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Steroid


DATA No : SST0042 INFORMANT : Hideaki Nishino

NAME : 17a,21-Dihydroxy-4-pregnene-3,11,20-trione / 17-Hydroxy-11-dehydrocorticosterone / 11-Dehydro-17-hydroxycorticosterone / D4-Pregnene-17a,21-diol-3,11,20-trione

COMMON NAME: Cortisone
SYMBOL:
FORMULA: C21H28O5 MOL.WT (average) : 360.444


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BIOLOGICAL ACTIVITY
Synthesis as a monoacetate from deoxycholic acid. (Ref. 0272) Improved preparation protocols. (Ref. 0273/0274/0275/0276/0277/0278/0279/0280/0281/0282/0283/0284) Total stereospecific synthesis as a cortisone acetate. (Ref. 0285)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:220-224degC (95% ethanol) (Ref. 0267/0268/0269/0270)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]25/D=+209deg (c=1.2 in 95% ethanol); [a]25/546=+248deg (c=0.1 to 0.2 in ethanol); [a]25/546=+269deg (c=0.125 in benzene) (Ref. 0270/0271)

DENSITY:

SOLUBILITY:Sol in cold methanol, ethanol, acetone. Sparingly so in ether, benzene, chloroform. Insol in water. (Ref. 0267/0268/0269/0270)
SPECTRAL DATA
UV SPECTRA:UVmax: 237nm (e=14,000) (Ref. 0270)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolation from adrenal glands. (Ref. 0267/0268/0269/0270)
CHEMICAL SYNTHESIS

METABOLISM
Action as a glucocorticoid. (Ref. 0270)
GENETIC INFORMATION

NOTE

REFERENCES
[0267]
AUTHOR:Pfiffner,J.J.,Wintersteiner,O.,and Vars,H.M.
TITLE:Chemical studies on the adrenal cortex. I. Fractionation studies on hormone concentrates.
JOURNAL:J. Biol. Chem.
VOL:111 PAGE : 585 -597 (1935)
[TOP]

[0268]
AUTHOR:Wintersteiner,O.,and Pfiffner,J.J.
TITLE:Chemical studies on the adrenal cortex. III. Isolation of two new physiologically inactive compounds.
JOURNAL:J. Biol. Chem.
VOL:116 PAGE : 291 -305 (1936)
[TOP]

[0269]
AUTHOR:Mason,H.L.,Myers,C.S.,and Kendall,E.C.
TITLE:The chemistry of crystalline substances isolated from the suprarenal gland.
JOURNAL:J. Biol. Chem.
VOL:114 PAGE : 613 -631 (1936)
[TOP]

[0270]
AUTHOR:Reichstein,T.
TITLE:Über Bestandteile der Nebennieren-Rinde VI. Trennungsmethoden, sowie Isolierung der Substanzen F. a. H und J.
JOURNAL:Helv. Chim. Acta
VOL:19 PAGE : 1107 -1126 (1936)
[TOP]

[0271]
AUTHOR:Mason,H.L.,Myers,C.S.,and Kendall,E.C.
TITLE:Chemical studies of the suprarenal cortex. II. The identification of a substance which possesses the qualitative action of cortin; Its conversion into a diketone closely related to androstenedione.
JOURNAL:J. Biol. Chem.
VOL:116 PAGE : 267 -276 (1936)
[TOP]

[0272]
AUTHOR:Sarett,L.H.
TITLE:Partial synthesis of pregnene-4-triol-17(b),20(b),21-dione-3,11 and pregnene-4-diol-17(b),21-trione-3,11,20 monoacetate.
JOURNAL:J. Biol. Chem.
VOL:162 PAGE : 601 -631 (1946)
[TOP]

[0273]
AUTHOR:Meystre,Ch.,and Wettstein,A.
TITLE:Seitenkettenabbau von Gallensäuren direkt zu Ketolen vom Typus der Nebennierenrinden-Hormone.
JOURNAL:Experientia
VOL:3 PAGE : 185 -188 (1947)
[TOP]

[0274]
AUTHOR:Meystre,Ch.,and Wettstein,A.
TITLE:Über Steroide (65. Mitteilung). Ein einfacher Abbau der Gallensaure-Seitenkette VIII. Überführung der Desoxy-cholsäure in 3,12-Disubstituierte Ketole vom Typus der Nebennierenrinden-Hormone.
JOURNAL:Helv. Chim. Acta
VOL:30 PAGE : 1037 -1047 (1947)
[TOP]

[0275]
AUTHOR:Meystre,CH.,and Wettstein,A.
TITLE:Über Steroide. Ein einfacher Abbau der Gallensauren-Seitenkette IX. Überführung der D5-3b-Oxy-cholensäure in 11-Desoxy-corticosteronester und -äther.
JOURNAL:Helv. Chim. Acta
VOL:30 PAGE : 1256 -1262 (1947)
[TOP]

[0276]
AUTHOR:Reich,H.,and Reichstein,T.
TITLE:Über Gallensäuren und verwandte Stoffe. 22. Mitteilung. 11a-Keto-und 11a-Oxy-cholansäure.
JOURNAL:Helv. Chim. Acta
VOL:26 PAGE : 562 -585 (1943)
[TOP]

[0277]
AUTHOR:Lardon,A.,and Reichstein,T.
TITLE:Über Gallensäuren und verwandte Stoffe. Derivate der ätio-cholansäure mit Sauerstoff in 3- und 11-Stellung.
JOURNAL:Helv. Chim. Acta
VOL:26 PAGE : 705 -715 (1943)
[TOP]

[0278]
AUTHOR:Hegner,P.,and Reichstein,T.
TITLE:Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 61. Mitteilung. 11-Keto-progesteron.
JOURNAL:Helv. Chim. Acta
VOL:26 PAGE : 721 -729 (1943)
[TOP]

[0279]
AUTHOR:Turner,R.B.,Mattox,V.R.,Engel,L.L.,Mckenzie,B.F.,and Kendel,E.D.
TITLE:Steroids derived from bile acids. V. Introduction of oxygen at C11.
JOURNAL:J. Biol. Chem.
VOL:166 PAGE : 345 -365 (1946)
[TOP]

[0280]
AUTHOR:Peterson,D.H.,and Murray,H.C.
TITLE:Microbiological oxygenation of steroids at carbon 11.
JOURNAL:J. Am. Chem. Soc.
VOL:74 PAGE : 1871 -1872 (1952)
[TOP]

[0281]
AUTHOR:Perlman,D.,Titus,E.,and Fried,J.
TITLE:Microbiological hydroxylation of progesterone.
JOURNAL:J. Am. Chem. Soc.
VOL:74 PAGE : 2126 -2126 (1952)
[TOP]

[0282]
AUTHOR:Sarett,L.H.
TITLE:A new method for the preparation of 17(a)-hydroxy-20-ketopregnanes.
JOURNAL:J. Am. Chem. Soc.
VOL:70 PAGE : 1454 -1458 (1948)
[TOP]

[0283]
AUTHOR:Sarett,L.H.
TITLE:Preparation of pregnane-17a,21-diol-3,11,20-trione acetate.
JOURNAL:J. Am. Chem. Soc.
VOL:71 PAGE : 2443 -2444 (1949)
[TOP]

[0284]
AUTHOR:Mattox,V.R.,and Kendall,E.C.
TITLE:The preparation of 3-keto-D4-steroids.
JOURNAL:J. Am. Chem. Soc.
VOL:70 PAGE : 882 -883 (1948)
[TOP]

[0285]
AUTHOR:Sarett,L.H.,Arth,G.E.,Lukes,R.M.,Beyler,R.E.,Poos,G.I.,Johns,W.F.,and Constantin,J.M.
TITLE:Stereospecific total synthesis of cortisone.
JOURNAL:J. Am. Chem. Soc.
VOL:74 PAGE : 4974 -4976 (1952)
[TOP]

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