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HomeProduct name listCOPROSTANOL

COPROSTANOL

Synonym(s):5β-Cholestan-3β-ol

  • CAS NO.:360-68-9
  • Empirical Formula: C27H48O
  • Molecular Weight: 388.68
  • MDL number: MFCD00068259
  • EINECS: 206-638-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-28 16:48:35
COPROSTANOL Structural

What is COPROSTANOL?

The Uses of COPROSTANOL

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).

The Uses of COPROSTANOL

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

What are the applications of Application

Coprostan-3-ol is a common biomarker for the presence of human faecal matter in the environment

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.]

Properties of COPROSTANOL

Melting point: 101°
Boiling point: 454.32°C (rough estimate)
alpha  D18 +28° (c = 1.8 in CHCl3)
Density  0.9506 (rough estimate)
refractive index  1.5250 (estimate)
storage temp.  Refrigerator
solubility  Chloroform (Slightly), Ethylacetate (Slightly)
pka 15.14±0.70(Predicted)
form  Solid
color  White to Off-White
EPA Substance Registry System Coprosterol (360-68-9)

Safety information for COPROSTANOL

Computed Descriptors for COPROSTANOL

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