7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid
• CAS No.: 4185-00-6
• Molecular Formula: C24H38O4
• Molecular Weight: 390.563
• UNII: 3MY7NM9XNW
• DSSTox Substance ID: DTXSID601272325
• Nikkaji Number: J324.807K
• Wikidata: Q27160049
• Metabolomics Workbench ID: 36402
• ChEMBL ID: CHEMBL271172
• Mol file: 4185-00-6.mol

Synonyms:4185-00-6;7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid;7a-Hydroxy-3-oxo-5b-cholanoic acid;3-oxochenodeoxycholic acid;3MY7NM9XNW;UNII-3MY7NM9XNW;(5beta,7alpha)-7-hydroxy-3-oxocholan-24-oic acid;CHEMBL271172;CHEBI:88097;3-Oxo-7alpha-hydroxycholan-24-oic acid;(4R)-4-[(5R,7R,8R,9S,10S,13R,14S,17R)-7-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;Cholan-24-oic acid, 7-hydroxy-3-oxo-, (5beta,7alpha)-;3-Keto-CDCA;3-dehydrochenodeoxycholic acid;SCHEMBL24001497;DTXSID601272325;BDBM50375578;LMST04010161;7alpha-Hydroxy-3-oxo-5beta-cholanoate;3-Oxo-7alpha-hydroxy-5beta-cholanoic Acid;7alpha-Hydroxy-3-oxo-5beta-cholanoic acid;3-Oxo-7alpha-hydroxy-5beta-cholan-24-oic acid;(5beta,7alpha)-7-Hydroxy-3-oxo-cholan-24-oate;3-OXO-7.ALPHA.-HYDROXYCHOLAN-24-OIC ACID;A902946;(5beta,7alpha)-7-Hydroxy-3-oxo-cholan-24-oic acid;Q27160049;7.ALPHA.-HYDROXY-3-OXO-5.BETA.-CHOLAN-24-OIC ACID;(5.BETA.,7.ALPHA.)-7-HYDROXY-3-OXOCHOLAN-24-OIC ACID;CHOLAN-24-OIC ACID, 7-HYDROXY-3-OXO-, (5.BETA.,7.ALPHA.)-

Chemical Property of 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid

Chemical Property:

• Melting Point: 111-114 °C
• Boiling Point: 545.9±25.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 74.60000
• Density: 1.124±0.06 g/cm3(Predicted)
• LogP: 4.68610
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (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:

98% ^*data from raw suppliers

3-Oxo-7α-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(CCC3C2C(CC4C3(CCC(=O)C4)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CCC(=O)C4)C)O)C
• Uses: 3-Oxo-7a-hydroxy-5β-cholanoic Acid is a keto bile acid derivative.

Technology Process of 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid

There total 4 articles about 7alpha-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: 86.0%

sodium chenodeoxycholate (2646-38-0) → Dehydrochenodeoxycholic acid (4185-00-6)

Guidance literature:

With DL-dithiothreitol; NAD; In water; ethyl acetate; for 40h; Ambient temperature; 3α-hydroxysteroid dehydrogenase, serum albumin, pyruvate/lactic dehydrogenase, potassium phosphate buffer pH=8.5;

DOI:10.1021/jo00236a018

Reference yield: 40.0%

chenodeoxycholic acid (474-25-9) → Dehydrochenodeoxycholic acid (4185-00-6) + 7α-hydroxy-3-oxochol-4-en-24-oic acid (14772-95-3) + (R)-4-((3R,5R,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-3-methoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

Guidance literature:

In water; at 37 ℃; for 120h; grown cells of the bacterium Alcaligenes recti (enzymic methylation);

DOI:10.1016/0039-128X(93)90057-T

Reference yield:

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3) → Dehydrochenodeoxycholic acid (4185-00-6)

Guidance literature:

With sodium hydroxide; In methanol; for 4h; Heating;

DOI:10.1016/j.tet.2006.02.052

upstream raw materials:

chenodeoxycholic acid

sodium chenodeoxycholate

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate

Downstream raw materials:

methyl 3β,7α-dihydroxy-5α-cholan-24-oate

7α-hydroxy-5β-cholanoic acid

Refernces

• 1、 Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Mari, Lara. "Two-way enantioselective control in the epoxidation of alkenes with the keto bile acid-Oxone system". . p. 4482 - 4490. Retrieved 2007/10/03.
• 2、 Mazumder, Ipsita,Mahato, Shashi B.. "Bile acid transformations by Alcaligenes recti". . p. 79 - 86. Retrieved 2007/10/02.