276. Allopregnan-3β-ol-20-one

Nomenclature

CAS number: 516-55-2
(3β,5α)-3-Hydroxypregnan-20-one; 3β-hydroxy-20-oxo-5α-pregnane.
C21H34O2; mol wt 318.49.
C 79.19%, H 10.76%, O 10.05%.

Description and references

Isoln from adrenal cortex: von Euw, Reichstein, Helv. Chim. Acta 24, 885 (1941); from corpus luteum: Butenandt, Mamoli, Ber. 68, 1847 (1935); Prelog, Meister, Helv. Chim. Acta 32, 2435 (1949); from human pregnancy urine: Lieberman et al., J. Biol. Chem. 172, 263 (1948); from human placenta: Pearlman, Cerceo, ibid. 194, 807 (1952). Prepn from 20-methyl-Δ20-allopregnen-3β-ol: Koechlin, Reichstein, Helv. Chim. Acta 27, 549 (1944); from pregnenolone: Mancera et al., J. Org. Chem. 16, 192 (1951); Pappas, Nace, J. Am. Chem. Soc. 81, 4556 (1959); by redn of allopregnane-3,20-dione with sodium borohydride: Mancera et al., ibid. 75, 1286 (1953); from progesterone 20-cycloethylene ketal: Sondheimer, Klibansky, Tetrahedron 5, 15 (1959).

Properties

Plates from dil methanol, mp 194-195°. [α]D27 +91.2° (c = 0.4 in ethanol).

Derivative

Acetate.
C23H36O3; mol wt 360.53.
C 76.62%, H 10.06%, O 13.31%.

Properties

Plates from methanol, mp 144-146°. [α]D25 +69° (chloroform).