2010Chemical Research and ApplicationRequires access

Synthesis of some cholic acid and deoxycholic acid oximes

Jianguo Cui

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Abstract

The carboxyl and hydroxys of cholic acid and deoxycholic acid were transformed into the carbonyl and esteryl by a series of reactions.Six steroidal oximes were synthesized by the oximation using hydroxylammonium chloride.They were methylester 7-hydroxy-12-keto-3-hydroximinocholic acid(5),methylester 7,12-diketo-3-hydroximinocholic acid(6),methylester 12-keto-3,7-dihydroximinocholic acid(7),methylester 3,7,12-trihydroximinocholic acid(8),methylester 12-keto-3-hydroximinodeoxycholic acid(12)and methylester 3,12-dihydroximinodeoxycholic acid(13).The structures of 5~10 were characterized by NMR and IR.

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What this paper is about

The carboxyl and hydroxys of cholic acid and deoxycholic acid were transformed into the carbonyl and esteryl by a series of reactions.Six steroidal oximes were synthesized by the oximation using hydroxylammonium chloride.They were methylester 7-hydroxy-12-keto-3-hydroximinocholic acid(5),methylester 7,12-diketo-3-hydroximinocholic acid(6),methylester 12-keto-3,7-dihydroximinocholic acid(7),methylester 3,7,12-trihydroximinocholic acid(8),methylester 12-keto-3-hydroximinodeoxycholic acid(12)and methylester 3,12-dihydroximinodeoxycholic acid(13).The structures of 5~10 were characterized by NMR and IR.

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Available abstract

The carboxyl and hydroxys of cholic acid and deoxycholic acid were transformed into the carbonyl and esteryl by a series of reactions.Six steroidal oximes were synthesized by the oximation using hydroxylammonium chloride.They were methylester 7-hydroxy-12-keto-3-hydroximinocholic acid(5),methylester 7,12-diketo-3-hydroximinocholic acid(6),methylester 12-keto-3,7-dihydroximinocholic acid(7),methylester 3,7,12-trihydroximinocholic acid(8),methylester 12-keto-3-hydroximinodeoxycholic acid(12)and methylester 3,12-dihydroximinodeoxycholic acid(13).The structures of 5~10 were characterized by NMR and IR.

Key concepts: Deoxycholic acid, Cholic acid, Chemistry, Bile acid, Chenodeoxycholic acid, Chloride, Organic chemistry, Biochemistry

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