Title: Pregnanediol
CAS Registry Number: 80-92-2
CAS Name: (3a,5b,20S)-Pregnane-3,20-diol
Molecular Formula: C21H36O2
Molecular Weight: 320.51
Percent Composition: C 78.69%, H 11.32%, O 9.98%
Literature References: A metabolite of progesterone, present in large amounts in pregnancy urine. Isoln from pregnancy urine of women: Marrian, Biochem. J. 23, 1090 (1929), Butenandt, Ber. 63, 659 (1930); of cows, mares, and chimpanzees: Fish et al., J. Biol. Chem. 143, 716 (1942). Prepn by reduction of pregn-16-ene-3,20-dione: Marker et al., US 2352852 (1944 to Parke, Davis). Conversion to progesterone: Butenandt, Schmidt, Ber. 67, 1893, 1901 (1934). Conversion to 3a-hydroxypregnan-20-one: Marker, US 2223377 (1940 to Parke, Davis). Prepn of the 3-acetate: Hirschmann, J. Biol. Chem. 140, 797 (1941); Ralls et al., ibid. 210, 709 (1954). Prepn of the 20-acetate: Hirschmann, loc. cit. Prepn of the diacetate: Johnson et al., J. Chem. Soc. 1954, 1302. Crystal structure: Haner, Norton, Acta Crystallogr. 16, 707 (1963). Review of metabolism, bioactivity and assay during pregnancy: P. J. Keller, Contrib. Gynecol. Obstet. 2, 75-91 (1976).
Properties: Crystals from acetone or ethanol, mp 239°. [a]D20 +27.4° (c = 0.7 in alc). Sparingly sol in organic solvents. Not precipitated by digitonin.
Melting point: mp 239°
Optical Rotation: [a]D20 +27.4° (c = 0.7 in alc)
Derivative Type: 3-Acetate
Additional Names: 3a-Acetoxypregnan-20a-ol
Molecular Formula: C23H38O3
Molecular Weight: 362.55
Percent Composition: C 76.20%, H 10.56%, O 13.24%
Properties: Crystals, mp 132°. [a]D25 +45° (CHCl3).
Melting point: mp 132°
Optical Rotation: [a]D25 +45° (CHCl3)
Derivative Type: 20-Acetate
Additional Names: 20a-Acetoxypregnan-3a-ol
Molecular Formula: C23H38O3
Molecular Weight: 362.55
Percent Composition: C 76.20%, H 10.56%, O 13.24%
Properties: Crystals, mp 174°.
Melting point: mp 174°
Derivative Type: Diacetate
Additional Names: 3a,20a-Diacetoxypregnane
Molecular Formula: C25H40O4
Molecular Weight: 404.58
Percent Composition: C 74.22%, H 9.97%, O 15.82%
Properties: Crystals from light petroleum, mp 180°, also reported as mp 182-183°. [a]D15 +35° (c = 1.1 in CHCl3).
Melting point: mp 180°; mp 182-183°
Optical Rotation: [a]D15 +35° (c = 1.1 in CHCl3)
Use: In manuf of progesterone. |