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Steroid


DATA No : SST0064 INFORMANT : Hideaki Nishino

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

COMMON NAME: b-Estradiol / (+)-Estradiol
SYMBOL:
FORMULA: C18H24O2 MOL.WT (average) : 272.382


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BIOLOGICAL ACTIVITY
Enantioselective synthesis from 1,3-dihydrobenzo[c] thiophene-2,2-dioxide (Ref. 0107)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:173-179degC. (Ref. 0378/0106)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]25/D=+76 to +83deg (dioxane). (Ref. 0378/0106)

DENSITY:

SOLUBILITY:Almost insol in water. Freely sol in alcohol, acetone, dioxane, other organic solvents. Sparingly sol in vegetable oils. (Ref. 0378/0106)
SPECTRAL DATA
UV SPECTRA:UVmax: 225, 280 nm (Ref. 0379)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolation from urine of pregnant mares. (Ref. 0103) Isolation from porcine ovary follicular fluid. (Ref. 0103)
CHEMICAL SYNTHESIS

METABOLISM
The strongest estrogen in mammals. (Ref. 0103)
GENETIC INFORMATION

NOTE
Properties, synthesis, and analysis as valerate. (Ref. 0380)
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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[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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[0378]
AUTHOR:Butenandt,A.,and Goergens,C.
TITLE:Über a- und b- Oestradiol.
JOURNAL:Z. Physiol. Chem.
VOL:248 PAGE : 129 -141 (1937)
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[0379]
AUTHOR:Inhoffen,H.H.,and Zühlsdorff,G.
TITLE:Übergang von Sterinen in aromatische Verbindungen, V. Mitteil.: Aromatisierung des Ringes A durch Methylwanderung.
JOURNAL:Ber.
VOL:74 PAGE : 604 -617 (1941)
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[0380]
AUTHOR:Florey,K. (1975) Estradiol valerate, in Analytical profiles of drug substances 4 (Florey,K., eds.) pp192-208, Academic Press, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.