(S)-Equol

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(S)-Equol
Equol structure.png
Systematic (IUPAC) name
(3S)-3-(4-Hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol
Identifiers
CAS Number 531-95-3
PubChem CID: 91469
ChemSpider 82594
Chemical data
Formula C15H14O3
Molecular mass 242.26986 g/mol
  • C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
  • 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
  • Key:ADFCQWZHKCXPAJ-GFCCVEGCSA-N

(S)-Equol, or (S)-(–)-4',7-isoflavandiol, is the (S)-enantiomer of the naturally-occurring isoflavandiol estrogen, equol.[1] It is a non-steroidal, selective agonist of ERβ (Ki = 16 nM), with 13-fold selectivity for ERβ over ERα.[1] Relative to (S)-equol, (R)-equol is less potent and, in contrast, binds to ERα (Ki = 50 nM) with 3.5-fold selectivity over ERβ.[1] Under the code name AUS-131, (S)-equol is under development for the treatment of menopausal symptoms such as hot flashes and benign prostatic hyperplasia.[2][3][1] Human intestinal bacteria metabolize the soy isoflavone daidzein into (S)-equol, and it has been determined that (S)-equol is exclusively produced.[4]

See also

References

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