(−)-Epicatechin gallate
SIAL/E3893 - ≥98% (HPLC), from green tea
Synonym: (−)-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
CAS Number: 1257-08-5
Empirical Formula (Hill Notation): C22H18O10
Molecular Weight: 442.37
MDL Number: MFCD00075936
Linear Formula: C22H18O10
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: E3893-10MG
| application(s) | metabolomics vitamins, nutraceuticals, and natural products |
| assay | ≥98% (HPLC) |
| biological source | green tea |
| InChI | 1S/C22H18O10/c23-11-6-14( |
| InChI key | LSHVYAFMTMFKBA-TZIWHRDSSA |
| Quality Level | 100  |
| SMILES string | Oc1cc(O)c2C[C@@H](OC(=O)c |
| storage temp. | 2-8°C |
| 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). |
| 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. |
| Packaging: | 10 mg in glass bottle |
| Symbol |  GHS07 |
| Signal word | Warning |
| Hazard statements | H315 - H319 - H335 |
| Precautionary statements | P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC) |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352205 |