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Equol (racemic), the racemic mixture of equol, is a medication that hinders the growth of human gastric cancer cells and may be used to treat acute thyroid disease. S-equol and R-equol are combined to form equol (racemic).
| Targets |
ERβ
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|---|---|
| ln Vitro |
Equol is subsequently discovered in the urine of goats, cows, hens, and sheep[1]. It is initially isolated and recognized from the urine of pregnant mares. Equol can exist as two different diastereoisomers because it has a chiral center, unlike the soy isoflavones genistein and daidzein. The sole byproduct of soy isoflavone synthesis in the human gut is s-equol, which is bioavailable in both enantiomers. While R-equol is comparatively inactive, S-equol exhibits a high affinity for estrogen receptor beta (Ki=0.73 nM)[2]. Equol may enhance rat osteoblast growth and differentiation by triggering the signaling pathway linked to ER-PKCα. Significant increases in alkaline phosphatase activity are also observed in all equol and 17β-estradiol (E2) groups. Additionally, equol dramatically raises osteocalcin levels[3].
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| ln Vivo |
Equol is a mild vasorelaxant and natriuretic in rats. Equol taken orally has about 8 times less potency than furosemide taken orally. Equol administration relaxes the contracted aorta in isolated aortic rings precontracted by phenylephrine administration (concentration for half-maximal activity: 58.9±16 μM)[4]. Equol has anticancer properties; in rats with mammary gland tumors, it inhibits the growth of tumors by inducing apoptosis. Moreover, equol protects the liver by lowering apoptosis and functioning as an antioxidant[5].
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| Cell Assay |
For 24 or 48 hours, 0.01-1 μM equol, 0.01-1 μM E2, or 0.01-1 μM equol/E2 combined with 1 μM ICI182780 are applied to primary rat osteoblasts. Each well is then filled with 10 mL of a 5 mg/mL MTT solution. Before taking measurements in a microplate reader, 100 mL of DMSO is added to each well and thoroughly mixed after the plates are incubated at 37°C for four hours[3]. The supernatant is then discarded.
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| Animal Protocol |
Rats: Groups of 3–9 rats are given oral doses of equol or furosemide (16, 40, and 100 mg/kg) in a volume of 16 mL/kg 5% arabic syrup (vehicle only is given to rats in the control group). Samples of urine are taken for six hours. Flame photometry is used to determine the sodium and potassium contents of the urine[3].
Mouse: Eight weeks after a single dose of DMBA (100 mg/kg), rats are given equol, which has been dissolved in water and given orally at a dose of 5 and 25 mg/kg BW. Rats are separated into vehicle alone and DMBA alone groups as controls. In the second phase, equol is given orally to ICR mice every day at a dose of 5 and 25 mg/kg BW for 7 weeks, prior to a single weekly dose of DMBA (34 mg/kg). Animals are observed nonstop for a week following equol administration. The six mice in each of the control groups are the same as in the previous group. Mammary gland tumors and mouse livers are separated, blotted, weighed, frozen in liquid nitrogen, and kept at -70°C until analysis[5]. |
| References |
| Molecular Formula |
C15H14O3
|
|---|---|
| Molecular Weight |
242.274
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| Exact Mass |
242.0943
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| Elemental Analysis |
C, 74.36; H, 5.82; O, 19.81
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| CAS # |
94105-90-5
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| Related CAS # |
(-)-(S)-Equol;531-95-3;(R)-Equol;221054-79-1
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| Appearance |
Solid powder
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| SMILES |
C1C(COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
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| InChi Key |
ADFCQWZHKCXPAJ-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol
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| Synonyms |
(±)-Equol; (-)-(S)-Equol; (-)-Equol; (3S)-Equol; (S)-Equol; AUS 131; Equol; S-Equol; SE 5OH
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~48 mg/mL (~198.1 mM)
Ethanol: ~48 mg/mL (~198.1 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (10.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05741060 | Recruiting | Drug: S-equol Drug: Placebo |
Arterial Stiffness Cognitive Decline |
Akira Sekikawa | June 29, 2023 | Phase 2 |
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