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Steroid


DATA No : SST0244 INFORMANT : Hideaki Nishino

NAME : 11b,17,21-Trihydroxypregn-4-ene-3,20-dione-4-pregnene-11b,17a,21-triol-3,20-dione / 17-Hydroxycorticosterone

COMMON NAME: Hydrocortisone / Cortisol / Ala-Cort / Cremesone / Cobadex / Cort-dome / Cortef / Cortifoam / Cortril / Dome cort / Efcorbin / Efcorlin / EF-cortelan / Efcortelin / Reichstein's Substance M / Scheroson F / Sigmacort / Texacort / Demacort / Proctocort / Epicort / Ficortril / Genacort (Lotion) / Hidro-colisona / HVB / Hydro-adreson / Hydrocortisyl / Hydrocortone / Lubricort / Meusicort
SYMBOL:
FORMULA: C21H30O5 MOL.WT (average) : 362.460


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:217-220degC (anhydrous ethanol or isopropanol) commercial sample 212-213deg (Ref. 0888), 207-210degC. (Ref. 0295)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]22/D=+167deg (abs. ethanol), commercial sample [a]22/D=+163deg (c=0.5 in methanol) (Ref. 0295)

DENSITY:

SOLUBILITY:Sol in water (0.28 mg/ml, 25deg), ethanol (15.0 mg/ml), methanol (6.2 mg/ml), acetone (9.3 mg/ml), chloroform (1.6 mg/ml), propyleneglycol (12.7 mg/ml), ether (about 0.35 mg/ml). (Ref. 0295)
SPECTRAL DATA
UV SPECTRA:UVmax: 242nm (E1%/1cm=445) (Ref. 0889)

IR SPECTRA:Complete identification in IR spectra. (Ref. 0892)

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Animals. Isolation from adrenal glands. (Ref. 0295/0888) Found in urine of Cushing's syndrome accompanied with severe diabetes. (Ref. 0889) Extraction from blood in adrenal glands of dogs dosed with ACTH. (Ref. 0890) Conversion from cholesterol in adrenal glands. (Ref. 0893) Synthesis from 11-oxygenation of 11-desoxy-17-hydroxycorticosterone in Streptomyces fradiae. (Ref. 0894)
CHEMICAL SYNTHESIS

METABOLISM
Glucocorticoid action. Application to domestic animals as adrenocortical steroid, glucocorticoid. Also applied as a topical anti-inflammatory medicine. (Ref. 0295/0888/0889/0890/0006/0891/0892/0893)
GENETIC INFORMATION

NOTE
Determination of stereochemical structure. (Ref. 0006/0891) Synthesis as 21-acetate from 20-cyano-17-pregnene-21-ol-3,11-dione as a starting material: m.p. 218.5-220.5deg, [a]25/D=+150.7deg (0.5 acetone), lmax (methanol) 2420A, E1%/1cm 371, not depressed mixed m.p. by authentic sample.
REFERENCES
[0006]
AUTHOR:von Euw,J., and Reichstein,T.
TITLE:Über Bestandteile der NebennierenRinde und Verwandte Stoffe. 56. Mitteilung. Substanz V und Konfigurations-Bestimmungen in der C21O5-Gruppe
JOURNAL:Helv.Chim.Acta
VOL:25 PAGE : 988 -1022 (1942)
[TOP]

[0295]
AUTHOR:Reichstein,T.
TITLE:Über Bestandteile der Nebennierenrinde (X). Zur Kenntnis des Cortico-sterons.
JOURNAL:Helv. Chim. Acta
VOL:20 PAGE : 953 -969 (1937)
[TOP]

[0888]
AUTHOR:Mason,H.L.,Hoehn,W.M.,and Kendall,E.C.
TITLE:Chemical studies of the suprarenal cortex. IV. Structures of compounds C, D, E, F, and G.
JOURNAL:J. Biol. Chem.
VOL:124 PAGE : 459 -474 (1938)
[TOP]

[0889]
AUTHOR:Mason,H.L.,and Sprague,R.G.
TITLE:Isolation of 17-Hydroxycorticosterone from the urine in a case of Cushing's syndrome associated with severe diabetes mellitus.
JOURNAL:J. Biol. Chem.
VOL:175 PAGE : 451 -456 (1948)
[TOP]

[0890]
AUTHOR:Reich, H., Nelson, D. H., and Zaffaroni, A.
TITLE:Isolation of 17-hydroxycorticosterone from blood obtained from adrenal veins of dogs PubMed ID:14794726
JOURNAL:J Biol Chem.
VOL:187 PAGE : 411-417 (1950)
[TOP]

[0891]
AUTHOR:von Euw,J.,and Reichstein,T.
TITLE:Über Bestandteile der Nebennierenrinde und verwandte Stoffe. (74. Mitteilung). Konfiguration der Cortico-Steroide.
JOURNAL:Helv. Chim. Acta
VOL:30 PAGE : 205 -217 (1947)
[TOP]

[0892]
AUTHOR:Wendler,N.L.,Graber,R.P.,Jones,R.E.,and Tishler,M.
TITLE:Synthesis of 11-hydroxylated cortical steroids. 17(a)-Hydroxycorticosterone.
JOURNAL:J. Am. Chem. Soc.
VOL:72 PAGE : 5793 -5794 (1950)
[TOP]

[0893]
AUTHOR:Zaffaroni,A.,Hechter,O.,and Pincus,G.
TITLE:Adrenal conversion of C14 labeled cholesterol and acetate to adrenal cortical hormones.
JOURNAL:J. Am. Chem. Soc.
VOL:73 PAGE : 1390 -1391 (1951)
[TOP]

[0894]
AUTHOR:Colingsworth, D. R., Karnemaat, J. N., Hanson, F. R., Brunner, M. P., Mann, K. M., and Haines, W. J.
TITLE:A partial microbiological synthesis of hydrocortisone PubMed ID:13084650
JOURNAL:J Biol Chem.
VOL:203 PAGE : 807-813 (1953)
[TOP]

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