3a,4b,7a,12a-Tetrahydroxy-5b-cholanoic acid

Base Information

• Chemical Name: 3a,4b,7a,12a-Tetrahydroxy-5b-cholanoic acid
• CAS No.: 122742-19-2
• Molecular Formula: C₂₄H₄₀O₆
• Molecular Weight: 424.578
• DSSTox Substance ID: DTXSID101195641
• Nikkaji Number: J258.761K
• Wikidata: Q76294473
• Metabolomics Workbench ID: 36357
• Mol file: 122742-19-2.mol

Synonyms:(4R)-4-[(3R,4R,5S,7R,8R,9S,10R,12S,13R,14S,17R)-3,4,7,12-tetrahydroxy-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;3a,4b,7a,12a-Tetrahydroxy-5b-cholanoic acid;122742-19-2;(3a,4b,5b,7a,12a)-3,4,7,12-tetrahydroxy-Cholan-24-oic acid;3alpha,4beta,7alpha,12alpha-Tetrahydroxy-5beta-cholan-24-oic Acid;LMST04010116;4beta-Hydroxycholic acid;SCHEMBL2552287;CHEBI:181843;DTXSID101195641;3a,4b,7a,12a-Tetrahydroxy-5b-cholanoate;3a,4b,7a,12a-Tetrahydroxy-5b-cholan-24-oate;3a,4b,7a,12a-Tetrahydroxy-5b-cholan-24-oic acid;3alpha,4beta,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid;(3alpha,4beta,5beta,7alpha,12alpha)-3,4,7,12-Tetrahydroxycholan-24-oic acid;"(R)-4-((3R,4R,5S,7R,8R,9S,10R,12S,13R,14S,17R)-3,4,7,12-tetrahydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid"

Chemical Property of 3a,4b,7a,12a-Tetrahydroxy-5b-cholanoic acid

Chemical Property:

• Vapor Pressure: 4.99E-17mmHg at 25°C
• Melting Point: 161 - 162 °C (aq. ethanol)
• Refractive Index: 1.574
• Boiling Point: 602.5°Cat760mmHg
• Flash Point: 332.2°C
• PSA: 118.22000
• Density: 1.242g/cm³
• LogP: 2.41950
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 424.28248899
• Heavy Atom Count: 30
• Complexity: 668

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4O)O)C)O)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]2[C@@H](C[C@H]4[C@@]3(CC[C@H]([C@@H]4O)O)C)O)O)C

Technology Process of 3a,4b,7a,12a-Tetrahydroxy-5b-cholanoic acid

There total 11 articles about 3a,4b,7a,12a-Tetrahydroxy-5b-cholanoic 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: 85.0%

methyl 4β,7α,12α-triacetoxy-3α-hydroxy-5β-cholan-24-oate (148785-48-2) → 3α,4β,7α,12α-tetrahydroxy-5β-cholanoic acid (122742-19-2)

Guidance literature:

With potassium hydroxide; Heating;

DOI:10.1016/0039-128X(93)90052-O

Reference yield:

methyl cholate (1448-36-8) → 3α,4β,7α,12α-tetrahydroxy-5β-cholanoic acid (122742-19-2)

Guidance literature:

Multi-step reaction with 5 steps

1: Jones reagent

2: Et₃N, N,N-dimethylaminopyridine

3: 71 percent / BF₃*Et₂O / acetic acid / 1 h / Ambient temperature

4: 90 percent / NaBH₄, MeOH / CH₂Cl₂ / 0.25 h / Ambient temperature

5: 85 percent / 2M methanolic KOH / Heating

With methanol; dmap; potassium hydroxide; sodium tetrahydroborate; jones reagent; boron trifluoride diethyl etherate; triethylamine; In dichloromethane; acetic acid;

DOI:10.1016/0039-128X(93)90052-O

Reference yield:

methyl 3-keto-7,12-diacetylcholate (4947-65-3) → 3α,4β,7α,12α-tetrahydroxy-5β-cholanoic acid (122742-19-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / BF₃*Et₂O / acetic acid / 1 h / Ambient temperature

2: 90 percent / NaBH₄, MeOH / CH₂Cl₂ / 0.25 h / Ambient temperature

3: 85 percent / 2M methanolic KOH / Heating

With methanol; potassium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; In dichloromethane; acetic acid;

DOI:10.1016/0039-128X(93)90052-O

upstream raw materials:

methyl 7α,12α-diacetoxy-3α,4β-dihydroxy-5β-cholanoate

methyl 4β,7α,12α-triacetoxy-3α-hydroxy-5β-cholan-24-oate

methyl 3-keto-7,12-diacetylcholate

methyl cholate