Stilbestrol: Difference between revisions
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* [[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) |
* [[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) |
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* [[Bifluranol]] |
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* [[Dienestrol]] |
* [[Dienestrol]] |
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** [[Dienestrol acetate]] |
** [[Dienestrol acetate]] |
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Revision as of 14:55, 13 September 2016
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| Names | |
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| IUPAC name
4-[(E)-2-(4-Hydroxyphenyl)ethenyl]phenol
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| Other names
4,4'-Dihydroxystilbene, 4,4'-stilbenediol
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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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]
The stilbestrol estrogens include the following:
- 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
- Diethylstilbestrol (stilbestrol)
- Diethylstilbestrol dipropionate
- Dimestrol (dianisylhexene, diethylstilbestrol dimethyl ether, dimethoxydiethylstilbene)
- Fosfestrol (diethylstilbestrol diphosphate)
- Furostilbestrol (diethylstilbestrol di(2-furoate))
- Mestilbol (diethylstilbestrol monomethyl ether)
- Hexestrol (dihydrodiethylstilbestrol)
- Methestrol (promethestrol; dimethylhexestrol)
- Methestrol dipropionate (promethestrol dipropionate)
Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol were the most well-known.[3]
The stilbestrol estrogens bind with high affinity to both ERα and ERβ.[4]
Resveratrol is a stilbenoid with estrogenic properties that is not a silbestrol derivative (it is 3,4',5-stilbenetriol).[5]
See also
- 3,4′-Dihydroxystilbene
- Triphenylethylene
- Methallenestril
- Ethamoxytriphetol
- Doisynolic acid
- Allenolic acid
- Chlorotrianisene
- Chrysene
- Phenanthrene
References
- ^ a b VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
- ^ William John Edward Jessop (12 May 2014). Fearon's Introduction to Biochemistry. Elsevier. pp. 408–. ISBN 978-1-4831-9556-8.
- ^ Actions and Uses of Drugs. Stanford University Press. pp. 234–. ISBN 978-0-8047-1505-8.
- ^ 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.
- ^ 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.
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