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Method for synthesizing acetyl-trans-resveratrol

A technology of acetylated resveratrol and resveratrol, which is applied in the field of synthesizing acetylated resveratrol, can solve the problems of high price of boron tribromide, violent reaction exotherm, inconvenient control, etc., and achieve wide application Foreground, less dosage, and the effect of reducing the generation of impurities

Active Publication Date: 2015-05-13
浙江新赛科药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This technical solution uses boron tribromide as the demethylation reagent, and the exothermic reaction is relatively violent, which is not easy to control and has certain safety risks. At the same time, the price of boron tribromide is high, and the molecular weight is large, and the dosage is large, resulting in an increase in cost.

Method used

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  • Method for synthesizing acetyl-trans-resveratrol
  • Method for synthesizing acetyl-trans-resveratrol
  • Method for synthesizing acetyl-trans-resveratrol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 1) Add 90ml of chlorobenzene into a 500ml dried four-neck flask, add 39.5g of anhydrous aluminum trichloride, after the addition is complete, replace with nitrogen twice, then continue to feed nitrogen, control the temperature at 0-30°C, and slowly drop Add 36g of triethylamine, drop triethylamine to control the temperature at 0-30°C, after dropping, keep warm for 30 minutes, add 16g of anhydrous sodium sulfate and 20g of 3,4',5-trimethoxystilbene, and finish adding, Nitrogen was replaced twice, and then nitrogen was continuously introduced, and the temperature of the reaction solution was raised to 110-115°C, kept warm for 6 hours, and samples were taken. After the reaction was completed, the temperature of the reaction solution was lowered to 30-40°C, and then added to ice water to control the water phase system. After the temperature was ≤30°C, the addition was completed, stirred for 2 hours, filtered, and dried to obtain 16.5 g of resveratrol, with a yield of 98%.

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Embodiment 2

[0072] 1) Add 50ml of chlorobenzene into a 500ml dried four-neck flask, add 43g of anhydrous aluminum trichloride, after the addition is completed, replace with nitrogen twice, then continue to feed nitrogen, control the temperature at 0-30°C, and slowly add 33g triethylamine, drop triethylamine to control the temperature 0-30°C, after dropping, keep warm for 30 minutes, add 21g anhydrous sodium sulfate and 20g 3,4',5-trimethoxystilbene, add nitrogen Replace twice, then continue to feed nitrogen, raise the temperature of the reaction solution to 110-115°C, keep it warm for 6 hours, take a sample, after the reaction is over, cool the reaction solution to 30-40°C, add ice water to control the temperature of the water phase system ≤30°C, the addition was completed, stirred for 2 hours, filtered, and dried to obtain 16.4 g of resveratrol, with a yield of 97%.

[0073] 2) Add 10g of resveratrol, 156ml of ethyl acetate, and 22.5g of acetic anhydride to a 250ml four-neck flask, add 8...

Embodiment 3

[0075] 1) Add 70ml of chlorobenzene into a 500ml dried four-neck flask, add 42g of anhydrous aluminum trichloride, after the addition is completed, replace with nitrogen twice, then continue to feed nitrogen, control the temperature at 0-30°C, and slowly drop 36g triethylamine, drop triethylamine to control the temperature 0-30°C, after dropping, keep warm for 30 minutes, add 18g anhydrous sodium sulfate and 20g 3,4',5-trimethoxystilbene, add nitrogen Replace twice, then continue to feed nitrogen, raise the temperature of the reaction solution to 110-115°C, keep it warm for 6 hours, take a sample, after the reaction is over, cool the reaction solution to 30-40°C, add ice water to control the temperature of the water phase system ≤30°C, the addition was completed, stirred for 2 hours, filtered, and dried to obtain 16.6 g of resveratrol, with a yield of 98%.

[0076] 2) Add 10g of resveratrol, 150.6ml of ethyl acetate, and 27g of acetic anhydride to a 250ml four-neck flask respe...

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Abstract

The invention discloses a method for synthesizing acetyl-trans-resveratrol. The method comprises the following steps: (1) using 3,4',5-trimethoxystilbene as a raw material, and adopting a complex prepared from aluminum trichloride and triethylamine as a demethylation reagentl; under the action of inorganic salt, and carrying out demethylating reaction so as to obtain trans-resveratrol; (2) under the action of triethylamine, carrying out acetylated reaction for the obtained trans-resveratrol and acetic anhydride so as to obtain the acetyl-trans-resveratrol. The method has the advantages of being high in yield, good in product quality, environment-friendly and low in cost, is suitable for industrialization, is simple in preparation, is suitable for industrialized operation, can reduce impurities, improves the product quality, and has a wide application prospect.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing acetylated resveratrol. Background technique [0002] Acetylated resveratrol (English name is Acetyl-trans-resveratrol), chemical name: 3,5,4'-triacetylstilbene, molecular formula: C 20 h 18 o 6 , Molecular weight: 354.24, structural formula as shown in formula I, CAS number: 42206-94-0, appearance: white to off-white powder or crystal. Acetylated resveratrol is a prodrug of resveratrol. Since resveratrol is a polyhydric phenolic compound, it is easy to be oxidized. After protecting the phenolic hydroxyl group with an acetyl group, the properties of the acetylated resveratrol obtained are Very stable, at the same time, acetylated resveratrol acts as a prodrug of resveratrol, which contributes to the extension of resveratrol half-life and the increase of bioavailability. [0003] [0004] In view of the promising application prospect of acetylated...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/18C07C67/08
CPCC07C37/055C07C67/08C07C69/18C07C39/21
Inventor 李洪武杨和军蒋栋郭拥政张喜郭洪巨俞文彬吕士华
Owner 浙江新赛科药业有限公司
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