Coprosterol

Title: Coprosterol
CAS Registry Number: 360-68-9
CAS Name: (3b,5b)-Cholestan-3-ol
Additional Names: 3b-coprostanol; stercorin
Molecular Formula: C27H48O
Molecular Weight: 388.67
Percent Composition: C 83.44%, H 12.45%, O 4.12%
Literature References: Found in feces of man and of carnivorous animals: Bondzynski, Humnicki, Z. Physiol. Chem. 22, 396 (1896); Wells et al., Arch. Biochem. Biophys. 57, 437 (1955); Samuel et al., J. Chromatogr. 14, 508 (1964). Prepn from coprostenone: Ruzicka et al., Helv. Chim. Acta 17, 1407 (1934); Shoppee, Summers, J. Chem. Soc. 1950, 687. From coprostenol: Schönheimer, Evans, J. Biol. Chem. 114, 567 (1936); Ruzicka et al., Helv. Chim. Acta 21, 498 (1938); Agashe, Summers, J. Chem. Soc. 1957, 3107; Dart, Henbest, ibid. 1960, 3563. Prepn from cholesterol: Rosenfeld, Gallagher, Steroids 4, 515 (1964).
Properties: Needles from methanol, mp 101°. [a]D18 +28° (c = 1.8 in CHCl3). Freely sol in ether, chloroform, benzene; slightly sol in methanol (one gram dissolves in 145 ml MeOH). Insol in water.
Melting point: mp 101°
Optical Rotation: [a]D18 +28° (c = 1.8 in CHCl3)
Coptine Coptis Cord Factor(s) Coriamyrtin Coriander

Coprostanol
Coprostanol
Identifiers
CAS number 360-68-9 YesY
ChemSpider 19951861 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C27H48O
Molar mass 388.6756 g/mol
Melting point 102 °C; 216 °F; 375 K
Hazards
Flash point Non-flammable
Related compounds
Related Stanols 24-ethyl coprostanol
5α-cholestanol
epi-coprostanol
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

5β-Coprostanol (5β-cholestan-3β-ol) is a 27-carbon stanol formed from the biohydrogenation of cholesterol (cholest-5en-3β-ol) in the gut of most higher animals and birds. This compound has frequently been used as a biomarker for the presence of human faecal matter in the environment.