3alpha,6beta,7beta,12beta-Tetrahydroxy-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 3alpha,6beta,7beta,12beta-Tetrahydroxy-5beta-cholan-24-oic Acid
• CAS No.: 140852-41-1
• Molecular Formula: C₂₄H₄₀O₆
• Molecular Weight: 424.578
• DSSTox Substance ID: DTXSID101197766
• Nikkaji Number: J468.299H
• Metabolomics Workbench ID: 36364
• Mol file: 140852-41-1.mol

Synonyms:140852-41-1;3alpha,6beta,7beta,12beta-Tetrahydroxy-5beta-cholanoic Acid;3alpha,6beta,7beta,12beta-Tetrahydroxy-5beta-cholan-24-oic Acid;3a,6b,7b,12b-Tetrahydroxy-5b-cholanoic acid;(4R)-4-[(3R,5R,6S,7R,8R,9S,10R,12R,13R,14S,17R)-3,6,7,12-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;SCHEMBL2547217;DTXSID101197766;LMST04010123;3a,6b,7b,12b-Tetrahydroxy-5b-cholanoate;(3a,5b,6b,7b,12b)-3,6,7,12-Tetrahydroxy-cholan-24-oic acid;(3alpha,5beta,6beta,7beta,12beta)-3,6,7,12-Tetrahydroxycholan-24-oic acid

Chemical Property of 3alpha,6beta,7beta,12beta-Tetrahydroxy-5beta-cholan-24-oic Acid

Chemical Property:

• Vapor Pressure: 4.99E-17mmHg at 25°C
• Refractive Index: 1.574
• Boiling Point: 602.5°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• 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:

99%min ^*data from raw suppliers

3α,6β,7β,12β-Tetrahydroxy-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(CC3C2C(C(C4C3(CCC(C4)O)C)O)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@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)O)C
• Uses: 3α,6β,7β,12β-Tetrahydroxy-5β-cholanoic Acid is a bile acid.

Technology Process of 3alpha,6beta,7beta,12beta-Tetrahydroxy-5beta-cholan-24-oic Acid

There total 3 articles about 3alpha,6beta,7beta,12beta-Tetrahydroxy-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:

(R)-4-((3R,5S,8R,9S,10S,12R,13R,14S,17R)-3,12-Diacetoxy-10,13-dimethyl-2,3,4,5,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester (140711-21-3) → 3α,6β,7β,12β-tetrahydroxy-5β-cholan-24-oic acid (140852-41-1)

Guidance literature:

With potassium hydroxide; osmium(VIII) oxide; 4-methylmorpholine N-oxide; Yield given. Multistep reaction; 1.) tertiary butanol, THF, water, RT, 18 h, 2.) reflux, 2 h;

DOI:10.1016/0039-128X(92)90067-J

Reference yield:

methyl ester of 3α,12β-dihydroxy-5β-chol-6-en-24-oic acid (140711-19-9) → 3α,6β,7β,12β-tetrahydroxy-5β-cholan-24-oic acid (140852-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 1.) N-methylmorpholine N-oxide, osmium tetroxide, 2.) 5percent methanolic KOH / 1.) tertiary butanol, THF, water, RT, 18 h, 2.) reflux, 2 h

With pyridine; potassium hydroxide; osmium(VIII) oxide; 4-methylmorpholine N-oxide;

DOI:10.1016/0039-128X(92)90067-J

Reference yield:

→ 3α,6β,7β,12α-Tetrahydroxy-5β-cholansaeure-(24) (63266-88-6,75110-48-4,80875-92-9,80875-93-0,117997-15-6,133269-41-7,133269-42-8,138233-70-2,140852-40-0,140852-41-1)

Guidance literature:

6β,7β-Dihydroxy-3α,12α-diacetoxy-5β-cholansaeure-methylester, 2n-NaOH/Methoxyethanol (Kochen);

upstream raw materials:

(R)-4-((3R,5S,8R,9S,10S,12R,13R,14S,17R)-3,12-Diacetoxy-10,13-dimethyl-2,3,4,5,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

methyl ester of 3α,12β-dihydroxy-5β-chol-6-en-24-oic acid

Refernces