Equol

Equol
Names
IUPAC name
(3S)-Isoflavan-4,7′-diol
Systematic IUPAC name
(3S)-3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
Other names
4',7-Isoflavandiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.749 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1 checkY
    Key: ADFCQWZHKCXPAJ-GFCCVEGCSA-N checkY
  • InChI=1/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1
    Key: ADFCQWZHKCXPAJ-GFCCVEGCBP
  • C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
  • Oc1ccc(cc1)[C@@H]2Cc3c(OC2)cc(O)cc3
Properties
C15H14O3
Molar mass 242.274 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Equol (4',7-isoflavandiol) is an isoflavandiol[1] estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines.[2][3] While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol.[4]

  1. ^ The structures of 7,4’-dihydroxy-isoflavan and its precursors is shown in 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).
  2. ^ Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). "Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium". Appl. Environ. Microbiol. 71 (1): 214–9. Bibcode:2005ApEnM..71..214W. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190.
  3. ^ Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). "Equol, a natural estrogenic metabolite from soy isoflavones". Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. PMID 15018930.
  4. ^ Frankenfeld CL, Atkinson C, Thomas WK, et al. (December 2005). "High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart". Br. J. Nutr. 94 (6): 873–6. doi:10.1079/bjn20051565. PMID 16351761.