Equol

Chembox new
ImageFile=Equol structure.pngImageSize=200px
IUPACName=(3"S")-3-(4-Hydroxyphenyl)-7-chromanol
OtherNames=4',7-Isoflavandiol
Section1= Chembox Identifiers
CASNo=531-95-3
PubChem=91469
SMILES=C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
Section2= Chembox Properties
Formula=C₁₅H₁₄O₃
MolarMass=242.27 g/mol
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Section3= Chembox Hazards
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Equol (4',7-isoflavandiol) is an isoflavandiolThe structures of 7,4’-dihydroxy-isoflavan and its precursors is shown in [http://dmd.aspetjournals.org/cgi/reprint/dmd.105.004929v1.pdf Structural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MS] by Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in "Drug Metabolism and Disposition" (2005, electronic publication).] metabolized from daidzein, a type of isoflavone, by bacterial flora in the intestines. [http://www.pubmedcentral.gov/articlerender.fcgi?tool=pubmed&pubmedid=15640190 Enantioselective Synthesis of S-Equol from Dihydrodaidzein by a Newly Isolated Anaerobic Human Intestinal Bacterium] by Xiu-Ling Wang, Hor-Gil Hur, Je Hyeon Lee, Ki Tae Kim and Su-Il Kim in "Applied and Environmental Microbiology" (2005) Volume 71 pages 214-219.] While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. However, only about 30-50% of people have intestinal bacteria that make equol."High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart" by C. L. Frankenfeld, C. Atkinson, W. K. Thomas, A. Gonzalez, T. Jokela, K. Wahala, S. M. Schwartz, S. S. Li and J. W. Lampe (2005) "The British journal of nutrition" volume 94, pages 873-876. Entrez Pubmed|16351761] Equol may have beneficial effects on the incidence of prostate cancer [http://jjco.oxfordjournals.org/cgi/content/full/34/2/86 Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents] by H. Akaza, N. Miyanaga, N. Takashima, S. Naito, Y. Hirao, T. Tsukamoto, T. Fujioka, M. Mori, W. J. Kim, J. M. Song and A. J. Pantuck (2004) "Japanese Journal of Clinical Oncology" Volume 34, pages 86-39.] and physiological changes after menopause. [http://cebp.aacrjournals.org/cgi/content/full/13/7/1156 Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women] by C. L. Frankenfeld, A. McTiernan, E. J. Aiello, W. k. Thomas, K. LaCroix, J. Schramm, S. M. Schwartz, V. L. Holt and J. W. Lampe in "Cancer Epidemiology, Biomarkers and Prevention" (2004) Volume 13 pages 1156-1162.] Other benefits may be realized in treating male pattern baldness, acne, and other problems because it functions as a DHT blocker. [http://www.biolreprod.org/cgi/content/full/70/4/1188 Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback] by T. D. Lund, D. J. Munson, M. E. Haldy, K. D. Setchell, E. D. Lephart and R. J. Handa (2004) "Biology of Reproduction" Volume 70 pages 1188-1195.] S-Equol preferentially activates estrogen receptor type β. [http://toxsci.oxfordjournals.org/cgi/content/full/80/1/14 Phytoestrogens and Their Human Metabolites Show Distinct Agonistic and Antagonistic Properties on Estrogen Receptor {α} (ER{α}) and ERβ in Human Cells] by Stefan O. Mueller, Stephanie Simon, Kun Chae, Manfred Metzler and Kenneth S. Korach in "Toxicological Sciences" (2004) Volume 80 pages 14-25.]

ee also

*Hormone replacement therapy
*Estrogen receptor

References