Miroestrol
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| General | ||||||||||
| Surname | Miroestrol | |||||||||
| other names |
Mirestrol |
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| Molecular formula | C 20 H 22 O 6 | |||||||||
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| properties | ||||||||||
| Molar mass | 358.39 g mol −1 | |||||||||
| Physical state |
firmly |
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| Melting point |
268-270 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
Miroestrol is a phytoestrogen . These are phytochemicals with the to the female sex hormones counting estrogens similar structure and biological activity. Miroestrol was isolated in 1960 from the Pueraria mirifica plant , a species of Pueraria in the legume family .
Occurrence
Pueraria mirifica has been used in Thai folk medicine for a long time. Its ingredients are said to have rejuvenating properties. The miroestrol content depends on the age and location of the plant and can be up to 45 milligrams per kilogram of dried Pueraria mirifica root.
presentation
A total synthesis of miroestrol has been attempted by several research groups due to its estrogenic properties. The first total synthesis was achieved by EJ Corey in 1993. Corey first attempted an intramolecular ring closure via a photochemically induced arene – olefin cyclization. However, this did not succeed, so that the ring closure finally took place via an intramolecular Diels-Alder reaction with subsequent double bond isomerism.
use
Miroestrol is used in medical research to study the pharmacological effects of phytoestrogens.
effect
The estrogenic effect of Miroestrol is used to market extracts from Pueraria Mirifica as a herbal dietary supplement for menopausal symptoms , as an anti-aging agent or for breast enlargement. However, there is no scientific basis for these uses.
It is now assumed that the actually effective component of the plant is the compound desoyxymiroestrol and that miroestrol is only produced as an oxidation product during isolation. In a comparative study it was found that the estrogenic properties of desoyxymiroestrol were comparable to other phytohormones such as coumestrol . Miroestrol, on the other hand, was less effective.
Individual evidence
- ^ A b John Buckingham: Dictionary of Natural Products . CRC Press, 1993, ISBN 0-412-46620-1 , pp. 4017 ( limited preview in Google Book search).
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ James C. Cain: "Miroestrol: an oestrogen from the plant Pueraria mirifica." In: Nature, London 188.4753 (1960): p. 774-7.
- ↑ A. Manosroi, J. Manosroi: Determination of Bioactive Compounds in Roots of Different Ages Pueraria mirifica, Airy Shaw Suvatabhandhu and Butea superba, Roxb. from Various Locations in Thailand. In: Pharmaceutical-Cosmetic Raw Materials and Natural Products Research and Development Center (PCRNC), Institute for Science and Technology Research and Development, Faculty of Pharmacy, Chiang Mai University, Thailand. Retrieved December 28, 2013 .
- ↑ a b E.J. Corey, Laurence I. Wu: Enantioselective total synthesis of miroestrol. In: Journal of the American Chemical Society. 115, 1993, pp. 9327-9328, doi : 10.1021 / ja00073a074 .
- ^ A b A. Matsumura, A. Ghosh, GS Pope, PD Darbre: Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. In: The Journal of Steroid Biochemistry and Molecular Biology. 94, 2005, pp. 431-443, doi : 10.1016 / j.jsbmb.2004.12.041 .