(S)-Equol

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Cat.No. 6158 - (S)-Equol | C15H14O3 | CAS No. 531-95-3
Description: Potent estrogen receptor β (ERβ) agonist; dihydrotestosterone antagonist
Chemical Name: (3S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature
Pathways

Biological Activity

Potent estrogen receptor β (ERβ) agonist (EC50 = 65 nM). Exhibits 13-fold selectivity for ERβ over ERα. Atheroprotective. Protects against t-BHP induced apoptosis and attenuates ER stress in HUVECs. Activates Nrf2 signaling in vitro and in vivo. Inhibits tumor growth. Also dihydrotestosterone antagonist in vivo.

Technical Data

M. Wt 242.27
Formula C15H14O3
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 531-95-3
PubChem ID 91469
InChI Key ADFCQWZHKCXPAJ-GFCCVEGCSA-N
Smiles OC1=CC=C([C@H]2COC3=CC(O)=CC=C3C2)C=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 24.23 100
ethanol 24.23 100

Preparing Stock Solutions

The following data is based on the product molecular weight 242.27. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 4.13 mL 20.64 mL 41.28 mL
5 mM 0.83 mL 4.13 mL 8.26 mL
10 mM 0.41 mL 2.06 mL 4.13 mL
50 mM 0.08 mL 0.41 mL 0.83 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Yuan et al (2016) Tyrosine phosphorylation regulates ERβ ubiquitination, protein turnover, and inhibition of breast cancer. Oncotarget. 7 42585 PMID: 27323858

Zhang et al (2016) Equol attenuates atherosclerosis in apolipoprotein e-deficient mice by inhibiting endoplasmic reticulum stress via activation of Nrf2 in endothelial cells. PLoS One. 11 PMID: 27907038

Muthyala et al (2004) 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 PMID: 15018930

Setchell et al (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 1079 PMID: 15883431


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Keywords: (S)-Equol, supplier, agonist, estrogen, receptor, beta, agonist, ERb, ERbeta, ERβ, Nrf2, Estrogen, and, Related, Receptors, Androgen, Receptor, Estrogen, and, Related, Receptors, Tocris Bioscience

Citations for (S)-Equol

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Pathways for (S)-Equol

Estrogen

Estrogen Signaling Pathway

Estrogen is a steroid hormone that is responsible for the regulation of growth, differentiation and function of the reproductive system. Estrogen signaling is often dysregulated in breast cancer and osteoporosis.