Sweetener Compositions and Preparation Methods Thereof

Abstract

An aqueous steviol glycoside solution comprises 5% by weight or more of one or more steviol glycosides and an amount of choline chloride such that the weight ratio of choline chloride to water is between 4 and 7. One or more steviol glycosides and choline chloride may be present in a weight ratio of 0.65 or less. One or more steviol glycosides and water may be present in a weight ratio of 4 or less. One or more steviol glycosides may comprise leboside D and leboside M. A method for increasing the solubility of a steviol glycoside composition comprises adding one or more steviol glycosides and choline chloride to an aqueous solution to form a steviol glycoside composition wherein the weight ratio of choline chloride to water is in the range of 4 to 7.

Description

[0001] Cross-reference to related applications

[0002] This application claims the benefit of European application number 23204789.4, filed on 20 October 2023, which is incorporated herein by reference in its entirety. Background Technology

[0003] Sugars such as sucrose, fructose, and glucose are used to provide a pleasant taste in beverages, foods, pharmaceuticals, and oral hygiene / cosmetic products. While sucrose provides excellent sweetness, it also contains calories. In the food and beverage industry, efforts have been made to reduce the amount of calorie sugar in products as consumers constantly seek low-calorie alternatives to high-calorie products. Although sugar substitutes can provide sweetness to products, there can be limitations to using them in product preparation. For example, consumers may find that the sensory and temporal properties of sugar substitutes differ from those found in calorie sweeteners such as glucose, sucrose, and / or fructose. These sensory properties limit the use of sugar substitutes in products, and these limitations increase with increasing sugar substitute concentration. Furthermore, the chemical and physical properties of sugar substitutes may differ from those of calorie sweeteners.

[0004] Stevia is a genus of about 240 species of herbaceous plants and shrubs in the sunflower family (Asteraceae), native to subtropical and tropical regions from Northwest America to South America. The species Stevia rebaudiana is commonly known as sweetleaf, sweet leaf, sugarleaf, or simply stevia, and is widely cultivated for its sweet leaves. Steviosides are a class of sweet-tasting glycosylated diterpenoid compounds, often derived from the leaves of Stevia rebaudiana. Various compounds of this class are known, each with different properties, taste characteristics, and chemical structures. Typical steviol glycosides are characterized by a single steviol backbone and one or more carbohydrate residues at C13 and C19. For example, lebodiin A contains a branched group with three glucosyl groups at C13 and a single β-glucosyl group at C19, while lebodiin D contains the same unit at C13 but a disaccharide group at C19. Steviosides can be used as powerful sweeteners even at low concentrations, providing approximately 150 to 450 times the sweetening effect of an equivalent amount of sugar.

[0005] Steviol glycosides provide calorie-free alternatives to traditional calorie sweeteners such as glucose, sucrose, and / or fructose. While steviol glycosides have a higher sweetness intensity than sugars, they are not very soluble in water. This limits their use in a variety of consumer products, particularly those attempting to use the highest concentrations of steviol glycosides. For example, leucoside D has been reported to be difficult to use in food products due to its low solubility and poor dissolution in water at room temperature. For instance, leucoside D requires heating to near boiling point for 2 hours to achieve complete dissolution at a concentration of 0.8%. At 23°C, only 300 to 450 ppm are soluble in water at most (see, for example, US 2013 / 0251881). Similarly, leucoside M, obtained from stevia (Steviarebaudiana), exhibits poor water solubility and dissolution quality in beverage formulations (see, for example, US 2014 / 0171519). Some methods for improving the solubility of levodocin are less than ideal because they are labor-intensive and require high processing temperatures. See, for example, WO 2013148177.

[0006] The sweetener composition needs further improvement. Summary of the Invention

[0007] This disclosure provides steviol glycoside compositions and methods for sweetening food or beverage products.

[0008] The aqueous steviol glycoside solution comprises 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, or 30% or more of one or more steviol glycosides; and an amount of choline chloride such that the 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. One or more steviol glycosides may be present with choline chloride at a weight ratio of 0.65 or less. One or more steviol glycosides may be present with water at a weight ratio of 4 or less.

[0009] The aqueous steviol glycoside solution comprises one or more steviol glycosides; choline chloride; and water, wherein the one or more steviol glycosides are present with choline chloride in a weight ratio of 0.65 or less, and the one or more steviol glycosides are present with water in a weight ratio of 4 or less.

[0010] Steviosides are present in a total concentration of less than 40% by weight, less than 38% by weight, less than 35% by weight, or 33.3% by weight or less. One or more steviol glycosides may comprise rebaudioside D and rebaudioside M. The solution may contain rebaudioside D and rebaudioside M in a total amount of 80% by weight or more, 90% by weight or more, or 95% by weight or more of total steviol glycosides. The solution may contain rebaudioside M in an amount of 50% by weight or more, 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of total steviol glycosides. The solution may contain rebaudioside D in an amount of 50% by weight or less, 25% by weight or less, 20% by weight or less, 15% by weight or less, or 10% by weight or less of total steviol glycosides, optionally wherein the solution may contain rebaudioside D in an amount of 5% by weight or more, or 10% by weight or more of total steviol glycosides. The solution may contain 5% or less, 2% or less, or 1% or less of total steviol glycosides, other than rebaudioside D and rebaudioside M.

[0011] The steviol glycoside composition comprises one or more steviol glycosides; and choline chloride, wherein at least 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, or 30% by weight of one or more steviol glycosides are dissolved in an aqueous solution containing the steviol glycoside composition such that the ratio of choline chloride is 5.5 parts to 1 part of water.

[0012] A method for increasing the 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 wherein the weight ratio of choline chloride to water is in the range of 4 to 7, 4.5 to 6.5, 5.0 to 6.0, or 5.25 to 5.75, and wherein the solubility of the steviol glycoside composition is higher than that when the steviol glycoside composition is added to an aqueous solution wherein the weight ratio of choline chloride to water is outside the range.

[0013] One or more steviol glycosides may be present in the steviol glycoside composition at a weight ratio of 0.65 or less with choline chloride. One or more steviol glycosides may be present in the steviol glycoside composition at a weight ratio of 4 or less with water. The steviol glycoside composition may contain a total of 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, or 30% or more of one or more steviol glycosides. The steviol glycoside composition may contain a total of 40% or less, less than 38% or less, less than 35% or less, or 33.3% or less of one or more steviol glycosides. One or more steviol glycosides may contain rebaudioside D and rebaudioside M. The steviol glycoside composition may contain steviol glycosides other than rebaudioside D and rebaudioside M at a concentration of 5% or less, 2% or less, or 1% or less. The steviol glycoside composition may contain 80% or more, 90% or more, or 95% or more of total steviol glycosides, of rebaudioside D and rebaudioside M. The steviol glycoside composition may contain 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of total steviol glycosides, ... The steviol glycoside composition may contain steviol glycosides other than rebaudioside D and rebaudioside M at a concentration of 5% or less, 2% or less, or 1% or less of total steviol glycosides. One or more steviol glycosides are present at a total concentration of less than 40%, less than 38%, less than 35%, or 33.3% or less.

[0014] This disclosure also provides the use of choline chloride to increase the solubility of one or more steviol glycosides. Attached Figure Description

[0015] This patent or application contains at least one color-drawn drawing. A copy of this patent or patent application publication with a color drawing will be provided by the Patent Office upon request and payment of the necessary fees.

[0016] The accompanying figures illustrate, in a manner that is not restrictive, various aspects described herein.

[0017] Figure 1Photographs are shown of a 30.3% Reb M / Reb D solution (ratio 18 / 82) (left beaker) and a 29.0% Reb D solution (right beaker). The 30.3% mixed solution is clear and completely soluble, while the 29.0% pure Reb D solution is clear but contains some crystals. Detailed Implementation

[0018] This disclosure relates to various compositions, such as sweetener compositions and other compositions, and specifically to steviol glycoside compositions having improved water solubility.

[0019] Unless otherwise specified, all scientific and technical terms used herein have their common meaning in the art. The definitions provided herein are for the purpose of facilitating understanding of certain terms frequently used herein and are not intended to limit the scope of this disclosure.

[0020] Values ​​expressed in range format should be interpreted flexibly to include not only the values ​​explicitly listed as limits of the range, but also all individual values ​​or subranges covered within the range, as if each value and subrange were explicitly listed. For example, a range of "about 0.1% to about 5%" or "about 0.1% to 5%" should be interpreted to include not only about 0.1% to about 5%, but also individual values ​​(e.g., 1%, 2%, 3%, and 4%) and subranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the specified range. Unless otherwise stated, the statement "about X to Y" has the same meaning as "about X to about Y". Similarly, unless otherwise stated, the statement "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z".

[0021] Unless otherwise specified, ppm (parts per million), percentages, and ratios are based on weight. Percentages based on weight are also referred to below as weight% or (weight)%.

[0022] Steviosides

[0023] This disclosure provides compositions comprising a steviol glycoside component or a mixture of multiple steviol glycosides. The compositions may optionally contain other steviol glycosides. The compositions may optionally contain other additional components.

[0024] The steviol glycoside component may contain one or more steviol glycosides. In some respects, the term steviol glycoside refers to Reb A (CAS# 58543-16-1), Reb B (CAS# 58543-17-2), Reb C (CAS# 63550-99-2), Reb D (CAS# 63279-13-0), Reb E (CAS# 63279-14-1), Reb EE (CAS# 63279-14-1), Reb F (CAS# 63279-14-1), 1,3-stevioside (Reb G or Reb G), Reb I (CAS# 63279-14-1), Reb J (CAS# 1313049-59-0), and Reb M (CAS# 63279-15-16-2). 1220616-44-3), RebN, RebO (CAS# 1220616-48-7), RebQ, RebV2, RebDG, Stevioside (CAS# 63849-39-4), Dulcoside A (CAS# 64432-06-0), Stevioside, 1,2-Steviol (CAS# 1220616-44-3), RebN, RebO (CAS# 63849-39-4), Stevioside A (CAS# 64432-06-0), Stevioside, 1,2-Steviol (CAS# 63849-39-4) 57817-89-7), steviol monoglycoside, steviol-13-monoglycoside, steviol-19-monoglycoside, steviol diglycoside, steviol-1,2-diglycoside (MassBank record: FU000299), steviol-1,3-diglycoside, steviol-13-O-glucoside (13-SMG), steviol-19-O-glucoside (19-SMG), OPS1-5 (corresponding to compound 4 from WO2016100689), 13-[(β-D-glucopyranosyl)oxy)kaurose-16-en-18-oic acid 2-O-β-D-glucopyranosyl-pD-glucopyranosyl ester, steviol glycosides having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more glycosides and their isomers. 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 prior to use. Rebaudiosides can be used in commercially available form (available from Cargill, Inc., Wayzata, MN).

[0025] Steviosides are sometimes used as blends, such as blends of Reb D and Reb M. Such blends may be expressed as "Reb D / M" or "Reb D / M" and may contain both Reb D / M glycosides, their related isomers (e.g., natural or synthetic) and / or their salts. This terminology can be used for compositions containing any other combination of glycosides, such as, but not limited to, Reb D / G, Reb D / M / O, Reb N / O, Reb D / E, etc.

[0026] Structurally, steviol glycosides comprise a steviol backbone, and differ in the presence and arrangement of carbohydrate residues at positions C13 and C19 of the steviol backbone according to the atomic arrangement shown below. The pyranosel residues represent groups R1 and R2 in the following formula:

[0027]

[0028] Steviosides differ not only in structure but also in their physical and sensory properties. Steviool is represented by the formula above when R1 and R2 are hydrogen atoms. Steviosides typically have the above formula, where steviol is the glycosidic aglycone backbone, and R1 and R2 can each be hydrogen atoms or one or more sugar moieties. These sugar moieties are most commonly glucose, rhamnose, or xylose, but steviol glycosides have been reported to contain fructose and deoxyglucose moieties. Table 1 below shows the various steviol glycosides and their corresponding R1 and R2 groups:

[0029] Table 1 .

[0030]

[0031] Glu: glucose; Rha: rhamnose; Xyl: xylose

[0032] Steviol glycosides differ structurally and also exhibit different properties (including solubility). Generally, steviol glycosides are less soluble in water than sugars. Furthermore, some steviol glycosides are less soluble than others. Different steviol glycosides also provide different sensory properties, such as taste and sweetness intensity. Steviol glycosides (containing three glucose units) and rebaudioside A (containing four glucose units) are more abundant in stevia extract and have specific sweetness properties. Both steviol glycosides and rebaudioside A contribute to sweetness but can also be perceived as exhibiting bitterness, especially at higher concentrations. Other steviol glycosides are present in lower abundance in stevia extract and can sometimes be referred to as “minor” steviol glycosides, even when they are used as a major component in a composition. For example, so-called minor steviol glycosides may include rebaudioside D and rebaudioside M, which are present in lower abundance in stevia extract and have different sweetness properties than the more abundant steviol glycosides. Compared to major steviol glycosides, some of the sweetness properties of these minor steviol glycosides may be preferred. For example, rebaudioside D and rebaudioside M exhibit reduced bitterness compared to rebaudioside A. However, some minor steviol glycosides may be less soluble in water and other aqueous solutions. Therefore, in some cases, it may be desirable to use steviol glycosides that provide the desired flavor characteristics and / or sweetness intensity but have low solubility in water. For example, rebaudioside D may have the desired sensory properties but has relatively low solubility and poor dissolution in water at room temperature. Similarly, rebaudioside M may have the desired sensory properties but has poor water solubility and dissolution quality in beverage formulations.

[0033] Composition

[0034] The steviol glycoside compositions discussed herein can be sweetener compositions or other compositions, such as food products containing steviol glycoside compositions. Although the following discussion refers to steviol glycoside compositions, it should be understood that the discussion also applies to sweetener compositions and other compositions, whether or not they are considered sweetener compositions.

[0035] According to one embodiment, the steviol glycoside composition of this disclosure comprises one or more steviol glycosides and a solubility enhancer. The solubility enhancer can improve the solubility of the one or more steviol glycosides in an aqueous solution. The solubility enhancer may be choline chloride. One or more steviol glycosides may be selected from steviol monoglycoside, steviol diglycoside, steviol glycoside, Reb A, Reb B, Reb C, Reb D, Reb DG, Reb E, Reb F, Reb J, Reb M, Reb N, Reb O, Reb V2, stevia glycoside, dulcitin A, steviol-13-monoglycoside, steviol-19-monoglycoside, 13-[(β-D-glucopyranoyl)oxy)kauridine-16-en-18-oic acid 2-O-β-D-glucopyranoyl-pD-glucopyranoyl ester, and combinations of two or more thereof. One or more steviol glycosides may be selected from Reb A, Reb B, Reb C, Reb D, Reb J, Reb M, Reb N, Reb O, and combinations of two or more thereof. In some embodiments, one or more steviol glycosides comprise Reb D. In some embodiments, one or more steviol glycosides comprise Reb M. In some embodiments, one or more steviol glycosides comprise Reb D and Reb M. Additional steviol glycosides may also be included. In some embodiments, one or more steviol glycosides consist of or are substantially composed of Reb D and Reb M.

[0036] The steviol glycoside composition can be an aqueous solution. That is, one or more steviol glycosides are in solution, dissolved in water or other aqueous liquids. The steviol glycoside composition contains an amount of choline chloride to improve the solubility of one or more steviol glycosides in the composition. The steviol glycoside composition may contain one or more steviol glycosides at a concentration that would not be completely soluble in an aqueous solution in the absence of choline chloride. Based on the weight of the aqueous solution, one or more steviol glycosides may be present in the steviol glycoside composition in amounts of 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, or 30% or more. Based on the weight of the aqueous solution, one or more steviol glycosides may be present in the steviol glycoside composition in amounts of less than 40% by weight, less than 38% by weight, less than 35% by weight, 33.3% or less by weight, 30% or less by weight, 25% or less by weight, 20% or less by weight, 15% or less by weight, or 10% or less by weight.

[0037] The steviol glycoside composition may contain Reb D and Reb M in amounts 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, the total steviol glycosides in the composition may contain greater than 80% by weight of Reb M (RM80), greater than 90% by weight of Reb M (RM90), greater than 95% by weight of Reb M (RM95), or greater than 99% by weight of Reb M (RM99). Reb M may be the dominant steviol glycoside in the composition and may be present in amounts such as 50% to 95% by weight, 70% to 90% by weight, or 75% to 85% by weight, based on the total weight of steviol glycosides in the composition. Reb D may be present together with Reb M. Reb D may be present at a lower concentration than Reb M, for example, in amounts of 1% to 25% by weight, 3% to 20% by weight, or 5% to 15% by weight, based on the total weight of steviol glycosides in the composition. In one example, based on the total weight of steviol glycosides in the composition, Reb M is at least 85% by weight, and Reb D is between 3% and 15% by weight. Based on the total weight of steviol glycosides in the composition, the steviol glycoside composition may contain at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 75% by weight, at least 80% by weight, at least 85% by weight, at least 90% by weight, at least 95% by weight, or at least 98% by weight of a combination of Reb M and Reb D. Other steviol glycosides may be present in the composition, but some steviol glycosides may be present only in small amounts. Based on the total weight of steviol glycosides in the composition, the amount of steviol glycosides other than Reb D and Reb M may be 50% by weight or less, 20% by weight or less, 10% by weight or less, 5% by weight or less, 2% by weight or less, or 1% by weight or less. For example, Reb A, Reb B and steviol glycosides may be present with Reb D and Reb M, but in amounts less than 5% by weight, less than 2% by weight or less than 1% by weight, based on the total weight of steviol glycosides in the composition.

[0038] The steviol glycoside composition contains an amount of choline chloride to improve the solubility of one or more steviol glycosides in the composition. Based on the weight of the aqueous solution, the amount of steviol glycosides in the solution can be 5% by weight or more, 10% by weight or more, 15% by weight or more, 20% by weight or more, 25% by weight or more, or 30% by weight or more. The solubility of steviol glycosides can be improved 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 steviol glycosides, or both. The weight ratio of choline chloride to water can be between 4 and 7, between 4.5 and 6.5, between 5.0 and 6.0, or between 5.25 and 5.75. One or more steviol glycosides may be present in a weight ratio of 0.65 or less with choline chloride. One or more steviol glycosides may be present in a weight ratio of 4 or less with water. One or more steviol glycosides may be present in a weight ratio of 0.65 or less with choline chloride, while one or more steviol glycosides may be present in a weight ratio of 4 or less with water. When the ratio of choline chloride is 5.5 parts to 1 part water, at least 5% by weight, at least 10% by weight, at least 15% by weight, at least 20% by weight, at least 25% by weight, or at least 30% by weight of one or more steviol glycosides are dissolved in an aqueous solution containing the steviol glycoside composition.

[0039] method

[0040] This disclosure also provides a method for improving 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 can be in the 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 that when the steviol glycoside composition is added to an aqueous solution in which the weight ratio of choline chloride to water is outside the range described above. The one or more steviol glycosides can be completely soluble, with concentrations up to 40% by weight, up to 38% by weight, up to 35% by weight, or up to 33.3% by weight.

[0041] Additional components

[0042] In addition to one or more steviol glycosides and choline chloride, the steviol glycoside composition may be supplemented with one or more additional sweeteners, emulsifiers, flavoring agents, or combinations thereof.

[0043] In some embodiments, the sweetener composition further comprises one or more additional non-stevia glycoside sweetener compounds. The sweetener composition may contain only a calorie-free sweetener. Alternatively, the sweetener composition may contain a combination of a calorie-free sweetener and a calorie sweetener. The additional non-stevia glycoside sweetener compound may be any type of sweetener, such as a sweetener obtained from plants or plant products, or a physically or chemically modified sweetener obtained from plants, or a synthetic sweetener. Exemplary non-stevia glycoside sweeteners that may be included in sweetener compositions include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, tagatose, trehalose, galactose, rhamnose, cyclodextrins (e.g., α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin), ribulose, threose, arabinose, xylose, lysolose, allose, atroose, mannose, idulose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palaginose or isomaltulose, erythritol, deoxyribose, gulose, idulose, tarose, erythritolose, xylulose, allulose, mesobiose, cellobiose, glucosamine, mannosamine, fucose, fucose, glucuronic acid, gluconic acid, gluconolactone, apicolithosaccharide, and arbicose. Galactosamine, xylooligosaccharides (xylotriose, xylobiose, etc.), gentiooligosaccharides (gentiobiose, gentiotriose, gentiotetraose, etc.), galactooligosaccharides, sorbitol, ketonetriose (dihydroxyacetone), propionose (glyceraldehyde), Aspergillus niger oligosaccharides, fructooligosaccharides (fructotriose, fructotetraose, etc.), maltotetraose, maltotriose alcohol, tetrasaccharides, mannose, maltomalooligosaccharides (maltotriose, maltotetraose, maltopentose, maltohexaose, maltoheptaose, etc.), dextrin, lactulose, melibiose, raffinose, rhamnose, ribose, sucralose, isomerized liquid sugars such as high fructose corn / starch syrup (HFCS / HFSS) (e.g., HFCS55, HFCS42, or HFCS90), conjugated sugars, soybean oligosaccharides, glucose syrup, and combinations thereof. When applicable, D-configuration or L-configuration or both may be used. Non-stevia glycoside sweeteners and related aspects are also described in PCT International Publications WO 2019 / 071220 and WO 2019 / 071182 and U.S. Patent Application Publications 2019 / 0223481 and 2019 / 0223483, the full text of each of these patents being incorporated herein by reference.

[0044] In various embodiments, the steviol glycoside composition may optionally include additional additives. In some embodiments, the steviol glycoside composition comprises one or more additives, including carbohydrates, polyols, amino acids and their corresponding salts, polyamino 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, flavoring agents and flavor components, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, thickeners, weighting agents, gums, antioxidants, coloring agents, flavonoids, alcohols, polymers, or combinations thereof. In some embodiments, the additives are used to improve the timing and flavor characteristics of the sweetener to provide a favorable taste to the steviol glycoside composition, such as a sucrose-like taste. Examples of such components and aspects thereof are described, for example, in PCT International Publications WO 2019 / 071220 and WO 2019 / 071182 and U.S. Patent Application Publications 2019 / 0223481 and 2019 / 0223483, the full text of each of which is incorporated herein by reference.

[0045] Food products

[0046] Stevia glycoside compositions may be incorporated into or used in the preparation of any known edible material or other compositions intended to be ingested and / or come into contact with by the mouth of humans or animals, such as, for example, pharmaceutical compositions, supplementary compositions (e.g., gummies, tablets, etc.), edible gel mixtures and compositions, dental and oral hygiene compositions, food ingredients (e.g., confectionery, condiments, chewing gum, cereal compositions, baked goods, baked goods, cooking aids, dairy products, and table sweetener compositions), and beverage products (e.g., beverages, beverage mixtures, beverage concentrates, etc.). Examples of such compositions and aspects thereof are shown in PCT International Publications WO 2019 / 071220 and WO 2019 / 071182 and in U.S. Patent Application Publications 2019 / 0223481 and 2019 / 0223483, the entire contents of each of which are incorporated herein by reference.

[0047] Stevia glycoside compositions can be beverage products or can be used to prepare beverage products. As used herein, "beverage product" can be ready-to-drink beverages, beverage concentrates, beverage syrups, frozen beverages, powdered beverages, etc. Suitable ready-to-drink beverages include carbonated and non-carbonated beverages. Carbonated beverages include, but are not limited to, energy drinks, cola, lemon-lime flavored soda, orange flavored soda, grape flavored soda, strawberry flavored soda, pineapple flavored soda, ginger ale, soft drinks, and sarsaparilla. Non-carbonated beverages include, but are not limited to, fruit juices, fruit-flavored juices, fruit juice drinks, nectar, vegetable juices, vegetable-flavored juices, sports drinks, energy drinks, energy drinks, vitamin-enhancing drinks, near-water drinks (e.g., water with natural or synthetic flavorings), coconut water, tea drinks (e.g., black tea, green tea, rooibos tea, oolong tea), coffee, cocoa drinks, beverages containing dairy components (e.g., milk drinks, coffee containing dairy components, milk coffee, milk tea, fruit milk drinks), beverages containing cereal extracts, smoothies, and combinations thereof. Examples of frozen beverages include, but are not limited to, shaved ice, frozen cocktails, daiquiri, chilled fruit rum, margaritas, milkshakes, frozen coffee, frozen lemonade, granitas, and smoothies. Beverages can be alcoholic (e.g., liqueurs or cream liqueurs) or non-alcoholic. Beverages can be brewed fermented beverages, such as beer or kombucha. Beverage concentrates and beverage syrups can be prepared using an initial volume of liquid matrix (e.g., water) and desired beverage ingredients. A full-concentration beverage is then prepared by adding an additional volume of water. Powdered beverages are prepared by dry-mixing all beverage ingredients in the absence of a liquid matrix. A full-concentration beverage is then prepared by adding the full volume of water, a liquid matrix, or an aqueous solution.

[0048] The steviol glycoside composition can be a food product or can be used to prepare a food product. The food product can be any calorie or calorie-free food product suitable for human consumption. Suitable food products include, but are not limited to, confectionery products (e.g., candy, candied nuts, candy bars, caramel, chocolate, chocolate bars, chocolate beans, hollow chocolate or any desired shape, filled chocolate bars, pralines, truffles, cereal bars, chewing gum, and pastries), condiments, chewing gum, cereal compositions, baked goods, baked products (e.g., bread, such as bagels, rolls, bread rolls, biscuits, and loaves); cookies; brownies; crispy muffins; desserts, such as cakes, cheesecakes, and pies; snack cakes; sweets such as donuts, Danish pastries, sweet rolls, cinnamon rolls, and coffee cookies), cooking condiments, dairy products (e.g., ice cream, yogurt, frozen desserts, puddings, mousses, custards, milkshakes, malt, cream cheese, cheese, fudge), dairy substitutes, frozen desserts (e.g., ice cream, sorbets, frozen yogurt, etc.), tabletop steviol glycoside compositions, seasonings, sauces, gravy, soups, condiments, snack products (e.g., oat bars, nutrition bars, etc.), etc. The compositions described herein can be used in any form in food products, such as melting or mixing into the formulation of the final product as fillings, inclusions, toppings, or coatings, or molding around other discrete ingredients such as nuts, fruits, dried fruits, cookies, candy blocks, or shapes, or combinations thereof. In frozen dessert compositions, the compositions can be used as coatings, inclusions (in block, sheet, or corrugated form), toppings, or fillings (soft or solid).

[0049] The invention can be better understood by referring to the following embodiments provided by way of example. The invention is not limited to the embodiments given herein.

[0050] Example

[0051] Materials and Methods

[0052] Table 2 lists the sources of the test materials and various components.

[0053] Table 2 .

[0054]

[0055] Example 1 - Steviosides and Choline Chloride

[0056] Prepare a mixture of steviol glycosides (Reb D / M), choline chloride, and water according to Table 3. Stir the mixture to dissolve the steviol glycosides and choline chloride. If dissolution is not achieved at room temperature, heat the mixture to a temperature of 50°C–80°C to dissolve the components. Visually observe the clarity of the mixture to determine solubility. Observe the heated mixture after allowing it to cool to room temperature (approximately 20°C–25°C).

[0057]

[0058] These results indicate that choline chloride can increase the solubility of steviol glycosides. Without choline chloride, the tested steviol glycoside combinations exhibited a maximum solubility of 0.1%. However, when choline chloride was added at a choline chloride to water ratio between 5 and 6 and a steviol glycoside to choline chloride ratio below 0.6, the solubility increased to over 20% by weight, and clearly reached at least 33.3% by weight and possibly higher.

[0059] Example 2 - Steviosides and Other Reagents

[0060] An attempt was made to dissolve steviol glycosides (Reb D / M) in water with benzalkonium chloride (“BAC”) and hexadecyltrimethylammonium bromide (“CTAB”). The mixture was 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.

[0061]

[0062] Example 3 - Lebodiin D and Choline Chloride

[0063] Prepare a mixture of steviol glycosides (lebaudin D and lebaudin M), choline chloride, and water according to Table 5. Stir the mixture at 80°C to dissolve the steviol glycosides and choline chloride. Add additional choline chloride sequentially until a clear solution is obtained; the final choline chloride concentration is reported in Table 5. Allow the mixture to cool to room temperature (approximately 20°C–25°C). Visually inspect the clarity of the mixture to determine its solubility.

[0064] Table 5.

[0065]

[0066] These results indicate that choline chloride can increase the solubility of reb D steviol glycoside solutions. Figure 1A comparison is shown between a 29.0% Reb D solution (right beaker) and a 30.3% Reb M and Reb D solution (ratio 18 / 82). While the 18 / 82 Reb M / Reb D combination remained clear, the 29% pure Reb D solution showed slight crystallization but was still a clear solution.

[0067] All references and publications cited herein are expressly incorporated in their entirety by way of citation, unless they may directly contradict this disclosure. Although specific embodiments have been illustrated and described herein, those skilled in the art will understand that various alternative and / or equivalent embodiments may be substituted for the specific embodiments shown and described without departing from the scope of this 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 such examples and embodiments are presented by way of example only, and the scope of this disclosure is intended to be limited solely by the claims set forth herein.

Claims

1. An aqueous steviol glycoside solution, said aqueous steviol glycoside solution comprising: One or more steviol glycosides, comprising 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, or 30% or more by weight; and Choline chloride is an amount of choline chloride in which the 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 according to claim 1, wherein the one or more steviol glycosides and the choline chloride are present in a weight ratio of 0.65 or less.

3. The aqueous steviol glycoside solution according to claim 1 or 2, wherein one or more steviol glycosides and water are present in a weight ratio of 4 or less.

4. An aqueous steviol glycoside solution, said aqueous steviol glycoside solution comprising: One or more steviol glycosides; Choline chloride; and water, The one or more steviol glycosides are present with choline chloride in a weight ratio of 0.65 or less, and The one or more steviol glycosides are present with water in a weight ratio of 4 or less.

5. The aqueous steviol glycoside solution according to 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 according to any one of claims 1 to 5, wherein the solution comprises 80% by weight or more, 90% by weight or more, or 95% by weight or more of total steviol glycosides, of rebaudioside D and rebaudioside M; and / or The solution contains 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of total steviol glycosides as lebodiin M; and / or The solution contains 50% or less, 25% or less, 20% or less, 15% or less, or 10% or less of total steviol glycosides, of rebaudioside D, optionally wherein the solution contains 5% or more, or 10% or more of total steviol glycosides, of rebaudioside D; and / or The solution contains 5% or less, 2% or less, or 1% or less of total steviol glycosides, other than rebaudioside D and rebaudioside M.

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

8. A steviol glycoside composition, said steviol glycoside composition comprising: One or more steviol glycosides; and Choline chloride, In an aqueous solution containing the steviol glycoside composition such that the ratio of choline chloride is 5.5 parts to 1 part water, at least 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, or 30% by weight of the one or more steviol glycosides are dissolved.

9. A method for increasing the solubility of a steviol glycoside composition, the method comprising: One or more steviol glycosides and choline chloride are added to an aqueous solution to form a steviol glycoside composition wherein the weight ratio of choline chloride to water is in the 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 that when the steviol glycoside composition is added to an aqueous solution wherein the weight ratio of choline chloride to water is outside the range.

10. The steviol glycoside composition according to claim 8 or the method according to claim 9, wherein one or more steviol glycosides and the choline chloride are present in the steviol glycoside composition in a weight ratio of 0.65 or less; and / or The one or more steviol glycosides are present in the steviol glycoside composition in a weight ratio of 4 or less with water.

11. The steviol glycoside composition or method according to any one of claims 8 to 10, wherein the steviol glycoside composition comprises a total of 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, or 30% or more of said one or more steviol glycosides; and / or The steviol glycoside composition comprises a total of 40% by weight, less than 38% by weight, less than 35% by weight, or 33.3% by weight or less of one or more of the steviol glycosides.

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

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

14. The steviol glycoside composition or method according to any one of claims 8 to 13, wherein the one or more steviol glycosides are present in a total concentration of less than 40% by weight, less than 38% by weight, less than 35% by weight, or 33.3% by weight or less.

15. The use of choline chloride to increase the solubility of one or more steviol glycosides.

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