267. Allopregnane-3α,20α-diol

Nomenclature

CAS number: 566-58-5
(3α,5α,20S)-Pregnane-3,20-diol; 5α-pregnane-3α,20α-diol; 3α,20α-dihydroxy-5α-pregnane.
C21H36O2; mol wt 320.51.
C 78.69%, H 11.32%, O 9.98%.

Description and references

Progesterone metabolite. Isoln from human pregnancy urine: Beall, Biochem. J. 31, 35 (1937); from bulls' urine: Marker et al., J. Am. Chem. Soc. 60, 2931 (1938). Prepn by reduction of 5α-pregn-1-ene-3,20-dione with lithium aluminum hydride: Schütt, Tamm, Helv. Chim. Acta 41, 1751 (1958).

Properties

Crystals from methanol, mp 243-245°. [α]D20 +17° (c = 0.148 in ethanol).

Derivative

Diacetate.
C25H40O4; mol wt 404.58.
C 74.22%, H 9.97%, O 15.82%.

Properties

Crystals, mp 139.5-140.5°. [α]D20 +18° (c = 0.408 in benzene).