2869. 11-Dehydrocorticosterone

Nomenclature

CAS number: 72-23-1
21-Hydroxypregn-4-ene-3,11,20-trione; Δ4-pregnen-21-ol-3,11,20-trione; 17-(1-keto-2-hydroxyethyl)-Δ4-androsten-3,11-dione; Kendall's compound A.
C21H28O4; mol wt 344.44.
C 73.23%, H 8.19%, O 18.58%.

Description and references

Found in adrenal cortex. 1000 lbs of beef glands yield 333 mg: Kendall, Cold Spring Harbor Symp. Quant. Biol. 5, 299 (1937). Isoln procedure: Mason et al., J. Biol. Chem. 114, 613 (1936); see also Kendall et al., Proc. Staff Meet. Mayo Clin. 12, 136 (1937). Prepn from corticosterone 21-acetate: Reichstein, Helv. Chim. Acta 20, 953 (1937); from desoxycholic acid: Lardon, Reichstein, ibid. 26, 747 (1943); Gallagher, Recent Progress in Hormone Research (New York, 1946) p 83; from 3α-acetoxy-11-ketobisnorcholanic acid: Sarett, J. Biol. Chem. 162, 601 (1946); J. Am. Chem. Soc. 68, 2478 (1946); from 3α-acetyl-11-ketolithocholic acid methyl ester: Wettstein, Meystre, Helv. Chim. Acta 30, 1262 (1947). Manuf: Wettstein, US 2778776 (1957 to Ciba).

Chemical structure

Properties

Large prisms from aq acetone, mp 178-180°. Can be distilled in high vacuum. [α]25546 +299°, also given as +347° (c = 0.23 in benzene); [α]D25 +258° (alc). Relatively good soly in benzene.

Derivative

Acetate.
C23H30O5; mol wt 386.48.
C 71.48%, H 7.82%, O 20.70%.

Properties

Needles from alc, mp 179-181°. [α]18546 +285° (dioxane); [α]D18 +233.7° (dioxane).