Compounds Produced From Stevia And Process For Producing The Same

Abstract

Various ingredients and compositions are prepared from Stevia rebaudiana Bertoni plant. The compositions can be used as bulking agents, and sweeteners in foods, beverages, cosmetics and pharmaceuticals.

Claims

1. A sweetener composition comprising: at least one isomerized Stevia compound; wherein the at least one isomerized Stevia compound has the formula: ##STR00001## and is selected from the group consisting of: (1) iso-Rubusoside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (2) iso-Steviolbioside, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (3) iso-Stevioside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (4) Isomerized steviol glycoside formula 4, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (5) iso-Rebaudioside E, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (6) iso-Rebaudioside B, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (7) DAQ3, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (8) iso-Rebaudioside D, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (9) iso-Rebaudioside I, where R.sub.1 is Glc.beta.(1-3)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (10) iso-Rebaudioside G, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Glc.beta.1-; (11) iso-Rebaudioside M, where R.sub.1 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (12) Isomerized steviol glycoside formula 12, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)Glc.beta.1-; (13) iso-Rebaudioside L, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (14) iso-Dulcoside A, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)Glc.beta.1-; (15) iso-Dulcoside B, where R.sub.1 is H, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (16) iso-Rebaudioside C, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (17) iso-Rebaudioside H, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (18) iso-Rebaudioside K, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (19) iso-Rebaudioside J, where R.sub.1 is Rha.alpha.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (20) iso-Rebaudioside N, where R.sub.1 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (21) iso-Rebaudioside O, where R.sub.1 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (22) Isomerized steviol glycoside formula 22, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)Glc.beta.1-; (23) iso-Rebaudioside F, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (24) Isomerized steviol glycoside formula 24, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Xy1.beta.(1-3)]Glc.beta.1-; (25) Isomerized steviol glycoside formula 25, where R.sub.1 is Xy1.beta.(1-6)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (26) Isomerized steviol glycoside formula 26, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Fru.beta.(1-3)]Glc.beta.1-; (27) Isomerized steviol glycoside formula 27, where R.sub.1 is Glc.alpha.(1-2)Glc.alpha.(1-4)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (28) Isomerized steviol glycoside formula 28, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-3)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (29) Isomerized steviol glycoside formula 29, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-4)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (30) Isomerized steviol glycoside formula 30, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxy Glc.beta.(1-2)Glc.beta.1-; (31) Isomerized steviol glycoside formula 31, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxyGlc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; and (32) Isomerized steviol glycoside formula 32, where R.sub.1 is 6-deoxyGlc.beta.1-, and R.sub.0.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; and at least one additional substance selected from the group consisting of steviol glycosides, stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, steviolbioside, rubusoside, glycosylated steviol glycosides, glucosylated steviol glycosides as well as other steviol glycosides found in Stevia rebaudiana plant and mixtures thereof, Stevia extract, Luo Han Guo extract, mogrosides, high-fructose corn syrup, corn syrup, invert sugar, fructooligosaccharides, inulin, inulooligosaccharides, coupling sugar, maltooligosaccharides, maltodextins, corn syrup solids, glucose, maltose, sucrose, lactose, aspartame, saccharin, sucralose, sugar alcohols and combination thereof.

2. A flavor composition comprising: at least one isomerized Stevia compound; wherein the at least one isomerized Stevia compound has the formula: ##STR00002## and is selected from the group consisting of: (1) iso-Rubusoside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (2) iso-Steviolbioside, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (3) iso-Stevioside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (4) Isomerized steviol glycoside formula 4, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (5) iso-Rebaudioside E, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (6) iso-Rebaudioside B, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (7) DAQ3, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (8) iso-Rebaudioside D, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (9) iso-Rebaudioside I, where R.sub.1 is Glc.beta.(1-3)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (10) iso-Rebaudioside G, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Glc.beta.1-; (11) iso-Rebaudioside M, where R.sub.1 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (12) Isomerized steviol glycoside formula 12, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)Glc.beta.1-; (13) iso-Rebaudioside L, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (14) iso-Dulcoside A, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)Glc.beta.1-; (15) iso-Dulcoside B, where R.sub.1 is H, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (16) iso-Rebaudioside C, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (17) iso-Rebaudioside H, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (18) iso-Rebaudioside K, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (19) iso-Rebaudioside J, where R.sub.1 is Rha.alpha.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (20) iso-Rebaudioside N, where R.sub.1 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (21) iso-Rebaudioside O, where R.sub.1 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (22) Isomerized steviol glycoside formula 22, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)Glc.beta.1-; (23) iso-Rebaudioside F, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (24) Isomerized steviol glycoside formula 24, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Xy1.beta.(1-3)]Glc.beta.1-; (25) Isomerized steviol glycoside formula 25, where R.sub.1 is Xy1.beta.(1-6)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (26) Isomerized steviol glycoside formula 26, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Fru.beta.(1-3)]Glc.beta.1-; (27) Isomerized steviol glycoside formula 27, where R.sub.1 is Glc.alpha.(1-2)Glc.alpha.(1-4)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (28) Isomerized steviol glycoside formula 28, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-3)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (29) Isomerized steviol glycoside formula 29, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-4)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (30) Isomerized steviol glycoside formula 30, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxy Glc.beta.(1-2)Glc.beta.1-; (31) Isomerized steviol glycoside formula 31, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxyGlc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; and (32) Isomerized steviol glycoside formula 32, where R.sub.1 is 6-deoxyGlc.beta.1-, and R.sub.0.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; and at least one additional flavoring agent selected from the group consisting of lemon, berry, orange, fruit, banana, grape, pear, pineapple, mango, bitter almond, cola, cinnamon, sugar, cotton candy, vanilla, terpenoid glycosides and combination thereof.

3. A food ingredient comprising: at least one isomerized Stevia compound; wherein the at least one isomerized Stevia compound has the formula: ##STR00003## and is selected from the group consisting of: (1) iso-Rubusoside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (2) iso-Steviolbioside, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (3) iso-Stevioside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (4) Isomerized steviol glycoside formula 4, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (5) iso-Rebaudioside E, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (6) iso-Rebaudioside B, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (7) DAQ3, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (8) iso-Rebaudioside D, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (9) iso-Rebaudioside I, where R.sub.1 is Glc.beta.(1-3)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (10) iso-Rebaudioside G, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Glc.beta.1-; (11) iso-Rebaudioside M, where R.sub.1 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (12) Isomerized steviol glycoside formula 12, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)Glc.beta.1-; (13) iso-Rebaudioside L, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (14) iso-Dulcoside A, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)Glc.beta.1-; (15) iso-Dulcoside B, where R.sub.1 is H, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (16) iso-Rebaudioside C, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (17) iso-Rebaudioside H, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (18) iso-Rebaudioside K, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (19) iso-Rebaudioside J, where R.sub.1 is Rha.alpha.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (20) iso-Rebaudioside N, where R.sub.1 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (21) iso-Rebaudioside O, where R.sub.1 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.0.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (22) Isomerized steviol glycoside formula 22, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)Glc.beta.1-; (23) iso-Rebaudioside F, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (24) Isomerized steviol glycoside formula 24, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Xy1.beta.(1-3)]Glc.beta.1-; (25) Isomerized steviol glycoside formula 25, where R.sub.1 is Xy1.beta.(1-6)Glc.beta.1-, and R.sub.0.2 is Glc.beta.(1-2)Glc.beta.1-; (26) Isomerized steviol glycoside formula 26, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Fru.beta.(1-3)]Glc.beta.1-; (27) Isomerized steviol glycoside formula 27, where R.sub.1 is Glc.alpha.(1-2)Glc.alpha.(1-4)Glc.beta.1-, and R.sub.0.2 is Glc.beta.(1-2)Glc.beta.1-; (28) Isomerized steviol glycoside formula 28, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-3)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (29) Isomerized steviol glycoside formula 29, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-4)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (30) Isomerized steviol glycoside formula 30, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxy Glc.beta.(1-2)Glc.beta.1-; (31) Isomerized steviol glycoside formula 31, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxyGlc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; and (32) Isomerized steviol glycoside formula 32, where R.sub.1 is 6-deoxyGlc.beta.1-, and R.sub.0.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; and at least one additional food ingredient selected from the group consisting of acidulants, organic and amino acids, coloring agents, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilisers, thickeners, gelling agents, and combination thereof.

4. A food, beverage, cosmetic, pharmaceutical product or other consumable comprising at least one isomerized Stevia compound; wherein the at least one isomerized Stevia compound has the formula: ##STR00004## and is selected from the group consisting of: (1) iso-Rubusoside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (2) iso-Steviolbioside, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (3) iso-Stevioside, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (4) Isomerized steviol glycoside formula 4, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.1-; (5) iso-Rebaudioside E, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (6) iso-Rebaudioside B, where R.sub.1 is H, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (7) DAQ3, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (8) iso-Rebaudioside D, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (9) iso-Rebaudioside I, where R.sub.1 is Glc.beta.(1-3)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (10) iso-Rebaudioside G, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Glc.beta.1-; (11) iso-Rebaudioside M, where R.sub.1 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (12) Isomerized steviol glycoside formula 12, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)Glc.beta.1-; (13) iso-Rebaudioside L, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-6)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (14) iso-Dulcoside A, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)Glc.beta.1-; (15) iso-Dulcoside B, where R.sub.1 is H, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (16) iso-Rebaudioside C, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (17) iso-Rebaudioside H, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (18) iso-Rebaudioside K, where R.sub.1 is Glc.beta.(1-2)Glc.beta.1-, and R.sub.2 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (19) iso-Rebaudioside J, where R.sub.1 is Rha.alpha.(1-2)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (20) iso-Rebaudioside N, where R.sub.1 is Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (21) iso-Rebaudioside O, where R.sub.1 is Glc.beta.(1-3)Rha.alpha.(1-2)[Glc.beta.(1-3)]Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (22) Isomerized steviol glycoside formula 22, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)Glc.beta.1-; (23) iso-Rebaudioside F, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Xy1.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (24) Isomerized steviol glycoside formula 24, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Xy1.beta.(1-3)]Glc.beta.1-; (25) Isomerized steviol glycoside formula 25, where R.sub.1 is Xy1.beta.(1-6)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (26) Isomerized steviol glycoside formula 26, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Fru.beta.(1-3)]Glc.beta.1-; (27) Isomerized steviol glycoside formula 27, where R.sub.1 is Glc.alpha.(1-2)Glc.alpha.(1-4)Glc.beta.1-, and R.sub.2 is Glc.beta.(1-2)Glc.beta.1-; (28) Isomerized steviol glycoside formula 28, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-3)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (29) Isomerized steviol glycoside formula 29, where R.sub.1 is Glc.beta.1-, and R.sub.2 is Glc.alpha.(1-4)Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; (30) Isomerized steviol glycoside formula 30, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxyGlc.beta.(1-2)Glc.beta.1-; (31) Isomerized steviol glycoside formula 31, where R.sub.1 is Glc.beta.1-, and R.sub.2 is 6-deoxyGlc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-; and (32) Isomerized steviol glycoside formula 32, where R.sub.1 is 6-deoxyGlc.beta.1-, and R.sub.2 is Glc.beta.(1-2)[Glc.beta.(1-3)]Glc.beta.1-.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0025] The accompanying drawings are included to provide a further understanding of the invention. The drawings illustrate embodiments of the invention and together with the description serve to explain the principles of the embodiments of the invention.

[0026] FIG. 1 shows the chemical structure of rebaudioside A.

[0027] FIG. 2 shows the chemical structure of DAQ3.

[0028] FIG. 3 shows the general chemical structures of isomerized steviol glycosides.

[0029] FIG. 4 shows a HPLC chromatogram of a reaction mixture containing DAQ3.

[0030] FIG. 5 shows a HPLC chromatogram of purified DAQ3.

DETAILED DESCRIPTION OF THE INVENTION

[0031] Advantages of the present invention will become more apparent from the detailed description given hereinafter. However, it should be understood that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.

[0032] In one aspect, the present invention provides a process of isomerizing reb A and other steviol glycosides. Briefly, the inventors of the present invention discovered that reb A and other steviol glycosides could be isomerized when contacted with ion-exchange resins in water or aqueous alcohol solutions.

[0033] Rebaudioside A product commercialized by PureCircle Sdn. Bhd. (Malaysia), containing, rebaudioside A (about 95-100%), stevioside (about 0-1%), rebaudioside C (about 0-1%), rebaudioside D (about 0-1%), rebaudioside F (about 0-1%), rebaudioside B (about 0.1-0.8%) and other glycosides amounting to total steviol glycosides' content of at least about 95%, was used as a starting material. In addition, Stevia extracts with different ratio of steviol glycosides may be used as starting materials.

[0034] It is also to be noted that the process of the present invention is also applicable for isomerization of other glycosides of steviol such as stevioside, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, steviolbioside, rubusoside, other steviol glycosides found in Stevia rebaudiana plant, glycosylated steviol glycosides, glucosylated steviol glycosides, enzymatically modified steviol glycosides and/or combinations thereof. The structures of isomers of exemplary glycosides are provided in FIG. 3.

[0035] The HPLC analysis of the raw materials and products was performed on an Agilent Technologies 1200 Series (USA) liquid chromarograph, equipped with Phenomenex Prodigy ODS3, 3 m (4.6250 mm) column at 55 C. The mobile phase was 32:68 mixture of acetonitrile and 10 mmol/L sodium phosphate buffer (about pH 2.6) at 1 mL/min. A diode array detector set at 210 nm was used as the detector. The reference standards of DAQ3 and iso-stevioside were obtained from Chromadex Inc., USA (Part #00009518 and #00009595).

[0036] In one embodiment of the present invention, reb A product was dissolved in water or aqueous alcohol solution. The concentration of reb A is about 0.001-50% (w/v) preferably about 1-10%. The preferred alcohols include methanol, ethanol, n-propanol, iso-propanol, butanol and/or mixtures thereof. Other solvents capable of dissolving the raw material, including pure water, may be used as well. The water to alcohol ratio in aqueous alcohol (vol./vol.) was in the range from 0.001%:99.999% to 99.999%:0.001%, preferably from about 40%:60% to 60%:40%. The pH of the prepared solution was in the range from pH 0 to pH 14, preferably from pH 6 to pH 8, more preferably neutral. The dissolved reb A product was contacted with ion-exchange resin at about 10-150 C., preferably about 30-100 C., for a period of about 0.5-48 hrs, preferably about 1-24 hrs. As a result reb A is completely or partially isomerized to DAQ3. Various process equipment known to art, which are capable of facilitating the contact of a liquid with ion-exchange resin can be used for this purpose. Non-limiting examples include: columns, reactors, vessels, tanks, simulated moving bed systems, continuous ion-exchange systems, chromatography systems, etc. Different equipments can be combined, and systems including multiple numbers of same equipment, connected in parallel or consecutively, can be use as well. The process can be conducted in one or several stages. The process can be run in batch, semi-batch, fed-batch and continuous modes. Preferably the process is conducted in continuous mode by using columns packed with ion-exchange resin.

[0037] In one embodiment the reb A product-dissolved solution is circulated through a column system packaged with ion-exchange resin until the desired level of DAQ3 is achieved.

[0038] In another embodiment the reb A product-dissolved solution is fed to a column system packaged with ion-exchange resin with at a rate sufficient to achieve the desired level of DAQ3 at the outlet of the system.

[0039] Various ion-exchange resins known to art can be used. Resins with various chemistry including acrylic, methacrylic, (linked with a di-functional monomer e.g. DVB), sulfonated copolymers of styrene and DVB, gel, microporous and macroporous, or mixtures thereof can be used. Weak or strong ion-exchange resins can be used. Weak or strong cation exchange resins can be used; preferably strong protonated cation exchange resin.

[0040] After contacting the reb A product-dissolved solution with ion-exchange resin a reaction mixture containing at least 1 mg/L of DAQ3 is obtained. Preferably the reaction medium is containing from 10,000 mg/L to 500,000 mg/L DAQ3.

[0041] In one embodiment the DAQ3 is crystallized from the obtained reaction mixture.

[0042] In one embodiment the DAQ3 is crystallized from the obtained reaction mixture containing 0.001% to 90% total solids, preferably 1% to 50% total solids.

[0043] In another embodiment the DAQ3 is crystallized from reaction mixture after addition of at least one other solvent.

[0044] In yet another embodiment the DAQ3 is crystallized from reaction mixture after removal of at least one of the solvents.

[0045] In one embodiment the pH of the reaction mixture is adjusted to pH 7.0 to pH 14.0, preferably pH 8 to pH 10 before crystallization of DAQ3.

[0046] In yet another embodiment the crystallization of DAQ3 is induced by addition of DAQ3 crystals as a starter.

[0047] In another embodiment the crystallization of DAQ3 is induced without addition of DAQ3 crystals.

[0048] In one embodiment the crystallization is repeated at least one time.

[0049] In another embodiment at least one step of crystallization is conducted in media comprising water from 0.0001% to 99.999% (vol./vol.) and at least one organic solvent from 0.0001% to 99.999% (vol./vol.).

[0050] In one embodiment the DAQ3 purification process includes at least one step of chromatographic purification by any chromatographic separation method known to art.

[0051] In another method the DAQ3 purification process includes at least one membrane filtration step using any type of membrane known to art.

[0052] In one embodiment the DAQ3 crystals were separated by any method known in the art such as filtration, centrifugation etc.

[0053] In one embodiment the DAQ3 crystals were dried by different drying methods, including but not limited to vacuum drying, belt vacuum drying, oven drying, microwave drying, fluid bed drying, spray drying, flash drying, freeze drying etc.

[0054] In yet another embodiment the DAQ3 powder particle size was adjusted by pulverization, granulation, agglomeration or any other method known to art to produce particles from 0.00001 m to 10 mm.

[0055] In yet another embodiment the DAQ3 crystals were subjected to various treatments by different chemical and physical agents know to art to yield various polymorphic forms, including amorphous forms.

[0056] In one particular embodiment, after the reaction, the alcohol was removed from the solution, and the aqueous solution was concentrated to about 1% to 90% total solids content. The pH of the solution was adjusted to pH 9 to pH 10 and the DAQ3 was crystallized during 24 hrs. The DAQ3 crystals were separated by filtration to produce first crystals. The obtained first crystals were dried under vacuum at about 60-105 C. to yield a glycoside mixture comprising DAQ3 about 5-95%, preferably about 10-95%, and more preferably about 30-90%.

[0057] In embodiment, after the reaction, the reaction mixture was dried. The dried powder was dispersed or dissolved in water or aqueous alcohol, the pH of the solution was adjusted to pH 9 to pH 10 and the DAQ3 was crystallized during 24 hrs. The ratio of the dried powder to water (wt/vol) or aqueous alcohol was from 1:1 to 1:10. The DAQ3 crystals were separated by filtration to produce first crystals. The obtained first crystals were dried under vacuum at about 60-105 C. to yield a glycoside mixture comprising DAQ3 about 5-95%, preferably about 10-95%, and more preferably about 30-90%.

[0058] In another embodiment, the first crystals were suspended in water, the pH of the mixture was adjusted to pH 9 to pH 10, and the mixture is subjected to continuous agitation over about 0.5-24 hrs, preferably about 1-3 hours, at about 50-100 C., preferably about 10-60 C. The ratio of the first crystals to water (wt/vol) was from 1:1 to 1:10. The DAQ3 crystals were separated by filtration to produce second crystals. The obtained second crystals were dried under vacuum at about 60-105 C. to yield a glycoside mixture comprising DAQ3 about 50-99%, preferably about 70-98, and more preferably about 80-97%.

[0059] In another embodiment, the first crystals were dissolved in water to produce a solution with about 1-90% total solids content. The pH of the solution was adjusted to pH 9 to pH 10, and the solution was subjected to continuous agitation over about 0.5-24 hrs, preferably about 16-22 hours, at about 5-100 C., preferably about 10-30 C. The DAQ3 crystals were separated by filtration to produce second crystals. The obtained second crystals were dried under vacuum at about 60-105 C. to yield a glycoside mixture comprising DAQ3 about 50-99%, preferably about 70-98%, and more preferably about 80-97%

[0060] In another embodiment, the first crystals were dissolved in aqueous alcohol to produce a solution with about 1-90% total solids content. The preferred alcohols include methanol, ethanol, n-propanol, iso-propanol, butanol and/or mixtures thereof, however other solvents capable of dissolving the first crystals, including pure alcohols, may be used as well. The water to alcohol ratio in aqueous alcohol (vol./vol.) was in the range from 0.001%:99.999% to 99.999%:0.001%, preferably from about 1%:99% to 50%:50%. The pH of the solution was adjusted to pH 9 to pH 10, and the solution was subjected to continuous agitation over about 0.5-24 hrs, preferably about 16-22 hours, at about 5-100 C., preferably about 10-30 C. The DAQ3 crystals were separated by filtration to produce second crystals. The obtained second crystals were dried under vacuum at about 60-105 C. to yield a glycoside mixture comprising DAQ3 about 50-99%, preferably about 70-98%, and more preferably about 80-97%.

[0061] In another embodiment, the second crystals were dissolved in water or aqueous alcohol to produce a solution with about 1-90% total solids content. The pH of the mixture was adjusted to pH 9 to pH 10, and the solution was subjected to continuous agitation over about 0.5-24 hrs, preferably about 16-22 hours, at about 5-100 C., preferably about 10-30 C. The DAQ3 crystals were separated by filtration to produce third crystals. The obtained third crystals were dried under vacuum at about 60-105 C. to yield a glycoside mixture comprising of DAQ3 with purity of >99%.

[0062] The compositions can be used as sweetener, flavor, sweetness enhancer, flavor enhancer, sweetness modifier, flavor modifier in various food and beverage products at the concentration from 0.1 ppm to 999, 999 ppm. Non-limiting examples of food and beverage products include carbonated soft drinks, ready to drink beverages, energy drinks, isotonic drinks, low-calorie drinks, zero-calorie drinks, sports drinks, sodas, colas, teas, fruit and vegetable juices, juice drinks, dairy drinks, yoghurt drinks, alcohol beverages, powdered beverages, bakery products, cookies, biscuits, baking mixes, cereals, confectioneries, candies, toffees, chewing gum, dairy products, flavored milk, yoghurts, flavored yoghurts, cultured milk, soy sauce and other soy base products, salad dressings, mayonnaise, vinegar, frozen-desserts, meat products, fish-meat products, bottled and canned foods, tabletop sweeteners, fruits and vegetables.

[0063] Additionally the compositions can be used in drug or pharmaceutical preparations and cosmetics, including but not limited to toothpaste, mouthwash, cough syrup, chewable tablets, lozenges, vitamin preparations, and the like, at the concentration from 0.1 ppm to 999,999 ppm.

[0064] The obtained compositions can be used as-is or in combination with other sweeteners, flavors and food ingredients.

[0065] Non-limiting examples of sweeteners include at least one sweetener selected from group including steviol glycosides, stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, steviolbioside, rubusoside, glycosylated steviol glycosides, glucosylated steviol glycosides, enzymatically modified steviol glycosides as well as other steviol glycosides found in Stevia rebaudiana plant and mixtures thereof, Stevia extract, Luo Han Guo extract, mogrosides, high-fructose corn syrup, corn syrup, invert sugar, fructooligosaccharides, inulin, inulooligosaccharides, coupling sugar, maltooligosaccharides, maltodextins, corn syrup solids, glucose, maltose, sucrose, lactose, aspartame, saccharin, sucralose, sugar alcohols.

[0066] Non-limiting examples of flavors include at least one flavor selected from the group including lemon, orange, berry, fruit, banana, grape, pear, pineapple, bitter almond, cola, cinnamon, sugar, cotton candy, vanilla flavors, terpenoid glycosides and/or combinations thereof.

[0067] Non-limiting examples of other food ingredients include at least one selected from group of flavors, acidulants, organic acids, amino acids, coloring agents, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilisers, thickeners, gelling agents and/or combinations thereof.

[0068] It is to be understood that the process described in the invention can be used for preparing similar compounds from other steviol glycosides. Non limiting examples of these steviol glycosides include: stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, steviolbioside, rubusoside, glycosylated steviol glycosides, glucosylated steviol glycosides, enzymatically modified steviol glycosides as well as other steviol glycosides found in Stevia rebaudiana plant and/or combinations thereof.

[0069] The following examples illustrate various embodiments of the invention. It will be understood that the invention is not limited to the materials, proportions, conditions and procedures set forth in the examples, which are only illustrative.

Example 1

[0070] Preparation of Stevia Sweetener

[0071] 80 g of rebaudioside A produced by PureCircle Sdn. Bhd. (Malaysia), containing, 98.3% rebaudioside A, 0.1% stevioside, 0.1% rebaudioside C, 0.2% rebaudioside F, 0.4% rebaudioside B, 0.2% DAQ3, and 0.5% rebaudioside D was dissolved in 50%:50% (vol./vol.) blend of absolute ethanol and ultrapure water to make 4,000 mL solution. The solution was fed to a 250 mL jacketed column packed with protonated cation exchange resin (Amberlite IR120, Rohm and Haas USA). The column temperature was maintained at 50 C. After 24 hrs the solution was assayed by HPLC. The solution contained (on dry anhydrous basis) 20.9% rebaudioside A, 11.3% rebaudioside B, 47.8% DAQ3, 19.9% iso-Reb B and traces of other glycosides. The solution was evaporated to remove ethanol and the remaining aqueous solution (pH 5) was diluted with water to about 2% total solids content. The pH was adjusted by NaOH to pH 10 and the solution was agitated at room temperature for about 24 hrs. The precipitated crystals were separated, dried under vacuum to yield about 30 g first crystals. HPLC assay show the first crystals contain (on dry anhydrous basis) 3.1% rebaudioside A, 0.7% rebaudioside B, 80.4% DAQ3, 15.5% iso-Reb B and traces of other glycosides.

Example 2

[0072] Preparation of Stevia Sweetener by Acid Treatment

[0073] 80 g of rebaudioside A produced by PureCircle Sdn. Bhd. (Malaysia), containing, 98.3% rebaudioside A, 0.1% stevioside, 0.1% rebaudioside C, 0.2% rebaudioside F, 0.4% rebaudioside B, 0.2% DAQ3, and 0.5% rebaudioside D was dissolved in ultrapure water to make 4,000 mL solution. The pH was adjusted to pH 2.0 by phosphoric acid and the solution was incubated at 50 C. for 7 days. After 1 day and 7 days the solution was analyzed by HPLC. The 1 day solution contained (on dry anhydrous basis) 90.4% rebaudioside A, 1.7% rebaudioside B, 5.1% DAQ3, 1.2% iso-Reb B and traces of other glycosides. The 7 day solution contained (on dry anhydrous basis) 38.9% rebaudioside A, 11.2% rebaudioside B, 40.9% DAQ3, 9.0% iso-Reb B and traces of other glycosides. The solution was diluted to about 2% total solids and the pH was adjusted by NaOH to pH 10. The solution was agitated at room temperature for about 24 hrs. The precipitated crystals were separated, dried under vacuum to yield about 22 g crystals. HPLC assay show the crystals contain (on dry anhydrous basis) 22.9% rebaudioside A, 6.2% rebaudioside B, 66.1% DAQ3, 4.1% iso-Reb B and traces of other glycosides.

Example 3

[0074] Preparation of Stevia Sweetener

[0075] 80 g of rebaudioside A produced by PureCircle Sdn. Bhd. (Malaysia), containing, 98.3% rebaudioside A, 0.1% stevioside, 0.1% rebaudioside C, 0.2% rebaudioside F, 0.4% rebaudioside B, 0.2% DAQ3, and 0.5% rebaudioside D was dissolved in 50%:50% (vol./vol.) blend of absolute ethanol and ultrapure water to make 4,000 mL solution. The solution was mixed with 250 mL protonated cation exchange resin (Amberlite IR120, Rohm and Haas USA) in a jacketed reactor. The mixture temperature was maintained at 50 C. After 24 hrs the resin was separated from solution by filtration. The obtained solution was assayed by HPLC. The solution contained (on dry anhydrous basis) 20.1% rebaudioside A, 12.4% rebaudioside B, 45.9% DAQ3, 21.6% iso-Reb B and traces of other glycosides. The solution was evaporated to remove ethanol and the remaining aqueous solution (pH 5) was diluted with water to about 2% total solids content. The pH was adjusted by NaOH to pH 10 and the solution was agitated at room temperature for about 24 hrs. The precipitated crystals were separated, dried under vacuum to yield about 28 g first crystals. HPLC assay show the first crystals contain (on dry anhydrous basis) 3.8% rebaudioside A, 1.0% rebaudioside B, 79.1% DAQ3, 16.1% iso-Reb B and traces of other glycosides.

Example 4

[0076] Preparation of Stevia Sweetener

[0077] 50 g of first crystals prepared according to EXAMPLE 1 were dissolved in ultrapure water to make 2,500 mL solution. The pH was adjusted by NaOH to pH 10 and the solution was agitated at room temperature for about 24 hrs. The precipitated crystals were dried under vacuum to yield about 35 g second crystals. HPLC assay show the second crystals contain (on dry anhydrous basis) 2.1% rebaudioside A, 0.3% rebaudioside B, 95.1% DAQ3, 2.5% iso-Reb B and traces of other glycosides. The procedure was repeated to produce about 27 g third crystals which contain (on dry anhydrous basis) 0.1% rebaudioside A, 0.2% rebaudioside B, 99.3% DAQ3, 0.5% iso-Reb B and traces of other glycosides.

Example 5

[0078] Preparation of Stevia Sweetener

[0079] 80 g of stevioside produced by PureCircle Sdn. Bhd. (Malaysia), containing, 98.4% stevioside, 0.5% rebaudioside A, 0.3% rebaudioside C, 0.7% steviolbioside, and 0.1% iso-stevioside, was dissolved in 50%:50% (vol./vol.) blend of absolute ethanol and ultrapure water to make 4,000 mL solution. The solution was fed to a 250 mL jacketed column packed with protonated cation exchange resin (Amberlite IR120, Rohm and Haas USA). The column temperature was maintained at 50 C. After 24 hrs the solution was assayed by HPLC. The solution contained (on dry anhydrous basis) 25.1% stevioside, 10.5% steviolbioside, 46.6% iso-stevioside, 17.8% iso-steviolbioside and traces of other glycosides. The solution was evaporated to remove ethanol and the remaining aqueous solution (pH 5) was diluted with water to about 2% total solids content. The pH was adjusted by NaOH to pH 10 and the solution was agitated at room temperature for about 24 hrs. The precipitated crystals were separated, dried under vacuum to yield about 29 g crystals. HPLC assay show the crystals contain (on dry anhydrous basis) 2.7% stevioside, 1.0% steviolbioside, 83.1% iso-stevioside, 13.2% iso-steviolbioside and traces of other glycosides. These crystals were dissolved in ultrapure water to make 5% solution. The pH was adjusted by NaOH to pH 10 and the solution was agitated at room temperature for about 24 hrs. The precipitated crystals were dried under vacuum to yield about 20 g crystals. The procedure was repeated to produce about 18 g crystals which contain (on dry anhydrous basis) 0.1% stevioside, 0.4% steviolbioside, 99.0% iso-stevioside, 0.5% iso-steviolbioside and traces of other glycosides.

Example 6

[0080] Zero-Calorie Carbonated Beverage

[0081] Carbonated beverages according to formula presented in Table 1 below were prepared.

TABLE-US-00001 TABLE 1 Formula for carbonated beverages Quantity, % Ingredients Stevia Extract Reb A EXAMPLE 4 Cola flavor 0.340 0.340 0.340 ortho-Phosphoric acid 0.100 0.100 0.100 Sodium citrate 0.310 0.310 0.310 Sodium benzoate 0.018 0.018 0.018 Citric acid 0.018 0.018 0.018 Stevia composition 0.050 0.050 0.050 Carbonated water to 100 to 100 to 100

[0082] The sensory properties were evaluated by 20 panelists. The results are summarized in Table 2.

TABLE-US-00002 TABLE 2 Evaluation of zero-calorie carbonated beverage samples Number of panelists detected the attribute Stevia Extract Reb A EXAMPLE 4 Taste attribute Bitter taste 15 12 0 Astringent taste 16 10 1 Aftertaste 17 11 2 Comments Quality of sweet taste Bitter aftertaste Bitter aftertaste Clean (14 of 20) (10 of 20) (18 of 20) Overall evaluation Satisfactory Satisfactory Satisfactory (0 of 20) (6 of 20) (18 of 20)

[0083] The above results showed that the beverages prepared using the composition obtained according to EXAMPLE 4 possessed the best organoleptic characteristics.

[0084] It is to be understood that the foregoing descriptions and specific embodiments shown herein are merely illustrative of the best mode of the invention and the principles thereof, and that modifications and additions may be easily made by those skilled in the art without departing for the spirit and scope of the invention, which is therefore understood to be limited only by the scope of the appended claims.