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Synthesis method for allicin derivative

A synthesis method and a technology of derivatives, which are applied in the field of synthesis of allicin derivatives, can solve the problems of being unsuitable for industrial production, harsh conditions, and cumbersome steps, and achieve clean and environmentally friendly reaction yields, mild reaction conditions, and high reaction yields. high effect

Active Publication Date: 2014-11-05
上海莱慎生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is a series of problems (J.Am.Chem.Soc., 1949,71 , 3565~3566 and J.Am.Chem.Soc., 1997, 119, 9309~9310 and J.Org.Chem., 1978, 43(13), 2728~2730), are not suitable for industrial production, so that affect the Widespread application of quasi-derivatives

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: Methyl methyl thiosulfinate preparation of

[0019] Dimethyl disulfide (20g) and L-proline (2g) were dissolved in acetonitrile (10ml), and hydrogen peroxide (30%, 40g) was added dropwise thereto at 0°C; stirred, and the temperature was naturally raised to 25°C, After the reaction is complete, remove acetonitrile under reduced pressure at 20°C; add dichloromethane to extract and separate layers, collect the organic layer, wash with saturated brine, and dry with anhydrous sodium sulfate; concentrate under reduced pressure at 20°C to remove the solvent , the obtained light yellow oily product is 18.7 g of methyl methyl thiosulfinate, the molar yield is 80%, and the HPLC purity is >90%.

Embodiment 2

[0020] Embodiment 2: methyl methyl thiosulfonate preparation of

[0021] Dimethyl disulfide (40g) and L-proline (4g) were dissolved in methyl tetrahydrofuran (10ml), and hydrogen peroxide (30%, 150g) was added dropwise thereto at 10°C; stirred and naturally warmed to 30 ℃, after the reaction is complete, remove methyl tetrahydrofuran under reduced pressure at 20°C; add dichloromethane to extract and separate layers, collect the organic layer, wash with saturated brine, and dry with anhydrous sodium sulfate; reduce pressure at 20°C Concentrate and remove the solvent to obtain a light yellow oily product, 46 g of methyl methyl thiosulfonate, with a molar yield of 85% and an HPLC purity of >90%.

Embodiment 3

[0022] Embodiment 3: Ethyl ethyl thiosulfinate preparation of

[0023] Diethyl disulfide (100g) and L-proline (5g) were dissolved in 1,2-dichloroethane (40ml), and hydrogen peroxide (30%, 160g) was added dropwise thereto at 10°C; stirred , raised the temperature to 40°C, after the reaction was complete, added dichloromethane to extract and separate the layers, collected the organic layer, washed with saturated brine, and dried with anhydrous sodium sulfate; concentrated under reduced pressure at 20°C, and removed the solvent to obtain The light yellow oily product was 90 g of ethyl thiosulfinate, the molar yield was 80%, and the HPLC purity was >90%.

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Abstract

The invention discloses a synthesis method for an allicin derivative. The allicin derivative has the structural general formula as the specification. The synthesis method comprises the following step of enabling R1-S-S-R2 as a raw material to react with hydrogen peroxide in a solvent by taking proline as a catalyst, wherein R1 and R2 are same or different and are C1-C4 alkanes or C2-C4 alkylenes. The synthesis method disclosed by the invention has the advantages of mild reaction condition, simplicity and convenience in operation, higher reaction yield, cleanness, environment friendliness and the like, meets the requirement of industrial production, and provides feasibility for wide popularization and application of the allicin derivative.

Description

technical field [0001] The invention relates to a synthesis method of allicin derivatives, belonging to the technical field of organic synthesis. Background technique [0002] Garlic (Alliiridum) is a traditional Chinese food and medicine plant. Allicin is an active ingredient extracted and isolated from garlic bulbs. The structural formula is CH 2 =CH-CH 2 -S-S-S-CH 2 -CH=CH 2 , the chemical name is diallyl trisulfide. Scientific research results show that allicin has various medical and health care functions, and it has different degrees of inhibition and killing effects on various bacteria, viruses, fungi and other pathogenic microorganisms and tumors. In addition, it also has blood pressure lowering, It has pharmacological activities such as lowering blood fat, lowering blood sugar, improving immunity and anti-oxidation. At present, allicin is mainly used clinically as an antibacterial drug, and has the reputation of a natural broad-spectrum antibiotic, which is sui...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/04C07C381/00
Inventor 姜标张琛李金华陈思远
Owner 上海莱慎生物科技股份有限公司