Title: Aldosterone
CAS Registry Number: 52-39-1
CAS Name: (11b)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al
Synonyms: 3,20-diketo-11b,18-oxido-4-pregnene-18,21-diol
Trademarks: Aldocorten (Novartis)
Molecular Formula: C21H28O5
Molecular Weight: 360.44
Percent Composition: C 69.98%, H 7.83%, O 22.19%
Literature References: Adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Isoln: Simpson
et al., Experientia 9, 333 (1953);
Helv. Chim. Acta 37, 1163 (1954); Mattox
et al., J. Am. Chem. Soc. 75, 4869 (1953); Harman
et al., ibid. 76, 5035 (1954). Solutions contain an equilibrium mixture of the aldehyde and the hemiacetal, the equilibrium favoring the latter. Structure: Tait
et al., Experientia 10, 132 (1954);
Helv. Chim. Acta 37, 1200 (1954). Crystal structure and molecular conformation: Duax, Hauptmann,
J. Am. Chem. Soc. 94, 5467 (1972). 13C-NMR spectrum: P. Gerard,
Org. Magn. Reson. 11, 478 (1978). Total synthesis: Schmidlin
et al., Helv. Chim. Acta 40, 1438 (1957); Johnson
et al., J. Am. Chem. Soc. 80, 2585 (1958);
85, 1409 (1963). Three-step synthesis from corticosterone: Barton, Beaton,
ibid. 82, 2640 (1960);
83, 4083 (1961). Alternate synthesis: D. H. R. Barton
et al., J. Chem. Soc. Perkin Trans. 1 1975, 2243; M. Miyano,
J. Org. Chem. 46, 1846 (1981). Biosynthesized in the zona glomerulosa and transported chiefly by albumin. In man, 400 mg secreted normally in one day. Secretion influenced by ACTH, growth hormone, plasma sodium and potassium, and the renin-angiotensin system. Causes reabsorption of Na+, Cl-, and HCO3- and diuresis of K+.
Review: L. F. Fieser, M. Fieser,
Steroids (Reinhold, New York, 1959) pp 701-720.
Properties: Hydrated crystals from dilute acetone, mp 108-112° (when anhydr mp 164°). [a]D23 +152.2° (anhydr; c = 2 in acetone). [a]D25 +161° (c = 0.1 in chloroform). uv max: 240 nm (log e 4.20 for the monohydrate; emol 15,000 for the anhydr).
Melting point: mp 108-112° (when anhydr mp 164°)
Optical Rotation: [a]D23 +152.2° (anhydr; c = 2 in acetone); [a]D25 +161° (c = 0.1 in chloroform)
Absorption maximum: uv max: 240 nm (log e 4.20 for the monohydrate; emol 15,000 for the anhydr)
Derivative Type: 21-Acetate
Molecular Formula: C23H30O6
Molecular Weight: 402.48
Percent Composition: C 68.64%, H 7.51%, O 23.85%
Literature References: Synthesis: Wettstein
et al.; Jeger,
US 3002972 and
US 3014029 (both 1958 to Ciba).
Properties: Flat needles from acetone + ether, mp 198-199°. [a]D24 +121.7° (c = 0.71 in chloroform).
Melting point: mp 198-199°
Optical Rotation: [a]D24 +121.7° (c = 0.71 in chloroform)
Therap-Cat: Mineralocorticoid.
Therap-Cat-Vet: Mineralocorticoid.
Keywords: Mineralocorticoid.
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