Novel Polymorphs of Rebaudioside C and Methods for Making and Using the Same
AssigneeRedpoint Bio Corporation
InventorsF. Raymond Salemme, Robert A. Daines
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Abstract
Embodiments of this invention encompass a method for producing and purifying rebaudioside C. In particular, this invention relates to a method for purifying rebaudioside C compositions to obtain a substantially pure rebaudioside C product using one or more crystallization steps. Resulting polymorphic forms of rebaudioside C, substantially pure rebaudioside C compositions and their uses are disclosed.
Claims49
1:
- Isolated rebaudioside C crystalline Form I, which has a powder X-ray diffraction pattern at Cu Kα wavelength 1.54 Å as shown in FIG. 2.
2:
- The isolated rebaudioside C crystalline Form I of claim 1, wherein the d-spacing distances (Å) of significant peaks as determined by powder X-ray diffraction are:
- 8.6, 9.8, 12.6, 13.6, 13.9, 14.2, 14.9, 15.6, 17.0, 17.4, 18.2, 19.9, 21.3, 22.6, 23.3, 25.5, 27.2, 28.4, 28.9, and 30.0.
3:
- A method for making the isolated rebaudioside C crystalline Form I of claim 1 comprising:
- (a) adding a crystallization solution comprising methanol and isopropanol to a substantially pure rebaudioside C solid to completely dissolve the rebaudioside;
- (b) allowing the solution of step (a) to dry completely at room temperature;
- and
- (c) recovering isolated rebaudioside C crystalline Form I crystals formed in step (b).
4:
- The method of claim 3, further comprising the presteps of:
- (i) adding a crystallization solution to a substantially pure rebaudioside C solid to completely dissolve said solid;
- (ii) allowing the crystallization solution of step (i) to evaporate completely at room temperature;
- and
- (iii) recovering rebaudioside C crystals as a substantially pure rebaudioside C solid.
5:
- The method of claim 4, wherein the crystallization solution of step (i) comprises acetone, acetonitrile, methanol, ethanol, propanol, isopropanol, butanol, 2-butanol, tert-butanol, or mixtures thereof.
6:
- The method of claim 5, wherein the crystallization solution comprises methanol and isopropanol present in a weight ratio ranging from about 5 parts to about 1 part isopropanol to about 1 part methanol.
7:
- The method of claim 3, wherein the substantially pure rebaudioside C solid and the crystallization solution are combined in a weight ratio from about 30 parts to about 1 part substantially pure rebaudioside C to about 1 part crystallization solution.
8:
- A method of purifying rebaudioside C comprising the steps of:
- (a) adding a crystallization solution to a Stevia extract solid or crude rebaudioside C solid to produce a crude rebaudioside C solution, wherein the Stevia extract solid contains at least 0.6% of rebaudioside C by dry weight, and the crude rebaudioside C solid contains at least 40% of rebaudioside C by dry weight;
- (b) seeding said crude rebaudioside C solution with isolated rebaudioside C crystalline Form I crystals of claim 1;
- (c) allowing said crude rebaudioside C solution to dry completely at room temperature;
- (d) recovering rebaudioside C crystals formed in step (c);
- (e) adding a crystallization solution comprising methanol and isopropanol to the rebaudioside C crystals of step (d) to completely dissolve said crystals;
- (f) allowing the solution of step (e) to dry completely at room temperature;
- and
- (g) recovering isolated rebaudioside C crystalline Form I crystals formed in step (f).
9:
- The method of claim 8, wherein the crystallization solvent comprises acetone, acetonitrile, methanol, ethanol, propanol, isopropanol, butanol, 2-butanol, tert-butanol, or mixtures thereof.
10:
- The method of claim 9, wherein the crystallization solvent comprises methanol and isopropanol present in a weight ratio from about 5 parts to about 1 part isopropanol to about 1 part methanol.
11:
- The method of claim 9, further comprising seeding the crystallization solution of step (e) with isolated rebaudioside C crystalline Form I crystals of claim 1 or claim 2.
12:
- A method of purifying rebaudioside C comprising the steps of:
- (a) adding a crystallization solution comprising methanol and isopropanol to a Stevia extract solid or crude rebaudioside C solid to produce a crude rebaudioside C solution, wherein the Stevia extract solid contains at least 0.6% of rebaudioside C by dry weight and the crude rebaudioside C solid contains at least 40% of rebaudioside C by dry weight;
- (b) seeding said crude rebaudioside C solution with the isolated rebaudioside C crystalline Form I crystals of claim 1;
- (c) allowing said crude rebaudioside C solution to dry completely at room temperature;
- and
- (d) recovering isolated rebaudioside C crystalline Form I crystals formed in step (c).
13:
- The method of claim 8, further comprising the step of heating the crude rebaudioside C solution.
14:
- The method of claim 13, further comprising the step of cooling the crude rebaudioside C solution.
15:
- The method of claim 8, wherein said crude rebaudioside C solid comprises substantially no rebaudioside D impurity and/or rebaudioside A impurity, and the method further comprises slurrying the isolated rebaudioside C crystalline Form I crystals in a slurry solution.
16:
- A method of enhancing a sweet taste of a carbohydrate sweetener, comprising administering to a subject the carbohydrate sweetener and isolated rebaudioside C crystalline Form I of claim 1 in an amount effective to provide the sweet taste enhancing effect without exhibiting an off-taste.
17:
- The method of claim 16, wherein the carbohydrate sweetener is sucrose, fructose, glucose, high fructose corn syrup, xylose, arabinose or rhamnose.
18:
- The method of claim 16, wherein the carbohydrate sweetener is a sugar alcohol.
19:
- The method of claim 18, wherein the sugar alcohol is erythritol, xylitol, mannitol, sorbitol, or inositol.
20:
- The method of claim 16, wherein the carbohydrate sweetener and isolated rebaudioside C crystalline Form I are administered in a consumable.
21:
- The method of claim 20, wherein the consumable is a food product, pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition, a tabletop sweetener, or a cosmetic product.
22:
- The method of claim 21, wherein the food product is a beverage or a drink.
23:
- The method of claim 16, wherein isolated rebaudioside C crystalline Form I is present at a concentration of from about 150 μM to about 600 μM.
24:
- The method of claim 16, wherein the consumable has a sweetness intensity equivalent to about 5-12% (w/v-%) sucrose solution.
25:
- A consumable comprising a carbohydrate sweetener and isolated rebaudioside C crystalline Form I of claim 1 in an amount effective to enhance the sweet taste of the carbohydrate sweetener without exhibiting an off-taste.
26:
- The consumable of claim 25, wherein isolated rebaudioside C crystalline Form I is present at a concentration of from about 150 μM to about 600 μM.
The consumable of claim 25, wherein the consumable has a sweetness intensity equivalent to about 5-12% (w/v-%) sucrose solution.
The consumable of claim 25, wherein the carbohydrate sweetener is sucrose, fructose, glucose, high fructose corn syrup, xylose, arabinose or rhamnose.
The consumable of claim 25, wherein the carbohydrate sweetener is a sugar alcohol.
The consumable of claim 25, wherein the consumable is a food product, pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition, a tabletop sweetener or a cosmetic product.
A method of decreasing the amount of a carbohydrate sweetener in a consumable, comprising adding isolated rebaudioside C crystalline Form I of claim 1 to the consumable and reducing the amount of the carbohydrate sweetener needed to exhibit a given level of sweetness.
A method of enhancing the sweetness of a consumable comprising a carbohydrate sweetener, comprising adding isolated rebaudioside C crystalline Form I of claim 1 to the consumable in an amount effective to enhance the sweetness of the consumable.
Dependencies are inferred from the claim text.