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Steroid


DATA No : SST0020 INFORMANT : Hideaki Nishino

NAME : 17b-Hydroxyandrost-4-en-3-one / D4-Androsten-17b-ol-3-one

COMMON NAME: Testosterone / Trans-testosterone / Geno-cristaux gremy / Malestrone (AMPS) / Orquisteron / Percutacrine androgenique / Primotest / Primoteston / Sustanon / Mertestate / Testobase / Virosterone / Virormone / Testryl / Testrone / Homosterone / Oreton-f / Teslen
SYMBOL:
FORMULA: C19H28O2 MOL.WT (average) : 288.424


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BIOLOGICAL ACTIVITY
Stimulates growth of the prostate and seminal vesicles, and promotes sperm maturation and development of male secondary sexual characteristics. (Ref. 0184/0187)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:154-154.5degC (Ref. 0179)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]24/D = +109deg (c = 4 in alcohol) (Ref. 0179)

DENSITY:

SOLUBILITY:Insol in water. Sol in alcohol, ether, other organic solvents. (Ref. 0184)
SPECTRAL DATA
UV SPECTRA:max. 238nm (loge = 4.23) (Ref. 0181/0185)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:E1%/1cm=582 (240nm, e = 16,800) (Ref. 0186)
CHROMATOGRAM DATA

SOURCE
Major hormone secreted from interstitial cells, e.g., Leydig cells in testis. (Ref. 0184/0187)
CHEMICAL SYNTHESIS
Synthesis from cholesterol via dehydroandrosterone. (Ref. 0184)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0179]
AUTHOR:Butenandt,A., and Hanisch,G.
TITLE:Über die Umwandlung des Dehydro-Androsterons in D4-Androsten-Ol-(17)-On-(3)(Testosteron); ein Weg Zur Darstellung des Testosterons aus Cholesterin (Vorläuf. Mitteil).
JOURNAL:Ber.
VOL:68 PAGE : 1859 -1862 (1935)
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[0181]
AUTHOR:Ruzicka,L., and Wettstein,A.
TITLE:Sexualhormone VII. Über die Künstliche Herstellung des Testikelhormons Testosteron (Androsten-3-On-17-Ol).
JOURNAL:Helv.Chim.Acta
VOL:18 PAGE : 1264 -1275 (1935)
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[0184]
AUTHOR:Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp1446-1446, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0185]
AUTHOR:Dawson,R.M.C., Elliott,D.C., Elliott,W.H., and Jones,K.M.(1987) Steroids in Data for Biochemical Research, 3rd ed. (Dawson,R.M.C., Elliott,D.C., Elliott,W.H., and Jones,K.M., eds.), pp192-193, Oxford Univ. Press, Oxford.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0186]
AUTHOR:Sober,H.A., (1968) Section F Steroids in Handbook of Biochemistery Selected Data for Molecular Biology (Sober,H.A., eds.) ppF4-F4, The Chemical Rubber, Cleveland.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0187]
AUTHOR:David,K., Dingemanse,E., Freud,J., and Laqueur,E.
TITLE:Über Krystallinisches Männliches Hormon als aus Harn oder aus Cholesterin Bereitetes Androsteron.
JOURNAL:Z.Physiol.Chem.
VOL:233 PAGE : 281 -282 (1935)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.