2242-12-8

Basic information

• Product Name: 3α-Acetyloxy-5β-chol-11-en-24-oic acid methyl ester
• Synonyms: 3α-Acetyloxy-5β-chol-11-en-24-oic acid methyl ester
• CAS NO: 2242-12-8
• Molecular Formula: C₂₇H₄₂O₄
• Molecular Weight: 430.61998
• Mol File: 2242-12-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3α-Acetyloxy-5β-chol-11-en-24-oic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3α-Acetyloxy-5β-chol-11-en-24-oic acid methyl ester(2242-12-8)
• EPA Substance Registry System: 3α-Acetyloxy-5β-chol-11-en-24-oic acid methyl ester(2242-12-8)

Safety Data

• Hazardous Substances Data: 2242-12-8(Hazardous Substances Data)

Upstream product

• 81644-38-4 methyl 3-oxo-5β-chol-11-en-24-oate 
• 1053-37-8 3β-hydroxy-5β-cholen-(11)-oic acid-(24) 
• 423767-61-7 3-keto-5β-chol-11-enic acid 
• 81644-41-9 3β-hydroxy-5β-cholen-(11)-oic acid-(24)-methyl ester 
• 108-24-7 acetic anhydride 
• 27240-83-1 methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate 
• 3245-38-3 methyl deoxycholate 
• 83-44-3 Deoxycholic acid 
• 1053-37-8 lithocholenic acid 
• 7647-01-0 hydrogenchloride 
• 7751-05-5 3α-acetoxy-11β-hydroxy-5β-cholan-24-oic acid methyl ester 
• 64-19-7 acetic acid 
• 4472-02-0 methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate 
• 141-52-6 sodium ethanolate 

Downstream Products

• 4472-02-0 methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate 
• 4651-66-5 methyl 3α-acetoxy-11-oxo-5β-cholan-24-oate 
• 4472-02-0 methyl 3β-hydroxy-5β-chol-9(11)-ene-12-one-24-oate acetate 
• 122441-65-0 methyl 3β-hydroxy-5β-cholan-11-one-24-oate acetate 
• 62797-60-8 3α-hydroxy-5β-chol-9(11)-en-24-oic acid 
• 3253-69-8 methyl 3α-acetoxy-5β-cholan-24-oate 
• 434-13-9 Lithocholic acid 
• 1053-37-8 lithocholenic acid 

Relevant articles and documents

Chemical Synthesis of Rare Natural Bile Acids: 11α-Hydroxy Derivatives of Lithocholic and Chenodeoxycholic Acids

A method for the preparation of 11α-hydroxy derivatives of lithocholic and chenodeoxycholic acids, recently discovered to be natural bile acids, is described. The principal reactions involved were (1) elimination of the 12α-mesyloxy group of the methyl esters of 3α-acetate-12α-mesylate and 3α,7α-diacetate-12α-mesylate derivatives of deoxycholic acid and cholic acid with potassium acetate/hexamethylphosphoramide; (2) simultaneous reduction/hydrolysis of the resulting △11-3α-acetoxy and △11-3α,7α-diacetoxy methyl esters with lithium aluminum hydride; (3) stereoselective 11α-hydroxylation of the △11-3α,24-diol and △11-3α,7α,24-triol intermediates with B2H6/tetrahydrofuran (THF); and (4) selective oxidation at C-24 of the resulting 3α,11α,24-triol and 3α,7α,11α,24-tetrol to the corresponding C-24 carboxylic acids with NaClO2 catalyzed by 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (TEMPO) and NaClO. In summary, 3α,11α-dihydroxy-5β-cholan-24-oic acid and 3α,7α,11α-trihydroxy-5β-cholan-24-oic acid have been synthesized and their nuclear magnetic resonance (NMR) spectra characterized. These compounds are now available as reference standards to be used in biliary bile acid analysis.

Synthesizing method of lithocholic acid

The invention discloses a synthesizing method of lithocholic acid. The synthesizing method is characterized in that deoxycholic acid is used as the raw material, and the deoxycholic acid is subjected to reactions such as methyl esterification protection, acetic anhydride protection of 3 hydroxyl groups, dewatering, hydrogenation and hydrolysis to synthesize the lithocholic acid. The synthesizing method is simple in step, few in side reaction, high in yield, easy in raw material obtaining, suitable for industrial production, and capable of solving the problems that the prior art is excessively high in synthesizing cost, low in yield and not suitable for large-scale industrial production.