Process of preparing trans-polyhydroxy diphenyl ethylene

A technology of polyhydroxy stilbene and stilbene, which is applied in the chemical industry, can solve the problems of complex steps and high cost, and achieve the effects of low reaction cost, mild reaction conditions and high yield

Inactive Publication Date: 2007-11-07
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the cost of this preparation method is relatively high, and the steps are more complicated, and it is necessary to carry out the isomerization of cis-to-trans-stilbene separately

Method used

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  • Process of preparing trans-polyhydroxy diphenyl ethylene
  • Process of preparing trans-polyhydroxy diphenyl ethylene
  • Process of preparing trans-polyhydroxy diphenyl ethylene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 15.22g (0.0373mol) of All 3 and 75ml of acetonitrile, then slowly dropwise added 2.70g (0.01mol) of (Z)-3,4',5-trimethoxystilbene dissolved in 5ml of acetonitrile, stirred and refluxed at 82°C for 3h, cooled, and the reaction The solution was concentrated to dryness, and a yellow-brown solid was produced, and an appropriate amount of water was added, and a light-yellow solid was obtained by suction filtration, and then recrystallized with ethanol / water to obtain 1.91 g of white needle-like crystals, namely (E)-3,4′,5- Trihydroxystilbene (resveratrol), the yield is 83.8%. The test data are as follows: Mp: 255-260°C. MS m / z (%): 228 (M + ). 1 H-NMR (CDCl 3 ): 6.27 (t, 1H, J = 2.2Hz), 6.54 (d, 2H, J = 2.4Hz), 6.96 (d, 2H, J = 16.4), 7.10 (d, 4H, J = 8.8Hz), 8.22 (s, 2H, 2 x OH), 8.50 (s, 1H, OH).

Embodiment 2

[0034] Add 15.22g (0.0373mol) of All 3 and 75ml of acetonitrile, then slowly dropwise added 2.70g (0.01mol) of (Z)-3,4',5-trimethoxystilbene dissolved in 5ml of acetonitrile, stirred at 65°C for 2h, cooled, and the reaction solution Concentrate to dryness, a yellow-brown solid is produced, add an appropriate amount of water, and filter with suction to obtain a light-yellow solid, and then recrystallize with ethanol / water to obtain 1.42 g of white needle-like crystals, namely (E)-3,4′,5-tri Hydroxystilbene (resveratrol), the yield is 62.3%.

Embodiment 3

[0036] Add 15.22g (0.0373mol) of All 3 and 75ml of acetonitrile, then slowly dropwise added 2.70g (0.01mol) of (Z)-3,4',5-trimethoxystilbene dissolved in 5ml of acetonitrile, stirred and refluxed at 90°C for 5h, cooled, and the reaction solution was Concentrate to dryness, a yellow-brown solid is produced, add an appropriate amount of water, and filter with suction to obtain a light-yellow solid, and then recrystallize with ethanol / water to obtain 1.71 g of white needle-like crystals, namely (E)-3,4′,5-tri Hydroxystilbene (resveratrol), the yield is 75%.

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Abstract

The present invention discloses process of preparing trans-polyhydroxy diphenyl ethylene. In solvent and at 50-100 deg.c, cis-polymethoxyl substituted diphenyl ethylene under the action of demethylating reagent produces demethylating and isomerizing reaction, and through subsequent cooling, suction filtering, concentrating, re-crystallization, trans-polyhydroxy diphenyl ethylene is prepared. The preparation process of the present invention has simple operation, low reaction cost, high yield and excellent industrial application foreground.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of trans polyhydroxy stilbene. Background technique [0002] Multi-substituted stilbene natural products have broad application prospects as pharmaceutical products because of their extensive and beneficial biological activities and important scientific research value. Many stilbene natural products and derivatives containing hydroxyl, methoxy or amino substitution have anti-platelet aggregation, lowering blood fat, lowering blood sugar, antibacterial and anti-inflammatory, preventing tissue cancer and tumor occurrence, and anti-vascular effects. The most representative ones are resveratrol, CA4, pterostylbene, AVE-8062, etc. The research on these compounds has become a hot spot and frontier field of scientific research. (E)-3,4 ', 5-trihydroxystilbene (resveratrol), its structure is as shown in formula (1): [0003] [0004] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/055
Inventor 邹永李国兴张学景魏文林慧贞
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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