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Method for preparing resveratrol

A technology of resveratrol and methoxyphenyl, applied in the field of preparing resveratrol, can solve the problems of low total yield of trans-resveratrol, high reaction temperature, long reaction time, etc. The effect of shortened time, low reaction temperature, and short reaction time

Inactive Publication Date: 2011-09-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the use of a large amount of copper powder catalyst in this method, it is difficult to operate in a large amount of synthesis, and the reaction time is longer, the reaction temperature is higher, and the product is Z / E The mixture needs to be separated by column chromatography, and the separation is difficult
Therefore the total yield of obtaining trans-resveratrol is not high, less than 30%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment one: ( E )-2-(4-methoxyphenyl)-3-(3,5-dimethoxyphenyl)-acrylic acid preparation

[0023] 3,5-dimethoxybenzaldehyde 8.50g (51.15mmol), 4-methoxyphenylacetic acid 9.35g (56.27mmol), anhydrous K 2 CO 3 3.53g (25.54mmol) was put into a 50mL round bottom flask, 20mL redistilled acetic anhydride was added, and the reaction was refluxed for 2h. After cooling, add water to precipitate a red oily substance, discard the water layer, and add 2mol.L to the oily substance -1 NaOH solution 30mL, refluxed for 1h, filtered. The filtrate was acidified with concentrated hydrochloric acid, and a precipitate was precipitated. After filtration, the filter residue was recrystallized with 80% ethanol to obtain 14.50 g of light yellow solid with a yield of 90.2%. mp: 294-295°C.

Embodiment 2

[0024] Embodiment two: Z - Preparation of 3, 4', 5-trimethoxystilbene

[0025] Will( E )-2-(4-methoxyphenyl)-3-(3,5-dimethoxyphenyl)-acrylic acid 5.00g (15.90mmol), CuBr 0.65g (4.53mmol) and KOH0.89g (15.90 mmol) was added to 50 mL of quinoline, and reacted for 0.5 h at 190°C. After the reaction is complete, dilute with 20mL ethyl acetate, and then use 1mol.L -1Hydrochloric acid, saturated brine washing, anhydrous MgSO 4 dry. The solvent was evaporated to dryness and recrystallized from ethanol-water to obtain 3.49 g of white crystals with a yield of 81.2%. mp: 57-58°C.

Embodiment 3

[0026] Embodiment three: Z - Preparation of 3, 4', 5-trimethoxystilbene

[0027] Will( E )-2-(4-methoxyphenyl)-3-(3,5-dimethoxyphenyl)-acrylic acid 5.00g (15.90mmol), CuBr 0.65g (4.53mmol) and NaOH 0.64g (16.0 mmol) was added to 50 mL of quinoline, and reacted for 0.5 h at 190°C. After the reaction is complete, dilute with 20mL ethyl acetate, and then use 1mol.L -1 Hydrochloric acid, saturated brine washing, anhydrous MgSO 4 dry. The solvent was evaporated to dryness and recrystallized from ethanol-water to obtain 3.47 g of white crystals with a yield of 80.7%. mp: 57-58°C.

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Abstract

The invention discloses a method for preparing resveratrol, which comprises the following steps of: (1) preparing an intermediate (E)-2-(4-methoxyphenyl)-3-(3,5-dimethoxyphenyl)-acrylic acid; (2) performing decarboxylation reaction on the intermediate to prepare Z-3,4',5-trimethoxystilbene; and (3) performing protecting group removal or isomerization on the Z-3,4',5-trimethoxystilbene to prepare E-3,4',5-trihydroxystilbene, namely trans-resveratrol. In the method for preparing the resveratrol, inorganic alkali or organic alkali is added into an organic solvent and copper salt with catalytic amount is taken as a catalyst in the step (2), so compared with a quinoline / Cu powder catalyst in the prior art, the copper salt catalyst ensures that reaction time is greatly shortened, the reaction temperature is obviously reduced and reactants are difficult to carbonize; and the obtained product is single and easy to separate and purify.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing resveratrol. Background technique [0002] Resveratrol (Resveratrol, Res), chemical name E -3,4',5-Trihydroxystilbene, which is widely found in grapes, knotweed, cassia, peanuts and other plants, is a natural polyphenol phytoalexin with many important biological activities, such as reducing blood lipids, Anti-platelet aggregation, anti-oxidation, anti-free radicals, anti-bacteria and anti-inflammation, anti-tumor, anti-osteoporosis, skin whitening and life extension, etc., have received increasing attention due to their various beneficial physiological functions. In 1997, Pezzuto et al. reported in the journal Science that resveratrol can inhibit the three main stages of cancer initiation, proliferation and expansion. At present, more than ten countries and regions in the world are developing resveratrol raw materials and preparations. It is ...

Claims

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Application Information

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IPC IPC(8): C07C39/21C07C37/055
CPCY02P20/55
Inventor 敖桂珍候丙波曹毅杨圣伟冯江江
Owner SUZHOU UNIV
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