Preparation of ursodeoxycholic acid from 7-ketone lithocholic acid by stereoselective electroreduction

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Preparation of ursodeoxycholic acid from 7-ketone lithocholic acid by stereoselective electroreduction

Background: Ursodeoxycholic acid (UDCA) is an important clinical drug in the treatment of liver disease. In previous work, ursodeoxycholic acid was prepared by traditional organic synthesis. The preparation of ursodeoxycholic acid through an electrochemical method with higher stereoselectivity and environmental friendliness is described herein. Results: Dimethyl sulfoxide (DMSO), dimethylformam...

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Ursodeoxycholic acid

Ursodeoxycholic acid is an epimer of chenodeoxycholic acid (DB06777). It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [PubChem] Indication: The drug reduces cholesterol absorption and is used to dis...

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Ursodeoxycholic acid, chenodeoxycholic acid, and 7-ketolithocholic acid are primary bile acids of the guinea pig.

Guinea pig gallbladder bile contains chenodeoxycholic acid (62 +/- 5%), ursodeoxycholic acid (8 +/- 5%), and 7-ketolithocholic acid (30 +/- 5%). All three bile acids became labeled to the same specific activity within 30 min after [3H]cholesterol was injected into bile fistula guinea pigs. When a mixture of [3H]ursodeoxycholic acid and [14C]chenodeoxycholic acid was infused into another bile fi...

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Metabolism of lithocholic acid in the rat: formation of lithocholic acid 3-0-glucuronide in vivo

Milligram amounts of [3P-3H]lithocholic (3a-hydroxy5P-cholanoic) acid were administered by intravenous infusion to rats prepared with a biliary fistula. Analysis of sequential bile samples by thin-layer chromatography (TLC) demonstrated that lithocholic acid glucuronide was present in bile throughout the course of the experiments and that its secretion rate paralleled that of total isotope secr...

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Separation of ursodeoxycholic acid by silylation crystallization

Background: Ursodeoxycholic acid is an important clinical drug in the treatment of liver disease. In our previous work, ursodeoxycholic acid was prepared by electroreduction of 7-ketolithocholic acid. The separation of ursodeoxycholic acid from the electroreduction product (47% (w/w) ursodeoxycholic acid) by silylation crystallization is described herein. Results: N,N-dimethylformamide was used...

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ژورنال

عنوان ژورنال: Bioresources and Bioprocessing

سال: 2015

ISSN: 2197-4365

DOI: 10.1186/s40643-015-0058-4