Allopregnan-3alpha-ol-20-one

Title: Allopregnan-3a-ol-20-one
CAS Registry Number: 516-54-1
CAS Name: 3a-Hydroxy-5a-pregnan-20-one
Additional Names: 5a-pregnan-3a-ol-20-one; epiallopregnanolone; allotetrahydroprogesterone
Molecular Formula: C21H34O2
Molecular Weight: 318.49
Percent Composition: C 79.19%, H 10.76%, O 10.05%
Literature References: Naturally occurring metabolite of progesterone. Prototype of the neuroactive steroids known as epalons that allosterically modulate g-aminobutyric acid type A (GABAA) receptors in the CNS. Isoln from human pregnancy urine: R. E. Marker et al., J. Am. Chem. Soc. 59, 616 (1937). Prepn from pregnenolone: G. Fleischer et al., ibid. 60, 79 (1938). Chromatographic determn in urine: F. J. Bègue et al., J. Chromatogr. Sci. 12, 763 (1974). Synthesis, metabolism and pharmacology: R. H. Purdy et al., J. Med. Chem. 33, 1572 (1990). Review of pharmacology and therapeutic potential of epalons: K. W. Gee et al., Crit. Rev. Neurobiol. 9, 207-227 (1995).
Properties: Crystals from abs alc, mp 176-178°. [a]D +87.7° (abs alc).
Melting point: mp 176-178°
Optical Rotation: [a]D +87.7° (abs alc)
Derivative Type: Acetate
Molecular Formula: C23H36O3
Molecular Weight: 360.53
Percent Composition: C 76.62%, H 10.06%, O 13.31%
Properties: Crystals from aq ethanol, mp 141-142°. [a]D22 +94.5° (abs ethanol).
Melting point: mp 141-142°
Optical Rotation: [a]D22 +94.5° (abs ethanol)
Allopregnan-3beta-ol-20-one Allopregnane Allopregnane-3alpha,11beta,17alpha,21-tetrol-20-one Allopregnane-3alpha,20alpha-diol Allopregnane-3alpha,20beta-diol