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

(R)-Equol Exclusive

Cayman Chemical Item Number 10010172

Isoequol; (+)-Equol (CAS 221054-79-1)

(R)-Equol (CAS 221054-79-1)

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Description

Equol is a non-steroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein by human intestinal microflora.1,2 It is a chiral molecule that exists in two enantiomeric forms.2 In contrast to the estrogen receptor (ER) selectivity of (S)-equol , (R)-equol is a weaker ER agonist that binds to ERα and ERβ with Ki values of 27.4 and 15.4 nM, respectively.1 The (R)-enantiomer demonstrates higher ER agonist activity at ERα compared to ERβ (EC50 = 66 and 330 nM, respectively).2

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).

Synonyms
  • Isoequol
  • (+)-Equol
Formal Name 3,​4-​dihydro-​3R-​(4-​hydroxyphenyl)-​2H-​1-​benzopyran-​7-​ol
CAS Number 221054-79-1
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

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).
Size Price Quantity Subtotal
1 mg $13.00 $0.00
5 mg $59.00 $0.00
10 mg $104.00 $0.00
25 mg $228.00 $0.00
Bulk Contact
Cart Total $0.00

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

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

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Warning This product is not for human or veterinary use.

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