271. Allopregnane-3β,17α-diol-20-one

Nomenclature

CAS number: 570-54-7
(3β,5α)-3,17-Dihydroxypregnan-20-one; 3β,17-dihydroxy-5α-pregnan-20-one; 3β,17-dihydroxy-20-oxo-5α-pregnane; 17-(1-ketoethyl)androstane-3,17-diol; Reichstein's substance L; Wintersteiner's compound G.
C21H34O3; mol wt 334.49.
C 75.41%, H 10.25%, O 14.35%.

Description and references

Isoln from adrenal cortex: Wintersteiner, Pfiffner, J. Biol. Chem. 116, 291 (1936). Structure: Reichstein, Gtzi, Helv. Chim. Acta 21, 1497 (1938). Prepn from allopregnan-3β-ol-20-one 3-acetate: Rosenkranz et al., J. Am. Chem. Soc. 72, 4081 (1950); from pregn-5-ene-3β-ol-20-one: Ramirez, Stafie, ibid. 77, 134 (1955).

Properties

Crystals from abs alcohol, mp 264-266°. [α]D21 +30.6° (c = 0.54 in abs alcohol).

Derivative

3-Acetate.
C23H36O4; mol wt 376.53.
C 73.37%, H 9.64%, O 17.00%.

Properties

Crystals from acetone, mp 187-189°. [α]D20 +18° (acetone).