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Steroid


DATA No : SST0028 INFORMANT : Hideaki Nishino

NAME : 4-Androstene-3,17-dione

COMMON NAME: Androstenedione / Androtex
SYMBOL:
FORMULA: C19H26O2 MOL.WT (average) : 286.409


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BIOLOGICAL ACTIVITY
Synthesis from 5-dehydroandrosterone (Ref. 0208/0209) Synthesis from 5-androsten-3-ol-17-one (Ref. 0210) Synthesis from 4,5-androsten-17-ol (Ref. 0211) Synthesis from 5,6-dibromo-3-keto-steroids by chromous chloride dehalogenation (Ref. 0212)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:142-144deg (acetone) (Ref. 0208) 173-174deg (hexane) (Ref. 0209)

BOILING POINT:

REFRACTIVE INDEX:[a]17/D = +2.26deg (Ref. 0210)

OPTICAL ROTATION:[a]30/D = +191deg (alcohol), [a]18/D = +185deg, [a]17/D = +197.4deg (chloroform) (Ref. 0210)

DENSITY:

SOLUBILITY:Sol in chloroform (Ref. 0210)
SPECTRAL DATA
UV SPECTRA:max. 235 nm (chloroform) (Ref. 0208)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Adrenal cortex (Ref. 0207)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0207]
AUTHOR:von Euw,J., and Reichstein,T.
TITLE:Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 51 Mitteilung. 17b-Oxy-progesteron.
JOURNAL:Helv.Chim.Acta
VOL:24 PAGE : 879 -889 (1941)
[TOP]

[0208]
AUTHOR:Butenandt,A., and Kudszus,H.
TITLE:Über Androstendion, einen hochwirksamen männlichen Prägungsstoff. Ein Beitrag zur Genese der Keimdrüsenhormone.
JOURNAL:Z.Physiol.Chem.
VOL:237 PAGE : 75 -87 (1935)
[TOP]

[0209]
AUTHOR:Ruzicka,L., and Wettstein,A.
TITLE:Sexualhormone V. Kunstliche Herstellung des männlichen Sexualhormons trans-Dehydro-androsteron und des Androsten-3,17-dions.
JOURNAL:Helv.Chim.Acta
VOL:18 PAGE : 986 -994 (1935)
[TOP]

[0210]
AUTHOR:Westphal,U., and Hellmann,H.
TITLE:Über Versuche zur partiellen Reduktion des Androstendions.
JOURNAL:Ber.
VOL:70 PAGE : 2136 -2140 (1937)
[TOP]

[0211]
AUTHOR:Marker,R.E., Wittle,E.L., and Tullar,B.F.
TITLE:Sterols. LXXXVI. Desoxotestosterone and its Conversion to Testosterone.
JOURNAL:J.Am.Chem.Soc.
VOL:62 PAGE : 223 -226 (1940)
[TOP]

[0212]
AUTHOR:Julian,P.L., Cole,W., Magnani,A., and Meyer,E.W.
TITLE:Sterols. III. A Method for the Dehalogenation of Steroids.
JOURNAL:J.Am.Chem.Soc.
VOL:67 PAGE : 1728 -1730 (1945)
[TOP]

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