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Novel polymorphs of rebaudioside C and methods for making and using the same

A technology of rebaudioside and baudioside, which is applied in the field of new polymorphs of rebaudioside C and its preparation and use, and can solve the problems of a large number of reaction steps, purification steps, etc.

Inactive Publication Date: 2012-07-18
REDPOINT BIO CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Previously reported attempts to manufacture and purify rebaudioside C required extensive reaction steps or repeated purification steps

Method used

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  • Novel polymorphs of rebaudioside C and methods for making and using the same
  • Novel polymorphs of rebaudioside C and methods for making and using the same
  • Novel polymorphs of rebaudioside C and methods for making and using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0140] Reb C (93.3% HPLC purity; ) were placed in each well of a polypropylene 96-well V-bottom plate: well A1, 5.8 mg; well D1, 5.5 mg; well G1, 5.4 mg. Add absolute ethanol (~300 μL 75% of pore volume) to A1, anhydrous methanol (75% of pore volume) to D1, and isopropanol (50% of pore volume) to G1 followed by anhydrous Water methanol (25% of pore volume). The plate was gently agitated until the material in the three wells was completely dissolved. The plates were left uncovered and the solvent was evaporated overnight at room temperature. This produced a glassy, ​​non-crystalline material in all three pores. The material in each well was dissolved again using the same method as above. The 96-well V-bottom plate containing the dissolved Reb C samples was covered with a second blank plate to slow down the evaporation rate and left overnight at room temperature. A colorless / white crystalline solid was obtained in each well. This material was transferred to vials labeled ...

Embodiment 2

[0143] Crude Stevia extract solids or crude Reb C solids (5 g), ethanol (95%, 12.5 mL), methanol (6 mL) and water (2 mL) were combined and heated to reflux for 10 minutes. The clear solution was cooled to 22 °C. The solution was seeded with 10 mg of 93-98% pure Form I Reb C crystals and the mixture was left at 22°C for 16 hours. The resulting white crystalline product was filtered, washed twice with ethanol-methanol (5 mL, 4:1, v / v) mixture and dried in a vacuum oven at 50 °C under reduced pressure (20 mm) for 16-24 hours to obtain The purified Reb C product was obtained. The purity of the Reb C product produced was evaluated by HPLC.

Embodiment 3

[0145] Crude Stevia extract solids or crude Reb C solids (5 g), propanol (95%, 12.5 mL) and methanol (7.5 mL) were combined and heated to reflux for 10 minutes. The clear solution was cooled to 22 °C. The solution was seeded with 10 mg of 93-98% pure Form I Reb C and the mixture was left at 22°C for 16 hours. The resulting white crystalline product was filtered, washed twice with ethanol-methanol (5 mL, 4:1, v / v) mixture and dried in a vacuum oven at 50 °C under reduced pressure (20 mm) for 16-24 hours to obtain The purified Reb C product was obtained. The purity of the Reb C product produced was evaluated by HPLC.

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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.

Description

[0001] introduction [0002] This application claims priority to US Provisional Application No. 61 / 244,803, filed September 22, 2009, the contents of which are hereby incorporated by reference in their entirety. Background of the invention [0003] The sweet diterpene glycosides of Stevia have been characterized and eight sweet glycosides of steviol have been identified. These glycosides accumulate in Stevia leaves where they can reach 10-20% of the leaf weight. A typical profile of the four major glycosides found in Stevia leaves includes 0.3% dulcoside, 0.6% rebaudioside C, 3.8% rebaudioside A on a dry weight basis and 9.1% stevioside. Other glycosides identified in stevia include rebaudiosides B, D, and E; and dulcosides A and B. Of the four major diterpene glycoside sweeteners present in Stevia leaves, only two (stevioside and rebaudioside A) have well-characterized physical and sensory properties. It is known that stevioside is 110-270 times sweeter than sucrose, reba...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A23L1/236C07H1/08A23L27/30
CPCC07H15/24A23V2002/00A23L1/2366A23L27/36A61K8/602A61Q19/00A61K2800/10A61Q11/00A61P3/02A23V2250/258A61K8/60A61K47/26
Inventor F·雷蒙德·塞尔弥罗伯特·A·戴尼斯
Owner REDPOINT BIO CORP
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