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S-Equol

S-Equol

Product ID E6782
Cas No. 531-95-3
Purity ≥99%
Product Unit SizeCostQuantityStock
5 mg $85.90 In stock
25 mg $321.90 In stock
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  • Product Info
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  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
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  • Custom Order

Description

(S)-Equol is a metabolite produced in humans and animals after consuming daidzein, a soy isoflavone. While equol exists in two enantiomeric forms S-equol and R-equol, it is the former that binds preferentially to the estrogen receptor beta. Equol exhibits anti-aging, antioxidative, estrogenic, anti-inflammatory, and chemopreventive activities. In vitro, equol increases expression of extracellular matrix proteins collagen and elastin as well as nerve growth factor (NGF) and decreases expression of aging genes and pro-inflammatory cytokines such as matrix metalloproteinases 1, 3, and 9 (MMP1/3/9), COX-1, IL-6, and IL-1α. In fibroblasts, equol inhibited ROS generation and oxidative stress. In animal models, equol increases activity of catalase, superoxide dismutase (SOD), glutathione peroxidase, and glutathione reductase. Additionally, equol inhibits TNF-α production, NF-κB activation, and IκB kinase degradation in macrophages. This compound increases activation of p53, caspase 3, and poly(ADP)-ribose polymerase (PARP), increases expression of p21 and Bax, and decreases expression of Bcl-2, resulting in apoptosis and inhibition of tumor formation in animal models.

Product Info

Cas No.

531-95-3

Purity

≥99%

Formula

C15H14O3

Formula Wt.

242.27

Chemical Name

(S)-3-(4-Hydroxyphenyl)chroman-7-ol

IUPAC Name

(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol

Synonym

(3S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol, (S)-(–)-4′,7-isoflavandiol, (S)-Equol, Equol

Melting Point

189.5°C

Solubility

Soluble in DMSO, ethanol, dilute aqueous base. Insoluble in water.

Shipping and Storage

Store Temp

-20°C

Ship Temp

Ambient

Downloads

MSDS

E6782 MSDS PDF

Info Sheet

E6782 Info Sheet PDF

References

Lephart ED. Protective effects of equol and their polyphenolic isomers against dermal aging: microarray/protein evidence with clinical implications and unique delivery into human skin. Pharm Biol. 2013 Nov;51(11):1393-400. PMID: 23862588.

Richardson TE, Simpkins JW. R- and S-equol have equivalent cytoprotective effects in Friedreich's ataxia. BMC Pharmacol Toxicol. 2012 Oct 22;13:12. PMID: 23088310.

Choi EJ, Kim GH. Anticancer mechanism of equol in 7,12-dimethylbenz(a)anthracene-treated animals. Int J Oncol. 2011 Sep;39(3):747-54. PMID: 21667019.

Muñoz Y, Garrido A, Valladares L. Equol is more active than soy isoflavone itself to compete for binding to thromboxane A(2) receptor in human platelets. Thromb Res. 2009 Mar;123(5):740-4. PMID: 18786699.

Kang JS, Yoon YD, Han MH, et al. Estrogen receptor-independent inhibition of tumor necrosis factor-alpha gene expression by phytoestrogen equol is mediated by blocking nuclear factor-kappaB activation in mouse macrophages. Biochem Pharmacol. 2005 Dec 19;71(1-2):136-43. PMID: 16288994.

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