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SML2147

Sigma-Aldrich

S-Equol

≥97% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C15H14O3
Numéro CAS:
531-95-3
Poids moléculaire :
242.27
Numéro CE :
208-522-2
Numéro MDL:
MFCD00200962
Code UNSPSC :
51111800
Nomenclature NACRES :
NA.77

Pureté

≥97% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

ADFCQWZHKCXPAJ-GFCCVEGCSA-N

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

Actions biochimiques/physiologiques

(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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Certificats d'analyse (COA)

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Yufei Liu et al.
Nutrition & metabolism, 16, 24-24 (2019-04-24)
Consumption of diet high in soy products is suggested to contribute to lower prostate cancer incidence in Asian men. But little has been known about the influences of dietary patterns on gut microbiota and microbiota-mediated isoflavone metabolism. Here, we determined
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BMC biology, 20(1), 43-43 (2022-02-18)
Mosquito control is a crucial global issue for protecting the human community from mosquito-borne diseases. There is an urgent need for the development of selective and safe reagents for mosquito control. Flavonoids, a group of chemical substances with variable phenolic
Zongliang Lu et al.
Current cancer drug targets, 16(5), 455-465 (2015-12-08)
Forkhead box O3 (FOXO3a) is a transcription factor with tumor suppressor functions that plays an important role in prostate cancer. Daidzein, one of the soy isoflavones present in soy-based foods, has been shown to exert anti-tumor effects in vitro and

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