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Method for synthesizing trans-resveratrol by combining hydroxyl groups and protective groups

A hydroxyl protecting group and resveratrol technology, which is applied in chemical instruments and methods, preparation of organic compounds, bulk chemical production, etc., can solve the disadvantages of resveratrol, reduce reaction temperature and reduce product cost , The effect of increasing the yield

Inactive Publication Date: 2011-06-01
HUBEI UNIV FOR NATITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the protecting group of the hydroxyl group at the 4′ position is still difficult to completely remove when the temperature rises to 160°C for 6 hours, which is very unfavorable to the thermally unstable compound resveratrol.

Method used

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  • Method for synthesizing trans-resveratrol by combining hydroxyl groups and protective groups

Examples

Experimental program
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Effect test

Embodiment 1

[0016] 3.5 grams of p-hydroxybenzaldehyde was dissolved in 100 milliliters of acetone, and 7.4 grams of potassium carbonate and 6.4 grams of benzyl bromide were added. After mixing, react at 50° C. for 24 hours under the protection of argon. After cooling to room temperature, it was filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate of the same volume as the reaction system, washed with an equal volume of 1M hydrochloric acid, then washed with an equal volume of saturated brine, dried over anhydrous sodium sulfate or anhydrous magnesium sulfate, filtered, and concentrated to dryness to obtain the intermediate 7.9 grams of p-benzyloxybenzaldehyde (containing impurities such as benzyl bromide).

[0017] 7.9 g of p-benzyloxybenzaldehyde containing benzyl bromide and other impurities, dissolved in 120 ml of methanol, slowly added 1.3 g of NaBH at 0-5 °C 4 , After 1.5 hours of reaction, the reaction was terminated with acetic acid. Methanol was recove...

Embodiment 2

[0021] 30.2 grams of p-hydroxybenzaldehyde was dissolved in 800 milliliters of acetone, and 64 grams of potassium carbonate and 46 grams of benzyl bromide were added. After mixing, react at 50° C. for 12 hours under the protection of argon. After cooling to room temperature, it was filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate of the same volume as the reaction system, washed with an equal volume of 1M hydrochloric acid, then washed with an equal volume of saturated brine, dried over anhydrous sodium sulfate or anhydrous magnesium sulfate, filtered, and concentrated to dryness to obtain the intermediate 66.2 grams of p-benzyloxybenzaldehyde (containing impurities such as benzyl bromide).

[0022] 66.2 grams of p-benzyloxybenzaldehyde containing benzyl bromide and other impurities, dissolved in 800 ml of methanol, slowly added 10 grams of NaBH at 0-5 °C 4 , After 2 hours of reaction, the reaction was terminated with acetic acid. Methanol was ...

Embodiment 3

[0026] 3.4 g of 3,5-dimethoxybenzaldehyde, dissolved in 40 ml of methanol, slowly added 0.5 g of NaBH at 0-5°C 4 , After 1.5 hours of reaction, the reaction was terminated with acetic acid. Methanol was recovered, 8 ml of ice water was added, cooled, and 3.2 g of intermediate 3,5-dimethoxybenzyl alcohol was obtained by filtration.

[0027] 3.2 g of 3,5-dimethoxybenzyl alcohol was stirred and dissolved in 40 ml of dichloromethane, protected by argon. The temperature was controlled below 0°C, and 1 ml of phosphorus tribromide was slowly added dropwise (5 ml of dichloromethane was dissolved and then added dropwise). After dropping, keep at 0°C for 1 hour, then cool to room temperature, pour into a container filled with 60 grams of ice, and separate layers after the ice completely melts. The organic layer (lower layer) was separated, and the aqueous layer was extracted twice with dichloromethane. The organic phases were combined, washed with water until neutral, dried over anhy...

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Abstract

The invention relates to a method for synthesizing trans-resveratrol by combining hydroxyl groups and protective groups. The method is characterized in that in the process of synthesizing the trans-resveratrol, the hydroxyl group at a 4' site in the molecular structure is protected by adopting a benzyl group, and hydroxyl groups at 3' and 5' sites in the molecular structure are protected by adopting methyl groups. By adopting the method for synthesizing the trans-resveratrol by combining the hydroxyl groups and the protective groups, the purposes of low cost and easy obtaining of raw materials, easy crystallization and separation of an intermediate product and moderate reaction condition of protective group removal can be achieved. The method has the characteristics of high reaction yield, low cost, simpleness of industrial operation, and the like and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing functional food additive trans-resveratrol. Background technique [0002] Resveratrol (resveratrol) is a non-flavonoid polyphenol substance containing stilbene structure, which is an important phytoalexin and mainly exists in natural plants such as grapes, knotweed, and peanuts. In January 1997, a research team led by Professor John Pezzuto of the School of Pharmacy at the University of Illinois at Chicago published a paper entitled "Anticancer Activity of the Natural Product Resveratrol of Grapes" in the famous American "SCIENCE" magazine. The paper caused a sensation in the medical science community. The paper proves that resveratrol can effectively inhibit cell activities related to various processes of cancer, that is to say, in the three main stages of cancer initiation, promotion and expansion, resveratrol has anti-cancer activity and has anti-ca...

Claims

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Application Information

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IPC IPC(8): C07C39/21C07C37/055
CPCY02P20/55
Inventor 王发松胡卫兵宋新建向家桂邓仕明冯驸
Owner HUBEI UNIV FOR NATITIES
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