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

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	:	140-141C, 152-153C (biphase). (Ref. 0209)

BOILING POINT	:

REFRACTIVE INDEX	:

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

DENSITY	:

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

SPECTRAL DATA

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)

[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)

[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)

[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)

[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)

[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)

[0733]

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

[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)