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SML2147

S-Equol

Name: S-Equol
Brand: SIGMA

≥97% (HPLC), Estrogen receptor beta agonist, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₄O₃

CAS Number:

531-95-3

Molecular Weight:

242.27

NACRES:

NA.77

UNSPSC Code:

51111800

EC Number:

208-522-2

MDL number:

MFCD00200962

Assay:

≥97% (HPLC)

Form:

powder

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Properties

Product Name

S-Equol, ≥97% (HPLC)

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

OC1=CC=C([C@H]2COC3=CC(O)=CC=C3C2)C=C1

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/t12-/m1/s1

InChI key

ADFCQWZHKCXPAJ-GFCCVEGCSA-N

Description

Application

S-Equol has been used:

as an estrogen receptor β (ERβ) agonist to study its effects on adipogenesis in mouse fibroblast cells
as a standard to study the effect of high dietary fats on S-equol metabolism and prostate carcinogenesis in the transgenic adenocarcinoma of mouse prostate (TRAMP) model
to study its mode of action on ecdysteroidogenic glutathione S-transferase Noppera-bo in Aedes aegypti

Biochem/physiol Actions

(S)-Equol is an estrogen receptor beta (ERβ) agonist, formed in some people by intestinal bacteria from the soy phytoestrogen daidzein. (S)-Equol has approximately 13-fold higher affinity for human ERβ over ERα and an EC50 value of 65nM for ERβ compared to an EC50 value of 85nM for ERα. It has been shown to have anti-inflammatory and neuroprotective activty.

S-Equol is an isoflavandiol derived from daidzein by bacterial flora in the intestines. It exhibits anti-cancer activity by the activation of forkhead box O3 (FOXO3a) via an Akt-specific pathway and inhibitory effects on mouse double minute 2 homolog (MDM2) expression.

Estrogen receptor beta ( ERβ) agonist from the soy phytoestrogen daidzein

Storage Class

11 - Combustible Solids

wgk

WGK 3

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