Allopregnane-3beta,17alpha-diol-20-one

Title: Allopregnane-3b,17a-diol-20-one
CAS Registry Number: 570-54-7
CAS Name: (3b,5a)-3,17-Dihydroxypregnan-20-one
Additional Names: 3b,17-dihydroxy-5a-pregnan-20-one; 3b,17-dihydroxy-20-oxo-5a-pregnane; 17-(1-ketoethyl)androstane-3,17-diol; Reichstein's substance L; Wintersteiner's compound G
Molecular Formula: C21H34O3
Molecular Weight: 334.49
Percent Composition: C 75.41%, H 10.25%, O 14.35%
Literature References: Isoln from adrenal cortex: Wintersteiner, Pfiffner, J. Biol. Chem. 116, 291 (1936). Structure: Reichstein, Gätzi, Helv. Chim. Acta 21, 1497 (1938). Prepn from allopregnan-3b-ol-20-one 3-acetate: Rosenkranz et al., J. Am. Chem. Soc. 72, 4081 (1950); from pregn-5-ene-3b-ol-20-one: Ramirez, Stafie, ibid. 77, 134 (1955).
Properties: Crystals from abs alcohol, mp 264-266°. [a]D21 +30.6° (c = 0.54 in abs alcohol).
Melting point: mp 264-266°
Optical Rotation: [a]D21 +30.6° (c = 0.54 in abs alcohol)
Derivative Type: 3-Acetate
Molecular Formula: C23H36O4
Molecular Weight: 376.53
Percent Composition: C 73.37%, H 9.64%, O 17.00%
Properties: Crystals from acetone, mp 187-189°. [a]D20 +18° (acetone).
Melting point: mp 187-189°
Optical Rotation: [a]D20 +18° (acetone)
Allopregnane-3beta,20alpha-diol Allopregnane-3beta,20beta-diol Allopregnane-3beta,21-diol-11,20-dione Allopurinol Allotetrahydrocortisone