By Robert P. Cook
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Additional resources for Cholesterol. Chemistry, Biochemistry, and Pathology
Example text
The molecular rotation of cholesterol [M] is given at various wavelengths from 300 to 650 τημ by: [Μ] = _ 4 8 . , 1955c). Cholesterol purified either by acetic acid crystallization or via the dibromide gives no color in the selenium dioxide test of Fieser (1953a) 7 (absence of A -cholestenol, e t c ) . The constants quoted above refer to anhydrous cholesterol which is obtained by crystallization from dry solvents. It then forms triclinic needles. From moist solvents, it separates as the monohydrate, rhombshaped triclinic plates, which lose water at 70-80° C.
From moist solvents, it separates as the monohydrate, rhombshaped triclinic plates, which lose water at 70-80° C. p. 110° C. p. 160° C. d e c ) . V. The Structure of Cholesterol As befits a compound of such profound biological importance, cholesterol has occupied the attention of organic chemists for a great number 25 CHEMISTRY of years. The structural relationship of the sterols and the bile acids was realized quite early, and to a large extent the structures assigned to the two classes of compounds are based on interrelated evidence.
T) Reduction of cholestan-l-one with L i A l H 4- E t 20 gave l a - and lß-alcohols in the ratio 2:1. Reduction with NaEtOH gave the products in the ratio 1:2 (Henbest and Wilson, 1956). Several alternative ways of preparing 1oxygenated cholestane derivatives were described by Striebel and Tamm (1954). The acetate of 1 α-hydroxy cholestane is difficult to hydrolyze, and can best be converted to the hydroxy compound with LiAlH 4 (Plattner et al, 1954). CH 2SHZnCl 2-Na 2S0 4; ( 2 ) Raney Ni-aq. dioxane (Hauptmann, 1947).