Miroestrol

Miroestrol

Names
IUPAC name (3R,13S,17R,18S)-7,13,16,17-Tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.0^3,12.0^4,9.0^13,18]nonadeca-4,6,8,11-tetraen-14-one
Other names (+)-Miroestrol
Identifiers
CAS Number	2618-41-9
ChemSpider	144658
Jmol interactive 3D	Image
KEGG	C08831
PubChem	165001
InChI InChI=1S/C20H22O6/c1-18(2)11-6-19(24)7-14(22)20(25,16(11)17(19)23)12-8-26-13-5-9(21)3-4-10(13)15(12)18/h3-5,8,11,15-17,21,23-25H,6-7H2,1-2H3/t11-,15+,16-,17+,19+,20-/m0/s1 Key: RJKLDOLOCIQYFS-PRTISISMSA-N InChI=1/C20H22O6/c1-18(2)11-6-19(24)7-14(22)20(25,16(11)17(19)23)12-8-26-13-5-9(21)3-4-10(13)15(12)18/h3-5,8,11,15-17,21,23-25H,6-7H2,1-2H3/t11-,15+,16-,17+,19+,20-/m0/s1 Key: RJKLDOLOCIQYFS-PRTISISMBT
SMILES CC1([C@@H]2C3=C(C=C(C=C3)O)OC=C2[C@]4([C@H]5C1CC([C@@H]5O)(CC4=O)O)O)C
Properties
Chemical formula	C20H22O6
Molar mass	358.385
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Miroestrol is a phytoestrogen, a plant-derived chemical that mimics the biological activity of the hormone estrogen. Miroestrol was first reportedly isolated from the Thai herb Pueraria 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.

Chemical structure of deoxymiroestrol

A comparative study of the estrogenic properties of phytoestrogens found that both deoxymiroestrol and miroestrol were comparable in activity in vitro to other known phytoestrogens such as coumestrol as 17β-oestradiol agonists.^[3] Because of their estrogenic activities, miroestrol, deoxymiroestrol, and other related compounds have been the targets of scientific research including total synthesis.^[4][5]

Extracts of Pueraria mirifica reportedly containing miroestrol are marketed as dietary supplements intended to lead to breast enhancement in women. However, there is no scientific basis for such claims. The Federal Trade Commission has taken legal action against marketers for these fraudulent claims.^[6]

References

1. Cain, J. C. (1960). "Miroestrol - An Estrogen from the Plant Pueraria mirifica". Nature 188 (4753): 774–777. doi:10.1038/188774a0. PMID 13689829.
2. Chansakaow, S.; Ishikawa, T.; Seki, H.; Sekine, K.; Okada, M.; Chaichantipyuth, C. (2000). "Identification of Deoxymiroestrol as the Actual Rejuvenating Principle of "Kwao Keur", Pueraria mirifica. The Known Miroestrol may be an Artifact". Journal of Natural Products 63 (2): 173–175. doi:10.1021/np990547v. PMID 10691701.
3. Matsumura, A.; Ghosh, A.; Pope, G. S.; Darbre, P. D. (2005). "Comparative Study of Estrogenic Properties of eight Phytoestrogens in MCF7 Human Breast Cancer Cells". Journal of Steroid Biochemistry and Molecular Biology 94 (5): 431–443. doi:10.1016/j.jsbmb.2004.12.041. PMID 15876408.
4. Corey, E. J.; Wu, L. I. (1993). "Enantioselective Total Synthesis of Miroestrol". Journal of the American Chemical Society 115 (20): 9327–9328. doi:10.1021/ja00073a074.
5. Ito, F.; Kumamoto, T.; Yamaguchi, K.; Ishikawa, T. (2009). "Synthetic Studies toward Miroestrols: Trials for Elongation of the Methyl Group of 5-Substituted 2-Methyl-2-Cyclohexanone to 3-Methyl-2-Butenyl Function". Tetrahedron 65 (4): 771–785. doi:10.1016/j.tet.2008.11.055.
6. "Federal Trade Commission v. Vital Dynamics" (PDF). FTC.