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Preparation method for trans-glycyrrhizic acid

A technology of glycyrrhizic acid and methyl glycyrrhizic acid, which is applied to the preparation of sugar derivatives, chemical instruments and methods, and steroids, can solve the problems of low yield, difficult operation, unsuitable recovery of cis-glycyrrhizic acid, etc., and achieve High yield, less side reactions, solve the effect of equipment post-treatment

Active Publication Date: 2012-07-18
杭州市第六人民医院
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Prior art: Generally, the conformational conversion of natural glycyrrhizic acid is obtained by base-catalyzed isomerization to obtain trans-glycyrrhizic acid, and the resulting product is a mixture of stereoisomers; Esterification or acylation of isomer mixture to produce trans-glycyrrhizic acid, but the operation is difficult and the yield is low, and unconverted cis-glycyrrhizic acid is not suitable for recovery

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  • Preparation method for trans-glycyrrhizic acid

Examples

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Embodiment 1

[0036] Take 100g (0.117mol) of diammonium glycyrrhizinate and 500g (15.606mol) of methanol, put them into a reaction tank to mix, stir evenly, add 20g (0.105mol) of p-toluenesulfonic acid, and react for 120 hours under r, t conditions , the crystallization of trans-methyl glycyrrhizinate is complete, filter, wash with methanol, drain, and dry to obtain 60g of high-purity trans-methyl glycyrrhizinate; add 3 times the amount of water to the filtrate, place it overnight, and pour off the supernatant , filtered, washed with appropriate amount of water, drained, and dried to obtain 35g of cis-glycyrrhizic acid (crude product).

[0037] ①Take 60g of trans methyl glycyrrhizinate, add 300ml of sodium hydroxide solution (2mol / L), saponify under r,t conditions until the solution is clear (about 2 hours), add dilute sulfuric acid to adjust the pH to 3.0, and use n-butyl Alcohol extraction to pH 4.0, reduced pressure, evaporated to dryness, and finally add 90% glacial acetic acid to disso...

Embodiment 2

[0045] Take 100g (0.117mol) of diammonium glycyrrhizinate and 350g (10.924mol) of methanol, put them into a reaction tank and mix them, stir evenly, add 8g (0.0816mol) of concentrated sulfuric acid, and react for 72 hours under r, t conditions, trans-glycyrrhizic acid Complete crystallization of methyl ester, filter, wash with methanol, drain, and dry to obtain 61g of high-purity methyl trans-glycyrrhizinate; add 3 times the amount of water to the filter solution, let it stand overnight, pour off the supernatant, filter, and appropriate amount Washed with water, drained and dried to obtain 33g of cis-glycyrrhizic acid (crude product).

[0046] ①Take 61g of trans-methyl glycyrrhizinate, add 305ml of sodium hydroxide solution (2mol / L), saponify under r,t conditions until the solution is clear (about 2 hours), add dilute sulfuric acid to adjust the pH to 3.0, and use n-butyl Alcohol extraction to pH 4.0, reduced pressure, evaporated to dryness, finally added 90% glacial acetic acid...

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Abstract

The invention relates to a preparation method for trans-glycyrrhizic acid. Diammonium glycyrrhizinate is directly placed in carbinol, a proper amount of protonic acid is added for catalysis, and under room temperature conditions, trans-glycyrrhizic acid methyl ester is selectively combined in automatic coherent type multicomponent reactive mode so as to change physical and chemical properties of a glycyrrhizic acid stereoisomer mixture, enable trans-glycyrrhizic acid methyl ester with weak polarity to be dissolved out from reaction liquid and filtered and obtain trans-glycyrrhizic acid methyl ester to be separated from cis-glycyrrhizic acid. Then, single-component trans-glycyrrhizic acid is prepared through saponification, acid neutralization and the like, and cis-glycyrrhizic acid is recycled. The preparation method resolves the technical problem that the glycyrrhizic acid stereoisomer mixture cannot be separated and has the advantages of being simple, low in energy consumption and high in yield and improving utilization ratio of natural glycyrrhizic acid.

Description

technical field [0001] The invention belongs to the technical field of glycyrrhizic acid preparation, in particular to a preparation method of trans glycyrrhizic acid. Background technique [0002] Trans-glycyrrhizic acid, also known as: 18α-glycyrrhizic acid (18α-Glycyrrhizic acid) and isoglycyrrhizinate (Isoglycyrrhizinate), is the epimer of cis-glycyrrhizic acid (18β-glycyrrhizic acid). A crystalline white powder, easily soluble in low-carbon alcohols, soluble in hot water, weakly acidic in aqueous solution, jelly-like after cooling, insoluble in ether, stable to heat, alkali and salt, solution when pH is less than 3 Precipitation will occur; UV, IR, 1 H-NMR, 13 C-NMR and MS spectral analysis confirmed that the α-body and the β-body have a common structure, and the only difference is that the H configuration at the C18 position is different, which are trans and cis respectively; after measuring the specific rotation, the trans-glycyrrhizic acid is significantly lower t...

Claims

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Application Information

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IPC IPC(8): C07J63/00C07H15/256C07H1/00
Inventor 田静刘金城
Owner 杭州市第六人民医院
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