Simple and effective preparation method for resveratrol

A technology for the protection of resveratrol and phenolic hydroxyl groups, applied in the field of medicine and chemical industry, can solve the problems of only 69% yield, inability to apply hydrogenolysis protection, incomplete reaction, etc., to reduce production costs, reduce corrosive and explosive Low, good purity effect

Inactive Publication Date: 2009-11-25
米启兮 +1
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Problems solved by technology

However, due to the stilbene structure of resveratrol, hydrogen deprotection cannot be applied
In Cushman et al.'s method (J.Med.Chem., 1993,36,2950-2955), aluminum trichloride has to be selected as an alternative method, which causes the reaction to be incomplete, and what is obtained is a partially protected mixture of phenolic hydroxyl groups, which needs to be used column chromatography for separation and purification, the yield only reaches 69%

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  • Simple and effective preparation method for resveratrol

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Embodiment Construction

[0011] The following are detailed implementation methods and results of the present invention. It should be pointed out that these specific reaction reagents and conditions and the operating process are only typical examples, realized by the replacement of the same function (as lithium aluminum hydride is replaced by sodium borohydride, dimethyl sulfate is replaced by bromoethane) Implementation method is still within the protection scope of the patent of the present invention.

[0012] [Form 1] methyl 3,5-dimethoxyhenzoate (2)

[0013] Take 1.54 grams of 3,5-dihydroxybenzoic acid and a small amount of sodium bisulfite and put them into a 50-milliliter three-neck flask equipped with a dropping funnel and a condenser tube with a Bunsen valve, and add them dropwise while stirring in an ice-water bath 30 ml of 8% sodium hydroxide solution. After all the solids are dissolved, add 1.9 ml of dimethyl sulfate dropwise to the bottle, keep the ice-water bath cooling, stir for 20 to 3...

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Abstract

The invention provides a simple and effective preparation method for a natural plant component resveratrol. The characteristic is following: 3,5-dihydric benzoic acid is used as initial material; steps of phenolic hydroxyl group protection, esterification, reduction, bromination, arbuzov reaction are adopted to prepare the key Intermediate 3,5 - dimethoxy-benzyl diethyl, processing the Widischy - Horner reaction with 4-methoxybenzaldehyde (anisaldehyde right) producing 3,4',5-trimethoxy-stilbene, finally removing the methyl protection to obtain the reaction formula resveratrol.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry and relates to a preparation method of natural plant components, in particular to a preparation method of polyphenol antitoxin with stilbene structure. Background technique [0002] Resveratrol (resveratrol), chemical name 3, 4', 5-trihydroxystilbene (3, 4', 5-trihydroxystilbene), is a kind that exists in Polygonum cuspidatum, Veratrum, Cassia, Polygonum multiflorum, Peanut, Natural polyphenolic antitoxins found in mulberries, pine trees, grapes and other plants. In recent years, the beneficial physiological functions of resveratrol, such as anti-tumor, anti-inflammation, anti-platelet aggregation and prevention of coronary heart disease and cardiovascular disease, have received increasing attention. For example, the World Health Organization (WHO)-sponsored survey of cardiovascular diseases in the world shows that compared with other countries in Western Europe, although the French ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/50
Inventor 米启兮曾冬利
Owner 米启兮
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