24-Hydroxycholesterol
Structural Formula Vector Image
Title: 24-Hydroxycholesterol
CAS Registry Number: 474-73-7
CAS Name: (3b,24S)-Cholest-5-ene-3,24-diol
Molecular Formula: C27H46O2
Molecular Weight: 402.65
Percent Composition: C 80.54%, H 11.52%, O 7.95%
Literature References: Two stereoisomers exist: cholest-5-ene-3b,24b-diol and cholest-5-ene-3b,24a-diol. Isoln of the naturally occurring 24b-epimer, from horse brain: Ercoli et al., Boll. Soc. Ital. Biol. Sper. 29, 494 (1953), C.A. 49, 4744i (1955); from beef spinal cord: Fieser et al., J. Org. Chem. 22, 1380 (1957). Prepn and separation of isomers: Ercoli, Ruggieri, Gazz. Chim. Ital. 83, 720 (1953); eidem, J. Am. Chem. Soc. 75, 3284 (1953). Configurations at C-24: Klyne, Stokes, J. Chem. Soc. 1954, 1979.
 
Derivative Type: 24b-Epimer
Additional Names: Cerebrostenediol; cerebrosterol
Properties: Needles from acetone, mp 175-176°. [a]D20 -48.2° (c = 1.06 in CHCl3).
Melting point: mp 175-176°
Optical Rotation: [a]D20 -48.2° (c = 1.06 in CHCl3)
 
Derivative Type: 24b-Epimer dibenzoate
Molecular Formula: C41H54O4
Molecular Weight: 610.87
Percent Composition: C 80.61%, H 8.91%, O 10.48%
Properties: Crystals from ether + acetone, mp 182-183°. aD -19° (c = 1.20 in CHCl3).
Melting point: mp 182-183°
Optical Rotation: aD -19° (c = 1.20 in CHCl3)
 
Derivative Type: 24a-Epimer
Properties: Crystals, mp 182-183°. [a]D20 -26.8° (c = 0.672 in CHCl3).
Melting point: mp 182-183°
Optical Rotation: [a]D20 -26.8° (c = 0.672 in CHCl3)
 
Derivative Type: 24a-Epimer dibenzoate
Properties: Crystals, mp 141-142°. [a]D26 -11.8° (c = 1 in CHCl3).
Melting point: mp 141-142°
Optical Rotation: [a]D26 -11.8° (c = 1 in CHCl3)

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