(±)-Equol

(±)-Equol is the racemate of equol. (±)-equol exhibits EC50s of 200 and 74 nM for human ERα and ERβ, respectively. Equol is a metabolite of the soy isoflavones, daidzin and daidzein.

Product information

CAS Number: 94105-90-5

Molecular Weight: 242.27

Formula: C15H14O3

Chemical Name: 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Smiles: OC1C=C2OCC(CC2=CC=1)C1C=CC(O)=CC=1

InChiKey: ADFCQWZHKCXPAJ-UHFFFAOYSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : ≥ 100 mg/mL (412.76 mM).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Equol is first isolated and identified from pregnant-mares' urine and later found in the urine of the goat, cow, hen and sheep. Equol, unlike the soy isoflavones daidzein or genistein, has a chiral center and therefore can occur as 2 distinct diastereoisomers. S-equol is the exclusive product of human intestinal bacterial synthesis from soy isoflavones and both enantiomers are bioavailable. S-equol has a high affinity for estrogen receptor beta (Ki=0.73 nM), whereas R-equol is relatively inactive. Equol could promote the proliferation and differentiation of rat osteoblasts through activating the ER-PKCα-related signaling pathway. The alkaline phosphatase activity also increases significantly in all of the equol and 17β-estradiol (E2 ) groups. Equol also significantly elevates the osteocalcin levels.

In Vivo:

Equol is a modest natriuretic and vasorelaxant agent in the rat. Orally administered equol is about 8-fold less potent than orally administered furosemide. In isolated aortic rings precontracted by administration of phenylephrine, administration of equol relaxes the contracted aorta (concentration for half-maximal activity 58.9±16 μM). Equol possesses anticancer activity that suppresses tumor formation via apoptosis induction in rats with DMBA-induced mammary gland tumors. In addition, equol shows a hepatic protective effect by acting as an antioxidant and by reducing apoptosis.

Products are for research use only. Not for human use.