WO2025085207A2 - Sweetener compositions and method for making the same - Google Patents

Abstract

An aqueous steviol glycoside solution includes 5 wt% or more of one or more steviol glycosides and choline chloride in an amount such that a weight ratio of choline chloride to water is between 4 and 7. The one or more steviol glycosides and the choline chloride may be present at a weight ratio of 0.65 or lower. The one or more steviol glycosides and water may be present at a weight ratio of 4 or lower. The one or more steviol glycosides may include rebaudioside D and rebaudioside M. A method for increasing the solubility of a steviol glycoside composition includes adding one or more steviol glycosides and choline chloride to an aqueous solution to form a steviol glycoside composition with a weight ratio of choline chloride to water is in a range of 4 to 7.

Description

SWEETENER COMPOSITIONS AND METHOD FOR MAKING THE SAME

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of European Application No. 23204789.4, filed October 20, 2023, which is incorporated by reference herein in its entirety.

BACKGROUND

[0002] Sugars, such as sucrose, fructose, and glucose, are utilized to provide a pleasant taste to beverages, foods, pharmaceuticals, and oral hygienic/cosmetic products. Although sucrose provides superior sweetness characteristics, it is caloric. Within the food and beverage industry, there continue to be efforts to reduce the amount of caloric sugars in products as consumers continue to seek low-calorie alternatives to calorie-rich products. While sugar substitutes can provide a sweetened taste to products, there may be limitations to preparing products with sugar substitutes. For example, consumers may find that the sensory and temporal characteristics of sugar substitutes differ from those found in caloric sweeteners such as glucose, sucrose, and/or fructose. These sensory characteristics can limit the use of sugar substitutes in products and become increasingly limiting as the concentration of sugar substitute increases. Further, the chemical and physical characteristics of sugar substitutes may differ from caloric sweeteners.

[0003] Stevia is a genus of about 240 species of herbs and shrubs in the sunflower family (Asteraceae), native to subtropical and tropical regions from western North America to South America. The species Stevia rebaudiana, commonly known as sweetleaf, sweet leaf, sugarleaf, or simply stevia, is widely grown for its sweet leaves. Steviol glycosides are a class of sweet-tasting glycosylated diterpene compounds commonly obtained from the leaves of Stevia rebaudiana. Various such compounds are known, each having differing properties, taste profiles, and chemical structures. A typical steviol glycoside is characterized by a single steviol backbone and contains one or more carbohydrate residues at C13 and Cl 9. For example, rebaudioside A contains a branched group of three glucosyl groups at C 13 and a single P-glucosyl at C 19, while rebaudioside D contains the same unit at Cl 3 but a diglucosyl at Cl 9. Steviol glycosides can serve as powerful sweeteners even at low concentrations — providing a sweetening effect approximately 150 to 450 times greater than an equivalent amount of sugar.

[0004] Steviol glycosides offer a non-caloric alternative to traditional caloric sweeteners such as glucose, sucrose, and/or fructose. Although steviol glycosides have higher sweetness intensity than sugar, they are less soluble in water. This can limit the use of steviol glycosides in various consumer products, particularly those which seek to use steviol glycosides in the highest concentrations. For example, it has been reported that rebaudioside D is difficult to use in food products because of its low solubility and poor dissolution in water at room temperature. For instance, rebaudioside D needs to be heated to near boiling water temperature for 2 hours in order to achieve complete dissolution at 0.8 % concentration. At most, only 300 to 450 ppm can be solubilized in water at 23 °C (e.g., see US 2013/0251881). As another example, rebaudioside M obtained from Stevia rebaudiana has poor water solubility and dissolution qualities in beverage formulations (e.g., see US 2014/0171519). Certain methods to improve rebaudioside solubility are less than desirable because they are labor intensive, requiring high processing temperatures. For example, see WO 2013148177.

[0005] Further improvements to sweetener compositions are desired.

SUMMARY

[0006] The present disclosure provides steviol glycoside compositions and methods for sweetening a food or beverage product.

[0007] An aqueous steviol glycoside solution includes 5 wt% or more, 10 wt% or more, 15 wt% or more, 20 wt% or more, 25 wt% or more, or 30 wt% or more, of one or more steviol glycosides; and choline chloride in an amount such that a weight ratio of choline chloride to water is between 4 and 7, between 4.5 and 6.5, between 5.0 and 6.0, or between 5.25 and 5.75. The one or more steviol glycosides and the choline chloride may be present at a weight ratio of 0.65 or lower. The one or more steviol glycosides and water may be present at a weight ratio of 4 or lower. [0008] An aqueous steviol glycoside solution includes one or more steviol glycosides; choline chloride; and water, the one or more steviol glycosides and choline chloride being present at a weight ratio of 0.65 or lower, and the one or more steviol glycosides and water being present at a weight ratio of 4 or lower.

[0009] The steviol glycosides are present at a total concentration of less than 40 wt%, less than 38 wt%, less than 35 wt%, or 33.3 wt% or less. The one or more steviol glycosides may include rebaudioside D and rebaudioside M. The solution may include rebaudioside D and rebaudioside M in a total amount of 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides. The solution may include rebaudioside M in an amount of 50 wt% or more, 60 wt% or more, 70 wt% or more, 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides. The solution may include rebaudioside D in an amount of 50 wt% or less, 25 wt% or less, 20 wt% or less, 15 wt% or less, or 10 wt% or less of total steviol glycosides, optionally wherein the solution may include rebaudioside D in an amount of 5 wt% or more or 10 wt% or more of total steviol glycosides. The solution may include steviol glycosides other than rebaudioside D and rebaudioside M at a concentration of 5 wt% or less, 2 wt% or less, or 1 wt% or less of total steviol glycosides.

[0010] A steviol glycoside composition includes one or more steviol glycosides; and choline chloride, wherein in an aqueous solution comprising the steviol glycoside composition such that the choline chloride is at a ratio of 5.5 parts to 1 part water, at least 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, or 30 wt% of the one or more steviol glycosides is solubilized.

[0011] A method for increasing solubility of a steviol glycoside composition includes adding one or more steviol glycosides and choline chloride to an aqueous solution to form a steviol glycoside composition with a weight ratio of choline chloride to water is in a range of 4 to 7, 4.5 to 6.5, 5.0 to 6.0, or 5.25 to 5.75 and the solubility of the steviol glycoside composition is higher than when the steviol glycoside composition is added to an aqueous solution with a weight ratio of choline chloride to water that is outside of the range.

[0012] The one or more steviol glycosides and the choline chloride may be present in the steviol glycoside composition at a weight ratio of 0.65 or lower. The one or more steviol glycosides and water may be present in the steviol glycoside composition at a weight ratio of 4 or lower. The steviol glycoside composition may include a total of 5 wt% or more, 10 wt% or more, 15 wt% or more, 20 wt% or more, 25 wt% or more, or 30 wt% or more, of the one or more steviol glycosides. The steviol glycoside composition may include a total of 40 wt%, less than 38 wt%, less than 35 wt%, or 33.3 wt% or less, of the one or more steviol glycosides. The one or more steviol glycosides may include rebaudioside D and rebaudioside M. The steviol glycoside composition may include steviol glycosides other than rebaudioside D and rebaudioside M at a concentration of 5 wt% or less, 2 wt% or less, or 1 wt% or less. The steviol glycoside composition may include rebaudioside D and rebaudioside M in a total amount of 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides. The steviol glycoside composition may include rebaudioside M in an amount of 50 wt% or more, 60 wt% or more, 70 wt% or more, 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides. The steviol glycoside composition may include rebaudioside D in an amount of 50 wt% or less, 25 wt% or less, 20 wt% or less, 15 wt% or less, or 10 wt% or less of total steviol glycosides, optionally wherein the steviol glycoside composition may include rebaudioside D in an amount of 5 wt% or more or 10 wt% or more of total steviol glycosides. The steviol glycoside composition may include steviol glycosides other than rebaudioside D and rebaudioside M at a concentration of 5 wt% or less, 2 wt% or less, or 1 wt% or less of total steviol glycosides. The one or more steviol glycosides are present at a total concentration of less than 40 wt%, less than 38 wt%, less than 35 wt%, or 33.3 wt% or less. [0013] The present disclosure further provides for use of choline chloride to increase solubility of one or more steviol glycosides.

BRIEF DESCRIPTION OF THE FIGURES

[0014] This patent or application contains at least one drawing executed in color. Copies of this patent or patent application publication with color drawings will be provided by the Office upon request and the payment of the necessary fee.

[0015] The drawings illustrate generally, by way of example, but not by way of limitation, various aspects discussed herein.

[0016] FIG. 1 shows a photo of a 30.3% solution of Reb M/Reb D in a ratio of 18/82 (left beaker) and a 29.0% solution of Reb D (right). The 30.3% mixed solution is clear and completely soluble, while the 29.0% solution of Reb D alone is clear but has some crystallization.

DETAILED DESCRIPTION

[0017] This disclosure relates to various compositions, such as sweetener compositions and other compositions, and in particular, steviol glycoside compositions which have improved water solubility.

[0018] All scientific and technical terms used herein have meanings commonly used in the art unless otherwise specified. The definitions provided herein are to facilitate understanding of certain terms used frequently herein and are not meant to limit the scope of the present disclosure. [0019] Values expressed in a range format should be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range were explicitly recited. For example, a range of “about 0. 1 % to about 5 %” or “about 0. 1 % to 5 %” should be interpreted to include not just about 0. 1 % to about 5 %, but also the individual values (e.g., 1 %, 2 %, 3 %, and 4 %) and the sub-ranges (e.g., 0.1 % to 0.5 %, 1.1 % to 2.2 %, 3.3 % to 4.4 %) within the indicated range. The statement “about X to Y” has the same meaning as “about X to about Y,” unless indicated otherwise. Likewise, the statement “about X, Y, or about Z” has the same meaning as “about X, about Y, or about Z,” unless indicated otherwise. [0020] Unless expressly stated, ppm (parts per million), percentage, and ratios are on a by weight basis. Percentage on a by weight basis is also referred to as wt% or % (wt) below.

Steviol Glycosides

[0021 ] The present disclosure provides compositions containing a steviol glycoside component or a mixture of a variety of steviol glycosides. The compositions may optionally include other steviol glycosides. The compositions may optionally include other additional components.

[0022] The steviol glycoside component can include one or more steviol glycosides. In some aspects, the term steviol glycoside refers to rebaudioside A (Reb A) (CAS # 58543-16-1), rebaudioside B (Reb B) (CAS # 58543-17-2), rebaudioside C (Reb C) (CAS # 63550-99-2), rebaudioside D (Reb D) (CAS # 63279-13-0), rebaudioside E (Reb E) (CAS # 63279-14-1), rebaudioside EE (Reb EE), rebaudioside F (Reb F) (CAS # 438045-89-7), 1,3-stevioside (rebaudioside G or Reb G), rebaudioside I (Reb I) (MassBank Record: FU000332), rebaudioside J (Reb J) (CAS # 1313049-59-0), rebaudioside M (Reb M) (CAS # 1220616-44-3), rebaudioside N (Reb N), rebaudioside O (Reb O) (CAS # 1220616-48-7), rebaudioside Q (Reb Q), rebaudioside V2 (Reb V2), rebaudioside DG (Reb DG), rubiisoside (CAS # 63849-39-4), dulcoside A (CAS # 64432-06-0), stevioside, 1,2-stevioside (CAS # 57817-89-7), steviolmonoside, steviol- 13- monoside, steviol- 19-monoside, steviolb ioside, steviol- 1,2-bioside (MassBank Record: FU000299), steviol- 1,3 -bioside, steviol- 13-O-glucoside (13-SMG), steviol- 19-O-glucoside (19- SMG), OPS 1-5 (corresponding to compound 4 from WO2016100689), 13-[(|3-D- glucopyranosy l)oxy)kaur- 16-en- 18-oic acid 2-O-|3-D-glucopyranosy 1-p-D-glucopyranosy 1 ester, steviol glycosides with 1, 2,3, 4, 5, 6, 7, 8, 9, 10 or more glycosides, and isomers thereof. Further discussion of steviol glycosides can be found in Harriet Wallin et al., Steviol Glycosides, 84th JECFA - Chemical and Technical Assessment (2017) Food Agric. Org. Rebaudiosides can be isolated and purified before use. Rebaudiosides can be used in commercially available form, obtainable from Cargill, Inc. (Wayzata, MN).

[0023] Steviol glycosides are sometimes used as blends, such as blends of Reb D and Reb M. Such blends may be notated as “rebaudioside D/M” or “Reb D/M”, and may include the two rebaudiosides, their related isomers (e.g., natural or synthetic), and/or salts thereof. This terminology format may be used for compositions having any other combination of glycosides, for example, but not limited to Reb D/G, Reb D/M/0, Reb N/O, Reb D/E, and the like.

[0024] Structurally, steviol glycosides comprise a steviol backbone and differ by the presence and arrangement of carbohydrate residues at the C 13 and C19 positions of the steviol backbone, according to the atom numbering on the base shown below. The glucopyranosyl residues represent groups Ri and R in the following formula:

[0025] Not only do steviol glycosides differ structurally, but the various steviol glycosides also have differing physical and sensory properties. Steviol is represented by the above formula when Ri and R2 are hydrogen. Steviol glycosides generally have the formula shown above where steviol is the aglycone backbone and Ri and R2 can each be hydrogen or one or more sugar moieties. These sugar moieties are most commonly glucose, rhamnose, or xylose, but steviol glycosides have been reported that include fructose and deoxyglucose sugar moieties. Table 1 below shows the various steviol glycosides and the corresponding Ri and R2 groups:

Table 1.

Glu: glucose; Rha: rhamnose; Xyl: xylose

[0026] Steviol glycosides differ structurally and also exhibit different properties, including solubility. In general, steviol glycosides are less soluble in water than sugar. Further, some steviol glycosides are less soluble than other steviol glycosides. Different steviol glycosides also provide different sensory properties, such as taste and sweetness intensity. Stevioside (comprising three glucose units) and rebaudioside A (comprising four glucose units) are found in greater abundance in stevia extracts and have particular sweetness attributes. Both stevioside and rebaudioside A add sweetness but can also be perceived as exhibiting bitterness attributes, especially at higher concentrations. Other steviol glycosides are found in much lower abundance in stevia extracts and can sometimes be termed “minor” steviol glycosides, even when they are used as a primary component in a composition. For example, so-called minor steviol glycosides can include rebaudioside D and rebaudioside M, which are found in lower abundance in stevia extracts and comprise different sweetness attributes than the more abundant steviol glycosides. Some of the sweetness attributes of these minor steviol glycosides can be preferred over the major steviol glycosides. For example, rebaudioside D and rebaudioside M exhibit reduced bitterness attributes compared to rebaudioside A. But some of the minor steviol glycosides may be less soluble in water and other aqueous solutions. Thus, in some cases, it may be desirable to use a steviol glycoside that provides a desired flavor profde and/or sweetness intensity but has a low solubility in water. For example, rebaudioside D may have desired sensory properties but has relatively low solubility and poor dissolution in water at room temperature. As another example, rebaudioside M may have desired sensory properties but has poor water solubility and dissolution qualities in beverage formulations.

Compositions

[0027] The steviol glycoside compositions discussed herein may be sweetener compositions or other compositions, such as foodstuffs, including the steviol glycoside composition. While the following discussion references steviol glycoside compositions, it should be understood that the discussion applies to sweetener composition and other compositions, as well, whether or not they would be considered sweetener compositions.

[0028] According to an embodiment, a steviol glycoside composition of the present disclosure includes one or more steviol glycosides and a solubility enhancer. The solubility enhancer increases the solubility of the one or more steviol glycosides in aqueous solutions. The solubility enhancer may be choline chloride. The one or more steviol glycosides may be selected from steviolmonoside, steviolbioside, stevioside, rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside DG (Reb DG), rebaudioside E (Reb E), rebaudioside F (Reb F), rebaudioside J (Reb J), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O), rebaudioside V2 (Reb V2), rubusoside, dulcoside A, steviol- 13-monoside, steviol- 19-monoside, 13-[(P-D-glucopyranosyl)oxy)kaur-16-en-18-oic acid 2-O-P- D-glucopyranosyl-p-D-glucopyranosyl ester, and combinations of two or more thereof. The one or more steviol glycosides may be selected from rebaudioside A (Reb A), rebaudioside B (Reb B), rebaudioside C (Reb C), rebaudioside D (Reb D), rebaudioside J (Reb J), rebaudioside M (Reb M), rebaudioside N (Reb N), rebaudioside O (Reb O), and combinations of two or more thereof. In some embodiments, the one or more steviol glycosides includes Reb D. In some embodiments, the one or more steviol glycosides includes Reb M. In some embodiments, the one or more steviol glycosides includes Reb D and Reb M. Additional steviol glycosides may be included. In some embodiments, the one or more steviol glycosides consist of or consist essentially of Reb D and Reb M.

[0029] The steviol glycoside composition may be an aqueous solution. That is, the one or more steviol glycosides are in solution, dissolved in water or other aqueous liquid. The steviol glycoside composition includes choline chloride in an amount that improves the solubility of the one or more steviol glycosides in the composition. The steviol glycoside composition may include one or more steviol glycosides at a concentration that, without the presence of choline chloride, would not be fully soluble in the aqueous solution. The one or more steviol glycosides may be present in the steviol glycoside composition in an amount of 5 wt% or more, 10 wt% or more, 15 wt% or more, 20 wt% or more, 25 wt% or more, or 30 wt% or more, based on the weight of the aqueous solution. The one or more steviol glycosides may be present in the steviol glycoside composition in an amount of less than 40 wt%, less than 38 wt%, less than 35 wt%, 33.3 wt% or less, 30 wt% or less, 25 wt% or less, 20 wt% or less, 15 wt% or less, or 10 wt% or less, based on the weight of the aqueous solution.

[0030] The steviol glycoside composition may include Reb D and Reb M in an amount greater than other steviol glycosides. The steviol glycosides in the composition may be described based on the content of Reb D and Reb M. For example, total steviol glycosides in the composition may include greater than 80 wt% Reb M (RM80), greater than 90 wt% Reb M (RM90), greater than 95 wt% Reb M (RM95), or greater than 99 wt% Reb M (RM99). Reb M can be the predominant steviol glycoside in the composition, and can be present, for example, in an amount between 50 wt% and 95 wt%, between 70 wt% and 90 wt%, or between 75 wt% and 85 wt% based on the total weight of steviol glycosides in the composition. Reb D may be present together with Reb M. The Reb D may be present at a lower concentration than the Reb M, for example, in an amount between 1 wt% and 25 wt%, between 3 wt% and 20 wt%, or between 5 wt% and 15 wt%, based on the total weight of steviol glycosides in the composition. In one example, Reb M is at least 85 wt% and Reb D is between 3 wt% and 15 wt% based on the total weight of the steviol glycosides in the composition. The steviol glycoside compositions may include ate least 50 wt%, at least 60 wt%, at least 70 wt%, at least 75 wt%, at least 80 wt%, at least 85 wt%, at least 90 wt%, at least 95 wt% or at least 98 wt% of the combination of Reb M and Reb D based on the total weight of steviol glycosides in the combinations. Other steviol glycosides may be present in the composition, but some may be present in only small amounts. The amount of steviol glycosides other than Reb D and Reb M may be 50 wt% or less, 20 wt% or less, 10 wt% or less, 5 wt% or less, 2 wt% or less, or lwt% or less based on total weight of steviol glycosides in the composition. For example, Reb A, Reb B, and stevioside may be present together with Reb D and Reb M but in an amount less than 5 wt%, less than 2 wt%, or less than 1 wt% based on total weight of steviol glycosides in the composition.

[0031 ] The steviol glycoside composition includes choline chloride in an amount that improves the solubility of the one or more steviol glycosides in the composition. The amount of steviol glycosides in solution may be 5 wt% or more, 10 wt% or more, 15 wt% or more, 20 wt% or more, 25 wt% or more, or 30 wt% or more, based on the weight of the aqueous solution. The solubility of steviol glycosides may be improved either by adjusting the amount of choline chloride relative to the amount of water in the solution, or by adjusting the amount of choline chloride relative to the amount of the steviol glycosides, or both. The weight ratio of choline chloride to water may be between 4 and 7, between 4.5 and 6.5, between 5.0 and 6.0, or between 5.25 and 5.75. The one or more steviol glycosides and choline chloride may be present at a weight ratio of 0.65 or lower. The one or more steviol glycosides and water may be present at a weight ratio of 4 or lower. The one or more steviol glycosides and choline chloride may be present at a weight ratio of 0.65 or lower, while the one or more steviol glycosides and water is present at a weight ratio of 4 or lower. When the choline chloride is at a ratio of 5.5 parts to 1 part water, at least 5 wt%, at least 10 wt%, at least 15 wt%, at least 20 wt%, at least 25 wt%, or at least 30 wt% of the one or more steviol glycosides is solubilized in an aqueous solution comprising the steviol glycoside composition.

Methods

[0032] The present disclosure further provides a method for increasing the solubility of one or more steviol glycosides. The method includes adding one or more steviol glycosides and choline chloride to an aqueous solution to form a steviol glycoside composition. The weight ratio of choline chloride to water may be in a range of 4 to 7, 4.5 to 6.5, 5.0 to 6.0, or 5.25 to 5.75 and the solubility of the steviol glycoside composition is higher than when the steviol glycoside composition is added to an aqueous solution with a weight ratio of choline chloride to water that is outside of the range. The one or more steviol glycosides may be fully soluble up to a concentration of 40 wt%, up to 38 wt%, up to 35 wt%, or up to 33.3 wt%.

Additional Components

[0033] In addition to the one or more steviol glycoside(s) and choline chloride, the steviol glycoside composition may additionally include one or more additional sweeteners, emulsifiers, flavorings, or combinations thereof.

[0034] In some embodiments, the sweetener composition also contains one or more additional non-steviol glycoside sweetener compounds. The sweetener composition may include only noncaloric sweeteners. Alternatively, the sweetener composition may include a combination of noncaloric and caloric sweeteners. The additional non-steviol glycoside sweetener compounds can be any type of sweetener, for example, a sweetener obtained from a plant or plant product, or a physically or chemically modified sweetener obtained from a plant, or a synthetic sweetener. Exemplary non-steviol glycoside sweeteners that may be included in the sweetener composition include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g., a-cyclodextrin, P-cyclodextnn. and y- 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, fuculose, glucuronic acid, gluconic acid, glucono-lactone, abequose, galactosamine, xylo-oligosaccharides (xylotriose, xylobiose and the like), gentio- oligosaccharides (gentiobiose, gentiotriose, gentiotetraose and the like), galacto-oligosaccharides, sorbose, ketotriose (dehydroxy acetone), aldotriose (glyceraldehyde), nigero-oligosaccharides, fructooligosaccharides (kestose, nystose and the like), maltotetraose, maltotriol, tetrasaccharides, mannan-oligosaccharides, malto-oligosaccharides (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the like), dextrins, lactulose, melibiose, raffinose, rhamnose, ribose, sucralose, isomerized liquid sugars such as high fructose com/starch syrup (HFCS/HFSS) (e.g., HFCS55, HFCS42, or HFCS90). coupling sugars, soybean oligosaccharides, glucose syrup, and combinations thereof. Either D- or L-configurations or both can be used when applicable. Non-steviol glycoside sweeteners and aspects thereof are also described in PCT International Publication Nos. WO 2019/071220 and WO 2019/071182 and in US Patent Application Publication Nos. 2019/0223481 and 2019/0223483, each of which is incorporated by reference herein in its entirety.

[0035] In various embodiments, the steviol glycoside composition may further optionally include additional additives. In some embodiments the steviol glycoside composition contains one or more additives including carbohydrates, polyols, amino acids and their corresponding salts, poly-amino acids and their corresponding salts, 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, flavorants and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, thickeners, weighing agents, gums, antioxidants, colorants, flavonoids, alcohols, polymers or combinations thereof. In some embodiments, the additives act to improve the temporal and flavor profile of the sweetener to provide a steviol glycoside composition with a favorable taste, such as a taste similar to sucrose. Examples of such ingredients and aspects thereof are described, for example, in PCT International Publication Nos. WO 2019/071220 and WO 2019/071182 and in US Patent Application Publication Nos. 2019/0223481 and 2019/0223483, each of which is incorporated by reference herein in its entirety. Food Products

[0036] The steviol glycoside composition may be incorporated in or used to prepare any known edible material or other composition intended to be ingested and/or contacted with the mouth of a human or animal, such as, for example, pharmaceutical compositions, supplement compositions (e.g.. gummy, tablet, etc.), edible gel mixes and compositions, dental and oral hygiene compositions, foodstuffs (e.g., confections, condiments, chewing gum, cereal compositions, baked goods, baking goods, cooking adjuvants, dairy products, and tabletop steviol glycoside compositions), and beverage products (e.g., beverages, beverage mixes, beverage concentrates, etc.). Examples of such compositions and aspects thereof are set forth in PCT International Publication Nos. WO 2019/071220 and WO 2019/071182 and in US Patent Application Publication Nos. 2019/0223481 and 2019/0223483, each of which is incorporated by reference herein in its entirety⁷.

[0037] The steviol glycoside composition may be a beverage product or can be used to prepare a beverage product. As used herein a “beverage product” may be a ready-to-drink beverage, a beverage concentrate, a beverage syrup, frozen beverage, a powdered beverage, or the like. Suitable ready-to-drink beverages include carbonated and non-carbonated beverages. Carbonated beverages include, but are not limited to, enhanced sparkling beverages, cola, lemon-lime flavored sparkling beverage, orange flavored sparkling beverage, grape flavored sparkling beverage, strawberry flavored sparkling beverage, pineapple flavored sparkling beverage, ginger- ale, soft drinks and root beer. Non-carbonated beverages include, but are not limited to fruit juice, fruit- flavored juice, juice drinks, nectars, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, enhanced water drinks, enhanced water with vitamins, near water drinks (e.g., water with natural or synthetic flavorants), coconut water, tea type drinks (e.g. black tea, green tea, red tea, oolong tea), coffee, cocoa drink, beverage containing milk components (e.g. milk beverages, coffee containing milk components, cafe au lait, milk tea, fruit milk beverages), beverages containing cereal extracts, smoothies and combinations thereof. Examples of frozen beverages include, but are not limited to, icees, frozen cocktails, daiquiris, pina coladas, margaritas, milk shakes, frozen coffees, frozen lemonades, granitas, and slushees. Beverages may be alcoholic (e.g., a liqueur or cream liqueur) or non-alcoholic beverages. The beverage may be a brewed for fermented beverage, for example, beer or kombucha. Beverage concentrates and beverage syrups can be prepared with an initial volume of liquid matrix (e.g., water) and the desired beverage ingredients. Full strength beverages are then prepared by adding further volumes of water. Powdered beverages are prepared by dry-mixing all of the beverage ingredients in the absence of a liquid matrix. Full strength beverages are then prepared by adding the full volume of water, liquid matrix, or aqueous solution.

[0038] The steviol glycoside composition can be a food product or can be used to prepare a food product. The food product may be any caloric or non-caloric food product suitable for human consumption. Suitable food products include, but are not limited to, confectionary products (e.g., candies, candied nuts, candy bars, caramels, chocolates, chocolate bars, chocolate drops, chocolate in the form of hollow figures or any desired shape, filled chocolate bars, pralines, truffles, cereal bars, chewing gum, and pastillage), condiments, chewing gum, cereal compositions, baked goods, bakery products (e.g.. breads such as bagels, buns, rolls, biscuits and loaf breads; cookies; brownies; muffins; desserts such as cakes, cheesecakes and pies; snack cakes; sweet goods such as doughnuts, Danish pastries, sweet rolls, cinnamon rolls, and coffee cakes), cooking adjuvants, dairy products (e.g., ice cream, yogurt, chilled desserts, pudding, mousse, custard, milk shakes, malts, cream cheeses, cheeses, fudge), dairy-alternatives, frozen desserts (e.g., ice cream, sorbet, frozen yoghurt, and the like), tabletop steviol glycoside compositions, seasoning, sauces, gravies, soups, dressings, snack products (e g., granola bars, nutrition bars, and the like), and the like. The compositions described herein may be used in food products in any form, such as melted or mixed into the recipe of the end product, in the form of a filling, inclusions, toppings, or coatings, molded around other discrete ingredients such as nuts, fruit, dried fruit, biscuits, candy pieces or shapes, combinations thereof, and the like. In frozen dessert compositions, the composition may be used as a coating, inclusion (chunks, flakes, or ripples), topping, or core (soft or solid).

[0039] The present invention can be better understood by reference to the following examples which are offered by way of illustration. The present invention is not limited to the examples given herein.

EXAMPLES

Materials and Methods

[0040] Table 2 lists the tested materials and source of various components.

Table 2.

Example 1 - Steviol Glycoside with Choline Chloride

[0041] Mixtures of steviol glycosides (Reb D/M), choline chloride, and water were prepared according to Table 3. The mixtures were stirred to dissolve the steviol glycosides and choline chloride. If dissolution was not obtained at room temperature, the mixture was heated to a temperature of 50-80 °C to dissolve the components. The clarity of the mixtures was observed visually to determine solubility. Mixtures that were heated were observed after the mixture was allowed to cool to room temperature (about 20-25 °C).

Table 3.

[0042] These results demonstrate that choline chloride can increase the solubility of steviol glycosides. Without the inclusion of choline chloride, the tested steviol glycoside combination has a maximum solubility of 0.1%. However, when choline chloride is added in a ratio of choline chloride to water between 5-6 and a ratio of steviol glycosides to choline chloride below 0.6, solubility is increased above 20 wt%, with evident of solubility up to at least 33.3wt% and likely higher.

Example 2 - Steviol Glycoside with Other Agents

[0043] Attempts were made to dissolve steviol glycosides (Reb D/M) in water with benzalkonium chloride (“BAC”) and cetyltrimethylammonium bromide (“CTAB”) were according to Table 4. The mixtures were heated and stirred. However, none of the compositions were able to dissolve the steviol glycosides, or if initial dissolution was achieved, the steviol glycosides crystallized upon cooling.

Table 4.

Example 3 - Rebaudioside D with Choline Chloride

[0044] Mixtures of steviol glycosides (Rebaudioside D and Rebaudioside M), choline chloride, and water were prepared according to Table 5. The mixtures were stirred at 80 °C to dissolve the steviol glycosides and choline chloride. Sequential additional of choline chloride were added until a clear solution was obtained, and the final choline chloride concentration is reported in Table 5. Mixtures were allowed to cool to room temperature (about 20-25 °C). The clarity of the mixtures was observed visually to determine solubility.

Table 5.

[0045] These results indicate that choline chloride can increase the solubility of reb D steviol glycoside solutions. FIG. 1 shows a comparison of 29.0% reb D (right) to 30.3% reb M and reb D at a 18/82 ratio. While the combination of 18/82 Reb M/Reb D remains clear, the 29% Reb D alone shows slight crystallization but a clear solution.

[0046] All references and publications cited herein are expressly incorporated herein by reference in their entirety into this disclosure, except to the extent they may directly contradict this disclosure. Although specific embodiments have been illustrated and described herein, it will be appreciated by those of ordinary skill in the art that a variety of alternate and/or equivalent implementations can be substituted for the specific embodiments shown and described without departing from the scope of the present disclosure. It should be understood that this disclosure is not intended to be unduly limited by the illustrative embodiments and examples set forth herein and that such examples and embodiments are presented by way of example only with the scope of the disclosure intended to be limited only by the claims set forth here.

Claims

1. An aqueous steviol glycoside solution comprising:

5 wt% or more, 10 wt% or more, 15 wt% or more, 20 wt% or more, 25 wt% or more, or 30 wt% or more, of one or more steviol glycosides; and choline chloride in an amount such that a weight ratio of choline chloride to water is between 4 and 7, between 4.5 and 6.5, between 5.0 and 6.0, or between 5.25 and 5.75.

2. The aqueous steviol glycoside solution of claim 1. wherein the one or more steviol glycosides and the choline chloride are present at a weight ratio of 0.65 or lower.

3. The aqueous steviol glycoside solution of claim 1 or 2, wherein the one or more steviol glycosides and water are present at a weight ratio of 4 or lower.

4. An aqueous steviol glycoside solution comprising: one or more steviol glycosides; choline chloride; and water, the one or more steviol glycosides and choline chloride being present at a weight ratio of 0.65 or lower, and the one or more steviol glycosides and water being present at a weight ratio of 4 or lower.

5. The aqueous steviol glycoside solution of any one of claims 1 to 4, wherein the one or more steviol glycosides comprise rebaudioside D and rebaudioside M.

6. The aqueous steviol glycoside solution of any one of claims 1 to 5, wherein the solution comprises rebaudioside D and rebaudioside M in a total amount of 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides; and/or wherein the solution comprises rebaudioside M in an amount of 50 wt% or more, 60 wt% or more, 70 wt% or more, 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides; and/or wherein the solution comprises rebaudioside D in an amount of 50 wt% or less, 25 wt% or less, 20 wt% or less, 15 wt% or less, or 10 \\1% or less of total steviol glycosides, optionally wherein the solution comprises rebaudioside D in an amount of 5 wt% or more or 10 wt% or more of total steviol glycosides; and/or wherein the solution comprises steviol glycosides other than rebaudioside D and rebaudioside M at a concentration of 5 wt% or less, 2 wt% or less, or 1 wt% or less of total steviol glycosides.

7. The aqueous steviol glycoside solution of any one of claims 1 to 6, wherein the one or more steviol glycosides are present at a total concentration of less than 40 wt%, less than 38 wt%, less than 35 wt%, or 33.3 wt% or less.

8. A steviol glycoside composition comprising: one or more steviol glycosides; and choline chloride, wherein in an aqueous solution comprising the steviol glycoside composition such that the choline chloride is at a ratio of 5.5 parts to 1 part water, at least 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, or 30 wt% of the one or more steviol glycosides is solubilized.

9. A method for increasing solubility of a steviol glycoside composition, the method comprising: adding one or more steviol glycosides and choline chloride to an aqueous solution to form a steviol glycoside composition with a weight ratio of choline chloride to w ater is in a range of 4 to 7, 4.5 to 6.5, 5.0 to 6.0, or 5.25 to 5.75 and the solubility of the steviol glycoside composition is higher than when the steviol glycoside composition is added to an aqueous solution with a weight ratio of choline chloride to w ater that is outside of the range.

10. The steviol glycoside composition of claim 8 or method of claim 9, wherein the one or more steviol glycosides and the choline chloride are present in the steviol glycoside composition at a weight ratio of 0.65 or low er: and/or wherein the one or more steviol glycosides and water are present in the steviol glycoside composition at a weight ratio of 4 or low er.

11. The steviol glycoside composition or method of any one of claims 8-10, wherein the steviol glycoside composition comprises a total of 5 wt% or more, 10 wt% or more, 15 wt% or more, 20 wt% or more, 25 wt% or more, or 30 \vt°/o or more, of the one or more steviol glycosides; and/or wherein the steviol glycoside composition comprises a total of 40 wt%, less than 38 wt%, less than 35 wt%, or 33.3 wt% or less, of the one or more steviol glycosides.

12. The steviol glycoside composition or method of any one of claims 8-11, wherein the one or more steviol glycosides comprise rebaudioside D and rebaudioside M.

13. The steviol glycoside composition or method of any one of claims 8-12, wherein the steviol glycoside composition comprises rebaudioside D and rebaudioside M in a total amount of 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides; and/or wherein the steviol glycoside composition comprises rebaudioside M in an amount of 50 wt% or more, 60 wt% or more, 70 wt% or more, 80 wt% or more, 90 wt% or more, or 95 wt% or more of total steviol glycosides; and/or wherein the steviol glycoside composition comprises rebaudioside D in an amount of 50 wt% or less, 25 wt% or less, 20 wt% or less, 15 wt% or less, or 10 wt% or less of total steviol glycosides, optionally wherein the steviol glycoside composition comprises rebaudioside D in an amount of 5 wt% or more or 10 wt% or more of total steviol glycosides; and/or wherein the steviol glycoside composition comprises steviol glycosides other than rebaudioside D and rebaudioside M at a concentration of 5 wt% or less, 2 wt% or less, or 1 wt% or less of total steviol glycosides.

14. The steviol glycoside composition or method of any one of claims 8-13, wherein the one or more steviol glycosides are present at a total concentration of less than 40 wt%, less than 38 wt%, less than 35 wt%, or 33.3 wt% or less.

15. Use of choline chloride to increase solubility of one or more steviol glycosides.