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Ursodesoxycholic acid preparation method

A technology for ursodeoxycholic acid and chenodeoxycholic acid, which is applied in the field of ursodeoxycholic acid preparation, can solve the problems of complicated processing, low conversion rate of chenodeoxycholic acid, etc., and achieves easy post-processing, environment-friendly, high conversion rate

Active Publication Date: 2016-08-17
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, chenodeoxycholic acid is mainly used as raw material at home and abroad to prepare ursodeoxycholic acid through oxidation and reduction two-step chemical reaction. During the reaction process, a large amount of solvents and oxidizing and reducing agents are used, and the conversion rate of chenodeoxycholic acid is low. , only about 80% of chenodeoxycholic acid is converted into ursodeoxycholic acid, and the post-processing is complicated

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 10g chenodeoxycholic acid, 50ml sec-butanol, 100ml PH7.4 PB buffer and stir to dissolve, add 10mg7-αHSDH and 10mg7-βHSDH freeze-dried powder, 10mg coenzyme II, adjust the pH of the solution to about 6.8, and control the temperature at 23 degree, react for 3 hours.

[0033] The temperature of the reaction solution is raised to 70-75 degrees, stirred for 2 hours, cooled to 25-30 degrees, the reaction solution is poured into a centrifuge bottle of a high-speed centrifuge, and the supernatant is poured into a separatory funnel to stand for stratification, and the lower layer of water phase Discard, add 1.1g of sodium hydroxide to the organic phase, remove the solvent by vacuum distillation, add 100ml of water to the distillation residue, adjust the acidic crystallization of the solution with 1:1 hydrochloric acid, and filter.

[0034] Add 50ml of acetone to the filter cake, heat to reflux for 2 hours, cool to 20°C, filter, and vacuum-dry at 70-75°C to obtain 7.9 grams o...

Embodiment 2

[0036] Add 10g chenodeoxycholic acid, 80ml sec-amyl alcohol, 100ml PH7.4PB buffer and stir to dissolve, add 30mg7-αHSDH and 30mg7-βHSDH freeze-dried powder, 10mg coenzyme II, adjust the pH of the solution to about 6.8, and control the temperature at 23 degree, react for 3 hours.

[0037] The temperature of the reaction solution is raised to 70-75 degrees, stirred for 2 hours, cooled to 25-30 degrees, the reaction solution is poured into a centrifuge bottle of a high-speed centrifuge, and the supernatant is poured into a separatory funnel to stand for stratification, and the lower layer of water phase Discard, add 1.1g of sodium hydroxide to the organic phase, remove the solvent by vacuum distillation, add 100ml of water to the distillation residue, adjust the acidic crystallization of the solution with 1:1 hydrochloric acid, and filter.

[0038] Add 60ml of acetone to the filter cake, heat to reflux for 2 hours, cool to 20°C, filter, and vacuum-dry at 70-75°C to obtain 8.1 gra...

Embodiment 3

[0040] Add 10g chenodeoxycholic acid, 50ml n-butanol, 100ml PH7.4PB buffer and stir to dissolve, add 10mg7-αHSDH and 10mg7-βHSDH freeze-dried powder, 10mg coenzyme II, adjust the pH of the solution to about 6.8, and control the temperature at 23 degree, react for 3 hours.

[0041] The temperature of the reaction solution is raised to 70-75 degrees, stirred for 2 hours, cooled to 25-30 degrees, the reaction solution is poured into a centrifuge bottle of a high-speed centrifuge, and the supernatant is poured into a separatory funnel to stand for stratification, and the lower layer of water phase Discard, add 1.1g of sodium hydroxide to the organic phase, remove the solvent by vacuum distillation, add 100ml of water to the distillation residue, adjust the acidic crystallization of the solution with 1:1 hydrochloric acid, and filter.

[0042] Add 80ml of ethyl acetate to the filter cake, heat to reflux for 2 hours, cool to 20°C, filter, and vacuum-dry at 70-75°C to obtain 7.8 gram...

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Abstract

The invention discloses an ursodesoxycholic acid preparation method. The method comprises the following steps: 1, adding chenodeoxycholic acid and a solvent A to a reaction container, stirring for dissolving, adding 7-alphaHSDH, 7-betaHSDH and a coenzyme II, and carrying out a reaction at a controlled temperature at a controlled pH value to convert chenodeoxycholic acid into ursodesoxycholic acid in order to obtain a conversion liquid; 2, heating the conversion liquid obtained in step 1 to denaturalize the 7-alphaHSDH and the 7-betaHSDH, centrifuging through a high speed centrifuge, removing proteins, adding a sodium hydroxide solution to the above obtained solution, distilling to remove the solvent A, adding water to dissolve obtained distillation residues, adding an acid, and crystallizing to obtain crude ursodesoxycholic acid; and 3, adding the crude ursodesoxycholic acid obtained in step 2 and a solvent B to the reaction container, heating and refluxing the crude ursodesoxycholic acid and the solvent B for 1h, cooling the obtained reaction product to normal temperature, and filtering the cooled product to obtain ursodesoxycholic acid with the purity being greater than 99%. The ursodesoxycholic acid preparation method has the advantages of simple technology, short synthesis route, high conversion rate, easy post-treatment and environmental protection.

Description

technical field [0001] The invention relates to a preparation method of ursodeoxycholic acid. Background technique [0002] The chemical name of ursodeoxycholic acid is: 3α, 7β-dihydroxy-5β-cholic acid, which has the same molecular formula as chenodeoxycholic acid and bovine cholic acid, but different three-dimensional structures. Chemically, the structures of these two compounds are Relationships become isomers. Ursodeoxycholic acid is a white crystalline powder, odorless and bitter. It is easily soluble in ethanol, chloroform, glacial acetic acid, dilute lye, slightly soluble in ether, hardly soluble in water and dilute mineral acid, with a melting point of 203°C. Ursodeoxycholic acid UDCA is a non-toxic hydrophilic cholic acid, which can competitively inhibit the absorption of toxic endogenous cholic acid in the ileum, by activating the signaling network composed of calcium ions and protein kinase C, and by activating the cleavage activity Protein-based enzymes to incr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P33/06
CPCC12P33/06
Inventor 秦和平张和平梁待亮欧松娄良沈惠宾阮宇峰王明宗
Owner ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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