Preparation method of 3š�-succinyl-18-disodium salt dehydro ursolic acid

A technology of ursolic acid disodium salt and succinyl, which is applied in the field of preparation of 3β-succinyl-18-dehydroursolic acid disodium salt, can solve the problems such as undescribed preparation methods, and achieve low production cost and high product quality. The effect of convenient separation and purification and simple synthesis process

Inactive Publication Date: 2003-10-08
GUANGZHOU HANFANG PHARMA
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  • Summary
  • Abstract
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AI Technical Summary

Problems solved by technology

[0004] At present, there is no report on the method of preparing 3β-succinyl-18-dehydroursolic acid disodium salt from 18-dehydroursolic acid, only mentioned in Guangdong Pharmacy 2001, Volume 11, Issue 1, Pages 4-6 Pentacyclic triterpenoids obtained by extracting and purifying 18-dehydroursolic acid (18-dehydroursolic acid) from holly root through succinylation, its structure is 3β-succinyl-18-dehydroursolic acid Disodium salt, but no description of its preparation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Take 100 kilograms of the roots / stems of holly and cut them into small pieces, place them in an extraction pot, and use 400 liters of 95% ethanol to heat reflux each time, extract 3 times in total, combine the filtrates, concentrate to 250 liters, add 10 3 liters of concentrated sulfuric acid was refluxed for hydrolysis for 3 hours, filtered after cooling, and the solid was washed with water until neutral and nearly white to obtain a crude product. The crude product was recrystallized with ethanol and activated carbon to obtain 206 g of white 18-dehydroursolic acid with a content of 97% and a melting point of 287-289 ° C. The 18-dehydro-ursolic acid was put into a three-necked flask, and pyridine was added. 1000ml, heated at 95℃ to dissolve, add 120g of succinic anhydride, add 10ml of concentrated sulfuric acid, react for 6 hours, add dilute hydrochloric acid to precipitate a precipitate, filter, wash with water until almost no pyridine smell, the solid is dissolved in e...

Embodiment 2

[0020] Extract 18-dehydroursolic acid with the method of Example 1, take by weighing 20g (content is 98.5%) of 18-dehydroursolic acid and place in a three-necked flask, add 100ml of pyridine, heat and dissolve at 90°C, add 24g of succinic anhydride , add 1ml of concentrated sulfuric acid, continue to heat and stir for the reaction, the reaction is complete after 8 hours, add dilute hydrochloric acid to precipitate the precipitate, filter, wash with water, the solid is dissolved in ethanol, add 30% NaOH solution under stirring, wait for the reaction to complete, set to low temperature After the crystallization was completed, it was filtered and recrystallized with 75% ethanol. Suction filtration and drying to obtain 21.5 g of 3β-succinyl-18-dehydroursolic acid disodium salt with a content of 98% and a yield of 81.22%.

Embodiment 3

[0021] Embodiment 3, take by weighing the 18-dehydroursolic acid of 20g (content is 98.5%) in a there-necked flask, add 100ml of pyridine, heat and dissolve in an oil bath, add 36g of succinic anhydride, continue to be heated to 115°C to react, After 10 hours of reaction, add dilute acid, filter, wash with water until neutral, dissolve the solid in ethyl acetate, add 10% NaOH solution with stirring, after the reaction is completed, set it to crystallize at low temperature, filter, recrystallize with water, set to 4 Crystallize overnight below ℃. The solid was filtered and dried to obtain 18.5 g of 3β-succinyl-18-dehydroursolic acid disodium salt, the content of which was greater than 98.5%, and the yield was 70.25%.

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Abstract

A process for preparing 3 beta-succinyl-18-disodium dehydroursolate includes reaction between 18-dehydroursolic acid and succinic acid anhydride in alkaline organic solvent at 80-202 deg.C for 5-12 hr, adding diluted acid, filter, water washing to remove pyridine, dissolving in C1-14 emtrol or ethyl acetate, adding sodium hydroxide solution, filter, recrystallizing and drying. Its advantage is high purity (more than 95%).

Description

Technical field [0001] The invention belongs to a preparation method of pentacyclic triterpenoid compound 3β-succinyl-18-dehydroursolic acid disodium salt. Background technique: [0002] 18-Dehydroursolic acid is a compound extracted from Ilex Pubescens Hook.et Arn. plants of the family Aquifoliaccae. Its properties are insoluble in water, so it is difficult to show physiological activity. Therefore, Convert 18-dehydroursolic acid into its a kind of pentacyclic triterpene compound 3β-succinyl-18-dehydroursolic acid disodium salt with strong physiological activity, thereby improving the solubility in water and showing obvious physiological activity . [0003] A series of studies on the evaluation of pharmacy, efficacy, toxicology and clinical efficacy of 3β-succinyl-18-dehydroursolic acid disodium salt. The experimental studies have proved that it has a certain effect on platelet aggregation induced by ADP or epinephrine. It has a certain anticoagulant effect and good antib...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00
Inventor 李漓钟鸣张素中
Owner GUANGZHOU HANFANG PHARMA
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