Benzestrol

Benzestrol

Names
IUPAC name p-[1,2-Diethyl-3-(p-hydroxyphenyl)butyl]phenol
Systematic IUPAC name 4,4'-(3-Ethyl-2,4-hexanediyl)diphenol
Other names 3-Ethyl-2,4-bis(p-hydroxyphenyl)hexane; 4,4'-(1,2-Diethyl-3-methyl-1,3-propanediyl)bisphenol; 4,4'-(1,2-Diethyl-3-methyltrimethylene)diphenol; 4,4'-(3-Ethylhexane-2,4-diyl)diphenol; Ocestrol; Chemestrogen
Identifiers
CAS Number	85-95-0
Beilstein Reference	2139461
ChEMBL	ChEMBL2104644
ChemSpider	6566
Jmol 3D model	Interactive image
PubChem	6827
InChI InChI=1S/C20H26O2/c1-4-19(14(3)15-6-10-17(21)11-7-15)20(5-2)16-8-12-18(22)13-9-16/h6-14,19-22H,4-5H2,1-3H3
SMILES Oc1ccc(cc1)C(C(CC)C(c2ccc(O)cc2)C)CC
Properties
Chemical formula	C20H26O2
Molar mass	298.43 g·mol−1
Density	1.063g/cm3
Melting point	164 °C (327 °F; 437 K)
Vapor pressure	0 mmHg @ 25°C
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzestrol (INN, BAN) (brand names Chemestrogen, Ocestrol, Octestrol, Octoestrol, Octofollin) is a synthetic, non-steroidal estrogen of the stilbestrol group that was formerly used medically but has since been discontinued. The stilbestrol estrogens, the most well-known of which is diethylstilbestrol (DES) were used extensively in the mid-1900s and were finally banned by the FDA due to them causing tumors in the children of women who used them.

Uses

Benzestrol and other stilbestrol were used as synthetic estrogens in order to prevent premature births. Based on the idea that premature births happened because the mother did not produce enough estrogen on her own, doctors prescribed benzestrol to mothers in order to increase their estrogen levels.

Studies have been done in the past on normal, mature and castrate female rats. Benzestrol produced the same type of estrus in the castrate rat when injected at 0.8 to 1.0 micrograms as when the rat was injected with 2.0 to 2.5 micrograms of estrone. This is significant because less benzestrol could be used to produce the same effect as estrone in increasing estrogen production. It has been used in the past as a nonsteroidal estrogen antagonist.

History

Benzestrol is a drug in the stilbestrol family of estrogens. These drugs were first produced in the late 1930s. In 1953, experiments began on benzestrol and other stilbestrols to see if they actually helped stop premature births. This study in 1953 found that benzestrol did not in fact help stop premature births. A study in 1971 found that benzestrol was the cause of a rare vaginal cancer in girls and women whose mothers had been on benzestrol while pregnant.

See also

• Dienestrol
• Fosfestrol
• Hexestrol
• Methestrol