Cholestanol

Title: Cholestanol
CAS Registry Number: 80-97-7
CAS Name: (3b,5a)-Cholestan-3-ol
Additional Names: Dihydrocholesterol; 3b-hydroxycholestane; b-cholestanol
Molecular Formula: C27H48O
Molecular Weight: 388.67
Percent Composition: C 83.44%, H 12.45%, O 4.12%
Literature References: Occurs in human feces, in gallstones, in eggs. Prepn by reduction of cholesterol: Willstätter, Mayer, Ber. 41, 2199 (1908); Ellis, Gardner, Biochem. J. 12, 72 (1918). From coprostenone: Diels, Abderhalden, Ber. 39, 884 (1906). See also Bruce, Ralls, Org. Synth. coll. vol. II, 191 (1943).
Properties: Monohydrate, scales from alc, mp 141.5-142°. [a]D22 +24.2° (c = 1.3 in chloroform). One gram dissolves in about 100 ml alcohol, in 200 ml dry methanol. Freely sol in hot alc, ether, chloroform. Pptd by digitonin.
Melting point: mp 141.5-142°
Optical Rotation: [a]D22 +24.2° (c = 1.3 in chloroform)
Derivative Type: Methyl ether
Molecular Formula: C28H50O
Molecular Weight: 402.70
Percent Composition: C 83.51%, H 12.51%, O 3.97%
Properties: Needles from acetone, mp 82.5-83°. [a]D20 +20.0°.
Melting point: mp 82.5-83°
Optical Rotation: [a]D20 +20.0°
Derivative Type: Acetate
Molecular Formula: C29H50O2
Molecular Weight: 430.71
Percent Composition: C 80.87%, H 11.70%, O 7.43%
Properties: Prisms from ethyl acetate + methanol, mp 111°. [a]D20 +13.3° (c = 2 in chloroform).
Melting point: mp 111°
Optical Rotation: [a]D20 +13.3° (c = 2 in chloroform)
Cholesterol Cholestyramine Resin Cholic Acid Choline Alfoscerate Choline Chloride

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.