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    Drug Metabolite
  3. (±)-Equol

(±)-Equol 

Cat. No.: HY-100583A Purity: 98.04%
Handling Instructions

(±)-Equol is the racemate of equol. Equol is a metabolite of the soy isoflavones, daidzin and daidzein.

For research use only. We do not sell to patients.

(±)-Equol Chemical Structure

(±)-Equol Chemical Structure

CAS No. : 94105-90-5

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Based on 1 publication(s) in Google Scholar

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Description

(±)-Equol is the racemate of equol. Equol is a metabolite of the soy isoflavones, daidzin and daidzein.

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[1]. 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[2]. 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[3].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

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)[4]. 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[5].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

242.27

Formula

C₁₅H₁₄O₃

CAS No.

94105-90-5

SMILES

OC1=CC=C2CC(C3=CC=C(O)C=C3)COC2=C1

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : ≥ 100 mg/mL (412.76 mM)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 4.1276 mL 20.6381 mL 41.2763 mL
5 mM 0.8255 mL 4.1276 mL 8.2553 mL
10 mM 0.4128 mL 2.0638 mL 4.1276 mL
*Please refer to the solubility information to select the appropriate solvent.
In Vivo:
  • 1.

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% saline

    Solubility: ≥ 2.5 mg/mL (10.32 mM); Clear solution

  • 2.

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in saline)

    Solubility: ≥ 2.5 mg/mL (10.32 mM); Clear solution

  • 3.

    Add each solvent one by one:  10% DMSO    90% corn oil

    Solubility: ≥ 2.5 mg/mL (10.32 mM); Clear solution

*All of the co-solvents are provided by MCE.
References
Cell Assay
[3]

Primary rat osteoblasts are treated with 0.01-1 μM equol, 0.01-1 μM E2 , or 0.01-1 μM equol/E2 combined with 1 μM ICI182780 for 24 or 48 hours. Then 10 mL 5 mg/mL MTT solution is added to each well. The plates are incubated at 37°C for 4 h, and then the supernatant is discarded and 100 mL DMSO is added to each well and mixed thoroughly before taking measurements in a microplate reader[3].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Administration
[3][5]

Rats: Equol or furosemide is administered orally at doses of 16, 40, and 100 mg/kg (in a volume of 16 mL/kg 5% arabic syrup) to groups of 3-9 rats (rats of a control group are administered vehicle only). Urine samples are collected for 6 h. Urinary sodium and potassium contents are measured by flame photometry[3].

Mouse: Equol is dissolved in water and administered orally to rats at a dose of 5 and 25 mg/kg BW for 8 weeks after a single dose of DMBA (100 mg/kg). As controls, rats are divided into vehicle alone and DMBA alone groups. In the second part, ICR mice are orally administered equol daily at a dose of 5 and 25 mg/kg BW for 7 weeks before a single dose of DMBA (34 mg/kg/week). After equol administration animals are followed for 1 week continuously. The control groups are the same as above and each group are comprised of six mice. Mice livers and mammary gland tumors are isolated, blotted, weighed, frozen in liquid nitrogen and stored at -70°C until assayed[5].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

References
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Keywords:

(±)-EquolEstrogen Receptor/ERRDrug MetaboliteInhibitorinhibitorinhibit

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(±)-Equol
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