Coprosterol

Base Information

• Chemical Name: Coprosterol
• CAS No.: 360-68-9
• Molecular Formula: C₂₇H₄₈O
• Molecular Weight: 388.678
• European Community (EC) Number: 206-638-8
• NSC Number: 18175,5060
• UNII: PPT67I3S74
• DSSTox Substance ID: DTXSID1052036
• Nikkaji Number: J5.697I
• Wikipedia: Coprostanol
• Wikidata: Q5168983
• Metabolomics Workbench ID: 34390
• ChEMBL ID: CHEMBL2048325
• Mol file: 360-68-9.mol

Synonyms:5 alpha Cholestan 3 alpha ol;5 alpha Cholestan 3 beta ol;5 alpha-Cholestan-3 alpha-ol;5 alpha-Cholestan-3 beta-ol;5 beta Cholestan 3 beta ol;5 beta-Cholestan-3 alpha-ol;5 beta-Cholestan-3 beta-ol;beta Cholestanol;beta-Cholestan-3 beta-ol, 5;beta-Cholestanol;beta-ol, 5 beta-Cholestan-3;Cholestan 3 ol;Cholestan-3-ol;Cholestanol;Cholestanol, (3alpha, 5beta)-Isomer;Coprostanol;Coprosterol;Dihydrocholesterol

Chemical Property of Coprosterol

Chemical Property:

• Appearance/Colour: WHITE POWDER
• Vapor Pressure: 3.26E-10mmHg at 25°C
• Melting Point: 101-103ºC
• Refractive Index: 1.5250 (estimate)
• Boiling Point: 455.5ºC at 760 mmHg
• PKA: 15.14±0.70(Predicted)
• Flash Point: 190.7ºC
• PSA: 20.23000
• Density: 0.956 g/cm³
• LogP: 7.46860
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethylacetate (Slightly)
• 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:

99.5% ^*data from raw suppliers

Coprostan-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Cholesterol and Derivatives
• 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: Coprostan-3-ol is a 27-carbon stanol resulted from biohydrogenation of cholesterol in the gut of most higher animals. It is a common biomarker for the presence of human faecal matter in the environment (1,2).This compound is a contaminant of emerging concern (CECs). It has been used as an internal standard for the determination of total amounts of cholesterol and 7-dehydrocholesterol reductase by GC/MS.

Technology Process of Coprosterol

There total 55 articles about Coprosterol 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: 84.0%

Trifluoro-methanesulfonic acid (3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester → 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 18-crown-6 ether; cesium acetate; In benzene; for 24h; Product distribution; Heating;

DOI:10.1016/0040-4039(96)01333-0

upstream raw materials:

ethanol

cholesterol

sodium ethanolate

epicoprostanol

Downstream raw materials:

coprostanone

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

O-Cholestanylselenobenzoat

epi-cholestanol benzoate

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.