(-)-Epicatechin

• CAT Number: I003727
• CAS Number: 490-46-0
• Molecular Formula: C15H14O6
• Molecular Weight: 290.3
• Purity: ≥95%
• Synonyms: (2R,3R)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol
• Target: Apoptosis
• Solubility: DMSO: 34 mg/mL
• Storage: Store at -20°C
• IUPAC Name: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• InChI: 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
• InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N
• SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

(-)-Epicatechin (CAT: I003727) is a natural flavonoid compound found in various plant sources, including tea, cocoa, and fruits. It is known for its antioxidant and anti-inflammatory properties. (-)-Epicatechin has been studied for its potential health benefits, including cardiovascular protection, improvement of blood flow, and prevention of oxidative stress. It has also been investigated for its potential role in the management of diabetes, neurodegenerative diseases, and cancer. (-)-Epicatechin has shown promising effects in preclinical studies, but further research is needed to fully understand its mechanisms of action and its potential therapeutic applications.

Reference

1:The effect of epicatechin on oxidative stress and mitochondrial damage induced by homocycteine using isolated rat hippocampus mitochondria. Shaki F, Shayeste Y, Karami M, Akbari E, Rezaei M, Ataee R.Res Pharm Sci. 2017 Apr;12(2):119-127. doi: 10.4103/1735-5362.202450. PMID: 28515764
2:Exploratory Studies of (-)-Epicatechin, a Bioactive Compound of Phyllanthus niruri, on the Antioxidant Enzymes and Oxidative Stress Markers in D-galactosamine-induced Hepatitis in Rats: A Study with Reference to Clinical Prospective. Shanmugam B, Shanmugam KR, Ravi S, Subbaiah GV, Ramakrishana C, Mallikarjuna K, Reddy KS.Pharmacogn Mag. 2017 Jan;13(Suppl 1):S56-S62. doi: 10.4103/0973-1296.203973. Epub 2017 Apr 7. PMID: 28479727 Free PMC Article
3:(-)-Epicatechin 3-O-β-D-allopyranoside prevent ovariectomy-induced bone loss in mice by suppressing RANKL-induced NF-κB and NFATc-1 signaling pathways. Hsiao HB, Wu JB, Lin WC.BMC Complement Altern Med. 2017 May 3;17(1):245. doi: 10.1186/s12906-017-1737-9. PMID: 28468652 Free PMC Article
4:Effect of ultrasound on the interaction between (-)-epicatechin gallate and bovine serum albumin in a model wine. Zhang QA, Fu XZ, García Martín JF.Ultrason Sonochem. 2017 Jul;37:405-413. doi: 10.1016/j.ultsonch.2017.01.031. Epub 2017 Jan 30. PMID: 28427650
5:(-)-Epicatechin Suppresses Angiotensin II-induced Cardiac Hypertrophy via the Activation of the SP1/SIRT1 Signaling Pathway. Dong ZX, Wan L, Wang RJ, Shi YQ, Liu GZ, Zheng SJ, Hou HL, Han W, Hai X.Cell Physiol Biochem. 2017 Apr 13;41(5):2004-2015. doi: 10.1159/000475396. [Epub ahead of print] PMID: 28420000 Free Article
6:Unique synergistic formulation of curcumin, epicatechin gallate and resveratrol, tricurin, suppresses HPV E6, eliminates HPV+ cancer cells, and inhibits tumor progression. Mukherjee S, Debata PR, Hussaini R, Chatterjee K, Baidoo JNE, Sampat S, Szerszen A, Navarra JP, Fata J, Severinova E, Banerjee P, Castellanos MR.Oncotarget. 2017 Mar 29. doi: 10.18632/oncotarget.16648. [Epub ahead of print] PMID: 28416754 Free Article
7:Simultaneous separation and purification of chlorogenic acid, epicatechin, hyperoside and phlorizin from thinned young Qinguan apples by successive use of polyethylene and polyamide resins. Sun L, Liu D, Sun J, Yang X, Fu M, Guo Y.Food Chem. 2017 Sep 1;230:362-371. doi: 10.1016/j.foodchem.2017.03.065. Epub 2017 Mar 14. PMID: 28407923
8:Epicatechin elicits MyoD-dependent myoblast differentiation and myogenic conversion of fibroblasts. Lee SJ, Leem YE, Go GY, Choi Y, Song YJ, Kim I, Kim DY, Kim YK, Seo DW, Kang JS, Bae GU.PLoS One. 2017 Apr 6;12(4):e0175271. doi: 10.1371/journal.pone.0175271. eCollection 2017. PMID: 28384253 Free PMC Article
9:(-)-Epicatechin-3-O-β-D-allopyranoside from Davallia formosana prevents diabetes and dyslipidemia in streptozotocin-induced diabetic mice. Lin CH, Wu JB, Jian JY, Shih CC.PLoS One. 2017 Mar 23;12(3):e0173984. doi: 10.1371/journal.pone.0173984. eCollection 2017. PMID: 28333970 Free PMC Article
10:Extraction of Epigallocatechin Gallate and Epicatechin Gallate from Tea Leaves Using β-Cyclodextrin. Cui L, Liu Y, Liu T, Yuan Y, Yue T, Cai R, Wang Z.J Food Sci. 2017 Feb;82(2):394-400. doi: 10.1111/1750-3841.13622. Epub 2017 Jan 10. PMID: 28071811