Cholan-24-oic acid,3,7-dihydroxy-12-oxo-, methyl ester, (3a,5b,7a)-

Base Information

• Chemical Name: Cholan-24-oic acid,3,7-dihydroxy-12-oxo-, methyl ester, (3a,5b,7a)-
• CAS No.: 10538-64-4
• Molecular Formula: C25H40 O5
• Molecular Weight: 420.59
• Mol file: 10538-64-4.mol

Synonyms:5b-Cholan-24-oic acid, 3a,7a-dihydroxy-12-oxo-, methyl ester (8CI); 5b-Cholanic acid, 3a,7a-dihydroxy-12-oxo-, methyl ester (6CI,7CI);12-Ketochenodeoxycholic acid methyl ester; 3a,7a-Dihydroxy-12-oxo-5b-cholanic acid methyl ester; Methyl 3a,7a-dihydroxy-12-oxo-5b-cholan-24-oate

Chemical Property of Cholan-24-oic acid,3,7-dihydroxy-12-oxo-, methyl ester, (3a,5b,7a)-

Chemical Property:

• Melting Point: 158-160 °C(Solv: acetone (67-64-1); ligroine (8032-32-4))
• Boiling Point: 540.0±50.0 °C(Predicted)
• PSA: 83.83000
• Density: 1.137±0.06 g/cm3(Predicted)
• LogP: 3.74530

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3α,?5β,?7α)?-3,?7-?Dihydroxy-?12-?oxocholan-?24-?oicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3α,?5β,?7α)?-3,?7-?Dihydroxy-?12-?oxocholan-?24-?oic Acid Methyl Ester is an intermediate in the synthesis of 12β-Hydroxyisocholic Acid (H943480), a bile acid. (3α,?5β,?7α)?-3,?7-?Dihydroxy-?12-?oxocholan-?24-?oic Acid Methyl Ester was found to increase the toxicity of verapamil, a cardioactive drug, in rats.

Technology Process of Cholan-24-oic acid,3,7-dihydroxy-12-oxo-, methyl ester, (3a,5b,7a)-

There total 12 articles about Cholan-24-oic acid,3,7-dihydroxy-12-oxo-, methyl ester, (3a,5b,7a)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate (28535-81-1) → methyl 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oate (10538-64-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 24h;

DOI:10.1007/s10870-014-0543-1

Reference yield: 82.1%

methanol (67-56-1) + 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid (2458-08-4) → methyl 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oate (10538-64-4)

Guidance literature:

With sulfuric acid; at 60 ℃; for 5h;

Reference yield: 76.0%

methyl 3,7,12-trioxo-5β-cholan-24-oate (7727-82-4) → methyl 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oate (10538-64-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1016/j.mencom.2011.04.007

upstream raw materials:

diazomethane

3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid

Dodecanoic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-acetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-12-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

methyl cholate

Downstream raw materials:

methyl cholate

methyl 3α-(tosyloxy)-7α-hydroxy-12-oxo-5β-cholanate

ursodeoxycholic acid

methyl 3α-(tosyloxy)-7β-hydroxy-12-oxo-5β-cholanate

Refernces

• 1、 Maslov, Mikhail A.,Morozova, Nina G.,Solomatina, Tatyana V.,Sergeeva, Olga A.,Cheshkov, Dmitry A.,Serebrennikova, Galina A.. "Synthesis of cholic acid amino analogues by oxime reduction with TiCl 3-NaBH3CN". . p. 137 - 139. Retrieved 2011.
• 2、 Berner,Lardon,Reichstein. "-". . p. 1542,1552. Retrieved 1947.
• 3、 -. "Chenodeoxycholic acid derivative or pharmaceutically acceptable salt thereof, and preparation method and applications thereof". . . Retrieved 2020/03/12.