21-Acetoxypregnenolone
Title: 21-Acetoxypregnenolone
CAS Registry Number: 566-78-9
CAS Name: (3b)-21-(Acetyloxy)-3-hydroxypregn-5-en-20-one
Additional Names: 3b,21-dihydroxypregn-5-en-20-one 21-acetate; 5-pregnene-3b,21-diol-20-one 21-acetate; 21-acetoxy-5-pregnen-3-ol-20-one; 3-hydroxy-21-acetoxy-5-pregnen-20-one; prebediolone acetate; A.O.P.
Trademarks: Acetoxanon (Organon); Artisone acetate (Wyeth)
Molecular Formula: C23H34O4
Molecular Weight: 374.51
Percent Composition: C 73.76%, H 9.15%, O 17.09%
Literature References: Intermediate product in the synthesis of desoxycorticosterone acetate: Steiger, Reichstein, Helv. Chim. Acta 20, 1164 (1937). Prepd by reacting 5,6-pregnen-3-ol-20-one with bromine in chloroform and treating the obtained oily bromide with potassium acetate in alcohol: Herloff, Inhoffen, US 2409043 (1946 to Schering).
Properties: Needles from acetone. Becomes opaque at about 80° or on prolonged standing. mp 184-185°. Very slightly sol in ether, in pentane; sol in chloroform, toluene. The esterified keto group is relatively stable to the action of chromic acid in cold and to such reducing agents as potassium iodide or zinc. On heating with aluminum isopropoxide in isopropyl alcohol it is reduced to 5-pregnene-3,20,21-triol.
Melting point: mp 184-185°
Therap-Cat: Anti-inflammatory.
Keywords: Glucocorticoid.

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