Stilbestrol

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Stilbestrol
Names
IUPAC name
4-[(E)-2-(4-Hydroxyphenyl)ethenyl]phenol
Other names
4,4'-Dihydroxystilbene, 4,4'-stilbenediol
Identifiers
3D model (JSmol)
  • C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O
Properties
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).
Not to be confused with diethylstilbestrol.

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 stilbestrol estrogens include diethylstilbestrol, diethylstilbestrol dipropionate, benzestrol, dienestrol, dienestrol acetate, dimestrol (dianisylhexene, diethylstilbestrol dimethyl ether, dimethoxydiethylstilbene), fosfestrol (diethylstilbestrol diphosphate), furostilbestrol, hexestrol (dihydrodiethylstilbestrol), hexestrol diacetate, hexestrol dicaprylate, hexestrol diphosphate, hexestrol dipropionate, mestilbol (diethylstilbestrol monomethyl ether), methestrol (promethestrol; dimethylhexestrol), methestrol dipropionate (promethestrol dipropionate), among others. The stilbestrol estrogens bind with high affinity to both ERα and ERβ.[3]

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

The term "stilbestrol" is often used incorrectly to refer to diethylstilbestrol.[1]

See also

References

  1. ^ a b 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. ^ 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.
  4. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)



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