epi-Coprostanol

Base Information

• Chemical Name: epi-Coprostanol
• CAS No.: 516-92-7
• Molecular Formula: C27H48 O
• Molecular Weight: 388.678
• Hs Code.: 2906130000
• NSC Number: 18182
• UNII: UFH3K1F9EG
• DSSTox Substance ID: DTXSID7046700
• Nikkaji Number: J39.847K
• Wikidata: Q27291059
• Metabolomics Workbench ID: 36782
• ChEMBL ID: CHEMBL1998721
• Mol file: 516-92-7.mol

Synonyms:3-alpha-hydroxy-5beta-cholestanol;epicoprostanol

Chemical Property of epi-Coprostanol

Chemical Property:

• Vapor Pressure: 3.26E-10mmHg at 25°C
• Boiling Point: 455.5°Cat760mmHg
• Flash Point: 190.7°C
• PSA: 20.23000
• Density: 0.956g/cm³
• LogP: 7.46860
• Storage Temp.: 2-8°C
• XLogP3: 9.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 388.370516150
• Heavy Atom Count: 28
• Complexity: 540

Purity/Quality:

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

Epicoprostanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• Uses: 5β-Cholestan-3α-ol was used as internal standard for analysis of sterols in plasma by GC and HPLC.

Technology Process of epi-Coprostanol

There total 68 articles about epi-Coprostanol 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: 100.0%

2-[(3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-furan (111222-20-9) → Coprostanol (80-97-7,360-68-9,516-92-7,516-95-0,566-84-7,14615-12-4,16720-60-8,17608-41-2,18769-46-5,27409-41-2,56193-35-2,57759-49-6,73465-18-6,103365-91-9,105119-51-5)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 1h; Ambient temperature;

DOI:10.1055/s-1987-27903

Reference yield: 97.0%

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxymethyl]-benzonitrile → Coprostanol (80-97-7,360-68-9,516-92-7,516-95-0,566-84-7,14615-12-4,16720-60-8,17608-41-2,18769-46-5,27409-41-2,56193-35-2,57759-49-6,73465-18-6,103365-91-9,105119-51-5)

Guidance literature:

With Triethylgermyl-natrium; In 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; at 50 ℃; for 15h;

DOI:10.1246/cl.2002.1032

Reference yield: 75.0%

coprostanone (601-53-6) → Coprostanol (80-97-7,360-68-9,516-92-7,516-95-0,566-84-7,14615-12-4,16720-60-8,17608-41-2,18769-46-5,27409-41-2,56193-35-2,57759-49-6,73465-18-6,103365-91-9,105119-51-5)

Guidance literature:

With hydrogen; carbon monoxide; In methanol; at 30 - 35 ℃; for 2.5h; under 51485.6 - 73550.8 Torr;

upstream raw materials:

ethanol

cholesterol

sodium ethanolate

coprostanone

Downstream raw materials:

Coprostanol

3α-(toluene-4-sulfonyloxy)-5β-cholestane

coprostanone

3.4-seco-5β-cholestanedioic acid-(3.4)

Refernces

• 1、 Villa, Giorgio,Povie, Guillaume,Renaud, Philippe. "Radical chain reduction of alkylboron compounds with catechols". supporting information; experimental part. p. 5913 - 5920. Retrieved 2011/06/16.
• 2、 Chen, Jian-Xin,Daeuble, John F.,Stryker, Jeffrey M.. "Phosphine effects in the copper(I) hydride-catalyzed hydrogenation of ketones and regioselective 1,2-reduction of α,β-unsaturated ketones and aldehydes. Hydrogenation of decalin and steroidal ketones and enones". . p. 2789 - 2798. Retrieved 2007/10/03.