WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H600131
CAS#: 490-46-0
Description: Epicatechin is a flavanol found in food sources such as tea, apples, berries and cocoa. Epicatechin has been reported to possess an immense antioxidant effect which contributes to its therapeutic effect against a handful of ailments. The consumption of epicatechin has been shown to reduce blood glucose levels in diabetic patients, while its anticancer effect was attributed to its antioxidant properties, antiangiogenic and direct cytotoxicity to cancer cells. Epicatechin lowers blood pressure and the associated end-organ damage.
Hodoodo Cat#: H600131
Name: Epicatechin
CAS#: 490-46-0
Chemical Formula: C15H14O6
Exact Mass: 290.08
Molecular Weight: 290.270
Elemental Analysis: C, 62.07; H, 4.86; O, 33.07
Related CAS #: 1257-08-5 (gallate) 490-46-0
Synonym: Epicatechol; (-)-epi-Catechin; (-)-Epicatechin; (-)-Epicatechol; (2R,3R)-(-)-Epicatechin; L-Epicatechin; epi-Catechin; epi-Catechol; Epicatechin; Epicatechol; l-Acacatechin; l-Epicatechin; l-Epicatechol; NSC 81161; NSC-81161; NSC81161;
IUPAC/Chemical Name: 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R)-
InChi Key: PFTAWBLQPZVEMU-UKRRQHHQSA-N
InChi Code: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
SMILES Code: O[C@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC3=CC(O)=CC(O)=C3C1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO.
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. |
| In vitro activity: | ROS, LDH, MDA, and SOD assays were performed in our study to evaluate the antioxidant activity of ECG. OGD/R induced an ROS level about 2.5-fold to control (normal), whereas ECG downregulated ROS significantly compared with the OGD/R group (P < 0.01) (Figure 2(a)). OGD/R induced oxidative stress, and the LDH level was used to assess cell death. ECG treatment significantly inhibited LDH leakage induced by OGD (P < 0.01) (Figure 2(b)). As shown in Figure 2(c), OGD/R upregulated intracellular MDA levels compared with control which was significantly decreased by ECG treatment (Figure 2(c)). As MDA was considered an indicator of lipid peroxidation, ECG may show inhibition of lipid peroxidation in HBMVECs that underwent OGD/R. In the OGD/R group, the SOD activities were significantly decreased compared with the control group (Figure 2(d)). ECG treatment significantly increased SOD activity (P < 0.01). Reference: Oxid Med Cell Longev. 2019 Mar 6;2019:7824684. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30962864/ |
| In vivo activity: | The acetic acid-induced writhing and hot plate models in mice were utilized to determine the analgesic effect of epicatechin gallate (ECG) isolated from Bauhinia hookeri. The anti-inflammatory activity of ECG was determined using carrageenan-induced paw edema model. The pro-inflammatory mediators (PGE2 , TNF-α, IL-1β, and IL-6) were estimated in the plasma of different treatment groups. ECG was tested at doses of 100, 200, and 400 mg/kg p.o. and diclofenac sodium was used as a standard drug (100 mg/kg) in all experiments. ECG significantly (p < .001) suppressed the writhing response in mice. The inhibition percentages were 32, 52, and 62%, at the tested doses of ECG, respectively as compared to the positive control group receiving acetic acid only. Furthermore, ECG significantly (p < .001) increased the reaction time in hot plate model. The maximum analgesic effect was evident after 120 min. ECG demonstrated a significant anti-inflammatory activity as evidenced by the inhibition of carrageenan-induced paw edema (46, 50, and 58%, at the tested doses, respectively). This effect was persistent all over the experimental period. ECG produced a significant (p < .001) reduction in plasma PGE2 (by 27, 38, and 50%), TNF-α (15, 33, and 41%), IL-1β (17, 25, and 33%), and IL-6 (22, 32, and 43%), at the tested doses, respectively. This study supports the use of ECG as both analgesic and anti-inflammatory agent. Reference: Drug Dev Res. 2018 Jun;79(4):157-164. https://doi.org/10.1002/ddr.21430 |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 56.8 | 195.78 | |
| DMSO:PBS (pH 7.2) (1:1) | 0.5 | 1.72 | |
| DMF | 12.5 | 43.06 |
The following data is based on the product molecular weight 290.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Fu B, Zeng Q, Zhang Z, Qian M, Chen J, Dong W, Li M. Epicatechin Gallate Protects HBMVECs from Ischemia/Reperfusion Injury through Ameliorating Apoptosis and Autophagy and Promoting Neovascularization. Oxid Med Cell Longev. 2019 Mar 6;2019:7824684. doi: 10.1155/2019/7824684. PMID: 30962864; PMCID: PMC6431361. 2. Al-Sayed E, Abdel-Daim MM. Analgesic and anti-inflammatory activities of epicatechin gallate from Bauhinia hookeri. Drug Dev Res. 2018 Jun;79(4):157-164. doi: 10.1002/ddr.21430. Epub 2018 May 6. PMID: 29732583. |
| In vitro protocol: | 1. Fu B, Zeng Q, Zhang Z, Qian M, Chen J, Dong W, Li M. Epicatechin Gallate Protects HBMVECs from Ischemia/Reperfusion Injury through Ameliorating Apoptosis and Autophagy and Promoting Neovascularization. Oxid Med Cell Longev. 2019 Mar 6;2019:7824684. doi: 10.1155/2019/7824684. PMID: 30962864; PMCID: PMC6431361. |
| In vivo protocol: | 1. Al-Sayed E, Abdel-Daim MM. Analgesic and anti-inflammatory activities of epicatechin gallate from Bauhinia hookeri. Drug Dev Res. 2018 Jun;79(4):157-164. doi: 10.1002/ddr.21430. Epub 2018 May 6. PMID: 29732583. |
1: Sabarathinam S, Dhanasekaran D, Ganamurali N. Insight on sarcopenic obesity and epicatechin as a promising treatment option. Diabetes Metab Syndr. 2023 Oct;17(10):102856. doi: 10.1016/j.dsx.2023.102856. Epub 2023 Sep 18. PMID: 37742361.
2: Dicks L, Haddad Z, Deisling S, Ellinger S. Effect of an (-)-Epicatechin Intake on Cardiometabolic Parameters-A Systematic Review of Randomized Controlled Trials. Nutrients. 2022 Oct 26;14(21):4500. doi: 10.3390/nu14214500. PMID: 36364762; PMCID: PMC9657629.
3: Hid EJ, Mosele JI, Prince PD, Fraga CG, Galleano M. ( -)-Epicatechin and cardiometabolic risk factors: a focus on potential mechanisms of action. Pflugers Arch. 2022 Jan;474(1):99-115. doi: 10.1007/s00424-021-02640-0. Epub 2021 Nov 23. PMID: 34812946.
4: Lee I. Regulation of Cytochrome c Oxidase by Natural Compounds Resveratrol, (-)-Epicatechin, and Betaine. Cells. 2021 May 29;10(6):1346. doi: 10.3390/cells10061346. PMID: 34072396; PMCID: PMC8229178.
5: Bernatova I, Liskova S. Mechanisms Modified by (-)-Epicatechin and Taxifolin Relevant for the Treatment of Hypertension and Viral Infection: Knowledge from Preclinical Studies. Antioxidants (Basel). 2021 Mar 16;10(3):467. doi: 10.3390/antiox10030467. PMID: 33809620; PMCID: PMC8002320.
6: Daussin FN, Heyman E, Burelle Y. Effects of (-)-epicatechin on mitochondria. Nutr Rev. 2021 Jan 1;79(1):25-41. doi: 10.1093/nutrit/nuaa094. PMID: 32989466.
7: Cremonini E, Iglesias DE, Kang J, Lombardo GE, Mostofinejad Z, Wang Z, Zhu W, Oteiza PI. (-)-Epicatechin and the comorbidities of obesity. Arch Biochem Biophys. 2020 Sep 15;690:108505. doi: 10.1016/j.abb.2020.108505. Epub 2020 Jul 14. PMID: 32679195.
8: Qu Z, Liu A, Li P, Liu C, Xiao W, Huang J, Liu Z, Zhang S. Advances in physiological functions and mechanisms of (-)-epicatechin. Crit Rev Food Sci Nutr. 2021;61(2):211-233. doi: 10.1080/10408398.2020.1723057. Epub 2020 Feb 23. PMID: 32090598.
9: Si H, Lai CQ, Liu D. Dietary Epicatechin, A Novel Anti-aging Bioactive Small Molecule. Curr Med Chem. 2021;28(1):3-18. doi: 10.2174/0929867327666191230104958. PMID: 31886745.
10: Cremonini E, Fraga CG, Oteiza PI. (-)-Epicatechin in the control of glucose homeostasis: Involvement of redox-regulated mechanisms. Free Radic Biol Med. 2019 Jan;130:478-488. doi: 10.1016/j.freeradbiomed.2018.11.010. Epub 2018 Nov 14. PMID: 30447350.
11: Haskell-Ramsay CF, Schmitt J, Actis-Goretta L. The Impact of Epicatechin on Human Cognition: The Role of Cerebral Blood Flow. Nutrients. 2018 Jul 27;10(8):986. doi: 10.3390/nu10080986. PMID: 30060538; PMCID: PMC6115745.
12: Fraga CG, Oteiza PI, Galleano M. Plant bioactives and redox signaling: (-)-Epicatechin as a paradigm. Mol Aspects Med. 2018 Jun;61:31-40. doi: 10.1016/j.mam.2018.01.007. Epub 2018 Feb 10. PMID: 29421170.
13: 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. doi: 10.1016/j.biotechadv.2018.01.009. Epub 2018 Feb 2. PMID: 29355598.
14: Borges G, Ottaviani JI, van der Hooft JJJ, Schroeter H, Crozier A. Absorption, metabolism, distribution and excretion of (-)-epicatechin: A review of recent findings. Mol Aspects Med. 2018 Jun;61:18-30. doi: 10.1016/j.mam.2017.11.002. Epub 2017 Nov 9. PMID: 29126853.
15: Abdulkhaleq LA, Assi MA, Noor MHM, Abdullah R, Saad MZ, Taufiq-Yap YH. Therapeutic uses of epicatechin in diabetes and cancer. Vet World. 2017 Aug;10(8):869-872. doi: 10.14202/vetworld.2017.869-872. Epub 2017 Aug 6. PMID: 28919675; PMCID: PMC5591471.
16: Shay J, Elbaz HA, Lee I, Zielske SP, Malek MH, Hüttemann M. Molecular Mechanisms and Therapeutic Effects of (-)-Epicatechin and Other Polyphenols in Cancer, Inflammation, Diabetes, and Neurodegeneration. Oxid Med Cell Longev. 2015;2015:181260. doi: 10.1155/2015/181260. Epub 2015 Jun 9. PMID: 26180580; PMCID: PMC4477097.
17: Jiménez R, Duarte J, Perez-Vizcaino F. Epicatechin: endothelial function and blood pressure. J Agric Food Chem. 2012 Sep 12;60(36):8823-30. doi: 10.1021/jf205370q. Epub 2012 Mar 29. PMID: 22440087.
18: Pan MH, Chiou YS, Wang YJ, Ho CT, Lin JK. Multistage carcinogenesis process as molecular targets in cancer chemoprevention by epicatechin-3-gallate. Food Funct. 2011 Feb;2(2):101-10. doi: 10.1039/c0fo00174k. Epub 2011 Jan 18. PMID: 21779554.
19: Fraga CG, Oteiza PI. Dietary flavonoids: Role of (-)-epicatechin and related procyanidins in cell signaling. Free Radic Biol Med. 2011 Aug 15;51(4):813-23. doi: 10.1016/j.freeradbiomed.2011.06.002. Epub 2011 Jun 12. PMID: 21699974.
20: Steffen Y, Schewe T, Sies H. Myeloperoxidase-mediated LDL oxidation and endothelial cell toxicity of oxidized LDL: attenuation by (-)-epicatechin. Free Radic Res. 2006 Oct;40(10):1076-85. doi: 10.1080/10715760600883247. PMID: 17015252.
