3b-Hydroxy-5-cholenoic acid

Base Information

• Chemical Name: 3b-Hydroxy-5-cholenoic acid
• CAS No.: 5255-17-4
• Molecular Formula: C24H38O3
• Molecular Weight: 374.564
• DSSTox Substance ID: DTXSID901317558
• Nikkaji Number: J21.489B
• Wikidata: Q27161420
• Metabolomics Workbench ID: 36442
• ChEMBL ID: CHEMBL169264
• Mol file: 5255-17-4.mol

Synonyms:3 beta-hydroxy-5-cholenic acid;3 beta-hydroxy-5-cholenoic acid;3 beta-hydroxy-delta 5-cholenic acid;3 beta-hydroxy-delta 5-cholenic acid, sodium salt;3beta-hydroxy-delta5-cholenic acid

Chemical Property of 3b-Hydroxy-5-cholenoic acid

Chemical Property:

• Appearance/Colour: WHITE TO OFF-WHITE POWDER
• Vapor Pressure: 4.99E-17mmHg at 25°C
• Melting Point: 232°C
• Refractive Index: -39.5 ° (C=1, Dioxane)
• Boiling Point: 522.8 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 284.1 °C
• PSA: 57.53000
• Density: 1.11 g/cm³
• LogP: 5.42720
• Storage Temp.: Refrigerator
• Solubility.: Dioxane (Slightly, Sonicated), DMF (Slightly), DMSO (Slightly, Heated,. Sonicate
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 374.28209507
• Heavy Atom Count: 27
• Complexity: 625

Purity/Quality:

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

5-Cholenic acid-3β-ol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Description: Cholenic acid is a monohydroxy bile acid. It is a cholesterol oxidation product formed by 7α-hydroxylation of 27-hydroxycholesterol (Item Nos. 14790 | 14791), as well as a precursor in the biosynthesis of chenodeoxycholic acid . Levels of cholenic acid are increased in patients with neonatal liver disease harboring mutations in CYP7A1, the gene encoding 7α-hydroxylase, as well as in patients with intrahepatic and extrahepatic cholestasis.
• Uses: 5-Cholenic Acid-3β-ol is a bile acid of which the metabolism in humans results in the primary bile acids lithocholic acid and chenodeoxycholic. It is found in hgher concentrations in meconium of premature human babies when compared to full term babies.

Technology Process of 3b-Hydroxy-5-cholenoic acid

There total 19 articles about 3b-Hydroxy-5-cholenoic 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: 89.6%

3β-acetoxy-5-cholenic acid (19462-13-6) → 3β-hydroxy-5-cholenoic acid (5255-17-4)

Guidance literature:

With sodium hydroxide; In methanol; for 4h; Ambient temperature;

DOI:10.1016/0040-4020(82)80080-X

Reference yield: 80.0%

methyl 5-cholenoate (20231-57-6) → 3β-hydroxy-5-cholenoic acid (5255-17-4)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; Inert atmosphere;

DOI:10.3390/md12063091

Reference yield:

3β-acetoxy-5α,6β-dibromocholestane (514-50-1) → prasterone acetate (853-23-6) + 3β-hydroxy-5-cholenoic acid (5255-17-4)

Guidance literature:

With chromium(VI) oxide; acetic acid; Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Erwaermen des erhaltenen Reaktionsprodukts mit methanol. Kalilauge;

DOI:10.1021/ja01311a036 DOI:10.1021/ja01851a038 DOI:10.1002/hlca.193501801132

upstream raw materials:

methyl 3α,6α-ditosyloxy-5β-cholan-24-oate

potassium acetate

Hyodeoxycholic Acid

3β-acetoxy-5α,6β-dibromocholestane

Downstream raw materials:

methyl 5-cholenoate

24,24-diphenyl-cholene-(5)-diol-(3β,24)

5α-cholanic acid-3,6-dione

3β-(t-butyldimethylsilyloxy)-5-cholenic acid methyl ester

Refernces

• 1、 Shen, Yuehai,Wen, Jianxun. "A new route for synthesizing cholesterol analogs with fluorocarbon side chains and their liquid-crystalline aliphatic esters". . p. 13 - 15. Retrieved 2007/10/03.
• 2、 Lehmann,Tepper,Hilgetag. "Progesterone from 3-alpha-hydroxy-6-oxo-5-alpha-cholic acid". . p. 176 - 181. Retrieved 2007/10/06.