269. Allopregnane-3β,20α-diol

Nomenclature

CAS number: 566-56-3
(3β,5α,20S)-Pregnane-3,20-diol; 5α-pregnane-3β,20α-diol; 3β,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 pregnant mares' urine: Brooks et al., Biochem. J. 51, 694 (1952). Prepn by heating 3α,20α-dihydroxy-5α-pregnane with sodium, or by hydrogenation of 5α-pregnane-20-ol-3-one in acid: Marker, US 2196220 and US 2250962 (1940, 1941, both to Parke, Davis); by reduction of allopregnan-3β-ol-20-one acetate with sodium: Klyne, Barton, J. Am. Chem. Soc. 71, 1500 (1949); by reduction of 5,16-pregnadien-3β-ol-20-one with Zn + acetic acid: Ercoli, De Ruggieri, Farm. Sci. Tec. 7, 11 (1952), C.A. 46, 10186b (1952).

Properties

Crystals from acetone, mp 218-219°. [α]D22 +23° (c = 0.93 in chloroform).

Derivative

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

Properties

Crystals from petr ether, mp 164-165°. [α]D19 +0.8° (c = 1.2 in chloroform).

Derivative

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

Properties

Crystals, mp 170.5-172°. [α]D20 +27.7° (c = 0.84 in chloroform).