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

BIOLOGICAL ACTIVITY

Most potent estrogenic activity. (Ref. 0103)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	173-179C (Ref. 0104)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]25/D= from +76 to +83(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

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)

[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 : - ()

[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 : - ()

[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)

[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)