A Facile Route to Ursodeoxycholic Acid Based on Stereocontrolled Conversion and Aggregation Behavior Research

Abstract

A facile route to ursodeoxycholic acid (UDCA) and its aggregation behavior in aqueous phase solution, which is rarely known, are reported. The starting material, hyodeoxycholic acid (HDCA), is a relatively less expensive material and more easily obtained compared with chenodeoxycholic acid (CDCA). A facile route was developed to synthesize UDCA from HDCA with a Shapiro reaction as the key step and in 26% overall yield. A new strategy using organosilane reagent considering its stability, nontoxicity, and abundance in nature was carried out for a more rapid route and higher yield. It was found that the critical micelle concentration value, which is a critical value for surfactants of bile salts, was influenced by the number of hydroxyl groups.

Key words

ursodeoxycholic acid - hyodeoxycholic acid - critical micelle concentration - facile route - Shapiro reaction - Clemmensen reaction

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