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Synthesis method of piceatannol

A technology of picatanol and synthetic methods, applied in organic chemical methods, skin care preparations, chemical instruments and methods, etc., can solve the problems of biological extraction that is difficult to meet market demand, target product structure is not single, and chemical synthesis operations are complex, etc. problems, to achieve high trans stereoselectivity, good development prospects, and high yield effects

Active Publication Date: 2018-10-19
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to overcome the existing methods of obtaining picatanol, biological extraction is difficult to meet the market demand, the cost is high, the environment is not friendly and the yield is very low, the chemical synthesis operation is complicated, the post-processing is difficult, and the structure of the target product is not single shortcoming

Method used

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  • Synthesis method of piceatannol
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Examples

Experimental program
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Effect test

Embodiment 1

[0026] (1) Synthesis of 3-hydroxy-4-methoxystyrene

[0027] Add 3-hydroxyl-4-methoxybenzaldehyde (2.0g, 13.14mmol) in 100mL round bottom flask, then add 50mL THF to dissolve it, then add potassium tert-butoxide (4.4g, 39.21mmol), finally Add methyltriphenylphosphine bromide (12.7 g, 35.55 mmol) and heat at 70° C. (Celsius). After 7 hours, TLC detects that the reaction is complete. Cool to room temperature, add 50mL of water, extract with ethyl acetate (50mL×3), combine the organic phases, wash with saturated brine (100mL×3), and finally dry with anhydrous sodium sulfate, spin dry to obtain 2.6g of yellow oil, Purified by column chromatography (ethyl acetate:petroleum ether=1:30, 1 L) to obtain 1.2 g of 3-hydroxy-4-methoxystyrene as a white solid, with a yield of 60.91%. 1 H NMR (300MHz, CDCl 3 )δ: 3.77 (s, 3H), 5.08 (d, J = 12.0Hz, 1H), 5.66 (d, J = 18.0Hz, 1H), 6.68 (dd, J = 18.0and12.0Hz, 1H), 6.88 ( m,3H), 9.00(s,1H).

[0028] (2) Synthesis of E-3-hydroxy-3',4,5'-trimet...

Embodiment 2

[0033]In step (1), the molar ratio of 3-hydroxyl-4-methoxybenzaldehyde, potassium tert-butoxide and methyltriphenylphosphine bromide is: 1:2.5:2.5, reaction temperature: 75°C, reaction time: 6h.

[0034] In step (2), 3-hydroxyl-4-methoxystyrene, 3,5-dimethoxybromobenzene, salt of wormwood, tetrabutylammonium bromide, the mol ratio of palladium acetate and triphenylphosphine are: 1:1.2:2.0:0.08:0.06:0.08, the reaction temperature is: 110°C, and the reaction time is 6.5h.

[0035] In step (3), the molar ratio of pyridine hydrochloride to E-3-hydroxy-3',4,5'-trimethoxystilbene is 60:1, the reaction temperature is 200°C, and the reaction time is: 1.5h.

Embodiment 3

[0037] In step (1), the molar ratio of 3-hydroxyl-4-methoxybenzaldehyde, potassium tert-butoxide and methyltriphenylphosphine bromide is: 1:3.5:3.5, reaction temperature: 80°C, reaction time: 8h.

[0038] In step (2), 3-hydroxyl-4-methoxystyrene, 3,5-dimethoxybromobenzene, salt of wormwood, tetrabutylammonium bromide, the mol ratio of palladium acetate and triphenylphosphine are: 1:1.5:2.2:0.12:0.08:0.1, the reaction temperature is: 130°C, and the reaction time is 9h.

[0039] In step (3), the molar ratio of pyridine hydrochloride to E-3-hydroxy-3',4,5'-trimethoxystilbene is 80:1, the reaction temperature is 260°C, and the reaction time is: 0.5h.

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Abstract

The invention provides piceatannol. A target product piceatannol is prepared through the steps of taking 3-hydroxyl-4-methoxybenzaldehyde as a starting raw material, carrying out wittig reaction to generate 3-hydroxyl-4-methoxystyrene, carrying out Heck reaction on the 3-hydroxyl-4-methoxystyrene and 3,5-dimethoxybromobenzene to obtain E-3-hydroxyl-3',4,5'-trimethoxystilbene and carrying out demethylation on the E-3-hydroxyl-3',4,5'-trimethoxystilbene. The Heck reaction is used as construction of a stilbene parent nucleus and the target product with a single configuration can be obtained; initial raw materials are cheap and easy to obtain, the operation is simple, conditions are moderate and the yield is relatively high.

Description

technical field [0001] The invention belongs to the field of synthesis, in particular to a synthesis method of picatanol. Background technique [0002] Picetanol is a natural extract of stilbenes, and it is a 3-hydroxylation analogue of resveratrol. It is found in grapes, blueberries, passion fruit, sugar cane and other plants. Pharmacological studies have shown that picatanol has many pharmacological activities, such as anti-cancer, anti-cell proliferation, anti-inflammation, immune regulation, anti-lipid oxidation, antibacterial and other pharmacological activities. Studies have shown that picatanol is also a good antioxidant and cardiovascular protective agent. With the continuous deepening of development, piceatanl has been widely used and recognized in the fields of health care products, cosmetics and pharmaceuticals. [0003] At present, picatanol mainly comes from plant extraction. This method is costly, unfriendly to the environment and the yield is very low. The...

Claims

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Application Information

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IPC IPC(8): C07C37/055C07C39/21A61K31/05A61P35/00A61P29/00A61P37/02A61P31/00A23L33/105A61K8/34A61Q19/08A61P39/06A61P9/00
CPCA23L33/105A23V2002/00A61K8/347A61K31/05A61P9/00A61P29/00A61P31/00A61P35/00A61P37/02A61P39/06A61Q19/08C07B2200/09C07C37/055C07C41/30C07C39/21C07C43/23A23V2250/21A23V2200/30
Inventor 任杰闫雪龙胡昆
Owner CHANGZHOU UNIV
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