SML2147

S-Equol

≥97% (HPLC)

• Synonym(s): (3S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol, (S)-(–)-4′,7-isoflavandiol, (S)-Equol, Equol
• Empirical Formula (Hill Notation): C₁₅H₁₄O₃
• CAS Number: 531-95-3
• Molecular Weight: 242.27
• EC Number: 208-522-2
• MDL number: MFCD00200962
• UNSPSC Code: 51111800
• NACRES: NA.77

Properties

• 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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3