(S)-Equol

(S)-Equol

Identifiers
IUPAC name (3S)-3-(4-Hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol
CAS Number	531-95-3
PubChem (CID)	91469
ChemSpider	82594
Chemical and physical data
Formula	C15H14O3
Molar mass	242.26986 g/mol
3D model (Jmol)	Interactive image
SMILES C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
InChI 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 (K_i = 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 (K_i = 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] 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

• Daidzein
• Genistein
• Liquiritigenin
• Menerba
• Prinaberel
• WAY-200070
• Diarylpropionitrile

References

1. 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.
2. Nilsson, Stefan; Koehler, Konrad F.; Gustafsson, Jan-Åke (2011). "Development of subtype-selective oestrogen receptor-based therapeutics". Nature Reviews Drug Discovery. 10 (10): 778–792. doi:10.1038/nrd3551. ISSN 1474-1776.
3. Jackson, Richard L.; Greiwe, Jeffrey S.; Desai, Pankaj B.; Schwen, Richard J. (2010). "Single-dose and steady-state pharmacokinetic studies of S-equol, a potent nonhormonal, estrogen receptor β-agonist being developed for the treatment of menopausal symptoms". Menopause: 1. doi:10.1097/gme.0b013e3181e9779c. ISSN 1072-3714.
4. Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, Handa RJ, Heubi JE (2005). "S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora". Am. J. Clin. Nutr. 81 (5): 1072–9. PMID 15883431.