14772-92-0

Basic information

• Product Name: Methyl 3-ketoallocholate
• Synonyms: Methyl 3-ketoallocholate;7α,12α-Dihydroxy-3-oxo-5α-cholan-24-oic acid methyl ester;Methyl 3-Keto-7α,12α-dihydroxy-5α-cholanoate;Methyl 3-keto-7alpha,12alpha-dihydroxy-5alpha-cholanoate;(5α,7α,12α)-7,12-Dihydroxy-3-oxo-cholan-24-oic Acid Methyl Ester
• CAS NO: 14772-92-0
• Molecular Formula: C₂₅H₄₀O₅
• Molecular Weight: 420.586
• Product Categories: Miscellaneous Reagents;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 14772-92-0.mol

Chemical Properties

• Melting Point: 120--123°C
• Boiling Point: 540°C at 760 mmHg
• Flash Point: 175.2°C
• Appearance: /
• Density: 1.137
• Vapor Pressure: 6.52E-14mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Methyl 3-ketoallocholate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-ketoallocholate(14772-92-0)
• EPA Substance Registry System: Methyl 3-ketoallocholate(14772-92-0)

Safety Data

• Hazardous Substances Data: 14772-92-0(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
Methyl 3-ketoallocholate is used as a research compound for studying the biochemical properties and characteristics of allocholic acid ring-containing compounds. Its application in this field aids in understanding the structure, function, and potential applications of these compounds in various scientific and medical contexts.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 3-ketoallocholate may be utilized as a starting material or intermediate in the synthesis of other compounds with potential therapeutic applications. Its unique structure and properties make it a valuable tool for drug discovery and development.
Used in Biochemical Studies:
Methyl 3-ketoallocholate is also used as a biochemical research tool to investigate the interactions and mechanisms of action of compounds containing the allocholic acid ring nucleus. This can provide insights into the development of new drugs or therapies targeting specific biological pathways.

InChI:InChI=1/C25H40O5/c1-14(5-8-22(29)30-4)17-6-7-18-23-19(13-21(28)25(17,18)3)24(2)10-9-16(26)11-15(24)12-20(23)27/h14-15,17-21,23,27-28H,5-13H2,1-4H3/t14?,15-,17?,18?,19?,20-,21+,23?,24?,25?/m1/s1

Upstream product

• 111102-58-0 methyl 3-oxo-7α,12α-dihydroxy-1,4-choladienate 
• 88674-56-0 3-oxo-7α,12α-diformyloxy-4-cholen-24-oic acid 
• 88674-54-8 3-oxo-4β-bromo-7α,12α-diformyloxy-5β-cholan-24-oic acid 
• 88674-52-6 3-oxo-7α,12α-diformoxy-5β-cholan-24-oic acid 
• 64986-86-3 3α-hydroxy-7α,12α-diformyloxy-5β-cholan-24-oic acid 
• 14772-99-7 3-oxo cholic acid methyl ester 
• 2304-89-4 7α,12α-dihydroxy-3-oxocholanoic acid 
• 125626-77-9 7α,12α-dihydroxy-3-oxochola-1,4-dien-24-oic acid 
• 111102-57-9 methyl 7α,12α-diformyloxy-3-oxo-1,4-choladienoate 
• 97412-89-0 methyl 3α-hydroxy-7α,12α-bis(formyloxy)-5β-cholan-24-oate 
• 1448-36-8 methyl cholate 
• 33744-75-1 methyl 3α,7α,12α-triformyloxy-5β-cholanoate 
• 13587-11-6 3-oxo-7α,12α-dihydroxy-4-cholen-24-oic acid 
• 67-56-1 methanol 

Downstream Products

• 28979-29-5 Petromyzonol 

Relevant articles and documents

Potential bile acid metabolites. XXI. A new synthesis of allochenodeoxycholic and allocholic acids

A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3α-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1,4-dien-3-oxo bydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.

Allomerization of cholic acid and conversion to petromyzonol

Petromyzonol, a rare bile substance, has been prepared from an abundant starting material, cholic acid.The critical conversion, the inversion of the configuration at C-5, was accomplished by oxidizing a suitably protected derivative of cholic acid to a 1,4-dien-3-one, which was then stereoselectively reduced to methyl allocholate.In a single oxidation step, the 3-hydroxy steroid was converted to the dienone by Barton's procedure using a catalytic amount of benzeneseleninic anhydride and m-iodoxybenzoic acid as the stoichiometric oxidant.The stereoselective reduction employed two steps: hydrogenation of the dienone to the saturated ketone (5α) in the presence of the Wilkinson catalyst, followed by reduction of the ketone with K-Selectride.Finally, methyl allocholate was reduced to petromyzonol with lithium aluminum hydride.

POTENTIAL BILE ACID METABOLITES. XI. SYNTHESES OF STEREOISOMERIC 7,12-DIHYDROXY-5α-CHOLANIC ACIDS

Three new compounds, 7α,12β-, 7β,12α-, and 7β,12β-dihydroxy-5α-cholanic acids, were synthesized.The principal reactions employed were 1) selective acylation at C-7 of a 7α,12α-dihydroxy ester with the propionic anhydride-4-dimethylaminopyridine system, 2) potassium superoxide-18-crown-6 ether inversion of the 7α-hydroxyl group, and 3) stereoselective reduction of the 12-ketones with the sodium borohydride-palladium chloride system and tert-butylamine-borane complex.High-performance liquid chromatography was of key impotance in characterizing the compounds and determining their purity.Keywords-- bile acid; allobile acid; 7,12-dihydroxy-5-α-cholanic acid; selective acylation; potassium superoxide-18-crown-6 ether reaction; sodium borohydride-palladium chloride reduction; tert-butylamine-borane complex reduction; HPLC