11-Dehydrocorticosterone
Title: 11-Dehydrocorticosterone
CAS Registry Number: 72-23-1
CAS Name: 21-Hydroxypregn-4-ene-3,11,20-trione
Additional Names: D4-pregnen-21-ol-3,11,20-trione; 17-(1-keto-2-hydroxyethyl)-D4-androsten-3,11-dione; Kendall's compound A
Molecular Formula: C21H28O4
Molecular Weight: 344.44
Percent Composition: C 73.23%, H 8.19%, O 18.58%
Literature 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 3a-acetoxy-11-ketobisnorcholanic acid: Sarett, J. Biol. Chem. 162, 601 (1946); J. Am. Chem. Soc. 68, 2478 (1946); from 3a-acetyl-11-ketolithocholic acid methyl ester: Wettstein, Meystre, Helv. Chim. Acta 30, 1262 (1947). Manuf: Wettstein, US 2778776 (1957 to Ciba).
Properties: Large prisms from aq acetone, mp 178-180°. Can be distilled in high vacuum. [a]25546 +299°, also given as +347° (c = 0.23 in benzene); [a]D25 +258° (alc). Relatively good soly in benzene.
Melting point: mp 178-180°
Optical Rotation: [a]25546 +299°; [a]D25 +258° (alc)
 
Derivative Type: Acetate
Molecular Formula: C23H30O5
Molecular Weight: 386.48
Percent Composition: C 71.48%, H 7.82%, O 20.70%
Properties: Needles from alc, mp 179-181°. [a]18546 +285° (dioxane); [a]D18 +233.7° (dioxane).
Melting point: mp 179-181°
Optical Rotation: [a]18546 +285° (dioxane); [a]D18 +233.7° (dioxane)

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