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Steroid


DATA No : SST0185 INFORMANT : Hideaki Nishino

NAME : 3b-Hydroxyandrost-5-en-17-one / D5-Androsten-3b-ol-17-one

COMMON NAME: Dehydroepiandrosterone / Dehydroisoandrosterone / Trans-Dehydroandrosterone / 17-Hormoforin / Diandron / Psicosterone / 17-Chetouis
SYMBOL:
FORMULA: C19H28O2 MOL.WT (average) : 288.424


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Praparation by degradation of g-sitosterol, which can be isolated from soya beans. (Ref. 0734) Preparation from cholesterol. (Ref. 0730/0209/0731)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:140-141degC, 152-153degC (biphase). (Ref. 0209)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]18/D=+10.9deg (c=0.4 in alc.). (Ref. 0734)

DENSITY:

SOLUBILITY:Sol in benzene, alcohol ether. Slightly sol in chloroform, petroleum ether. (Ref. 0209)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Animals. Isolation from male urine. (Ref. 0005/0729) Dehydroandrosterone is isolated as an epimer from male urine. (Ref. 0731)
CHEMICAL SYNTHESIS

METABOLISM
Androgen activity. (Ref. 0005/0729)
GENETIC INFORMATION

NOTE
Ppt with digitonin. (Ref. 0730/0209/0731/0732/0733)
REFERENCES
[0005]
AUTHOR:Butenandt,A., and Tscherning,K.
TITLE:Über Androsteron, ein Krystallisiertes Männliches Sexualhormon. I Isolierung und Reindarstellung aus Männerharn
JOURNAL:Z.Physol.Chem.
VOL:229 PAGE : 167 -184 (1934)
[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]

[0729]
AUTHOR:Butenandt,A.,and Dannenbaum,H.
TITLE:Über Androsteron. III. Isolierung eines neuen, physiologisch unwirksamen Sterinderivates aus Männerharn, seine Verknüpfung mit Dehydro-androsteron und Androsteron: ein Beitrag zur Konstitution des Androsterons.
JOURNAL:Z. Physiol. Chem.
VOL:229 PAGE : 192 -208 (1934)
[TOP]

[0730]
AUTHOR:Butenandt,A.,Dannenbaum,H.,Hanisch,G.,and Kudszus,H.
TITLE:Über Dehydro-androsteron.
JOURNAL:Z. Physiol. Chem.
VOL:237 PAGE : 57 -74 (1935)
[TOP]

[0731]
AUTHOR:Wallis,E.S.,and Fernholz,E.
TITLE:The constitution of dehydro-androsterone and its preparation from cholesterol.
JOURNAL:J. Am. Chem. Soc.
VOL:57 PAGE : 1379 -1380 (1935)
[TOP]

[0732]
AUTHOR:Wallis,E.S.,and Fernholz,E.
TITLE:The preparation of dehydroandrosterone from cholesterol.
JOURNAL:J. Am. Chem. Soc.
VOL:57 PAGE : 1504 -1506 (1935)
[TOP]

[0733]
AUTHOR:Schoeller,W.,Serini,A.,and Gehrke,M.
TITLE:Über die Konstitution des Dehydro-androsterons.
JOURNAL:Naturwiss.
VOL:23 PAGE : 337 -337 (1935)
[TOP]

[0734]
AUTHOR:Oppenauer,R.V.
TITLE:Synthesis of dehydroandrosterone by the decomposition of g-sitosterol from soya beans.
JOURNAL:Nature
VOL:135 PAGE : 1039 -1039 (1935)
[TOP]

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