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Steroid


DATA No : SST0205 INFORMANT : Hideaki Nishino

NAME : 3b-Hydroxy-5a-androstan-17-one / 3b-Hydroxy-17-androstanone / 3b-Androstanol-17-one / 3b-Hydroxyetioallocholan-17-one

COMMON NAME: Epiandrosterone / Isoandrosterone
SYMBOL:
FORMULA: C19H30O2 MOL.WT (average) : 290.440


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BIOLOGICAL ACTIVITY
Synthesis method. (Ref. 0791/0792/0793)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:dl-Form: 161-162degC, d-form: 174.5degC (ethyl acetate+petr. ether) (Ref. 0791/0792/0793)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:d-form: [a]20/D=+88deg (methanol). (Ref. 0791/0792/0793)

DENSITY:

SOLUBILITY:d-form: Insol in water. Sol in organic solvents. (Ref. 0791/0792/0793)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Animals. The trace amount is present in healthy human urine.(Ref. 0793)
CHEMICAL SYNTHESIS

METABOLISM
Androgen activity, weaker than androsterone. (Ref. 0793)
GENETIC INFORMATION

NOTE
d-Form: ppt with digitonin. (Ref. 0791)
REFERENCES
[0791]
AUTHOR:Cardwell,H.M.E.,Cornforth,J.W.,Duff,S.R.,Holtermann,H.,and Robinson,R.
TITLE:Experiments on the synthesis of substances related to the sterols. Part LI. Completion of the syntheses of androgenic hormones and of the cholesterol group of sterols.
JOURNAL:J. Chem. Soc.
VOL:1953 PAGE : 361 -384 (1953)
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[0792]
AUTHOR:Johnson,W.S.,Bannister,B.,Bloom,B.M.,Kemp,A.D.,Pappo,R.,Rogier,E.R.,and Szmuszkovicz,J.
TITLE:Total synthesis of epiandrosterone.
JOURNAL:J. Am. Chem. Soc.
VOL:75 PAGE : 2275 -2276 (1953)
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[0793]
AUTHOR:Johnson,W.S.,Bannister,B.,and Pappo,R.
TITLE:Steroid total synthesis. Hydrochrysene approach. VII. Metal-in-ammonia reduction of the aromatic nucleus. dl-Epiandrosterone and the lumi epimer.
JOURNAL:J. Am. Chem. Soc.
VOL:78 PAGE : 6331 -6339 (1956)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.