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(-)-(S)-Equol

Catalog No. T6491 CAS 531-95-3

Synonyms: (−)-Equol, Equol, 4',7-Dihydroxyisoflavan, 4',7-Isoflavandiol

(-)-(S)-Equol (4',7-Dihydroxyisoflavan) is an orally bioavailable, non-steroidal estrogen naturally produced by the metabolism of the isoflavonoid daidzein by human intestinal microflora, with potential chemoprotective and estrogen receptor (ER) modulating activities. S-equol preferentially binds to and activates the beta isoform of ER in certain target tissues, while having an antagonistic effect in other tissues. This modulates the expression of ER-responsive genes in a tissue-specific manner. This agent may increase bone mineral density, affect vasomotor symptoms, and may decrease the proliferation rate of susceptible cancer cells. In addition, this agent interferes with the activity of enzymes involved in steroid biosynthesis. S-equol inhibits dihydrotestosterone (DHT) production and may inhibit the proliferation of androgen-driven prostate cancer. S-equol is the biologically active enantiomer while R-equol is essentially inactive and has a weak affinity for alpha-ER.

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(-)-(S)-Equol, CAS 531-95-3

Pack Size	Availability	Price/USD
5 mg	In stock	$ 43.00
10 mg	In stock	$ 61.00
25 mg	In stock	$ 101.00
50 mg	In stock	$ 173.00
100 mg	In stock	$ 303.00
500 mg	In stock	$ 743.00
1 mL * 10 mM (in DMSO)	In stock	$ 48.00

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Purity: 99.61%

Purity: 97.15%

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Storage & Solubility Information

Description	(-)-(S)-Equol (4',7-Dihydroxyisoflavan) is an orally bioavailable, non-steroidal estrogen naturally produced by the metabolism of the isoflavonoid daidzein by human intestinal microflora, with potential chemoprotective and estrogen receptor (ER) modulating activities. S-equol preferentially binds to and activates the beta isoform of ER in certain target tissues, while having an antagonistic effect in other tissues. This modulates the expression of ER-responsive genes in a tissue-specific manner. This agent may increase bone mineral density, affect vasomotor symptoms, and may decrease the proliferation rate of susceptible cancer cells. In addition, this agent interferes with the activity of enzymes involved in steroid biosynthesis. S-equol inhibits dihydrotestosterone (DHT) production and may inhibit the proliferation of androgen-driven prostate cancer. S-equol is the biologically active enantiomer while R-equol is essentially inactive and has a weak affinity for alpha-ER.
Targets&IC50	ERRβ:0.73 nM(Ki)
In vitro	Equol is a metabolite produced from the soy phytoestrogen daidzein by the action of gut microflora. Equol has higher affinity for both ERs (estrogen receptors including ERalpha and ERbeta). Equol exists as the enantiomers R-equol and S-equol. S-equol has a high binding affinity, preferential for ERbeta with a Ki of 16 nM whereas R-equol binds more weakly and with a preference for ERalpha K with a Ki of 50 nM. [1] Equol is superior to all other isoflavones in its antioxidant activity. [2] Equol has antioestrogenic properties. [3] Equol is a 100-fold more potent than daidzein in stimulating an oestrogenic response. Equol is also more effective than daidzein in competing with 3 H-oestradiol for binding to the ER. Equol stimulates the growth of MCF-7 cells in a concentration-dependent manner. Although equol exhibits oestrogenic activity, exposure of MCF-7 cells to equol simultaneously with oestradiol is effective in reducing pS2 mRNA expression. Equol results in the downregulation of ER mRNA expression. [4]
Cell Research	Each well of a 24-well plate is seeded with 1 × 105 MCF-7 cells in 1 mL of media B. Twenty-four hours after plating, equol at the indicated concentration is added. Equol is dissolved in ethanol (final concentration of ethanol in the medium is 1%). The medium is changed every 24 hours and equol is replenished with each change. Cell growth is determined on the sixth day by the sulphorhodamine colorimetric assay. After colour development, aliquots are pipetted into a 96-well microtitre plate and the absorbance is determined at 570 nm using an Elisa microplate reader.(Only for Reference)
Source	Natural Products > Fabaceae > Glycine

Synonyms	(−)-Equol, Equol, 4',7-Dihydroxyisoflavan, 4',7-Isoflavandiol
Molecular Weight	242.27
Formula	C15H14O3
CAS No.	531-95-3

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: 24.2 mg/mL (100 mM)

Ethanol: 24.2 mg/mL (100 mM)

References and Literature

1. Muthyala RS, et al. Bioorg Med Chem, 2004, 12(6), 1559-1567. 2. Setchell KD, et al. J Nutr, 2002, 132(12), 3577-3584. 3. Adlercreutz H, et al. Lancet, 1982, 2(8311), 1295-1299. 4. Sathyamoorthy N, et al. Eur J Cancer, 1997, 33(14), 2384-2389.

Related compound libraries

This product is contained In the following compound libraries：

Anti-Neurodegenerative Disease Compound Library Anti-Cancer Active Compound Library Inhibitor Library Ferroptosis Compound Library Bioactive Compound Library Anti-Alzheimer's Disease Compound Library NO PAINS Compound Library Human Endogenous Metabolite Compound Library Plus Human Metabolite Library Nuclear Receptor Compound Library

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Pipendoxifene hydrochloride Erteberel Estrogen receptor modulator 8 Estrogen receptor modulator 7 Giredestrant Giredestrant tartrate Delphinidin chloride Gypenoside XVII

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Keywords

(-)-(S)-Equol 531-95-3 Endocrinology/Hormones Metabolism Estrogen/progestogen Receptor Estrogen Receptor/ERR Endogenous Metabolite Inhibitor inhibit (−)-Equol Equol 4',7-Dihydroxyisoflavan ( ) (S) Equol 4',7-Isoflavandiol ()(S)Equol inhibitor

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