3beta,7alpha-Dihydroxy-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 3beta,7alpha-Dihydroxy-5beta-cholan-24-oic Acid
• CAS No.: 566-24-5
• Molecular Formula: C24H40 O4
• Molecular Weight: 392.579
• DSSTox Substance ID: DTXSID001266009
• Nikkaji Number: J21.478G
• Wikidata: Q27105124
• Metabolomics Workbench ID: 36276
• ChEMBL ID: CHEMBL3342076
• Mol file: 566-24-5.mol

Synonyms:566-24-5;3beta,7alpha-Dihydroxy-5beta-cholan-24-oic Acid;Isochenodeoxycholic acid;(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid;(4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid;CHEBI:88102;3beta,7alpha-Dihydroxy-5beta-cholanic acid;Cholan-24-oic acid, 3,7-dihydroxy-, (3beta,5beta,7alpha)-;3b,7a-dihydroxy-5b-cholanoic acid;3-epichenodeoxycholic acid;3beta-chenodeoxycholic acid;3-epi-chenodeoxycholic acid;3b,7a-Dihydroxy-5b-cholanoate;SCHEMBL1043258;CHEMBL3342076;DTXSID001266009;3b,7a-dihydroxy-5b-cholan-24-oate;LMST04010034;3b,7a-dihydroxy-5b-cholan-24-oic acid;3beta,7alpha-Dihydroxy-5beta-cholanoic acid;C17660;Q27105124

Chemical Property of 3beta,7alpha-Dihydroxy-5beta-cholan-24-oic Acid

Chemical Property:

• Vapor Pressure: 2.98E-14mmHg at 25°C
• Boiling Point: 547.1°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 298.8°C
• PSA: 77.76000
• Density: 1.128g/cm³
• LogP: 4.47790
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly, Heated), Methanol (Slightly)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 392.29265975
• Heavy Atom Count: 28
• Complexity: 605

Purity/Quality:

97% ^*data from raw suppliers

IsochenodeoxycholicAcid ^*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(C4)O)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(CC[C@@H](C4)O)C)O)C
• Uses: Isochenodeoxycholic Acid is an epimer of common bile acid Chenodeoxycholic Acid (C291900), present in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate.

Technology Process of 3beta,7alpha-Dihydroxy-5beta-cholan-24-oic Acid

There total 17 articles about 3beta,7alpha-Dihydroxy-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:

→ 4-((3R,7R)-3,7-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid (128-13-2,474-25-9,566-24-5,15357-34-3,30627-76-0,30634-99-2,41195-65-7,51446-79-8,78919-26-3,105227-28-9)

Guidance literature:

aus 3α.7α-Diacetoxy-12-oxo-5β-cholanoic Saeure;

Reference yield:

5β-3,7-diacetoxycholanic acid isopropyl ester (944409-55-6) → chenodeoxycholic acid (474-25-9) + 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Guidance literature:

5β-3,7-diacetoxycholanic acid isopropyl ester; With methanol; sodium hydroxide; water; for 7h; Heating / reflux;

With hydrogenchloride; water;

Reference yield:

sodium chenodeoxycholate (2646-38-0) → 3β,7α-dihydroxy-5β-cholan-24-oic acid (566-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / NAD, DTT / ethyl acetate; H2O / 40 h / Ambient temperature; 3α-hydroxysteroid dehydrogenase, serum albumin, pyruvate/lactic dehydrogenase, potassium phosphate buffer pH=8.5

2: 81 percent / NADH, DTT / ethanol; H2O / 30 h / 3β-hydroxysteroid dehydrogenase, formate/formate dehydrogenase, potassium phosphate buffer pH=7.2

With 1,4-dihydronicotinamide adenine dinucleotide; DL-dithiothreitol; NAD; In ethanol; water; ethyl acetate;

DOI:10.1021/jo00236a018

upstream raw materials:

sodium chenodeoxycholate

5β-3,7-diacetoxycholanic acid isopropyl ester

Downstream raw materials:

methyl (5β)-3,7-bis[2-[[(4-bromophenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate

methyl (5β)-3,7-bis[2-[[(3-fluorophenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate

C₃₃H₄₇N₃O₄S

C₃₂H₄₄FN₃O₃S