12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid
• CAS No.: 4185-01-7
• Molecular Formula: C24H38O4
• Molecular Weight: 390.563
• UNII: ID36RLU01B
• Nikkaji Number: J324.809G
• Wikidata: Q27160053
• Metabolomics Workbench ID: 36409
• Mol file: 4185-01-7.mol

Synonyms:3-oxodeoxycholic acid;4185-01-7;12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid;12alpha-Hydroxy-3-oxo-5beta-cholanoic acid;CCRIS 3989;3-dehydrodeoxycholic acid;ID36RLU01B;(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]pentanoic acid;3-oxodeoxycholate;3-Dehydrodeoxycholate;12alpha-hydroxy-3-keto-5beta-cholan-24-oic acid;12-ALPHA-HYDROXY-3-OXO-5-BETA-CHOLANOICACID;(5beta,12alpha)-12-hydroxy-3-oxocholan-24-oic acid;(5beta,12alpha)-12-hydroxy-3-oxocholan-24-oate;3-Keto-DCA;UNII-ID36RLU01B;SCHEMBL10946232;CHEBI:88104;12a-Hydroxy-3-oxo-5b-cholanoate;3-Oxo-12-hydroxy-5-cholanoic Acid;LMST04010168;12a-Hydroxy-3-oxo-5b-cholanoic acid;5beta-Cholanic acid-12alpha-ol-3-one;12alpha-Hydroxy-3-oxo-5beta-cholanoate;12a-Hydroxy-3-oxo-5b-cholan-24-Oate;12a-Hydroxy-3-keto-5b-cholan-24-Oate;12a-Hydroxy-3-oxo-5b-cholan-24-Oic acid;12alpha-hydroxy-3-keto-5beta-cholanic acid;LS-188319;12a-Hydroxy-3-keto-5b-cholan-24-Oic acid;3-Oxo-12alpha-hydroxy-5beta-cholanoic Acid;(5b,12a)-12-Hydroxy-3-oxocholan-24-Oate;12alpha-Hydroxy-3-keto-5beta-cholan-24-Oate;(5b,12a)-12-Hydroxy-3-oxocholan-24-Oic acid;A902947;3-OXO-12.ALPHA.-HYDROXYCHOLAN-24-OIC ACID;Q27160053;12.ALPHA.-HYDROXY-3-OXO-5.BETA.-CHOLANOIC ACID;3-OXO-12.ALPHA.-HYDROXY-5.BETA.-CHOLANOIC ACID;12.ALPHA.-HYDROXY-3-KETO-5.BETA.-CHOLANOIC ACID;5.BETA.-CHOLANIC ACID, 12.ALPHA.-HYDROXY-3-OXO-;12.ALPHA.-HYDROXY-3-OXO-5.BETA.-CHOL-24-OIC ACID

Chemical Property of 12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid

Chemical Property:

• Vapor Pressure: 3.42E-14mmHg at 25°C
• Melting Point: >105°C (dec.)
• Boiling Point: 545.9°Cat760mmHg
• Flash Point: 298°C
• PSA: 74.60000
• Density: 1.124g/cm³
• LogP: 4.68610
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 390.27700969
• Heavy Atom Count: 28
• Complexity: 645

Purity/Quality:

97% ^*data from raw suppliers

3-Oxo-12α-hydroxy-5β-cholanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(=O)C4)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[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: 3-Oxo-12a-hydroxy-5β-cholanoic Acid is a keto bile acid derivative.

Technology Process of 12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid

There total 6 articles about 12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid 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: 61.0%

sodium cholate (302-95-4) → 3-keto-12α-hydroxy-5β-cholan-24-oic acid (4185-01-7) + 3,12-dioxo-7-deoxycholic acid (2958-05-6)

Guidance literature:

With Rhodococcus erythropolis ECS₂₅; In water; at 28 ℃; for 24h; Microbiological reaction;

DOI:10.1002/cbdv.201500300

Reference yield:

Deoxycholic acid (83-44-3) → cholic acid (81-25-4) + 3-keto-12α-hydroxy-5β-cholan-24-oic acid (4185-01-7)

Guidance literature:

With scopulariopsis brevicaulis VKM F-406; In methanol; at 29 ℃; for 240h; Reagent/catalyst; Microbiological reaction;

DOI:10.1016/j.steroids.2015.12.015

Reference yield:

methyl deoxycholate (3245-38-3) → 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 aluminum tri-tert-butoxide; acetone; benzene;

DOI:10.1021/ja01235a011

upstream raw materials:

methyl deoxycholate

cyclohexanone

(R)-methyl 4-((5R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Deoxycholic acid

Downstream raw materials:

methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate

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

12-keto-5β-cholan-24-oic acid methyl ester