2284-36-8

Basic information

• Product Name: methyl 3alpha,7alpha-diacetoxy-5beta-chol-11-en-24-oate
• Synonyms: methyl 3alpha,7alpha-diacetoxy-5beta-chol-11-en-24-oate;3α,7α-Bis(acetyloxy)-5β-chol-11-en-24-oic acid methyl ester;3α,7α-Diacetoxy-5β-cholan-11-en-24-oic acid methyl ester;Einecs 218-923-4
• CAS NO: 2284-36-8
• Molecular Formula: C₂₉H₄₄O₆
• Molecular Weight: 488.65606
• EINECS: 218-923-4
• Mol File: 2284-36-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 530°Cat760mmHg
• Flash Point: 221.1°C
• Appearance: /
• Density: 1.12g/cm³
• CAS DataBase Reference: methyl 3alpha,7alpha-diacetoxy-5beta-chol-11-en-24-oate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3alpha,7alpha-diacetoxy-5beta-chol-11-en-24-oate(2284-36-8)
• EPA Substance Registry System: methyl 3alpha,7alpha-diacetoxy-5beta-chol-11-en-24-oate(2284-36-8)

Safety Data

• Hazardous Substances Data: 2284-36-8(Hazardous Substances Data)

Upstream product

• 81-25-4 cholic acid 
• 1448-36-8 methyl cholate 
• 3749-87-9 methyl 3α,7α-diacetoxy-12α-hydroxy cholanate 
• 58896-97-2 methyl 3α,7α-diacetoxy-12α-mesyloxy-5β-cholan-24-oate 

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.

Introducing Δ11 unsaturation into steroid compounds

A process for the introduction of Δ11 unsaturation into steroid compounds having a C-12 sulfonate ester group is described. Dehydrosulfonation is carried out by reacting the sulfonate with a hexaalkylphosphoric triamide. The process is particularly useful with steroid compounds that also contain a blocked C-7 hydroxy group. The process yields the 11-enate in preference to the 6,11-dienate. The yield of the process can be increased by carrying out the reaction in the presence of a weak base.