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Steroid


DATA No : SST0013 INFORMANT : Hideaki Nishino

NAME : Estra-1,3,5(10)-triene-3b,17b-diol

COMMON NAME: b-Estradiol / Cis-estradiol / Estradiol / 3,17-Epidihydroxyestratriene / Dihydrofollicular hormone / Dihydrofolliculin / Dihydroxyestrin / Dihydrotheelin / Compudose 365 / Dihydromenformon / Dimenformon / Diogyn / Estrovite / Femestral / Gynergon / Gynoestryl / Lamdiol / Macrodiol / Oestergon / Ovahormon / Ovasterol / Ovocyclin / Ovocylin / Perlatanol / Primofol / Profoliol / Progynon-dh
SYMBOL:
FORMULA: C18H24O2 MOL.WT (average) : 272.382


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BIOLOGICAL ACTIVITY
Most potent estrogenic activity. (Ref. 0103)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:173-179degC (Ref. 0104)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]25/D= from +76 to +83deg(dioxane) (Ref. 0104)

DENSITY:

SOLUBILITY:Hardly sol in water. Sol in organic solvents like alcohol, acetone, dioxane. Slightly sol in vegetable oil. (Ref. 0104)
SPECTRAL DATA
UV SPECTRA:max. 225, 280nm (Ref. 0104)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:e=2,120 (281nm), E1%/1cm=78 (Ref. 0105)
CHROMATOGRAM DATA

SOURCE
Ovary, placenta, testis, adrenal cortex of animals. (Ref. 0104)
CHEMICAL SYNTHESIS
Total synthesis from the optically active CD-building block and m-methoxyphenacyl bromide (Ref. 0106) or (+)-carboxylic acid. (Ref. 0107)
METABOLISM

GENETIC INFORMATION

NOTE
Very weak estrogenic activity in 17a-form. (Ref. 0103)
REFERENCES
[0103]
AUTHOR:Maccorquodale,D.W., Thayer,S.A., and Doisy,E.A.
TITLE:The Isolation of the Principal Estrogenic Substance of Liquor Folliculi.
JOURNAL:J.Biol.Chem.
VOL:115 PAGE : 435 -448 (1936)
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[0104]
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), pp583-583, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0105]
AUTHOR:Sober,H.A., (1968) Section F Steroids in Handbook of Biochemistery Selected Data for Molecular Biology (Sober,H.A., eds.) ppF11-F11, The Chemical Rubber, Cleveland
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0106]
AUTHOR:Eder,U., Gibian,H., Haffer,G., Neef,G., Sauer,G., and Wiechert,R.
TITLE:Total Synthesis of Optically Active Steroids, XIV Synthesis of Estradiol.
JOURNAL:Chem.Ber.
VOL:109 PAGE : 2948 -2953 (1976)
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[0107]
AUTHOR:Oppolzer,W., and Roberts,D.A.
TITLE:The Enantioselective Synthesis of (+)-Estradiol From 1,3-Dihydrobenzo-[c] Thiophene-2,2-Dioxide by Successive Thermal SO2-Extrusion and Cycloaddition Reactions.
JOURNAL:Helv.Chim.Acta
VOL:63 PAGE : 1703 -1705 (1980)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.