Steviol glycoside isomers
Steviol glycoside isomers are provided having the formula: wherein R 1 may be hydrogen, 1-β-D-glucopyranosyl, or 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 may be hydrogen, 1-β-D-glucopyranosyl, 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, or 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl. Methods for making steviol glycoside isomers are also disclosed. These compounds may be present in food and beverage products as non-nutritive sweeteners.
1. A compound of formula II:
wherein R 1 is 1-β-D-glucopyranosyl or 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is hydrogen, 1-β-D-glucopyranosyl, 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, or 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
2. The compound of claim 1 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
3. The compound of claim 1 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
4. The compound of claim 1 , wherein R 1 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl and R 2 is 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
5. The compound of claim 1 , wherein R 1 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl and R 2 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
6. The compound of claim 1 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 1-β-D-glucopyranosyl.
7. The compound of claim 1 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
8. The compound of claim 1 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is hydrogen.
9. The compound of claim 1 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl.
10. The compound of claim 1 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
11. The compound of claim 1 , wherein the compound is isolated and purified.
12. A beverage product comprising:
an aqueous liquid, and
a compound of formula II:
wherein R 1 is 1-β-D-glucopyranosyl or 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is hydrogen, 1-β-D-glucopyranosyl, 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, or 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
13. The beverage product of claim 12 , wherein the beverage product is selected from the group consisting of carbonated beverages, non-carbonated beverages, fountain beverages, frozen carbonated beverages, powdered concentrates, beverage concentrates, fruit juices, fruit juice-flavored drinks, fruit-flavored drinks, sports drinks, energy drinks, fortified/enhanced water drinks, soy drinks, vegetable drinks, grain-based drinks, malt beverages, fermented drinks, yogurt drinks, kefir, coffee beverages, tea beverages, dairy beverages, and mixtures of any of them.
14. The beverage product of claim 12 , further comprising a sweetener selected from the group consisting of a steviol glycoside, Stevia rebaudiana extracts, Lo Han Guo, Lo Han Guo juice concentrate, Lo Han Guo powder, mogroside V, thaumatin, monellin, brazzein, monatin, erythritol, tagatose, sucrose, liquid sucrose, fructose, liquid fructose, glucose, liquid glucose, high fructose corn syrup, invert sugar, medium invert sugar, maple syrup, maple sugar, honey, chicory syrup, Agave syrup, brown sugar molasses, cane molasses, sugar beet molasses, sorghum syrup, sorbitol, mannitol, maltitol, xylitol, glycyrrhizin, malitol, maltose, lactose, xylose, arabinose, isomalt, lactitol, trehalulose, ribose, fructo-oligosaccharides, aspartame, neotame, alitame, sodium saccharin, calcium saccharin, acesulfame potassium, sodium cyclamate, calcium cyclamate, neohesperidin dihydrochalcone, sucralose, polydextrose, and mixtures of any of them.
15. The beverage product of claim 12 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, wherein the beverage product is a beverage concentrate, and further comprising rebaudioside A.
16. The beverage product of claim 12 , wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, wherein the beverage product is a carbonated beverage, and further comprising rebaudioside A.
17. A food product comprising:
a food component, and
a compound of formula II:
wherein R 1 is 1-β-D-glucopyranosyl or 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is hydrogen, 1-β-D-glucopyranosyl, 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, or 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
18. The food product of claim 17 , wherein the food product is selected from the group consisting of oatmeal, cereal, baked goods, cookies, crackers, cakes, brownies, breads, snack foods, potato chips, tortilla chips, popcorn, snack bars, rice cakes, and grain-based food products.
19. The food product of claim 17 , further comprising a sweetener selected from the group consisting of a steviol glycoside, Stevia rebaudiana extracts, Lo Han Guo, Lo Han Guo juice concentrate, Lo Han Guo powder, mogroside V, thaumatin, monellin, brazzein, monatin, erythritol, tagatose, sucrose, liquid sucrose, fructose, liquid fructose, glucose, liquid glucose, high fructose corn syrup, invert sugar, medium invert sugar, maple syrup, maple sugar, honey, chicory syrup, Agave syrup, brown sugar molasses, cane molasses, sugar beet molasses, sorghum syrup, sorbitol, mannitol, maltitol, xylitol, glycyrrhizin, malitol, maltose, lactose, xylose, arabinose, isomalt, lactitol, trehalulose, ribose, fructo-oligosaccharides, aspartame, neotame, alitame, sodium saccharin, calcium saccharin, acesulfame potassium, sodium cyclamate, calcium cyclamate, neohesperidin dihydrochalcone, sucralose, polydextrose, and mixtures of any of them.
20. The food product of claim 19 , wherein the steviol glycoside is rebaudioside A, and wherein R 1 is 1-β-D-glucopyranosyl and R 2 is 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
21. A sweetener comprising a compound of formula II:
wherein R 1 is 1-β-D-glucopyranosyl or 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is hydrogen, 1-β-D-glucopyranosyl, 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2,3-bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, or 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
22. The sweetener of claim 21 , further comprising at least one of a filler, bulking agent, and an anticaking agent.
23. A compound of formula II:
wherein R 1 is 1-β-D-glucopyranosyl or 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is 1-β-D-glucopyranosyl, 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, glucopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, or 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
24. The compound of claim 1 , wherein R 1 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is hydrogen.
25. The compound of claim 1 , wherein R 1 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is 1-β-D-glucopyranosyl.
26. The compound of claim 1 , wherein R 1 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is 2-(1-α-L-rhamnopyranosyl)-1-β-D-glucopyranosyl.
27. The compound of claim 1 , wherein R 1 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is 2-(1-α-L-rhamnopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.
28. The compound of claim 1 , wherein R 1 is 2-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, and R 2 is 2-(1-β-D-xylopyranosyl)-3-(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl.