(S)-Equol (Synonyms: 4',7Dihydroxyisoflavan, (-)Equol, 4',7Isoflavandiol) |
| Catalog No.GC49520 |
(S)-Equol is an isoflavone compound produced by the gut microbiota of some individuals, primarily derived from the metabolism of daidzein in soybeans by specific gut bacteria. (S)-Equol exhibits significant estrogenic activity and antioxidant properties, binding to estrogen receptors with an affinity for ERβ of Ki=0.73±0.2nM and for ERα of Ki=6.41±1nM.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 531-95-3
Sample solution is provided at 25 µL, 10mM.
(S)-Equol is an isoflavone compound produced by the gut microbiota of some individuals, primarily derived from the metabolism of daidzein in soybeans by specific gut bacteria[1]. (S)-Equol exhibits significant estrogenic activity and antioxidant properties, binding to estrogen receptors with an affinity for ERβ of Ki=0.73±0.2nM and for ERα of Ki=6.41±1nM[2]. (S)-Equol also has antioxidant effects, scavenging free radicals in the body to reduce oxidative stress and prevent the development of cardiovascular diseases and certain chronic conditions[3]. (S)-Equol has demonstrated antitumor activity by regulating the cell cycle and inducing apoptosis, inhibiting tumor cell growth and spread, and providing new insights for cancer prevention and adjuvant therapy[4].
In vitro, 30μM (S)-Equol pre-treatment of rat primary chondrocytes for 24h, followed by stimulation with 0.8mM Sodium nitroprusside (SNP; 50μM) for 24h, significantly activated the PI3K/Akt signaling pathway, reducing SNP-induced cell death, oxidative stress, apoptosis, and proteoglycan loss, while inhibiting the expression of matrix metalloproteinases (MMPs) and p53[5]. 0.1-10μM (S)-Equol pre-treatment of rat insulinoma beta cell line INS-1 cells, followed by stimulation with high glucose (26.2mM) for 48h, significantly enhanced insulin secretion, decreased cell apoptosis, and inhibited the Chrebp/Txnip signaling pathway, activating PKA/PP2A activity[6].
In vivo, (S)-Equol (20, 40, 80mg/kg) administered daily via gavage for 12 weeks in a diabetic osteoporosis (DOP) rat model significantly increased bone density, improved bone microstructure, and enhanced bone formation markers while reducing bone resorption markers, ameliorating DOP[7]. (S)-Equol (2mg/kg/d) administered orally daily for 8 weeks in a Sprague–Dawley (SD) rat model of varying degrees of menopausal osteoarthritis (OA) significantly reduced OA pathological damage, oxidative stress, and cartilage matrix degradation[8].
References:
[1] Chen LR, Chen KH. Utilization of Isoflavones in Soybeans for Women with Menopausal Syndrome: An Overview. Int J Mol Sci. 2021 Mar 22;22(6):3212.
[2] Setchell KD, Clerici C, Lephart ED, et al. S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr. 2005 May;81(5):1072-9.
[3] Sekikawa A, Wharton W, Butts B, et al. Potential Protective Mechanisms of S-equol, a Metabolite of Soy Isoflavone by the Gut Microbiome, on Cognitive Decline and Dementia. Int J Mol Sci. 2022 Oct 7;23(19):11921.
[4] Zhang J, Ren L, Yu M, et al. S-equol inhibits proliferation and promotes apoptosis of human breast cancer MCF-7 cells via regulating miR-10a-5p and PI3K/AKT pathway. Arch Biochem Biophys. 2019 Sep 15;672:108064.
[5] Huang LW, Huang TC, Hu YC, et al. S-Equol Protects Chondrocytes against Sodium Nitroprusside-Caused Matrix Loss and Apoptosis through Activating PI3K/Akt Pathway. Int J Mol Sci. 2021 Jun 30;22(13):7054.
[6] Chen K, Lang H, Wang L, et al. S-Equol ameliorates insulin secretion failure through Chrebp/Txnip signaling via modulating PKA/PP2A activities. Nutr Metab (Lond). 2020 Jan 14;17:7.
[7] Xu Z, Xu J, Li S, et al. S-Equol enhances osteoblastic bone formation and prevents bone loss through OPG/RANKL via the PI3K/Akt pathway in streptozotocin-induced diabetic rats. Front Nutr. 2022 Oct 21;9:986192.
[8] Hu YC, Huang TC, Huang LW, et al. S-Equol Ameliorates Menopausal Osteoarthritis in Rats through Reducing Oxidative Stress and Cartilage Degradation. Nutrients. 2024 Jul 21;16(14):2364.
| Cell experiment [1]: | |
Cell lines | INS-1 cells (rat insulinoma beta cells) |
Preparation Method | INS-1 cells were cultured in RPMI 1640 medium containing 10% fetal bovine serum (FBS), 1% penicillin/streptomycin, 1mM sodium pyruvate, 2mM L-glutamine, 10mM HEPES, and 0.05mM 2-mercaptoethanol at 37°C, 5% CO₂. Cells were treated with (S)-Equol (0.1μM, 1μM, 10μM) in the presence of high glucose (26.2mM) for 48 hours. |
Reaction Conditions | 0.1-10μM; 48 hours |
Applications | (S)-Equol treatment enhanced glucose-stimulated insulin secretion (GSIS) in high glucose-cultured INS-1 cells. (S)-Equol also reduced cell apoptosis, as evidenced by decreased apoptotic cell numbers. (S)-Equol significantly increased the expression of preproinsulin (PPI) mRNA and Glut2 protein, while decreasing UCP-2 protein levels. |
| Animal experiment [2]: | |
Animal models | Sprague–Dawley (SD) rats |
Preparation Method | Rats were subjected to bilateral ovariectomy (OVX) to induce estrogen deficiency and intra-articular injection of mono-iodoacetate (MIA) to induce osteoarthritis (OA). Rats were divided into sham, OVX, OVX with low-dose MIA (0.1mg), and OVX with high-dose MIA (1mg) groups. (S)-Equol (2mg/kg/d) was administered orally for 8 weeks. |
Dosage form | 2mg/kg/d; oral administration |
Applications | (S)-Equol supplementation significantly reduced body weight gain, serum triglyceride levels, and oxidative stress markers. (S)-Equol also decreased cartilage degradation biomarkers, matrix-degrading enzymes, and improved histopathological changes in the knee joint, indicating its potential to mitigate menopausal OA progression. |
References: | |
| Cas No. | 531-95-3 | SDF | |
| Synonyms | 4',7Dihydroxyisoflavan, (-)Equol, 4',7Isoflavandiol | ||
| Canonical SMILES | OC1=CC=C2C(OC[C@H](C3=CC=C(O)C=C3)C2)=C1 | ||
| Formula | C15H14O3 | M.Wt | 242.3 |
| Solubility | DMF: 15 mg/ml,DMSO: 20 mg/ml,Ethanol: 20 mg/ml,Ethanol:PBS (pH 7.2) (1:10): 0.1 mg/ml | Storage | -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.1271 mL | 20.6356 mL | 41.2712 mL |
| 5 mM | 825.4 μL | 4.1271 mL | 8.2542 mL |
| 10 mM | 412.7 μL | 2.0636 mL | 4.1271 mL |
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Quality Control & SDS
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- Purity: >98.00%
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Average Rating: 5 (Based on Reviews and 35 reference(s) in Google Scholar.)
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