270. Allopregnane-3β,20β-diol

Nomenclature

CAS number: 516-53-0
(3β,5α,20R)-Pregnane-3,20-diol; 3β,20β-dihydroxy-5α-pregnane.
C21H36O2; mol wt 320.51.
C 78.69%, H 11.32%, O 9.98%.

Description and references

Progesterone metabolite. Isoln from pregnant mares' urine: Brooks et al., Biochem. J. 51, 694 (1952). Prepn by catalytic reduction of allopregnane-3,20-dione: Marker et al., GB 512940 (1939 to Parke, Davis); by hydrogenation of pregn-5-ene-3β-ol-20-one: Klyne, Barton, J. Am. Chem. Soc. 71, 1500 (1949); by hydrogenation of pregn-5-ene-3β,20β-diol: Klyne, Miller, J. Chem. Soc. 1950, 1972.

Properties

Leaflets from ethyl acetate + petr ether, mp 194.5-195.5°. [α]D +4.4° (c = 1.04 in chloroform).

Derivative

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

Properties

Needles from ethyl acetate + petr ether, mp 141-142.5°. [α]D20 +21° (c = 1 in chloroform).

Derivative

Dibenzoate.
C35H44O4; mol wt 528.72.
C 79.51%, H 8.39%, O 12.10%.

Properties

Crystals, mp 237.5-239°. [α]D20 10.1° (c = 2.08 in chloroform).