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A new crystal form of resveratrol trimethyl ether and its preparation method

A technology for resveratrol trimethyl ether and crystal form, which is applied to the new crystal form of resveratrol trimethyl ether and the field of preparation thereof, can solve the problems of difficult drying, troublesome post-processing, poor stability and the like, and achieves easy drying , the effect of good anti-tumor activity

Active Publication Date: 2015-09-30
GREAT FOREST BIOMEDICAL LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The resveratrol trimethyl ether obtained by the above-mentioned two types of methods reported in the literature is a viscous liquid or a mixture of cis-trans isomerism before obtaining the pure product, and the post-processing is troublesome; the obtained pure product is basically powdery, and the melting point Between 47-57°C, it is not easy to dry, and the stability is poor

Method used

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  • A new crystal form of resveratrol trimethyl ether and its preparation method
  • A new crystal form of resveratrol trimethyl ether and its preparation method
  • A new crystal form of resveratrol trimethyl ether and its preparation method

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Embodiment 1

[0035] Embodiment 1: Preparation of resveratrol trimethyl ether

[0036] Add 40g (0.214mol) of 3,5-dimethoxybenzyl chloride and 54g (0.428mol) of trimethyl phosphite into a 250ml four-necked flask, heat to an oil bath temperature of 140°C, follow the reaction by TLC, and react after about 24 hours Completely, use water pump (oil bath temperature at about 120°C) and Roots pump (oil bath temperature at about 120°C) to recover and remove trimethyl phosphite under reduced pressure to obtain 3,5-dimethoxybenzyl phosphoric acid The remaining reaction liquid of dimethyl ester is about 57g.

[0037] Add 27g of DMSO and 26.9g (0.198mol) of p-methoxybenzaldehyde to the remaining 57g of the reaction solution, cool it to 10°C in a water bath, and start adding KOH after the temperature stabilizes, adding about 2g each time, once every 20 minutes, and adding a total of 19g (0.339mol). Maintain the reaction temperature at 10°C. During the reaction, solids are gradually precipitated. TLC is...

Embodiment 2

[0057] Embodiment 2: Preparation of resveratrol trimethyl ether

[0058] The amount of trimethyl phosphite was changed to 40.5 g (0.321 mol), and the other reaction conditions were the same as in Example 1 to obtain 48 g of resveratrol trimethyl ether with a yield of 83.1%.

Embodiment 3

[0059] Embodiment 3: Preparation of resveratrol trimethyl ether

[0060] The amount of trimethyl phosphite was changed to 108 g (0.857 mol), and the remaining reaction conditions were the same as in Example 1 to obtain 52.2 g of resveratrol trimethyl ether with a yield of 90.3%.

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Abstract

The invention discloses a novel trimethoxystilbene crystal form and a preparation method. According to the invention, 2 theta diffraction angle in X-ray powder diffraction of the crystal form has characteristic peaks at the ranges between 15.1 and 15.5, between 16.5 and 16.9, between 17.0 and 17.4, between 17.5 and 17.7, between 19.8 and 20.0, between 20.0 and 20.2, between 22.2 and 22.6, between 24.2 and 24.6, between 25.4 and 25.8, and between 27.8 and 28.0. The method comprises the following steps: reacting 3,5-dimethoxy benzyl chloride and trimethyl phosphite under heating condition to obtain a residual reaction solution after the reaction is completed; then adding DMSO and p-anisaldehyde, cooling and adding KOH, adding DMF after the reaction is completed, heating to the temperature of 40-60 DEG C, insulating for 0.5-1.5 hours, cooling to 10-15 DEG C and then crystallizing, washing to neutrality by using water, and drying to obtain the product. The melting point of the novel trimethoxystilbene crystal form is high, the novel trimethoxystilbene crystal form has the advantages of easy drying, and has good antineoplastic activity.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis medicine, and relates to a new crystal form of resveratrol trimethyl ether and a preparation method thereof. technical background [0002] Resveratrol trimethyl ether, chemical name trans-3,4',5-trimethoxystilbene, CAS No.: [22255-22-7], molecular formula: C 17 h 18 o 3 , molecular weight: 270.32, structure as shown in the following formula: [0003] [0004] Resveratrol trimethyl ether is a methylated derivative of resveratrol, which has obvious anti-angiogenesis and anti-mitosis effects, can significantly cause microtubule decomposition and tubulin depolymerization, and is used for anti-tumor therapy; Veratrol trimethyl ether has anti-allergic, gastric mucosal damage protection and anti-aging effects; in addition, resveratrol trimethyl ether and resveratrol have similar anti-inflammatory effects, both of which can improve the condition of osteoarthritis, white Veratrol trimethy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/215C07C41/30A61P35/00
CPCC07B2200/13C07C41/30C07C43/215C07F9/4808
Inventor 汪劲松张习坤李小玲胡杨群王克猛陈亮
Owner GREAT FOREST BIOMEDICAL LTD
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