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(±)-Equol

Cayman Chemical Item Number 13184

(CAS 94105-90-5)

(±)-Equol (CAS 94105-90-5)

See more	Flavonoids (20) Receptor Agonist (48) Cancer (606) Endocrinology (335)

Description

Equol is a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein by human intestinal microflora.^1,2 The estrogen receptor (ER) binding activity of the naturally occurring (S)-enantiomer demonstrates greater affinity toward ERβ while the (R)-enantiomer demonstrates greater affinity towards ERα.^1,2 Synthesized as a racemic mixture, (±)-equol exhibits EC₅₀ values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM.^2,3

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 Liu, H., Du, J., Hu, C., et al. Delayed activation of extracellular-signal-regulated kinase ½ is involved in genistein- and equol-induced cell proliferation and estrogen-receptor-a-mediated transcription in MCF-7 breast cancer cells. J Nutr Biochem (2009).

Formal Name	3,4-dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol
CAS Number	94105-90-5
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	Copy SMILES to clipboard OC1=CC=C(CC(C2=CC=C(O)C=C2)CO3)C3=C1

Background Reading

Liu, H., Du, J., Hu, C., et al. Delayed activation of extracellular-signal-regulated kinase ½ is involved in genistein- and equol-induced cell proliferation and estrogen-receptor-a-mediated transcription in MCF-7 breast cancer cells. J Nutr Biochem (2009).

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).

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).

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(±)-Equol is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

Size	Price	Quantity	Subtotal
5 mg	$26.00		$0.00
10 mg	$49.00		$0.00
25 mg	$117.00		$0.00
50 mg	$208.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-11. 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.

Related Products

Daidzein

Estrogen Receptor Polyclonal Antibody

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