25-Hydroxycholesterol
Title: 25-Hydroxycholesterol
CAS Registry Number: 2140-46-7
CAS Name: (3b)-Cholest-5-ene-3,25-diol
Additional Names: D5-cholestene-3b,25-diol
Molecular Formula: C27H46O2
Molecular Weight: 402.65
Percent Composition: C 80.54%, H 11.52%, O 7.95%
Literature References: An important intermediate in the synthesis of 25-hydroxycholecalciferol, q.v. Synthesis: A. Ryer et al., J. Am. Chem. Soc. 72, 4247 (1950); W. G. Dauben, H. L. Bradlow, ibid. 4248. Isoln from autoxidation products of cholesterol, q.v.: L. F. Fieser et al., J. Org. Chem. 22, 1380 (1957). Prepn from pregnenolone, q.v.: T. A. Narwid, M. R. Uskokovic, US 3856780 (1974). Alternate syntheses: M. Morisaki et al., Chem. Pharm. Bull. 21, 457 (1973); A. Rotman, Y. Mazur, Chem. Commun. 1974, 15; J. J. Partridge et al., Helv. Chim. Acta 57, 764 (1974); T. A. Narwid et al., ibid. 771; W. G. Salmond et al., Tetrahedron Lett. 1977, 987, 1237, 1695; K. Ochi et al., Chem. Pharm. Bull. 27, 252 (1979); M. Riediker, J. Schwartz, Tetrahedron Lett. 22, 4655 (1981).
Properties: Colorless needles from methanol, mp 178-180°. [a]D25 -39.0° (c = 1.05 in chloroform).
Melting point: mp 178-180°
Optical Rotation: [a]D25 -39.0° (c = 1.05 in chloroform)
 
Derivative Type: 20(S)-isomer
Properties: Crystals from chloroform, mp 189.5-190.5°. [a]D25 -41.50°(c = 0.9278 in chloroform).
Melting point: mp 189.5-190.5°
Optical Rotation: [a]D25 -41.50°(c = 0.9278 in chloroform)

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