141417-49-4

Basic information

• Product Name: Cholestan-26-oic acid, 3,7-bis(acetyloxy)-12-[[(4-methylphenyl)sulfonyl]hydrazono]-, methyl ester, (3a,5b,7a,25S)-
• CAS NO: 141417-49-4
• Molecular Formula: C39H58N2O8S
• Molecular Weight: 714.964
• Mol File: 141417-49-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Cholestan-26-oic acid, 3,7-bis(acetyloxy)-12-[[(4-methylphenyl)sulfonyl]hydrazono]-, methyl ester, (3a,5b,7a,25S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cholestan-26-oic acid, 3,7-bis(acetyloxy)-12-[[(4-methylphenyl)sulfonyl]hydrazono]-, methyl ester, (3a,5b,7a,25S)-(141417-49-4)
• EPA Substance Registry System: Cholestan-26-oic acid, 3,7-bis(acetyloxy)-12-[[(4-methylphenyl)sulfonyl]hydrazono]-, methyl ester, (3a,5b,7a,25S)-(141417-49-4)

Safety Data

• Hazardous Substances Data: 141417-49-4(Hazardous Substances Data)

Upstream product

• 141505-55-7 (2S,6R)-6-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-Diacetoxy-12-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptanoic acid methyl ester 
• 23740-21-8 (25R)-methyl 3α,7α,12α-trihydroxy-5β-cholestan-26-oate 
• 23047-29-2 (25R)-3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid 
• 141505-56-8 (2S,6R)-6-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-Diacetoxy-10,13-dimethyl-12-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptanoic acid methyl ester 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 38408-28-5 methyl 3α,7α-diacetoxy-12α-hydroxy-5β-cholestan-26-oate 
• 96478-80-7 (R)-2-Methyl-6-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-heptanoic acid methyl ester 
• 547-98-8 Trihydroxycholestanoic acid 
• 38408-29-6 methyl 3α,7α-diacetoxy-12-oxo-5β-cholestan-26-oate 

Downstream Products

• 17974-66-2 (25RS)-3α,7α-dihydroxy-5β-cholestan-26-oic acid 

Relevant articles and documents

Synthesis of 3α,7α-dihydroxy-5β-cholestan-26-oic acid from 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid: configuration in the bile of Alligator mississippiensis

Synthesis of 25R- and 25S-diastereoisomers of 3α,7α-dihydroxy-5β-cholestan-26-oic acid from 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid is described.The 25S-diastereoisomer of 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid was obtained by vigorous hydrolysis of the bile of Alligator mississippiensis followed by repeated crystallization of the hydrolysate, and the 25R-diastereoisomer was isolated by hydrolysis of the bile salts in bile of A mississippiensis with rat feces.Acetylation of the 25R- or 25S-diastereoisomer of methyl 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid under controlled conditions yielded the corresponding 3α,7α-diacetate in approximately 70percent yield.The diacetate was quantitatively oxidized to methyl 3α,7α-diacetoxy-12-oxo-5β-cholestan-26-oate, which was converted into the 12-tosylhydrazone in approximately 58percent yield.Reduction of the tosylhydrazone with sodium borohydride in acetic acid yielded the 25R- or the 25S-diastereoisomer of 3α,7α-dihydroxy-5β-cholestan-26-oic acid as the major product.Purification via column chromatography yielded the pure diastereoisomers in approximately 25percent overall yield.The two diastereoisomers were resolved on thin-layer chromatography and high-performance liquid chromatography.When the bile of A mississippiensis was hydrolyzed with rat fecal bacteria, the 3α,7α-dihydroxy-5β-cholestan-26-oic acid isolated via chromatographic purification was shown to be the 25R-diastereoisomer.Keywords: 3α,7α-dihydroxy-5β-cholestan-26-oic acid; 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid; diastereoisomers; alligator bile; thin-layer chromatography; high-performance liquid chromatography; Alligator mississippiensis; steroids