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(±)-Equol

Item № 13184
CAS № 94105-90-5
Purity ≥98%
product image
                (CAS 94105-90-5)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     5 mg $26.00 0.00
     10 mg $49.00 0.00
     25 mg $117.00 0.00
     50 mg $208.00 0.00

Pricing updated 2019-06-15. Prices are subject to change without notice.

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

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Technical Information
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
Purity
≥98%
Formulation
A crystalline solid
λmax
206, 225, 281 nm
SMILES
OC1=CC=C(CC(C2=CC=C(O)C=C2)CO3)C3=C1
InChI Code
InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2
InChI Key
ADFCQWZHKCXPAJ-UHFFFAOYSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

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References & Product Citations
Product Description References

1. Setchell, K.D.R., Clerici, C., Lephart, E.D., et al. S-equol, a potent ligand for estrogen receptor ß, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora American Journal of Clinical Nutrition 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 Bioorganic & Medicinal Chemistry 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-α-mediated transcription in MCF-7 breast cancer cells Journal of Nutritional Biochemistry (2009).

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