360-68-9

Basic information

• Product Name: COPROSTANOL
• Synonyms: 5BETA(H)-CHOLESTAN-3BETA-OL;5-BETA-CHOLESTANE-3-BETA-OL;5BETA-CHOLESTAN-3BETA-OL;COPROSTEROL;COPROSTANOL;COPROSTAN-3B-OL;COPROSTAN-3-OL;(3-beta,5-beta)-cholestan-3-o
• CAS NO: 360-68-9
• Molecular Formula: C27H48O
• Molecular Weight: 388.67
• EINECS: 206-638-8
• Mol File: 360-68-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 101°
• Boiling Point: 454.32°C (rough estimate)
• Flash Point: 190.7ºC
• Appearance: WHITE POWDER
• Density: 0.9506 (rough estimate)
• Vapor Pressure: 3.26E-10mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethylacetate (Slightly)
• PKA: 15.14±0.70(Predicted)
• CAS DataBase Reference: COPROSTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: COPROSTANOL(360-68-9)
• EPA Substance Registry System: COPROSTANOL(360-68-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 360-68-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 360-68-9 differently. You can refer to the following data:
1. 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).
2. It has been used as an internal standard for the determination of total amounts of cholesterol and 7-dehydrocholesterol reductase by GC/MS.

General Description

Coprostan-3-ol is a cholesterol derivative that can be prepared from 5β-cholestan-3-one via reduction.

Purification Methods

A possible impurity is the 3-ol from which it can be separated by chromatography on Al2O3 and eluting with Et2O/*C6H6 (1:24) whereby the 3-ol runs first (m 116-117o) and further elution gives the pure coprosterol (m 99-101o). Crystallise it from MeOH or aqueous EtOH. Its solubility is 0.79% in H2O at 25o. [Bridgewater & Shoppee J Chem Soc 1709 1953, Shoppee & Summers J Chem Soc 687 1950.]

InChI:InChI=1/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21-,22-,23-,24-,25-,26-,27+/m0/s1

Upstream product

• 64-17-5 ethanol 
• 57-88-5 cholesterol 
• 141-52-6 sodium ethanolate 
• 601-53-6 coprostanone 
• 54947-68-1 ethyl-(3β-hydroxy-cholesten-(5)-yl-(7α))-ether 
• 113349-59-0 5β-cholesta-8,14-dien-3β-ol 
• 517-10-2 allocholesterol 
• 516-92-7 epicoprostanol 
• 115792-56-8 5β-cholestan-3β-ylamine 
• 601-57-0 Cholest-4-en-3-one 
• 71-41-0 pentan-1-ol 
• 1941-84-0 sodium pentanolate 
• 3986-89-8 (20S)-3-oxopregn-4-ene-20-carboxaldehyde 
• 40736-33-2 (20S)-20-hydroxymethylpregn-4-en-3-one 

Downstream Products

• 56784-81-7 phthalic acid mono-(5β-cholestan-3β-yl ester) 
• 601-53-6 coprostanone 
• 1177-97-5 3.4-seco-5β-cholestanedioic acid-(3.4) 
• 566-88-1 cholestan-3-one 
• 4525-03-5 1'H-5β-cholest-3-eno[3,4-b]indole 
• 102582-57-0 trans-cinnamic acid-(5β-cholestanyl-(3β)-ester) 
• 51646-11-8 3β-benzoyloxy-5β-cholestane 
• 18880-50-7 3β-trimethylsilyloxy-5β-cholestan 
• 64714-04-1 α-Cholestanyloxystyrol 
• 64714-01-8 O-benzyl β-cholestanol 
• 14582-65-1 Phenyl-3α-cholestansulfid 

Relevant articles and documents

Method for synthesizing cholesterol by taking BA as raw material

The invention discloses a method for synthesizing cholesterol by taking BA as a raw material. A plant source raw material 21-hydroxy-20-methylpregna-4-en-3-one, also known as Shuangjiangchun or BA is taken as a raw material, and the cholesterol is synthesized by the steps of oxidation, Wittig reaction, acetylation, reduction, selective hydrogenation reduction and the like. The raw materials for synthesizing cholesterol are plant sources, the price is low, the safety is high, the risk of pathogenic bacteria and virus infection is avoided, and the synthesis method is easy to operate, high in yield, few in side reaction, environmentally friendly, good in economical efficiency and convenient for industrial production; and the invention solves the safety problem of the existing cholesterol product and the problems of high cost, environmental unfriendliness and unsuitability for large-scale industrial production in the synthesis technology.

Cleavage of a p-cyanobenzyl group from protected alcohols, amines, and thiols using triethylgermyl sodium

Alcohols, amines, and thiols protected with a p-cyanobenzyl group can be easily and quantitatively deprotected using triethylgermyl sodium under mild conditions.

The reaction of alkyl peroxy radicals

Secondary alkyl peroxy radicals generated from 4-phenyl-2-butyl-, 2-nonyl- and 3α-cholestanyl hydroperoxides at 45°C undergo Russell termination reactions in preference to non-terminating decomposition reactions. Non-terminating decomposition of 2-nonyl peroxy radicals afforded 2,5-nonanedione and 2,5-nonanediol due to intramolecular hydrogen abstraction reactions of alkoxy radicals. The radicals derived from 2-methyl-4-phenyl-2-butyl-, 2-methyl-5-phenyl-2-pentyl- and 2-methyl-6-phenyl-2-hexyl hydroperoxides afforded benzylic functionalized products due to intermolecular reactions. 2-Hexylperoxy radicals generated in excess alcohols ineffectively abstracted the α-hydrogens of alcohols. These results demonstrate the low reactivity of alkyl peroxy radicals.