Basic information Safety Supplier Related

COPROSTANOL

Basic information Safety Supplier Related

COPROSTANOL Basic information

Product Name:
COPROSTANOL
Synonyms:
  • 5BETA(H)-CHOLESTAN-3BETA-OL
  • 5-BETA-CHOLESTANE-3-BETA-OL
  • 5BETA-CHOLESTAN-3BETA-OL
  • (3-beta,5-beta)-cholestan-3-o
  • 3beta-Hydroxy-5beta-cholestanol
  • 3-beta-Hydroxycholestane
  • 5beta-cholestanol
  • Cholestan-3-ol
CAS:
360-68-9
MF:
C27H48O
MW:
388.68
EINECS:
206-638-8
Mol File:
360-68-9.mol
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COPROSTANOL Chemical Properties

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
optical activity
+2818 (c 1.8, CHCl3)
EPA Substance Registry System
Coprosterol (360-68-9)
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Safety Information

WGK Germany 
3
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COPROSTANOL Usage And Synthesis

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.]

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