(±)-Equol

www.equol.us

(±)-Equol (CAS 94105-90-5)

Formal Name
4',7-Isoflavandiol
Molecular Formula
C15H14O3
Formula Weight
242.3
Purity
≥99%
Stability
2 years
Storage
Refrigerated

 

Size
USD
EUR
CHF
 
10gr
$ 1,290.00
€ 960.00
Fr. 1,260.00
50gr
$ 5,500.00
€ 4,080.00
Fr. 5,295.00
100gr
$ 9,800.00
€ 7,280.00
Fr. 9,490.00
500gr
$ 44,000.00
32,612.00
Fr. 41,080.00

 

Sold for laboratory or study purposes only; not for human, medical, veterinary, food, or household use!

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 ERß 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 ERß, 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).

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).