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Steroid


DATA No : SST0002 INFORMANT : Hideaki Nishino

NAME : 3a-Hydroxy-5a-androstan-17-one

COMMON NAME: Androsterone / Cis-androsterone / 3a-Hydroxy-17-androstanone / Androstan-3(a)-ol-17-one / 3(a)-Hydroxyetioallocholan-17-one / 3-Epihydroxyetioallocholan-17-one
SYMBOL:
FORMULA: C19H30O2 MOL.WT (average) : 290.440


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BIOLOGICAL ACTIVITY
Androgenic activity. Sex determination in fetus. Maintenance of genitalia functions. (Ref. 0005/0006)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:185-185.5 degC (Ref. 0006)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]15/D=+87.8pm1.5deg, [a]15/5461=+107.3pm1.5deg (c=1.5379 in dioxan) (Ref. 0006)

DENSITY:

SOLUBILITY:Sol in most organic solvents. Barely sol in water. (Ref. 0007)
SPECTRAL DATA
UV SPECTRA:max. 292.5pm1.0 nm, min. 232.5pm2.5 nm (ethanol) (Ref. 0008)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolation from male urine. (Ref. 0005/0006)
CHEMICAL SYNTHESIS
Synthesis from cholesterol. (Ref. 0009/0010)
METABOLISM

GENETIC INFORMATION

NOTE
Not precipitated by digitonin. (Ref. 0007)
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]

[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]

[0007]
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), pp101-101, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0008]
AUTHOR:Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P.
TITLE:The Absorption Spectra of Compounds Related to the Sterols
JOURNAL:J.Biol.Chem.
VOL:120 PAGE : 239 -256 (1937)
[TOP]

[0009]
AUTHOR:Ruzicka,L., Goldberg,M.W., and Brügger,H.
TITLE:Zur Kenntnis der Sexualhormone I. Über die Gewinnung von 3-Chlor- und 3-Oxy-Ätio-Allocholanon-(17). Synthese einer Verbindung von den Eigenschaften des Testikelhormons
JOURNAL:Helv.Chim.Acta
VOL:17 PAGE : 1389 -1394 (1934)
[TOP]

[0010]
AUTHOR:Marker,R.E.
TITLE:Androsterone
JOURNAL:J.Am.Chem.Soc.
VOL:57 PAGE : 1755 -1756 (1935)
[TOP]

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