Allopregnane-3beta,20alpha-diol

Title: Allopregnane-3b,20a-diol
CAS Registry Number: 566-56-3
CAS Name: (3b,5a,20S)-Pregnane-3,20-diol
Additional Names: 5a-pregnane-3b,20a-diol; 3b,20a-dihydroxy-5a-pregnane
Molecular Formula: C21H36O2
Molecular Weight: 320.51
Percent Composition: C 78.69%, H 11.32%, O 9.98%
Literature References: Progesterone metabolite. Isoln from pregnant mares' urine: Brooks et al., Biochem. J. 51, 694 (1952). Prepn by heating 3a,20a-dihydroxy-5a-pregnane with sodium, or by hydrogenation of 5a-pregnane-20-ol-3-one in acid: Marker, US 2196220 and US 2250962 (1940, 1941, both to Parke, Davis); by reduction of allopregnan-3b-ol-20-one acetate with sodium: Klyne, Barton, J. Am. Chem. Soc. 71, 1500 (1949); by reduction of 5,16-pregnadien-3b-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°. [a]D22 +23° (c = 0.93 in chloroform).
Melting point: mp 218-219°
Optical Rotation: [a]D22 +23° (c = 0.93 in chloroform)
Derivative Type: Diacetate
Molecular Formula: C25H40O4
Molecular Weight: 404.58
Percent Composition: C 74.22%, H 9.97%, O 15.82%
Properties: Crystals from petr ether, mp 164-165°. [a]D19 +0.8° (c = 1.2 in chloroform).
Melting point: mp 164-165°
Optical Rotation: [a]D19 +0.8° (c = 1.2 in chloroform)
Derivative Type: Dibenzoate
Molecular Formula: C35H44O4
Molecular Weight: 528.72
Percent Composition: C 79.51%, H 8.39%, O 12.10%
Properties: Crystals, mp 170.5-172°. [a]D20 +27.7° (c = 0.84 in chloroform).
Melting point: mp 170.5-172°
Optical Rotation: [a]D20 +27.7° (c = 0.84 in chloroform)
Allopregnane-3beta,20beta-diol Allopregnane-3beta,21-diol-11,20-dione Allopurinol Allotetrahydrocortisone Alloxan