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Synthesis method for high-purity gastrodin

A synthesis method and technology for gastrodin are applied in the field of synthesis of high-purity gastrodin, can solve problems such as acetyl group cannot be completely removed, and achieve the effects of less by-products, high yield and simple operation

Inactive Publication Date: 2020-11-24
TOPFOND PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The chemical name of the gastrodin series is 4-hydroxymethyl-β-D-glucopyranoside, and its preparation methods mainly include direct hydrolysis after reduction of tetraacetylglucopyranose, and transesterification of pentaacetylgastroside with sodium methoxide. The former will require repeated recrystallization to remove inorganic impurities, while the latter cannot completely remove the acetyl group due to the existence of the by-product methyl acetate

Method used

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  • Synthesis method for high-purity gastrodin
  • Synthesis method for high-purity gastrodin
  • Synthesis method for high-purity gastrodin

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Embodiment 1

[0023] A synthetic method of high-purity gastrodin, the process is as follows:

[0024] Add 20g of pentaacetylgastroside, 1g of strongly acidic cation exchange resin (001×7), and 60g of methanol into the reactor, stir at room temperature for 0.5h, heat up to 64-65°C and reflux for 3h, filter, and concentrate the filtrate under reduced pressure, then Add 80g of methanol and 5g of sodium methoxide methanol solution (the concentration of sodium methoxide is 0.2mol / L), reflux at 64-65°C for 0.5h, add 90g of chloroform, heat to reflux (64-65°C) and filter while hot, and cool the filtrate to 0-5°C, filter, use 40g of mixed solvent of methanol and acetone (first mix methanol and acetone according to V / V=1:30 and then weigh, the same below) to recrystallize to obtain 11.6g of product, weight yield: 58%, the purity of gastrodin was tested by HPLC, by figure 1 It can be seen that its purity is 99.98%.

Embodiment 2

[0026] A synthetic method of high-purity gastrodin, the process is as follows:

[0027] Add 20g of pentaacetylgastroside, 1.5g of macroporous strongly acidic cation exchange resin (D001), and 60g of methanol into the reactor, first stir at room temperature for 0.5h, heat up to 64-65°C and reflux for 5h, filter, and concentrate the filtrate under reduced pressure. Then add 80g of methanol and 3g of sodium methoxide methanol solution (the concentration of sodium methoxide is 0.2mol / L), reflux at 64-65°C for 0.5h, add 75g of chloroform, heat to reflux (64-65°C) and filter while it is hot, and cool the filtrate to 0-5°C, filter, use 30g of methanol and acetone mixed solvent (V / V=1:30) to recrystallize to obtain 11.2 g of product, weight yield: 56%, test the purity of gastrodin by HPLC, by figure 2 It can be seen that its purity is 99.81%.

Embodiment 3

[0029] A synthetic method of high-purity gastrodin, the process is as follows:

[0030] Add 20g of pentaacetyl gastroside, 1.0g of macroporous strong acidic cation exchange resin (D001) and 0.2g of strong acidic cation exchange resin (001×7) mixture, 60g of methanol into the reactor, first stir at room temperature for 0.5h, and heat up to 64 Reflux at -65°C for 4h, filter, and concentrate the filtrate under reduced pressure, then add 80g of methanol and 6g of sodium methoxide methanol solution (the concentration of sodium methoxide is 0.2mol / L), reflux at 64-65°C for 0.5h, add 60g of chloroform, and heat to 64 After reflux at -65°C, filter while hot, cool the filtrate to 0-5°C, filter, and use 45g of methanol and acetone mixed solvent (V / V=1:30) to recrystallize to obtain 11.3 g of the product, weight yield: 56.5%, The purity of gastrodin was tested by HPLC, by image 3 It can be seen that its purity is 99.96%.

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Abstract

The invention discloses a synthesis method for high-purity gastrodin. The synthesis method comprises the following steps: adding penta-acetyl gastrodin, acid resin and methanol into a reactor; firstlyperforming stirring at room temperature for 15 min-1h; performing heating to reflux and performing stirring for 3-5h; performing filtering; performing decompression concentration on filtrate; subsequently, adding a methanol solution of sodium methylate for refluxing and performing stirring for 15 min-1h; adding chloroform; performing hot filtering after refluxing, cooling filtrate, and performingfiltering, and recrystallization to obtain the high-purity gastrodin. According to the synthesis method for the high-purity gastrodin provided by the invention, firstly most of the acetyl is removedwith the acid resin, and then transesterification is conducted; and the synthesis method has the advantages of few by-products, simple operation, high repeatability, high yield and the like.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a method for synthesizing high-purity gastrodin. Background technique [0002] Gastrodin is a natural compound and the core active ingredient of Gastrodia elata. Gastrodin has various physiological activities such as sedative, hypnotic, and anticonvulsant, and is mainly used clinically to treat dizziness, headache, deafness, tinnitus, and neurasthenia. In the late 1970s, Zhou Jun and others isolated a new compound from the traditional Chinese medicine Gastrodia elata, which was identified as 4-hydroxymethylphenyl-β-D-glucopyranoside. Pharmacological studies showed that this compound has sedative properties. , Hypnotic effect, considered to be the active ingredient of the traditional Chinese medicine Gastrodia elata, named gastrodin. In 1980, Zhou Jun and others completed the chemical synthesis of gastrodin, and after the continuous research and improvement of the synthesis method ...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H15/203
Inventor 杨明王俊臣樊振张宏周徐文斌李青丽赵臻钱丹苏济功年蓓蕾张玉斌刘继方
Owner TOPFOND PHARMA CO LTD