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Steroid


DATA No : SST0014 INFORMANT : Hideaki Nishino

NAME : Estra-1,3,5(10)-triene-3,16,17-triol / 3,16a,17b-Trihydroxy-D1,3,5-estratriene

COMMON NAME: estriol / 16a-Hydroxyestradiol / Follicular hormone hydrate / Oestriol / Trihydroxyestrin / Aacifemine / Colpogyn / Destriol / Gynasan / Hormomed / Klimax E / Klimoral / Oekolp / Ortho-gynest / Ovesterin / Ovestin / Ovo-vinces / Theelol / Tridestrin / Triovex
SYMBOL:
FORMULA: C18H24O3 MOL.WT (average) : 288.381


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BIOLOGICAL ACTIVITY
Male and female sex hormones, influences secondary sexual characteristics, regulates female reproduction cycles. A metabolite of, and less potent than, 17b-estradiol. (Ref. 0114/0115/0116/0117/0118)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:282degC (alcohol) / 268.5-269.5degC (methanol) (Ref. 0110/0111)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]25/D=+58pm5deg (Ref. 0110/0111)

DENSITY:

SOLUBILITY:Insol in water. Sol in alcohol, dioxane, chloroform, ether, vegetable oils. Freely sol in pyridine. (Ref. 0112)
SPECTRAL DATA
UV SPECTRA:max. 280nm (Ref. 0113)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:E1%/1cm=75, e=2,150 (280nm) (Ref. 0113)
CHROMATOGRAM DATA

SOURCE
Human pregnancy urine (Ref. 0114/0115) , Human placenta (Ref. 0116/0117) , Plant sources, e.g., pussywillows (Ref. 0118)
CHEMICAL SYNTHESIS
Partial synthesis from estrone by transforming a-keto to a-glycol with sodium amalgam in dilute ethanolic acetic acid (Ref. 0111) , Synthesis from zinc-acetic acid reduction of 16-oximino-17-ketosteroids and 16,17-diketosteroids. (Ref. 0119) Synthesis from 3b-hydroxyandrostane-17-one by formation of an enol acetate of a 17-ketosteroid followed by epoxidation with perbenzoic acid. (Ref. 0120)
METABOLISM

GENETIC INFORMATION

NOTE
Precipitable by digitonin. (Ref. 0108/0109)
REFERENCES
[0108]
AUTHOR:Huffman,M.N., and Lott,M.H.
TITLE:The Steric Structure of Estriol and Related Steroids.
JOURNAL:J.Am.Che.Soc.
VOL:69 PAGE : 1835 -1835 (1947)
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[0109]
AUTHOR:Cooper, A., Norton, D. A., and Hauptman, H.
TITLE:Estrogenic steroids. 3. The crystal and molecular structure of estriol PubMed ID:5819633
JOURNAL:Acta Crystallogr B.
VOL:25 PAGE : 814-828 (1969)
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[0110]
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), pp584-584, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0111]
AUTHOR:Huffman,M.N.
TITLE:16-Substituted Steroids III. The Partial Synthesis Estriol.
JOURNAL:J.Biol.Chem.
VOL:169 PAGE : 167 -172 (1947)
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[0112]
AUTHOR:Ruchelman,M.W., and Howe,C.D.
TITLE:Solubility Studies of Estriol in Organic Solvents Using Gas-Liquid Chromatography.
JOURNAL:J.Chromatogr.Sci.
VOL:7 PAGE : 340 -347 (1969)
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[0113]
AUTHOR:Sober,H.A., (1968) Section F Steroids in Handbook of Biochemistery Selected Data for Molecular Biology (Sober,H.A., eds.) ppF12-F12, The Chemical Rubber, Cleveland
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0114]
AUTHOR:Marrian,G.F.
TITLE:The Chemistry of Oestrin. I. Preparation from Urine and Separation from an Unidentified Solid Alcohol.
JOURNAL:Biochem.J.
VOL:23 PAGE : 1090 -1098 (1929)
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[0115]
AUTHOR:Cohen,S.L., and Marrian,G.F.
TITLE:The Hydrolysis of the Combined Forms of Oestron and Oestriol Present in Human Pregnancy Urine.
JOURNAL:Biochem.J.
VOL:29 PAGE : 1577 -1585 (1935)
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[0116]
AUTHOR:Collip,J.B.
TITLE:Placental Hormones.
JOURNAL:Brit.Med.J.
VOL:1930 PAGE : 1080 -1081 (1930)
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[0117]
AUTHOR:Collip,J.B., Brown,J.S.L., and Thomson,D.L.
TITLE:The Chemical Nature of Emmenin.
JOURNAL:Endocrinology
VOL:18 PAGE : 71 -74 (1934)
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[0118]
AUTHOR:Skarzynsky,B.
TITLE:An Oestrogenic Substance from Plant Material.
JOURNAL:Nature
VOL:131 PAGE : 766 -766 (1933)
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[0119]
AUTHOR:Huffman,M.N., and Lott,M.H.
TITLE:16-Sustituted Steroids. VI. The Steric Structure of Steroidal 16,17-Ketols and 16,17-Glycols.
JOURNAL:J.Am.Chem.Soc.
VOL:71 PAGE : 719 -728 (1949)
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[0120]
AUTHOR:Leeds,N.S., Fukushima,D.K., and Gallagher,T.F.
TITLE:Studies of Steroid Ring D Epoxides of Enol Acetates; A New Synthesis of Estriol and Androstane-3b, 16a,17b-Triol.
JOURNAL:J.Am.Chem.Soc.
VOL:76 PAGE : 2943 -2948 (1954)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.