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
PubChem	5282363
SMILES C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O
Properties
Chemical formula	C14H12O2
Molar mass	212.24388 g/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.^[1][2] The term "stilbestrol" is often used incorrectly to refer to diethylstilbestrol, but they are not the same compound.^[1]

Stilbestrol derivatives

The stilbestrol estrogenic drugs include the following:

• Acefluranol (an antiestrogen)
• Benzestrol (technically not a stilbestrol derivative due to its elongated central chain, but a very close analogue and grouped with the stilbestrol estrogens in any case)
• Bifluranol
• Dienestrol
  • Dienestrol acetate
• Diethylstilbestrol (stilbestrol)
  • Diethylstilbestrol diacetate
  • Diethylstilbestrol dilaurate
  • Diethylstilbestrol dipalmitate
  • Diethylstilbestrol dipropionate
  • Diethylstilbestrol disulfate
  • Diethylstilbestrol monobenzyl ether
  • Dimestrol (dianisylhexene, diethylstilbestrol dimethyl ether, dimethoxydiethylstilbene)
  • Fosfestrol (diethylstilbestrol diphosphate)
  • Furostilbestrol (diethylstilbestrol difuroate)
  • ICI-85966 (diethylstilbestrol bis[di(2-chloroethyl)carbamate)
  • Mestilbol (diethylstilbestrol monomethyl ether)
• Hexestrol (dihydrodiethylstilbestrol)
  • Diaethiphenum (hexestrol bis(2-diethylaminoethyl) ether) (a coronary vasodilator)
  • Hexestrol diacetate
  • Hexestrol dicaprylate
  • Hexestrol diphosphate
  • Hexestrol dipropionate
  • Phenestrol (hexestrol bis[4-[bis(2-chloroethyl)amino]phenylacetate)
• Methestrol (promethestrol; dimethylhexestrol)
  • Methestrol dipropionate (promethestrol dipropionate)
• Pentafluranol
• Terfluranol

Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol are the most well-known.^[3]

Mechanism of action

The stilbestrol estrogens bind with high affinity to both ERα and ERβ.^[4]

Closely related compounds

Triphenylethylene.

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).^[5]

See also

• 3,4′-Dihydroxystilbene
• Quadrosilan
• Doisynolic acid
• Allenolic acid
• Methallenestril
• Zeranol

References

1. VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
2. William John Edward Jessop (12 May 2014). Fearon's Introduction to Biochemistry. Elsevier. pp. 408–. ISBN 978-1-4831-9556-8.
3. Actions and Uses of Drugs. Stanford University Press. pp. 234–. ISBN 978-0-8047-1505-8.
4. Kuiper, George G. J. M.; Carlsson, Bo; Grandien, Kaj; Enmark, Eva; Häggblad, Johan; Nilsson, Stefan; Gustafsson, Jan-Åke (1997). "Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β". Endocrinology. 138 (3): 863–870. doi:10.1210/endo.138.3.4979. ISSN 0013-7227.
5. Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM; Lantvit; Christov; Mehta; Moon; Pezzuto (October 2001). "Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models". Cancer Res. 61 (20): 7456–63. PMID 11606380.