in solution.

[0086] Steviol glycoside solubility enhancers according to embodiments of the invention may maintain steviol glycosides in solution for a shelf-life measured according to this standardized solubility test of at least 3 days, at least 5 days, or at least 6 days. The shelf-life is desirably at least 7 days, at least 10 days, at least 14 days, at least 21 days, or at least 28 days. Particularly commercially useful steviol glycoside solubility enhancers may maintain steviol glycosides in solution for a shelf-life of at least 6 weeks, at least 8 weeks, or at least 12 weeks. This may enable beverage slosh syrups or water-fortified beverage concentrates to have commercially relevant shelf-life even when they do not contain C1-C4 alcohols. Ratio of steviol glycoside to steviol glycoside solubility enhancer

[0087] In some embodiments, the amount of steviol glycoside solubility enhancer effective to increase the solubility of steviol glycosides is such that the solubility enhancer comprises a weight ratio of steviol glycoside to solubility enhancer of 1:0.3 to 1:3. In other embodiments, the amount of solubility enhancer effective to increase the solubility of steviol glycosides is such that the solubility enhancer comprises a weight ratio of steviol glycoside to solubility enhancer of 1:1 to 1:3. The amount of solubility enhancer effective to increase the solubility of steviol glycosides can be such that the solubility enhancer comprises a weight ratio of steviol glycoside to solubility enhancer of 1:0.1 to 1:10. In some embodiments, the amount of solubility enhancer effective to increase the solubility of steviol glycosides can be such that the solubility enhancer comprises a weight ratio of steviol glycosides to solubility enhancer of about 1:0.1 to 1:5, about 1:0.5 to 1:4, about 1:0.3 to 1:3, or about 1:1 to 1:3. In other embodiments, the amount of solubility enhancer effective to increase the solubility of steviol glycosides can be such that the solubility enhancer comprises a weight ratio of steviol glycosides to solubility enhancer of about 1:0.1, 1:0.5, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, or 1:10. In some embodiments, the amount of solubility enhancer effective to increase the solubility of steviol glycosides can be an amount such that the solubility enhancer comprises a weight ratio of steviol glycosides to solubility enhancer of about 1:0.3 to 1:3.

[0088] In some embodiments, the amount of solubility enhancer effective to increase the solubility of steviol glycosides is a final concentration of the solubility enhancer greater than 100 ppm, 200 ppm, 300 ppm, 400 ppm, 700 ppm, 800 ppm, 900 ppm, or 1000 ppm. The final concentration of the solubility enhancer can be greater than 1100 ppm, 1200 ppm, 1300 ppm, 1400 ppm, 1500 ppm, 1600 ppm, 1700 ppm, 1800 ppm, or 1900 ppm. The final concentration of the solubility enhancer can be greater than 2100 ppm, 2200 ppm, 2300 ppm, 2400 ppm, 2500 ppm, 2600 ppm, 2700 ppm, 2800 ppm, or 2900 ppm. The final concentration of the solubility enhancer can be greater than 3100 ppm, 3200 ppm, 3300 ppm, 3400 ppm, 3500 ppm, 3600 ppm, 3700 ppm, 3800 ppm, or 3900 ppm. The final concentration of the solubility enhancer can be greater than 3000 ppm, 4000 ppm, 5000 ppm, 6000 ppm, 7000 ppm, 8000 ppm, or 9000 ppm. The final concentration of the solubility enhancer can be greater than 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or more.

[0089] In some embodiments, the steviol glycoside composition comprises an increased solubility when dissolved in a predominantly aqueous solution comprising predominantly water. The predominantly aqueous solution may also comprise less than 45%, 40%, 30%, 20%, 15%, 10%, 5%, or 1% by weight of C1-C4 alcohols. In one commercially relevant case, the predominantly aqueous solution may be substantially free of C1-C4 alcohols, e.g., non-alcoholic beverages (less than 0.2% by weight). In other embodiments, the predominantly aqueous solution is essentially free of C1-C4 alcohols (less than 0.05% by weight). In some embodiments, the predominantly aqueous solution comprises less than 1% stevioside. The predominantly aqueous solution may comprise less than 3% rebaudioside B. The predominantly aqueous solution may comprise less than 1% steviolbioside. The predominantly aqueous solution may comprise less than 1% 13-SMG. In other embodiments, the primarily aqueous solution comprises less than one or more of 1% stevioside, 1% rebaudioside B, 1% steviolbioside, and 1% 13-SMG.

[0090] The predominantly aqueous solution may have any suitable pH, for example, from 0-7, from 1-6, or from 1.5-4.

[0091] Beverages can be made with steviol glycoside solubility enhancers and steviol glycosides, and because the steviol glycoside solubility enhancers allow more steviol glycosides to go into solution, such beverages can be zero calorie beverages sweetened solely with steviol glycosides at a higher sweetness level than might otherwise be possible. EXAMPLES

[0092] The following examples are provided to illustrate the present disclosure but are not intended to limit its scope. All parts and percentages are by weight unless otherwise indicated. Example 1.

[0093] Various steviol glycoside solubility enhancer compounds are found in stevia leaves and other plant parts, such as artichoke stems, and may be in other leaves (such as tea leaves) or plant parts. In one embodiment, the solubility enhancer compounds are mono-, di-, or tri-hydroxycinnamic acid esters of quinic acid, such as chlorogenic acid, cynarin, neochlorogenic acid, cryptochlorogenic acid, 3-5-dicaffeoylquinic acid. Exemplary methods for purifying these solubility enhancers are described below. Refined from stevia leaves

[0094] Chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, cynarin, and other cynarin isomers comprise approximately 7% of the material in stevia leaves on a dry weight basis. Steviol glycoside solubility enhancer compounds in salt form

[0095] Stevia leaves may be first extracted with 50% (vol / vol) ethanol to liberate all steviol glycosides and steviol glycoside solubility enhancers from the solids. Once extracted, the solids may be removed (e.g., via filtration and / or centrifugation) and the resulting extract may be acidified to a pH of 2-2.5 with a common inorganic acid such as hydrochloric or phosphoric acid. The acidified extract may then be extracted with ethyl acetate via liquid-liquid extraction to produce purified fractions, separating the steviol glycoside compounds (aqueous layer) from the solubility enhancer compounds (organic layer). Each phase may then be further purified separately to obtain the desired end product.

[0096] The ethyl acetate layer with the steviol glycoside solubility enhancer compound can be further purified by adding a basic solution to the water (e.g., 0.05% calcium hydroxide, 0.1% sodium bicarbonate, etc.) and performing another liquid-liquid extraction. The colored species will remain in the ethyl acetate phase and can be discarded, while the aqueous phase contains the solubility enhancer compound and can be dried directly. Steviol Glycoside Solubility Enhancer Compounds in Acid Form

[0097] Stevia leaves may be first extracted with 50% (vol / vol) ethanol to liberate all steviol glycoside and steviol glycoside solubility enhancer compounds from the solids. After extraction, the solids may be removed (e.g., via filtration and / or centrifugation) and the resulting extract may be extracted with ethyl acetate via liquid-liquid extraction to remove colored species. The organic phase may be discarded and the aqueous layer may be acidified to pH 2-2.5 with a common inorganic acid such as hydrochloric or phosphoric acid. Fresh ethyl acetate may be added and another liquid-liquid extraction may be performed to produce purified fractions and separate the steviol glycosides (aqueous layer) from the steviol glycoside solubility enhancer compounds (organic layer). The aqueous phase containing the steviol glycoside compounds may be further purified for the desired steviol glycoside-based product and the organic phase may be directly dried to produce the desired steviol glycoside solubility enhancer product in acid form. Resin Purification

[0098] Resins such as polystyrene divinylbenzene and polymethacrylate can be used to purify these compounds. When using these resins, pH control allows for the purification of chlorogenic acid and cynarin isomers.

[0099] For polymethacrylate resins under acidic conditions, chlorogenic acid elutes before steviol glycoside compounds and cynarin isomers elute after steviol glycoside compounds using an ethanol / water elution. Under neutral conditions, both cynarin isomers and chlorogenic acid elute before steviol glycoside compounds.

[0100] In the case of polystyrene divinylbenzene under acidic conditions, chlorogenic acid elutes before steviol glycoside compounds, and cynarin isomers elute with steviol glycoside compounds using an ethanol / water elution. Under neutral conditions, both cynarin isomers and chlorogenic acid elute before steviol glycoside compounds.

[0101] Other hydrophobic resins and stationary phases can be used to purify these compounds. Purification of Cynarin (and its isomers) only

[0102] To purify only cynarin and its isomers (removing chlorogenic acid and its isomers), purification can begin by making a highly concentrated aqueous solution of the SE material. Higher concentrations of cynarin usually contain some base, such as ½ molar NaOH, to give a solution with a pH of about 4. This material can be loaded onto a polymethacrylate resin and washed with water (to remove excess acid). Chlorogenic acid (and its isomers) can be eluted with 15% (vol / vol) ethanol and dried separately to form one product. The column can then be treated with 60% (vol / vol) ethanol to elute cynarin and its isomers. This material can then be dried, for example, in the absence of strong acid or high heat, to form a cynarin-only SE material. Example 2. Long-term solubility testing of steviol glycoside solubility enhancers containing steviol glycosides

[0103] Samples were prepared via the design shown in Table 6 in weight to volume percentages. The appropriate amount of steviol glycoside (SG) was weighed into a 10 mL glass vial and diluted with the appropriate volume of pH 4 citrate buffer (e.g., 0.6% level), diluting 27 mg into 4.5 mL of buffer. This was repeated for all conditions in Table 1. Samples designed for pH 2.5 were then adjusted dropwise to pH 2.5 via phosphoric acid and a pH meter. For these samples, the same lot of steviol glycoside solubility enhancer (SE) derived from stevia leaves was used. Two different steviol glycosides were used: RM80 (>80% Reb M on a dry weight basis) and RA95 (>95% Reb A on a dry weight basis).

[0104] At each time point, the solution was centrifuged at 10,000 rpm for 2 minutes to remove any insoluble material from the analysis (even if it was not visible). An aliquot of the supernatant was diluted in 55% methanol for analysis by UHPLC-UV. Chromatographic analysis was performed on a C18-based reversed-phase chromatography column at elevated temperature under gradient conditions using trifluoroacetic acid in water and acetonitrile. SG was detected using a UV detector set at 210 nm. A linear calibration curve was applied using high purity (>99%) Reb A standard as the reference solution. [Table 6]

[0105] Briefly, this long-term storage solubility study shows that SG solutions with SE stored at 4° C., room temperature (approximately 22° C.), pH 4, and pH 2.5 demonstrated greater than 94% recovery of SG after 48+ weeks of storage. The long-term solubility data is shown in Table 7. A value of NM means that no measurement was made at that time point. [Table 7-1] [Table 7-2]

[0106] Long-term storage chemical stability data is shown in Table 8. The same samples were also evaluated for absolute concentration of dissolved steviol glycoside compounds. The data presented in Table 8 shows the concentration of steviol at each time point. In some of the vials, there was some evaporation of solvent during the one-year experiment. Thus, the concentration increased over time in most samples, but no crystals were observed at any time point in any sample. A value of NM means that no measurement was made at that time point. [Table 8]

[0107] This example shows that steviol glycoside solubility enhancers are effective at solubilizing steviol glycosides over time. SE is effective at solubilizing steviol glycoside solutions at 4° C., room temperature, pH 4, and / or pH 2.5 over 48 weeks with greater than 94% recovery of steviol glycosides. Example 3.

[0108] A series of solubility assays were performed with steviol glycoside enhancer compositions and steviol glycosides. Steviol glycoside enhancer compositions containing various ratios of dicaffeoylquinic acid and dicaffeoylquinate to monocaffeoylquinic acid and monocaffeoylquinate and monocaffeoylquinate were prepared and tested for their ability to solubilize steviol glycoside compositions. Accelerated solubility assays were performed with high concentrations of steviol glycosides (50,000 ppm, or 5% by weight) and high concentrations of steviol glycoside solubility enhancer (35,714 ppm) to reduce the amount of time that steviol glycosides can remain in solution and to determine the effect of various ratios of dicaffeoylquinic acid and dicaffeoylquinate to monocaffeoylquinic acid and monocaffeoylquinate on the solubility of steviol glycoside compounds.

[0109] Chlorogenic acid, monocaffeoylquinic acid was obtained commercially (Penta Manufacturing Company, Livingston, New Jersey). Dicaffeoylquina component was isolated from yerba mate. It contained 15% (wt) 3,4-dicaffeoylquinic acid, 45% (wt) 3,5-dicaffeoylquinic acid, 34% (wt) 4,5-dicaffeoylquinic acid, and less than 5% (wt) total monocaffeoylquinic acid. Steviol glycosides were 89% rebaudioside M and 8.2% rebaudioside D. A stock solution of monocaffeoylquinic acid was prepared and pH adjusted with concentrated sodium hydroxide to obtain a stock solution of monocaffeoylquinic acid of approximately 70% monocaffeoylquina sodium salt. A stock solution of dicaffeoylquinic acid was prepared and pH adjusted with concentrated sodium hydroxide to obtain a stock solution of dicaffeoylquinic acid of approximately 70% dicaffeoylquina sodium salt. Three control compositions and seven test compositions were prepared using the stock solution, steviol glycosides, and distilled water at the concentrations and ratios shown in Table Ex-1 below. The control and test compositions were prepared, aliquoted into glass vials, capped, and heated at 80°C for 5-10 minutes with periodic mixing. The vials were cooled to room temperature (approximately 22°C) and then stored at room temperature. The vials were visually inspected for crystal formation daily for the first two weeks and once a week thereafter. The storage period that each composition remained in solution before crystals were observed is shown in Table Ex-1 below.

[0110] Three control compositions contained steviol glycosides without a steviol glycoside solubility enhancer: one had 50,000 ppm (5% wt / vol), one had 30,000 ppm (3% wt / vol), and the third had 20,000 ppm (2% wt / vol) of steviol glycosides. Each of the test compositions contained 50,000 ppm (5% wt / vol) of steviol glycosides and 35,714 ppm (3.57% wt / vol) of steviol glycoside solubility enhancer, with a ratio of steviol glycosides to steviol glycoside solubility enhancer of about 1.4. Test compositions 1-7 contained a steviol glycoside solubility enhancer having a weight ratio of DCQ component to MCQ component (i.e., the weight of the DCQ component divided by the weight of the MCQ component) of 10, 5, 3, 1, 0.33, 0.2, and 0.1, respectively. [Table 9]

[0111] Table Ex-1 shows that each of the tests containing a steviol glycoside solubility enhancer was able to effectively solubilize 5% (wt / vol) steviol glycoside. A control composition with the same steviol glycoside concentration of 5% (wt / vol) did not dissolve even after several hours at 80° C. Even when the steviol glycoside concentration in the control was reduced to 2% (wt / vol), it still went into solution at 80° C., and SG degraded out of solution in less than an hour, which is consistent with the equilibrium solubility of Rebaudioside M and Rebaudioside D noted above. This alone demonstrates the remarkable effectiveness of the steviol glycoside solubility enhancer.

[0112] Surprisingly, test compositions having a DCQ component to MCQ component ratio of greater than 1 had a shelf life in solution, i.e., without visible precipitation, of greater than 10 days, which was more than double the shelf life of compositions having a DCQ component to MCQ component ratio of 0.1 or 0.2, and more than 50% longer than samples having a ratio of 0.33. Thus, steviol glycoside solubility enhancers with increased DCQ component to MCQ component ratios are more effective at solubilizing steviol glycosides, with ratios greater than 1 having a greater effect.

[0113] The test composition with equal amounts of DCQ and MCQ components was able to maintain a 5% (wt / vol) concentration of steviol glycosides in solution for 11 days, a feat in itself. All of the compositions with a DCQ to MCQ ratio of 3 or greater maintained steviol glycosides in solution for over 4 weeks upon drift and can remain in solution much longer.

[0114] All publications, patents, and patent applications are incorporated herein by reference. In the foregoing specification, the invention has been described with respect to certain preferred embodiments thereof, and numerous details have been set forth for purposes of illustration, and it will be apparent to those skilled in the art that the invention is susceptible to additional embodiments and that the specific details herein may be modified considerably without departing from the underlying principles of the invention. [Aspect 1] A steviol glycoside solubility enhancer comprising: a monocaffeoylquina (MCQ) component containing at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof; and a dicaffeoylquina (DCQ) component containing at least one compound selected from the group consisting of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and salts thereof, A steviol glycoside solubility enhancer, wherein the MCQ component and the DCQ component together comprise more than 50% (by weight) of the steviol glycoside solubility enhancer, preferably more than 60% (by weight), more than 70% (by weight), more than 80% (by weight), more than 90% (by weight), or more than 95% (by weight) of the steviol glycoside solubility enhancer. [Aspect 2] 2. The steviol glycoside solubility enhancer of embodiment 1, comprising less than 0.3% (by weight) of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, or malic acid, or less than 0.05% (by weight) of pyruvate, pyruvic acid, fumarate, fumaric acid, tartrate, tartaric acid, sorbate, sorbic acid, acetate, or acetic acid, or less than about 0.05% (by weight) of chlorophyll. [Aspect 3] The steviol glycoside solubility enhancer of embodiment 2, wherein the steviol glycoside solubility enhancer is free of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, and malic acid, or free of pyruvate, pyruvic acid, fumarate, fumaric acid, tartrate, tartaric acid, sorbate, sorbic acid, acetate, and acetic acid, or free of chlorophyll. [Aspect 4] A steviol glycoside solubility enhancer comprising: a monocaffeoylquina (MCQ) component containing at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof; and a dicaffeoylquina (DCQ) component containing at least one compound selected from the group consisting of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and salts thereof, the MCQ component and the DCQ component together comprise more than 50% (by weight) of the steviol glycoside solubility enhancer, preferably more than 60% (by weight), more than 70% (by weight), more than 80% (by weight), more than 90% (by weight), or more than 95% (by weight); the steviol glycoside solubility enhancer contains less than 5% by weight, preferably less than 4% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or less than 0.10% by weight of steviol glycoside compounds, or more preferably is substantially free of steviol glycoside compounds; 0-5% (by weight) of one or more of quercetin, kaempferol, myricetin, fisetin, galangin, isorhamnetin, pachypodol, rhamnadin, pyranofuranobol, furanofuranobol, luteolin, apigenin, tangeretin, taxifolin (or dihydroquercetin), dihydrokaempferol, hesperetin, naringenin, eriodictyol, homoeriodictyol, genistein, daidzein, glycitein, hesperidin, naringin, rutin, quercitrin, luteolin-glucoside, quercetin-xyloside, cyanidin, delphinidin, malvidin, pelargonidin, peonidin, and petunidin, or 0-3% (by weight) of one or more of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, malic acid, citrate, and citric acid; or 0-1% (by weight) of one or more of sulfate, sulfate, phosphate, phosphoric acid, nitrate, nitric acid, nitrite, nitrous acid, chloride, hydrochloric acid, ammonia, ammonium, tannic acid, monoglycerides, diglycerides, triglycerides, glucose, fructose, sucrose, galactose, ribose, trehalose, trehalulose, lactose, maltose, isomaltose, isomaltulose, mannose, tagatose, arabinose, rhamnose, xylose, dextrose, erythrose, threose, maltotriose, panose, glycerol, sorbitol, mannitol, xylitol, maltitol, lactitol, erythritol, isomalt, and inositol; or 0-0.5% (by weight) of a steviol glycoside solubility enhancer comprising one or more of tartrate, tartaric acid, pyruvate, pyruvic acid, fumarate, fumaric acid, ascorbic acid, sorbate, sorbic acid, acetate, acetic acid, and chlorophyll. [Aspect 5] Less than 0.1% (by weight) of: Alanine, Arginine, Asparagine, Aspartic Acid, Cysteine, Glutamine, Glutamic Acid, Glycine, Histidine, Isoleucine, Leucine, Lysine, Methionine, Phenylalanine, Proline, Serine, Threonine, Tryptophan, Tyrosine, Valine, Acacia (Arabic) Gum, Agar, Alginate, Arabinoxylan, Beta-Glucan, Beta-Mannan, Carrageenan Gum, Carob or The steviol glycoside solubility enhancer according to any one of Aspects 1 to 4, further comprising one or more of locust bean gum, fenugreek gum, galactomannan, gellan gum, glucomannan or konjac gum, guar gum, hemicellulose, inulin, karaya gum, pectin, polydextrose, psyllium husk mucilage, resistant starch, tara gum, tragacanth gum, xanthan gum, cellulose, chitin, and chitosan. [Aspect 6] The steviol glycoside solubility enhancer according to any one of Aspects 1 to 5, wherein the DCQ component comprises 10% (by weight) or more, 15% (by weight) or more, 20% (by weight) or more, 25% (by weight) or more, 30% (by weight) or more, 35% (by weight) or more, 40% (by weight) or more, 45% (by weight) or more, 50% (by weight) or more, 60% (by weight) or more, 70% (by weight) or more, 80% (by weight) or more, or 90% (by weight) or more of the steviol glycoside solubility enhancer. [Aspect 7] The steviol glycoside solubility enhancer according to any one of Aspects 1 to 4, wherein the weight ratio of the DCQ component to the MCQ component is at least 0.2, at least 0.33, at least 0.5, preferably at least 1, at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, or at least 10. [Aspect 8] The steviol glycoside solubility enhancer according to any one of aspects 1 to 4, wherein the weight ratio of the DCQ component to the MCQ component is 1 to 20, preferably 1 to 10, 2 to 10, 3 to 10, 4 to 10, or 5 to 10. [Aspect 9] The steviol glycoside solubility enhancer according to any one of aspects 1 to 4, wherein a weight ratio of the DCQ component to the MCQ component is 0.33 to 5. [Aspect 10] 5. The steviol glycoside solubility enhancer of any one of Aspects 1-4, wherein the weight ratio of the DCQ component to the MCQ component is at least 1, and the DCQ component and the MCQ component together comprise greater than 70% (by weight) of the steviol glycoside solubility enhancer. [Aspect 11] The steviol glycoside solubility enhancer according to any one of Aspects 1 to 10, further comprising one or more compounds selected from the group consisting of caffeic acid, ferulic acid, p-coumaric acid, sinapic acid, quinic acid, 3-(3,4-dihydroxyphenyl)lactic acid, tartaric acid, chicoric acid, caftaric acid, monoferuloylquinic acid, diferuloylquinic acid, monocoumaroylquinic acid, dicumaroylquinic acid, and salts thereof. [Aspect 12] The steviol glycoside solubility enhancer according to any one of aspects 1 to 10, further comprising one or more compounds selected from the group consisting of caffeic acid, monoferuloyl quinic acid, diferuloyl quinic acid, and salts thereof. [Aspect 13] 13. The steviol glycoside solubility enhancer of any one of aspects 1-12, wherein steviol glycosides comprising 89% rebaudioside M and 8% rebaudioside D are maintained in solution under a solubility test for a storage period of at least 10 days, wherein the solubility test comprises: (a) adding the steviol glycoside and the steviol glycoside solubility enhancer to distilled water, wherein the steviol glycoside is added at 5% (wt / vol of the water) and the steviol glycoside solubility enhancer is added at 3.57% (wt / vol of the water), (b) heating the composition of step (a) to 80° C. for 10 minutes with periodic mixing to form a solution, (c) cooling the solution to 22° C., and (d) maintaining the solution at 22° C. during the storage period. [Aspect 14] 14. An aqueous steviol glycoside solution comprising the steviol glycoside solubility enhancer according to any one of aspects 1 to 13. [Aspect 15] A non-alcoholic beverage comprising the steviol glycoside solubility enhancer according to any one of aspects 1 to 14 and a steviol glycoside. [Aspect 16] 16. A non-alcoholic beverage according to embodiment 15, having a pH of 1.5 to 4.

Claims

1. A steviol glycoside solubility enhancer prepared from yerba mate, comprising: a mono-caffeoylquina (MCQ) component comprising at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof; and a dicaffeoylquina (DCQ) component comprising at least one compound selected from the group consisting of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and salts thereof, the MCQ component and the DCQ component collectively comprise more than 70% (by weight) of the steviol glycoside solubility enhancer; A steviol glycoside solubility enhancer, wherein the weight ratio of said DCQ component to said MCQ component is at least 0.

2.

2. A steviol glycoside solubility enhancer prepared from yerba mate, comprising: a mono-caffeoylquina (MCQ) component comprising at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof; and a dicaffeoylquina (DCQ) component comprising at least one compound selected from the group consisting of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and salts thereof, the MCQ component and the DCQ component collectively comprise more than 70% (by weight) of the steviol glycoside solubility enhancer; the steviol glycoside solubility enhancer comprises less than 5% (by weight) of steviol glycoside compounds; 0-5% (by weight) of one or more of quercetin, kaempferol, myricetin, fisetin, galangin, isorhamnetin, pachypodol, rhamnadin, pyranofuranobol, furanofuranobol, luteolin, apigenin, tangeretin, taxifolin (or dihydroquercetin), dihydrokaempferol, hesperetin, naringenin, eriodictyol, homoeriodictyol, genistein, daidzein, glycitein, hesperidin, naringin, rutin, quercitrin, luteolin-glucoside, quercetin-xyloside, cyanidin, delphinidin, malvidin, pelargonidin, peonidin, and petunidin, or 0-3% (by weight) of one or more of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, malic acid, citrate, and citric acid; or 0-1% (by weight) of one or more of sulfate, sulfate, phosphate, phosphoric acid, nitrate, nitric acid, nitrite, nitrous acid, chloride, hydrochloric acid, ammonia, ammonium, tannic acid, monoglycerides, diglycerides, triglycerides, glucose, fructose, sucrose, galactose, ribose, trehalose, trehalulose, lactose, maltose, isomaltose, isomaltulose, mannose, tagatose, arabinose, rhamnose, xylose, dextrose, erythrose, threose, maltotriose, panose, glycerol, sorbitol, mannitol, xylitol, maltitol, lactitol, erythritol, isomalt, and inositol; or 0-0.5% (by weight) of one or more of tartrate, tartaric acid, pyruvate, pyruvic acid, fumarate, fumaric acid, ascorbic acid, sorbate, sorbic acid, acetate, acetic acid, and chlorophyll; A steviol glycoside solubility enhancer, wherein the weight ratio of said DCQ component to said MCQ component is at least 0.

2.

3. A steviol glycoside solubility enhancer prepared from yerba mate, comprising a mono-caffeoylquina (MCQ) component comprising at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof, and a dicaffeoylquina (DCQ) component comprising at least one compound selected from the group consisting of 1,3-dicaffeoylquina acid, 1,4-dicaffeoylquina acid, 1,5-dicaffeoylquina acid, 3,4-dicaffeoylquina acid, 3,5-dicaffeoylquina acid, 4,5-dicaffeoylquina acid, and salts thereof, wherein the MCQ component and the DCQ component together comprise more than 80% (by weight) of the steviol glycoside solubility enhancer, A steviol glycoside solubility enhancer, wherein the weight ratio of said DCQ component to said MCQ component is at least 0.

33.

4. A steviol glycoside solubility enhancer prepared from yerba mate, comprising a mono-caffeoylquina (MCQ) component comprising at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof, and a dicaffeoylquina (DCQ) component comprising at least one compound selected from the group consisting of 1,3-dicaffeoylquina acid, 1,4-dicaffeoylquina acid, 1,5-dicaffeoylquina acid, 3,4-dicaffeoylquina acid, 3,5-dicaffeoylquina acid, 4,5-dicaffeoylquina acid, and salts thereof, wherein the MCQ component and the DCQ component collectively comprise more than 90% (by weight) of the steviol glycoside solubility enhancer, A steviol glycoside solubility enhancer, wherein the weight ratio of said DCQ component to said MCQ component is at least 0.

33.

5. Less than 0.1% (by weight) of alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, acacia (arabic) gum, agar, alginate, arabinoxylan, beta-glucan, beta-mannan, carrageenan gum, carob or The steviol glycoside solubility enhancer of any one of claims 1 to 4, further comprising one or more of locust bean gum, fenugreek gum, galactomannan, gellan gum, glucomannan or konjac gum, guar gum, hemicellulose, inulin, karaya gum, pectin, polydextrose, psyllium husk mucilage, resistant starch, tara gum, tragacanth gum, xanthan gum, cellulose, chitin, and chitosan.

6. The steviol glycoside solubility enhancer of any one of claims 1 to 5, wherein the DCQ component comprises 25% (by weight) or more of the steviol glycoside solubility enhancer.

7. The steviol glycoside solubility enhancer of any one of claims 1 to 6, wherein the weight ratio of the DCQ component to the MCQ component is at least 1.

8. The steviol glycoside solubility enhancer according to any one of claims 1 to 7, wherein the weight ratio of the DCQ component to the MCQ component is 1 to 10.

9. The steviol glycoside solubility enhancer according to any one of claims 1 to 6, wherein the weight ratio of the DCQ component to the MCQ component is 0.33 to 5.

10. 4. The steviol glycoside solubility enhancer of any one of claims 1 to 3, wherein the weight ratio of the DCQ component to the MCQ component is at least 1, and the DCQ and MCQ components collectively comprise more than 80% (by weight) of the steviol glycoside solubility enhancer.

11. The steviol glycoside solubility enhancer according to any one of claims 1 to 10, further comprising one or more compounds selected from the group consisting of caffeic acid, ferulic acid, p-coumaric acid, sinapic acid, quinic acid, 3-(3,4-dihydroxyphenyl)lactic acid, tartaric acid, chicoric acid, caftaric acid, monoferuloyl quinic acid, diferuloyl quinic acid, monocoumaroyl quinic acid, dicumaroyl quinic acid, and salts thereof.

12. The steviol glycoside solubility enhancer according to any one of claims 1 to 11, further comprising one or more compounds selected from the group consisting of caffeic acid, monoferuloyl quinic acid, diferuloyl quinic acid, and salts thereof.

13. 13. The steviol glycoside solubility enhancer of any one of claims 1 to 12, wherein steviol glycosides comprising 89% rebaudioside M and 8% rebaudioside D are maintained in solution for a storage period of at least 7 days under a solubility test comprising: (a) adding the steviol glycoside and the steviol glycoside solubility enhancer to distilled water, wherein the steviol glycoside is added at 5% (wt / vol of the water) and the steviol glycoside solubility enhancer is added at 3.57% (wt / vol of the water), (b) heating the composition of step (a) to 80°C for 10 minutes with periodic mixing to form a solution, (c) cooling the solution to 22°C, and (d) maintaining the solution at 22°C during the storage period.

14. 1. A method for increasing the solubility of steviol glycosides in an aqueous solution, comprising:

14. A method comprising adding to the aqueous solution a steviol glycoside and a steviol glycoside solubility enhancer of any one of claims 1 to 13, wherein the solubility of the steviol glycoside is greater than a comparable composition without the steviol glycoside solubility enhancer.

15. 15. The method of claim 14, wherein the steviol glycoside comprises rebaudioside A, rebaudioside B, rebaudioside M, rebaudioside D, rebaudioside I, rebaudioside J, rebaudioside Q, rebaudioside N, rebaudioside O, stevioside, or any combination thereof.

16. 16. The method of claim 14 or 15, wherein the steviol glycosides include rebaudioside D and / or rebaudioside M.

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