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Sulforaphane isolation and purification

A technology of sulforaphane and cyclodextrin, which is applied in organic chemistry, active ingredients of esters, active ingredients of nitrile/isonitrile, etc., can solve the problems of difficult manufacture and distribution of sulforaphane, and achieve the effect of simple cost-effectiveness

Active Publication Date: 2015-05-20
FAMAGRA LAB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This makes sulforaphane extraordinarily difficult to manufacture and distribute

Method used

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  • Sulforaphane isolation and purification

Examples

Experimental program
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Effect test

Embodiment 1

[0095] This example relates to an embodiment of the invention demonstrating an improved method for purifying sulforaphane.

[0096] A sample of sulforaphane (production department: Beijing Hunda Qunxing Science and Technology Co.; batch #20091101) (8.23 g, 11.3 mmol of sulforaphane, 24.3% purity) was loaded into a 250 mL round bottom flask equipped with a magnetic stirrer And add 43.9 mL of 0.257M cyclodextrin solution (manufacturer: Wacker; batch #60F212; 11.3 mmol of cyclodextrin). The cyclodextrin solution was prepared by heating 288.9 g of cyclodextrin in 1 L of water at 70°C using ultrasound to give a total volume of 1155 mL after the cyclodextrin was completely dissolved.

[0097] The mixture was stirred at room temperature for one hour, sonicated for 10 minutes, and then stirred for another two hours. A small amount of precipitate formed. Stirring was continued overnight, which caused an increase in the amount of precipitate. The mixture was cooled in a refrigerator at 4°...

Embodiment 2

[0102] This example relates to a further embodiment of the invention demonstrating an improved method for purifying sulforaphane.

[0103] A sample of sulforaphane (production department: Beijing Hunda Qunxing Science and Technology Co.; batch #20091101) (3.2 g, 11.3 mmol of sulforaphane, 62.9% purity) was loaded into a 250 mL round bottom flask equipped with a magnetic stirrer And add 43.9 mL of 0.257M cyclodextrin in water to the flask. The cyclodextrin solution was prepared by heating 288.9 g of cyclodextrin in 1 L of water at 70°C using ultrasound to give a total volume of 1155 mL after the cyclodextrin was completely dissolved.

[0104] The solution was stirred at room temperature for 1 hour, sonicated for 10 minutes, and then stirred for another 2 hours. After the precipitate formed, the mixture was cooled overnight at 4°C in the refrigerator. After more solids precipitated, the mixture was filtered to give 11.9 g (92% yield, 96% HPLC purity) of light yellow solid. HPLC an...

Embodiment 3

[0109] The sulforaphane-cyclodextrin complex (2.2 g, 1.9 mmol) obtained in Example 2 was loaded into a 20 mL scintillation vial and 6 mL of water was added. The mixture is sonicated at about 70°C until the dissolution of the solid particles is complete. The tube was then removed from the ultrasonic bath and kept at room temperature for one hour. Solids began to precipitate out of solution. The tube was moved to a refrigerator at 4°C for 30 minutes and filtered to give an off-white solid, which was dried in a vacuum oven at 30°C overnight. Recrystallization yielded 1.5 g of off-white solid (68% yield, 98% HPLC purity).

[0110] 1 HNMR(D 2 O,400MHz); δ2.01(br,4H),2.78(s,3H),3.01(br,2H), 3.65(m,12H), 3.75(br,2H), 3.91(m,24H), 5.15 (d, 6H).

[0111] 13 CNMR(D 2 O, 100MHz); δ129.98, 101.79, 81.39, 74.01, 71.95, 71.83, 60.31, 52.01, 44.95, 37.04, 29.33, 20.08.

[0112] 13 C NMR analysis and 1 Both H NMR analysis (Figure 8 and Figure 9) are consistent with the 1:1.02 ratio of sulforaph...

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Abstract

The present invention relates to methods of isolating and purifying sulforaphane. More specifically, the present invention relates to methods of isolating and purifying sulforaphane from natural sources. The present invention also relates to methods of forming high purity complexes of sulforaphane with cyclodextrin.

Description

Invention field [0001] The present invention relates to a method for separating and purifying sulforaphane or its analogs. More specifically, the present invention relates to a method for separating and purifying sulforaphane or its analogs from natural sources. The present invention also relates to a method for forming a high-purity complex of sulforaphane or its analogue and cyclodextrin. Background of the invention [0002] It is known that sulforaphane has antimicrobial activity and the ability to inhibit cancer and tumorigenesis. Therefore, sulforaphane is a potentially useful agent for the treatment and prevention of microbial infections and / or cancer. [0003] Sulforaphane is found in cruciferous vegetables, such as cabbage, cauliflower, broccoli sprouts, Brussels sprouts, cauliflower, cauliflower sprouts, cabbage, kale, kale, arugula, Brussels sprouts, mustard, radishes, carrots and Watercress. In plants, it exists as glucoraphanin and glucosinolate in a combined form. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K31/26C07C331/20C08B37/16C08L5/16
CPCC07C331/20C08B37/0015C08L5/16B82Y5/00A61K47/61A61K47/6951A61K31/275A61P31/04A61P35/00
Inventor 萨哈戴瓦·雷迪·达米莱迪卡帕卡珀·安布鲁瓦兹·阿库尔贾瑞德·K·尼尔森阿尔贝托·罗杰·弗里斯比彼得·怀亚特·纽瑟姆
Owner FAMAGRA LAB INC
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