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

Base Information

• Chemical Name: 3alpha,6beta,7alpha,12alpha-Tetrahydroxy-5beta-cholan-24-oic Acid
• CAS No.: 80875-93-0
• Molecular Formula: C24H40 O6
• Molecular Weight: 424.578
• DSSTox Substance ID: DTXSID201261162
• Nikkaji Number: J353.599A
• Wikidata: Q63392374
• Metabolomics Workbench ID: 36361
• Mol file: 80875-93-0.mol

Synonyms:3alpha,6beta,7alpha,12alpha-Tetrahydroxy-5beta-cholan-24-oic Acid;(4R)-4-[(3R,5R,6S,7S,8R,9S,10R,12S,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;80875-93-0;3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid;3alpha,6beta,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid;SCHEMBL1492077;CHEBI:166709;DTXSID201261162;LMST04010120;3a,6b,7a,12a-Tetrahydroxy-5b-cholanoate;3a,6b,7a,12a-Tetrahydroxy-5b-cholan-24-oic acid;Q63392374

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

Chemical Property:

• 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

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

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

There total 12 articles about 3alpha,6beta,7alpha,12alpha-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: 84.0%

methyl 3α,12α-diacetoxy-6β,7α-dihydroxy-5β-cholanoate (133181-59-6) → 3α,6β,7α,12α-tetrahydroxy-5β-cholan-24-oic acid (80875-93-0)

Guidance literature:

With potassium hydroxide; In methanol; for 10h; Heating;

DOI:10.1016/0039-128X(90)90048-G

Reference yield:

7-ketodeoxycholic acid (911-40-0) → 3α,6β,7α,12α-tetrahydroxy-5β-cholan-24-oic acid (80875-93-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrogenchloride / Reflux

2.1: pyridine / dmap / dichloromethane / 12 h / 20 °C

3.1: bromine; acetic acid / 48 h / 20 °C

4.1: zinc(II) tetrahydroborate / benzene; diethyl ether / 22 h / 20 °C

4.2: 1 h / Reflux

5.1: 2,6-di-tert-butyl-4-methyl-phenol; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / Reflux

6.1: boron trifluoride diethyl etherate / N,N-dimethyl-formamide / 1 h / 20 °C

7.1: potassium hydroxide / methanol / 10 h / Reflux

With pyridine; hydrogenchloride; zinc(II) tetrahydroborate; 2,6-di-tert-butyl-4-methyl-phenol; boron trifluoride diethyl etherate; bromine; acetic acid; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; dmap; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

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:

methyl 3α,12α-diacetoxy-5β-chol-6-en-24-oate

methyl 3α,12α-diacetoxy-6β,7α-dihydroxy-5β-cholanoate

(R)-4-((3R,5R,8R,9S,10R,12S,13R,14S,17R)-3,12-Diacetoxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[6,7]cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

methyl 6α-bromo-3α,12α-acetoxy-7-oxo-5β-cholanoate

Refernces

• 1、 Yoshii, Michiko,Kihira, Kenji,Shoda, Junichi,Osuga, Toshiaki,Hoshita, Takahiko. "Identification of 3,6,7,12-tetrahydroxy-5β-cholan-24-oic acids in human biologic fluids". . p. 512 - 515. Retrieved 2007/10/02.
• 2、 Kurosawa,Mahara,Nittono,Tohma. "Synthesis of 6-hydroxylated bile acids and identification of 3α,6α,7α,12α-tetrahydroxy-5β-cholan-24-oic acid in human meconium and neonatal urine". . p. 557 - 559. Retrieved 2007/10/02.