Back to HOME

Steroid


DATA No : SST0129 INFORMANT : Hideaki Nishino

NAME : 11b,21-Dihydroxy-3,20-dioxopregn-4-en-18-ol; 3,20-Diketo-11b,18-oxido-4-pregnene-18,21-diol

COMMON NAME: Aldosterone / Elektrocortin / Electrocortin / Aldocortin
SYMBOL:
FORMULA: C21H28O5 MOL.WT (average) : 360.444


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Total synthesis. (Ref. 0577) Synthesis via three steps from corticosterone. (Ref. 0578)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:164-169degC (hydrated, 105deg) (Ref. 0574)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]23/D=+152.2deg (anhydr; c=2 in acetone), [a]25/D=+161deg (c=0.1 in chloroform) (Ref. 0571/0574)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:UVmax: 240nm (loge=4.20 for the monohydrate; e mol 15,000 for the anhydr.) (Ref. 0574)

IR SPECTRA:Hydroxyl band at 2.92m, D4-3-keto band at 6.05 and 6.18m, saturated carbonyl at 5.87m. (Ref. 0574)

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A mineral corticoid secreted from adrenal cortex. (Ref. 0579) Isolation. (Ref. 0571/0572/0573/0574)
CHEMICAL SYNTHESIS

METABOLISM
Adrenocortical steroid regulates matabolism of electrolyte and water. Synthesized in zona glomerulosa, transported by albumin. Secreted 400mg/day in human male adult. The secretion is influenced by ACTH, GH, plasma sodium/potassium ions, and renin-angiotensin system, which induces resorbing of sodium, chloride, bicarbonate ions and potassium ion from uresis. Activity can be detected at the dose of 0.05-0.01mg in rat urinary sodium retention assay. 16mg Desoxycorticosterone acetate must be needed to retain the same activity. (Ref. 0579)
GENETIC INFORMATION

NOTE

REFERENCES
[0571]
AUTHOR:Simpson, S. A., Tait, J. F., Wettstein, A., Neher, R., Von Euw, J., and Reichstein, T.
TITLE:[Isolation from the adrenals of a new crystalline hormone with especially high effectiveness on mineral metabolism.] PubMed ID:13107656
JOURNAL:Experientia.
VOL:9 PAGE : 333-335 (1953)
[TOP]

[0572]
AUTHOR:Simpson,S.A.,Tait,J.F.,Wettstein,A.,Neher,R.,von Euw,J.,Schindler,O.,and Reichstein,T.
TITLE:Aldosteron. Isolierung und Eigenschaften. Über Bestandteile der Nebennierenrinde und verwandte Stoffe.
JOURNAL:Helv. Chim. Acta
VOL:37 PAGE : 1163 -1200 (1954)
[TOP]

[0573]
AUTHOR:Mattox,V.R.,Mason,H.L.,Albert,A.,and Code,C.F.
TITLE:Properties of a sodium-retaining principle from beef adrenal extract.
JOURNAL:J. Am. Chem. Soc.
VOL:75 PAGE : 4869 -4870 (1953)
[TOP]

[0574]
AUTHOR:Harman,R.E.,Ham,E.A.,DeYoung,J.J.,Brink,N.G.,and Sarett,L.H.
TITLE:Isolation of aldosterone (electrocortin).
JOURNAL:J. Am. Chem. Soc.
VOL:76 PAGE : 5035 -5036 (1954)
[TOP]

[0577]
AUTHOR:Schmidlin,J.,Anner,G.,Billeter,J.-R.,Heusler,K.,Ueberwasser,H.,Wieland,P.,and Wettstein,A.
TITLE:Totalsynthese des Aldosterons. B. (18 to11)-Lacton der d,l-D5-3-äthylendioxy-11b-hydroxy-20-oxo-pregnen-18-säure. Über Steroide, 148. Mitteilung.
JOURNAL:Helv. Chim. Acta
VOL:40 PAGE : 1438 -1455 (1957)
[TOP]

[0578]
AUTHOR:Johnson,W.S.,Collins,J.C.,Pappo,R.,and Rubin,M.B.
TITLE:Total synthesis of aldosterone.
JOURNAL:J. Am. Chem. Soc.
VOL:80 PAGE : 2585 -2586 (1958)
[TOP]

[0579]
AUTHOR:Fieser,L.F.,and Fieser,M. (1959) Aldosterone, in Steroids (Fieser,L.F.,And Fieser,M., eds), pp701-720, Reinhold Publishing Co., New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.