176. Adrenosterone

Nomenclature

CAS number: 382-45-6
Androst-4-ene-3,11,17-trione; Reichstein's substance G.
C19H24O3; mol wt 300.39.
C 75.97%, H 8.05%, O 15.98%.

Description and references

Prepn: Reichstein, Helv. Chim. Acta 19, 29, 1107 (1936); Kendall et al., J. Biol. Chem. 116, 267 (1936); Reichstein, Helv. Chim. Acta 20, 817, 953 (1937). Total synthesis: Velluz et al., Compt. Rend. 250, 1293 (1960). Crystal structure: Ohrt et al., Acta Crystallogr. 19, 479 (1965). Metabolism: Bradlow et al., Steroids 10, 233 (1967).

Chemical structure

Properties

Needles from alcohol, mp 220-224°. Sublimes in high vacuum. Soly in water: 9.85 (23°), 15.2 (37°) mg/100 ml. Sol in alcohol, acetone, ether. [α]D20 +262° (abs alcohol); [α]255461 +364 ± 5° (c = 0.18 in abs alc). uv max: 235 nm.