Nomenclature
CAS number: 516-47-2
3β,17,21-Trihydroxy-5α-pregnan-20-one; 3α,17,21-trihydroxy-20-oxo-5α-pregnane; Reichstein's substance P.
C
21H
34O
4; mol wt 350.49.
C 71.96%, H 9.78%, O 18.26%.
Description and references
Isoln from adrenal glands: Steiger, Reichstein, Helv. Chim. Acta 21, 546 (1938);
Reichstein, Gatzi, ibid. 1185. Partial synthesis from
cholesterol: Reichstein, von Euw, ibid. 24, 401 (1941). Prepn from allopregnan-3β-ol-20-one:
Rosenkranz et al., J. Am. Chem.
Soc. 72, 4081 (1950); from 3β-acetoxy-21-bromo-17α-hydroxy-2-oxoallopregnane:
Kaufmann et al., US 2596562 (1952 to Syntex).
Properties
Pointed needles from abs ethanol, decomp 230-239°.
[α]D20 +48.0° (c = 0.938 in abs ethanol). Freely sol in alcohol,
acetone. Sparingly sol in ether, water.Derivative
3,21-Diacetate.
C
25H
38O
6; mol wt 434.57.
C 69.10%, H 8.81%, O 22.09%.
Properties
Crystals from benzene, mp 208-210°. [α]D20 +41.5° (chloroform).Status
This monograph has been retired and is no longer subject
to revision or update.