3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid

Base Information

• Chemical Name: 3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid
• CAS No.: 547-98-8
• Molecular Formula: C27H46O5
• Molecular Weight: 450.659
• DSSTox Substance ID: DTXSID80862168
• Nikkaji Number: J40.090D
• Wikidata: Q27103052
• Metabolomics Workbench ID: 36683
• Mol file: 547-98-8.mol

Synonyms:3 alpha,7 alpha,12 alpha-trihydroxy-5-beta-cholestan-26-oic acid;3,7,12-trihydroxycholestan-26-oic acid;3,7,12-trihydroxycholestan-26-oic acid, (25R)-isomer;3,7,12-trihydroxycholestan-26-oic acid, (25S)-isomer

Chemical Property of 3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid

Chemical Property:

• Vapor Pressure: 7.56E-08mmHg at 25°C
• Boiling Point: 409.4°C at 760 mmHg
• Flash Point: 215.5°C
• PSA: 97.99000
• Density: 1.134g/cm³
• LogP: 4.47490
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Ethanol (Slightly), Methanol (Sl
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 450.33452456
• Heavy Atom Count: 32
• Complexity: 696

Purity/Quality:

98%,99%, ^*data from raw suppliers

Trihydroxycholestanoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)C(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C(=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](C4)O)C)O)O)C
• Uses: 3α,7α,12α-Trihydroxycoprostanic Acid is a precursor of Cholic Acid (C432600), it undergoes side chain oxidation during the synthesis of bile acids. It was found that Zellweger’s syndrome patients have abnormal mitochondrial structure, the organelle that is responsible for the side chain oxidation, and as a consequence, excess amounts of 3α,7α,12α-Trihydroxycoprostanic Acid.

Technology Process of 3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid

There total 9 articles about 3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-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: 60.0%

3α,7α,12α-trihydroxy-25-carboxy-5β-cholestan-26-oic acid (264128-73-6) → Trihydroxycholestanoic acid (547-98-8)

Guidance literature:

With lithium chloride; In dimethyl sulfoxide; at 160 ℃; for 1h;

DOI:10.1016/S0039-128X(99)00099-9

Reference yield:

3α,7α,12α-Trihydroxy-5β-cholesten-24-26-saeure (5226-26-6) → Trihydroxycholestanoic acid (547-98-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; In acetic acid;

Reference yield:

3α,7α,12α-trihydroxy-5β-cholan-24-al (6542-40-1) → Trihydroxycholestanoic acid (547-98-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) benzene, (ii) KOH, MeOH

2: H₂ / PtO₂ / acetic acid

With hydrogen; platinum(IV) oxide; In acetic acid;

upstream raw materials:

3α,7α,12α-Trihydroxy-5β-cholesten-24-26-saeure

3α,7α,12α-trihydroxy-25-carboxy-5β-cholestan-26-oic acid

cholic acid triformate

3α,7α,12α-triformyloxy-5β-24-hydroxy-cholane

Downstream raw materials:

(25RS)-3α,7α-dihydroxy-5β-cholestan-26-oic acid

methyl 3α,7α-diacetoxy-12-oxo-5β-cholestan-26-oate-12-tosylhydrazone

cholic acid

Refernces

• 1、 Briggs. "Partial synthesis of 25D- and 25L-cholestanoic acids from some common bile acids.". . p. 1431 - 1434. Retrieved 2007/10/15.