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	:	142-144 (acetone) (Ref. 0208) 173-174 (hexane) (Ref. 0209)

BOILING POINT	:

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

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

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[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)

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[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)

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[0210]

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

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[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)

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[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)

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