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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

(S)-Equol

Cayman Chemical Item Number 10010173

4',7-Isoflavandiol; 4',7-Dihydroxyisoflavan; (−)-Equol (CAS 531-95-3)

(S)-Equol (CAS 531-95-3)

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Description

Equol is a non-steroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzen by human intestinal microflora.1,2 The estrogen receptor (ER) agonist activity of the naturally occurring (S)-enantiomer (EC50 = 85 and 65 nM for human ERα and ERβ, respectively) is similar to that of genistein but exceeds that of daidzein.2 (S)-Equol preferentially binds ERβ (Ki = 0.73 nM) and demonstrates approximately 9-fold lower affinity for ERα (Ki = 6.41 nM).1 (S)-equol is also a potent antagonist of dihydrotestosterone, which has important implications for prostate cancer and other androgen-mediated pathologies.3

1 Setchell, K.D.R., Clerici, C., Lephart, E.D., et al. S-equol, a potent ligand for estrogen receptor b, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr 81 1072-1079 (2005).

2 Muthyala, R.S., Ju, Y.H., Sheng, S., et al. Equol, a natural estrogenic metabolite from soy isoflavones: Convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta. Bioorg Med Chem 12 1559-1567 (2004).

3 Lund, T.D., Munson, D.J., Haldy, M.E., et al. Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback. Biol Reprod 70 1188-1195 (2004).

Synonyms
  • 4',7-Isoflavandiol
  • 4',7-Dihydroxyisoflavan
  • (-)-Equol
Formal Name (S)-​3,​4-​dihydro-​3-​(4-​hydroxyphenyl)-​2H-​1-​benzopyran-​7-​ol
CAS Number 531-95-3
Molecular Formula C15H14O3
Formula Weight 242.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OC1=CC=C2C(OC[C@H]​(C3=CC=C(O)​C=C3)​C2)​=C1

Background Reading

Lund, T.D., Munson, D.J., Haldy, M.E., et al. Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback. Biol Reprod 70 1188-1195 (2004).

Muthyala, R.S., Ju, Y.H., Sheng, S., et al. Equol, a natural estrogenic metabolite from soy isoflavones: Convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta. Bioorg Med Chem 12 1559-1567 (2004).

Heemstra, J.M., Kerrigan, S.A., Doerge, D.R., et al. Total synthesis of (S)-equol. Org Lett 8(24) 5441-5443 (2006).

Setchell, K.D.R., Clerici, C., Lephart, E.D., et al. S-equol, a potent ligand for estrogen receptor b, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr 81 1072-1079 (2005).

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Size Price Quantity Subtotal
1 mg $16.00 $0.00
5 mg $72.00 $0.00
10 mg $128.00 $0.00
25 mg $280.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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(R)-Equol Exclusive
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