COPROSTANOL Property

Melting point:

101°

alpha 

D18 +28° (c = 1.8 in CHCl3)

Boiling point:

454.32°C (rough estimate)

Density 

0.9506 (rough estimate)

refractive index 

1.5250 (estimate)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Ethylacetate (Slightly)

form 

Solid

pka

15.14±0.70(Predicted)

color 

White to Off-White

EPA Substance Registry System

Coprosterol (360-68-9)

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

COPROSTANOL Chemical Properties,Usage,Production

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).

Uses

It has been used as an internal standard for the determination of total amounts of cholesterol and 7-dehydrocholesterol reductase by GC/MS.

Definition

ChEBI: Coprostanol is a member of the class of phytosterols that is 5beta-cholestane carrying a hydroxy substituent at the 3beta-position. It has a role as a plant metabolite, a human urinary metabolite and an environmental contaminant. It is a cholestanoid, a 3-hydroxy steroid and a member of phytosterols. It derives from a hydride of a 5beta-cholestane.

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.]