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| Names | |
|---|---|
| IUPAC name (3R,13S,17R,18S)-7,13,16,17-Tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.03,12.04,9.013,18]nonadeca-4,6,8,11-tetraen-14-one | |
| Other names (+)-Miroestrol | |
| Identifiers | |
3D model (JSmol) | |
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| Properties | |
| C20H22O6 | |
| Molar mass | 358.385 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Miroestrol is aphytoestrogen, a plant-derived chemical that mimics thebiological activity of the hormoneestrogen. Miroestrol was first reportedly isolated from the Thai herbPueraria mirifica in 1960 and thought to be responsible for the supposed rejuvenating properties of the plant.[1] However, more recent studies have suggested that the active ingredient may actually be the closely related chemical compound deoxymiroestrol (shown below), and the reported presence of miroestrol may only have been an artifact of the isolation procedure.[2] When deoxymiroestrol is exposed to the oxygen in air, it is converted to miroestrol.
A comparative study of the estrogenic properties of phytoestrogens found that both deoxymiroestrol and miroestrol were comparable in activityin vitro to other known phytoestrogens such ascoumestrol as 17β-oestradiolagonists.[3] Because of their estrogenic activities, miroestrol, deoxymiroestrol, and other related compounds have been the targets of scientific research includingtotal synthesis.[4][5]
Extracts ofPueraria mirifica reportedly containing miroestrol are marketed as dietary supplements intended to lead to breast enhancement in women. However, there is a lack of conclusive evidence for such claims. TheFederal Trade Commission has taken legal action against marketers for these unproven claims.[6]
