E3893

(−)-Epicatechin gallate

≥98% (HPLC), from green tea

• Synonym(s): (−)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (−)-cis-3,3′,4′,5,7-Pentahydroxyflavane 3-gallate, 3-O-Galloylepicatechin
• Empirical Formula (Hill Notation): C₂₂H₁₈O₁₀
• CAS Number: 1257-08-5
• Molecular Weight: 442.37
• MDL number: MFCD00075936
• UNSPSC Code: 12352205
• PubChem Substance ID: 24894531
• NACRES: NA.21

Properties

• biological source: green tea
• Assay: ≥98% (HPLC)
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4ccc(O)c(O)c4
• InChI: 1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
• InChI key: LSHVYAFMTMFKBA-TZIWHRDSSA-N
• Gene Information: human ... CYP1A2(1544)

Description

General description

(−)-Epicatechin gallate is one of the major polyphenols present in green tea. It belongs to the catechin gallates group of organic compounds. ECG has a chemical structure like that of (−)-epigallocatechin gallate (EGCG), the other major polyphenol found in green tea.

Application

(−)-Epicatechin gallate has been used:

• in cell proliferation assays on the human brain microvascular endothelial cells (HBMVECs) to understand its effectiveness against anti-ischemic/reperfusion injury
• as an inhibitor in Human Salivary α-Amylase (HAS) and α-Glucosidase (AGH) in inhibition assays
• may be used as a cancer chemopreventive polyphenol in two human colorectal cell lines HCT-116 and SW-480
• as an inhibitor to in vitro collagenase and elastase enzymes
• as a supplement in spermatozoa incubation to check its effectiveness against oxidative stress

Biochem/physiol Actions

(−)-Epicatechin gallate (ECG), a potent free-radical scavenger has an inhibitory effect on collagenase and elastase enzymes making it an anti-aging agent. It displays antiproliferative effects on human colorectal cells and hence is a chemo-preventative agent. It influences cell survival, preventing apoptosis or autophagy by promoting cell proliferation in oxygen-glucose deprived human brain microvascular endothelial cells. Being structurally and functionally similar to EGCG, ECG might be involved in balancing the mammalian target of rapamycin (mTOR)-AMP-activated protein kinase (AMPK) pathways in endoplasmic reticulum stress. It prevents cell death in this scenario by showing resistance against oxygen-deprived cells. ECG may contribute in preventing oxidative stress. It effectively inhibits secretory sphingomyelinase in many disease states and provides protection for human spermatozoa in Assisted reproductive technology (ART).

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves