Stilbestrol

Stilbestrol

Names
IUPAC name 4-[(E)-2-(4-Hydroxyphenyl)ethenyl]phenol
Other names 4,4'-Dihydroxystilbene, 4,4'-stilbenediol
Identifiers
CAS Number	659-22-3
3D model (Jmol)	Interactive image Interactive image
ChemSpider	4445526
PubChem CID	5282363
InChI InChI=1S/C14H12O2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h1-10,15-16H/b2-1+ Key: XLAIWHIOIFKLEO-OWOJBTEDSA-N
SMILES C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O c1cc(ccc1/C=C/c2ccc(cc2)O)O
Properties
Chemical formula	C14H12O2
Molar mass	212.24388 g/mol
Magnetic susceptibility (χ)	-130·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid and the parent compound of a group of non-steroidal estrogens that includes, most notably, diethylstilbestrol. The term "stilbestrol" is often used incorrectly to refer to diethylstilbestrol, but they are not the same compound.

The stilbestrol estrogenic drugs include the following:

Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol are the most well-known.

The stilbestrol estrogens bind with high affinity to both ERα and ERβ.

Estrogens closely related to the stilbestrols include paroxypropione (a metabolite of diethylstilbestrol) and the anise and fennel-derived compounds anol, dianol, anethole, dianethole, and photoanethole (from which the stilbestrol estrogens were actually originally derived). The triphenylethylene group of estrogenic drugs that includes triphenylethylene itself, estrobin, chlorotrianisene, broparestrol, ethamoxytriphetol, clomifene, tamoxifen, and more recently developed derivatives is also very closely related structurally to the stilbestrols.

Resveratrol is a stilbenoid with estrogenic properties that is not technically a silbestrol derivative (it is 3,4',5-stilbenetriol).