Methyl 12alpha-hydroxy-3-oxo-5beta-cholan-24-oate

Base Information

• Chemical Name: Methyl 12alpha-hydroxy-3-oxo-5beta-cholan-24-oate
• CAS No.: 10538-58-6
• Molecular Formula: C25H40 O4
• Molecular Weight: 404.59
• European Community (EC) Number: 234-115-4
• UNII: SAO85TC57K
• DSSTox Substance ID: DTXSID80909481
• Nikkaji Number: J226.982A
• Wikidata: Q27289112
• Mol file: 10538-58-6.mol

Synonyms:10538-58-6;Methyl 12alpha-hydroxy-3-oxo-5beta-cholan-24-oate;UNII-SAO85TC57K;SAO85TC57K;EINECS 234-115-4;methyl (4R)-4-[(5R,8R,9S,10S,12S,13R,14S,17R)-12-hydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate;Methyl (5,12)-12-hydroxy-3-oxocholan-24-oate;Obeticholic Acid Intermediates;DTXSID80909481;MFCD00271400;AKOS032949943;Methyl 12-hydroxy-3-oxocholan-24-oate;H11552;Methyl(5,12)-12-hydroxy-3-oxocholan-24-oate;Q27289112;METHYL (5?,12?)-12-HYDROXY-3-OXOCHOLAN-24-OATE;METHYL 12.ALPHA.-HYDROXY-3-OXO-5.BETA.-CHOLANATE;METHYL-3-KETO-12.ALPHA.-HYDROXY-5.BETA.-CHOLANOATE;12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid methyl ester;METHYL (5BETA,12ALPHA)-12-HYDROXY-3-OXOCHOLAN-24-OATE;METHYL 12.ALPHA.-HYDROXY-3-OXO-5.BETA.-CHOLAN-24-OATE;5.BETA.-CHOLANIC ACID, 12.ALPHA.-HYDROXY-3-OXO-, METHYL ESTER;5.BETA.-CHOLAN-24-OIC ACID, 12.ALPHA.-HYDROXY-3-OXO-, METHYL ESTER;CHOLAN-24-OIC ACID, 12-HYDROXY-3-OXO-, METHYL ESTER, (5.BETA.,12.ALPHA.)-

Chemical Property of Methyl 12alpha-hydroxy-3-oxo-5beta-cholan-24-oate

Chemical Property:

• Melting Point: 145 °C
• Boiling Point: 505.7°Cat760mmHg
• PKA: 14.90±0.70(Predicted)
• Flash Point: 162.2°C
• PSA: 63.60000
• Density: 1.085g/cm³
• LogP: 4.77450
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 404.29265975
• Heavy Atom Count: 29
• Complexity: 659

Purity/Quality:

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

Methyl 3-Oxo-desoxycholate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(C(CC3C2CCC4C3(CCC(=O)C4)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC(=O)C4)C)O)C
• Uses: Methyl 3-Oxo-desoxycholate is used in the preparation of bile acid-based amino sterols with antimicrobal activity.

Technology Process of Methyl 12alpha-hydroxy-3-oxo-5beta-cholan-24-oate

There total 24 articles about Methyl 12alpha-hydroxy-3-oxo-5beta-cholan-24-oate 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: 98.0%

methyl deoxycholate (3245-38-3) → methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate (10538-58-6)

Guidance literature:

With Ag₂CO₃ on Celite; In toluene; Reflux; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.05.140

Reference yield: 26.0%

methyl 12α-hydroxy-3-ketochola-1,4-dienoate (106759-10-8) → methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate (10538-58-6) + methyl 3-oxo-12α-hydroxy-5α-cholan-24-oate

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4h; under 735.5 Torr; Ambient temperature;

DOI:10.1016/0039-128X(89)90022-6

Reference yield:

3-keto-12α-hydroxy-5β-cholan-24-oic acid (4185-01-7) → methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate (10538-58-6)

Guidance literature:

With methanol; acetyl chloride;

DOI:10.1021/ja01235a011

upstream raw materials:

diazomethane

3-keto-12α-hydroxy-5β-cholan-24-oic acid

methyl deoxycholate

cyclohexanone

Downstream raw materials:

1β,3α,12α-trihydroxy-5β-cholan-24-oic acid

3α,4β,12α-trihydroxy-5β-cholan-24-oic acid

12α-hydroxychol-4-en-3-one-24-coic acid methyl ester

C₃₂H₄₈N₂O₅S

Refernces

• 1、 Sasaki, Tomoaki,Nakamori, Ryusei,Yamaguchi, Takeru,Kasuga, Yuka,Iida, Takashi,Nambara, Toshio. "The application of dimethyldioxirane for the selective oxidation of polyfunctional steroids". . p. 135 - 143. Retrieved 2001.
• 2、 Sneeden,Turner. "-". . p. 190. Retrieved 1955.
• 3、 Rocheblave, Luc,de Ravel, Marc Rolland,Monniot, Elodie,Tavenard, Jeremy,Cuilleron, Claude-Yves,Grenot, Catherine,Radix, Sylvie,Matera, Eva-Laure,Dumontet, Charles,Walchshofer, Nadia. "Deoxycholic acid derivatives as inhibitors of P-glycoprotein-mediated multidrug efflux". . p. 5 - 12. Retrieved 2016.
• 4、 Jones,Webb,Smith. "-". . p. 2164,2167. Retrieved 1949.
• 5、 Tohma,Mahara,Takeshita,Kurosawa,Ikegawa,Nittono. "Synthesis of the 1β-hydroxylated bile acids and identification of 1β,3α,7α-trihydroxy- and 1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acids in human meconium". . p. 3071 - 3073. Retrieved 1985.