(-)-Epicatechin (Synonyms: epi-Catechin, NSC 81161) |
Catalog No.GN10461
One-Click Copy Product Info
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(-)-Epicatechin is an orally active flavan-3-ol polyphenol and a COX-1 inhibitor (IC50=3.2μM).
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 490-46-0
Sample solution is provided at 25 µL, 10mM.
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(-)-Epicatechin is an orally active flavan-3-ol polyphenol and a COX-1 inhibitor (IC50=3.2μM). (-)-Epicatechin can activate the PI3K/Akt pathway to phosphorylate endothelial nitric oxide synthase and inhibit NADPH oxidase, thereby increasing nitric oxide bioavailability and improving vascular endothelial function. (-)-Epicatechin can activate Nrf2 antioxidant signaling and promote mitochondrial biogenesis. (-)-Epicatechin can be used in research related to cardiovascular diseases, metabolic diseases, muscle-related diseases, cancer, inflammation, diabetes, and neurodegenerative diseases[1-4].
In vitro, pretreatment of Caco-2 cells with 0.5-5μM (-)-Epicatechin for 6 hours followed by treatment with 20ng/mL tumor necrosis factor alpha (TNF-α) inhibited TNF-α-triggered NADPH oxidase-mediated increase in oxidant generation, NF-κB and ERK1/2 activation, and prevented the decrease in transepithelial electrical resistance and cell monolayer permeabilization[5]. Treatment of PMA and IL-1α-activated EL4.BU.OU6 cells with 200-400μM (-)-Epicatechin for 24 hours dose-dependently reduced IL-2Rα expression, inhibited IL-2 secretion, and did not change cell viability[6]. Treatment of HepG2 cells with 1-100μM (-)-Epicatechin for 18 hours reduced cell viability, promoted cell proliferation, and decreased reactive oxygen species generation[7].
In vivo, feeding C57BL/6J mice a diet supplemented with 20mg/kg (-)-Epicatechin for 15 weeks improved glucose tolerance and insulin tolerance, reduced fasted and fed plasma glucose and insulin levels, decreased plasma triglyceride and free fatty acid concentrations, and attenuated body weight gain[8]. Feeding C57BL/6J mice a diet supplemented with 20mg/kg (-)-Epicatechin for 15 weeks increased plasma glucagon-like peptide 1 concentration, upregulated ileal proglucagon mRNA levels, and decreased plasma dipeptidyl peptidase IV activity[9]. Feeding high fat diet-fed C57BL/6J mice a diet supplemented with 20mg/kg (-)-Epicatechin for 15 weeks prevented thoracic periaortic adipose tissue expansion, attenuated high fat diet-induced fat whitening, and suppressed the increase in plasma glucose and total cholesterol[10].
References:
[1] Daussin FN, Heyman E, Burelle Y. Effects of (-)-epicatechin on mitochondria. Nutr Rev. 2021 Jan 1;79(1):25-41.
[2] Bernatova I. Biological activities of (-)-epicatechin and (-)-epicatechin-containing foods: Focus on cardiovascular and neuropsychological health. Biotechnol Adv. 2018 May-Jun;36(3):666-681.
[3] Lee I. Regulation of Cytochrome c Oxidase by Natural Compounds Resveratrol, (-)-Epicatechin, and Betaine. Cells. 2021 May 29;10(6):1346.
[4] Ávila-Avilés RD, Bahena-Culhuac E, Hernández-Hernández JM. (-)-Epicatechin metabolites as a GPER ligands: a theoretical perspective. Mol Divers. 2025 Jun;29(3):2099-2115.
[5] Contreras TC, Ricciardi E, Cremonini E, et al. (-)-Epicatechin in the prevention of tumor necrosis alpha-induced loss of Caco-2 cell barrier integrity. Arch Biochem Biophys. 2015 May 15;573:84-91.
[6] Ramiro E, Franch A, Castellote C, et al. Effect of Theobroma cacao flavonoids on immune activation of a lymphoid cell line. Br J Nutr. 2005 Jun;93(6):859-66.
[7] Granado-Serrano AB, Marín MA, Izquierdo-Pulido M, et al. Molecular mechanisms of (-)-epicatechin and chlorogenic acid on the regulation of the apoptotic and survival/proliferation pathways in a human hepatoma cell line. J Agric Food Chem. 2007 Feb;55(5):2020-7.
[8] Cremonini E, Bettaieb A, Haj FG, et al. (-)-Epicatechin improves insulin sensitivity in high fat diet-fed mice. Arch Biochem Biophys. 2016 Jun;599:13-21.
[9] Cremonini E, Daveri E, Mastaloudis A, et al. (-)-Epicatechin and anthocyanins modulate GLP-1 metabolism: evidence from C57BL/6J mice and GLUTag cells. J Nutr. 2021 Jun;151(6):1497-506.
[10] Hid EJ, Fischerman L, Piotrkowski B, et al. (-)-Epicatechin protects thoracic aortic perivascular adipose tissue from whitening in high-fat fed mice. Food Funct. 2020 Jul;11(7):5709-22.
| Cell experiment [1]: | |
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Cell lines |
EL4.BU.OU6 cells (murine thymoma lymphoid cell line) |
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Preparation Method |
EL4.BU.OU6 cells were maintained in Dulbecco's Modified Eagle Medium High Glucose supplemented with 10% fetal calf serum at 37°C, 5% CO2. EL4.BU.OU6 cells were treated with (-)-Epicatechin at 200-400μM simultaneously with or 2h before activation with 10ng/mL PMA and 0.2ng/mL IL-1α for 24h. After treatment, cell viability (propidium iodide), IL-2Rα(CD25) expression (flow cytometry), and IL-2 and IL-4 secretion (ELISA) were assessed. |
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Reaction Conditions |
200-400μM; 24h |
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Applications |
(-)-Epicatechin did not modify cell viability. (-)-Epicatechin reduced IL-2Rα(CD25) expression on activated cells in a dose-dependent manner. (-)-Epicatechin reduced IL-2 secretion. (-)-Epicatechin enhanced IL-4 release by about 4.5-fold in 10% fetal calf serum medium. |
| Animal experiment [2]: | |
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Animal models |
Male C57BL/6J mice |
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Preparation Method |
Mice were fed a control diet (~10% kcal from fat) or a high fat diet (HFD, ~60% kcal from fat) for 15 weeks. The control and HFD groups were supplemented with 20mg/kg (-)-Epicatechin in the diet. After 15 weeks, mice were fasted overnight, then intraperitoneally injected with saline or insulin (10U/kg) and sacrificed after 10min; blood, liver and epididymal adipose tissue were collected. Plasma glucose, insulin, TG, FFA, total cholesterol, and tissue phosphorylation of IR, IRS1, ERK1/2, Akt, IKK, JNK, PKCδ and PTP1B protein levels were assessed. |
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Dosage form |
20mg/kg; p.o.; 15 weeks |
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Applications |
(-)-Epicatechin reduced HFD-induced body weight gain. (-)-Epicatechin prevented HFD-induced increase in plasma TG and FFA but not total cholesterol. (-)-Epicatechin lowered fasted and fed plasma glucose and insulin in HFD-fed mice. (-)-Epicatechin improved ITT and GTT and prevented HFD-elevated plasma insulin during GTT. (-)-Epicatechin restored insulin-stimulated phosphorylation of IR, IRS1, Akt in liver and of IR, IRS1, Akt, ERK1/2 in adipose tissue. (-)-Epicatechin prevented HFD-induced activation (phosphorylation) of IKK, JNK in liver and adipose tissue and of PKCδ in adipose tissue. (-)-Epicatechin prevented HFD-induced upregulation of PTP1B in liver and adipose tissue. |
References: [1] Ramiro E, Franch A, Castellote C, et al. Effect of Theobroma cacao flavonoids on immune activation of a lymphoid cell line. Br J Nutr. 2005;93(6):859-66. [2] Cremonini E, Bettaieb A, Haj FG, et al. (-)-Epicatechin improves insulin sensitivity in high fat diet-fed mice. Arch Biochem Biophys. 2016 Jun;599:13-21. | |
| Cas No. | 490-46-0 | SDF | |
| Synonyms | epi-Catechin, NSC 81161 | ||
| Chemical Name | (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol | ||
| Canonical SMILES | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O | ||
| Formula | C15H14O6 | M.Wt | 290.27 |
| Solubility | DMF: 12.5 mg/ml,DMSO: 12.5 mg/ml,DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml | Storage | Store at -20°C |
| 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 | 3.4451 mL | 17.2253 mL | 34.4507 mL |
| 5 mM | 689 μL | 3.4451 mL | 6.8901 mL |
| 10 mM | 344.5 μL | 1.7225 mL | 3.4451 mL |
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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Quality Control & SDS
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- Purity: >99.00% Appearance: A solid
- COA (Certificate of Analysis)
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Average Rating: 5 (Based on Reviews and 30 reference(s) in Google Scholar.)