Crystal of (2R,4R)-monatin potassium salt and sweetener composition containing same

• US 20060014819A1
• Filed: 07/14/2005
• Published: 01/19/2006
• Est. Priority Date: 07/14/2004
• Status: Active Grant

• Current Assignee: Ajinomoto Co., Inc.
• Original Assignee: Ajinomoto Co., Inc.
• Inventors: Takemoto, Tadashi, Mori, Ken-ichi, Ono, Eriko
• Granted Patent: US 7,553,974 B2
• Time in Patent Office: Days
• US Class Current: 514/419
• CPC Class Codes: C07D 209/20 substituted additionally by nitrogen atoms, e.g. tryptophane

Abstract

Crystals of (2R,4R)-monatin potassium salt which exhibit an X-ray powder diffraction pattern having characteristic peaks at diffraction angles 2θ of 5.5°, 7.2°, 8.1°, 8.9°, and 16.3°, by powder X-ray diffraction (Cu—Kα radiation), are superior in sweetness, preservation stability, solubility, and color stability.

Claims

1. A crystal of (2R,4R)-monatin potassium salt which exhibits an X-ray powder diffraction pattern having characteristic peaks at diffraction angles 2θ

of 5.5°

, 7.2°

, 8.1°

, 8.9° and

16.3°

, by powder X-ray diffraction using Cu—

Kα

radiation.

2. The crystal of claim 1, which has a molar ratio of potassium to (2R,4R)-monatin within the range of 1.2 to 2.

3. The crystal of claim 1, which has a molar ratio of water to (2R,4R)-monatin within the range of 0.9 to 1.7.

6. A sweetener composition, comprising the crystal of (2R,4R)-monatin potassium salt of claim 1.

7. The sweetener composition of claim 6, wherein said crystal of (2R,4R)-monatin potassium salt has a molar ratio of potassium to (2R,4R)-monatin within the range of 1.2 to 2.

8. The sweetener composition of claim 6, wherein said crystal of (2R,4R)-monatin potassium salt has a molar ratio of water to (2R,4R)-monatin within the range of 0.9 to 1.7.

9. The sweetener composition of claim 6, further comprising at least one ingredient selected from the group consisting of a carrier, extender, additive, flavoring and mixtures thereof.

10. The sweetener composition of claim 6, further comprising at least one ingredient selected from the group consisting of sucrose, invert sugar, isomerized sugar, glucose, fructose, lactose, maltose, trehalose, xylose, multitol, sorbitol, mannitol, erythritol, xylitol, lactitol, oligosaccharides, dietary fiber, aspartame, saccharin, acesulfame K, sucralose, and mixtures thereof.

4. A crystal of (2R,4R)-monatin potassium salt having a molar ratio of potassium to (2R,4R)-monatin within the range of 1.2 to 2.

5. The crystal of claim 4, which has a molar ratio of water to (2R,4R)-monatin within the range of 0.9 to 1.7.

11. A sweetener composition comprising the crystal of (2R,4R)-monatin potassium salt of claim 4.

12. The sweetener composition of claim 11, wherein said crystal of (2R,4R)-monatin potassium salt has a molar ratio of water to (2R,4R)-monatin within the range of 0.9 to 1.7.

13. The sweetener composition of claim 12, further comprising at least one ingredient selected from the group consisting of a carrier, extender, additive, flavoring and mixtures thereof.

14. The sweetener composition of claim 12, further comprising at least one ingredient selected from the group consisting of sucrose, invert sugar, isomerized sugar, glucose, fructose, lactose, maltose, trehalose, xylose, multitol, sorbitol, mannitol, erythritol, xylitol, lactitol, oligosaccharides, dietary fiber, aspartame, saccharin, acesulfame K, sucralose, and mixtures thereof.

15. A method of preparing crystals of the (2R,4R)-monatin potassium salt, comprising:

(a) dispersing crystals of (2R,4R)-monatin monopotassium salt in a solvent, preferably in ethanol or aqueous ethanol solution, to obtain a suspension;

(b) adding an aqueous ethanol solution containing a potassium compound, preferably potassium hydroxide, to said suspension to dissolve said crystals and obtain a solution; and

(c) cooling said solution to obtain said crystals of the (2R,4R)-monatin monopotassium salt.

16. The method of claim 15, wherein the volume ratio of ethanol/water in said solution is not less than 20/1.

17. The method of claim 15, wherein said crystals of the (2R,4R)-monatin potassium salt exhibit an X-ray powder diffraction pattern having characteristic peaks at diffraction angles 2θ

of 5.5°

, 7.2°

, 8.1°

, 8.9° and

16.3°

, by powder X-ray diffraction using Cu—

Kα

radiation.

18. The method of claim 15, wherein said crystals of (2R,4R)-monatin monopotassium salt have a molar ratio of potassium to (2R,4R)-monatin within the range of 1.2 to 2.

19. The method of claim 15, wherein said crystals of (2R,4R)-monatin monopotassium salt have a molar ratio of water to (2R,4R)-monatin within the range of 0.9 to 1.7.