Cholesterol
Title: Cholesterol
CAS Registry Number: 57-88-5
CAS Name: (3b)-Cholest-5-en-3-ol
Additional Names: cholesterin
Molecular Formula: C27H46O
Molecular Weight: 386.65
Percent Composition: C 83.87%, H 11.99%, O 4.14%
Literature References: Principal sterol of the higher animals. Found in all body tissues, esp in the brain, spinal cord, and in animal fats or oils. Main constituent of gallstones. Prepd commercially from the spinal cord of cattle by petr ether extraction of the nonsaponifiable matter. Also produced from wool grease. Cholesterol from animal organs always contains cholestanol (dihydrocholesterol) and other satd sterols. Purification by repeated bromination: Schoenheimer, J. Biol. Chem. 105, 355 (1934); Fieser, Org. Synth. coll. vol. IV, 195 (1963). Laboratory procedure for isoln from gallstones: L. F. Fieser, Organic Experiments (Heath, Boston, 3rd ed., 1964) p 70. Total synthesis: Keana, Johnson, Steroids 4, 457 (1964). Reviews and bibliographies: Fieser, Fieser, Steroids (Reinhold, New York, Chapman & Hall, London, 1959); Lettré et al., Ueber Sterine, Gallensäuren und verwandte Naturstoffe (Stuttgart, 2nd ed., 1955); R. P. Cook, Cholesterol (Chemistry, Biochemistry and Pathology) (Academic Press, New York, 1958) 542 pp; J. T. Gwynne, J. F. Strauss, Endocr. Rev. 3, 299-329 (1982).
Properties: Monohydrate, pearly leaflets or plates from dil alcohol. Becomes anhydr at 70-80°. When anhydr mp 148.5°. Has been sublimed as orthorhombic needles. bp0.5 233°; bp760 360° (some decompn). d 1.03 (monohydrate); d1919 1.052 (anhydr). [a]D20 -31.5° (c = 2 in ether); [a]D20 -39.5° (c = 2 in chloroform). Absorption spectrum: Heilbron et al., J. Chem. Soc. 1928, 47. Practically insol in water (about 0.2 mg/100 ml H2O). Slightly sol in alc (1.29% w/w at 20°), more sol in hot alc (100 g of satd 96% alcoholic soln contains 28 g at 80°). One gram dissolves in 2.8 ml ether, in 4.5 ml chloroform, in 1.5 ml pyridine. Also sol in benzene, petr ether, oils, fats. Soly in aq solns of bile salts: Rosin, Z. Physiol. Chem. 124, 282 (1923). Solubilization: Gemant, Life Sci. 1, 233 (June 1962). Is pptd by digitonin. Gives intense red color with rosaniline in chloroform soln.
Melting point: mp 148.5°
Boiling point: bp0.5 233°; bp760 360° (some decompn)
Optical Rotation: [a]D20 -31.5° (c = 2 in ether); [a]D20 -39.5° (c = 2 in chloroform)
Density: d 1.03 (monohydrate); d1919 1.052 (anhydr)
 
Derivative Type: Methyl ether
Molecular Formula: C28H48O
Molecular Weight: 400.68
Percent Composition: C 83.93%, H 12.07%, O 3.99%
Properties: Crystals from acetone, mp 84°. [a]D20 -45.8° (c = 1.2 in chloroform).
Melting point: mp 84°
Optical Rotation: [a]D20 -45.8° (c = 1.2 in chloroform)
 
Derivative Type: Acetate
Molecular Formula: C29H48O2
Molecular Weight: 428.69
Percent Composition: C 81.25%, H 11.29%, O 7.46%
Properties: Needles from acetone, mp 115-116°. [a]D20 -47.4° (c = 2 in chloroform).
Melting point: mp 115-116°
Optical Rotation: [a]D20 -47.4° (c = 2 in chloroform)
 
Derivative Type: Benzoate
Molecular Formula: C34H50O2
Molecular Weight: 490.76
Percent Composition: C 83.21%, H 10.27%, O 6.52%
Properties: mp 145.5° (the melt becomes clear at 180°). [a]D25 -13.7° (c = 0.9 in chloroform).
Melting point: mp 145.5° (the melt becomes clear at 180°)
Optical Rotation: [a]D25 -13.7° (c = 0.9 in chloroform)
 
Use: Pharmaceutic aid (emulsifying agent).

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