E3893

(−)-Epicatechin-Gallat

≥98% (HPLC), from green tea

• Synonym(e): (−)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol-3-gallat, (−)-cis-3,3′,4′,5,7-Pentahydroxy-flavan-3-gallat, 3-O-Galloylepicatechin
• Empirische Formel (Hill-System): C₂₂H₁₈O₁₀
• CAS-Nummer: 1257-08-5
• Molekulargewicht: 442.37
• NACRES: NA.21
• PubChem Substance ID: 24894531
• UNSPSC Code: 12352205
• MDL number: MFCD00075936

Eigenschaften

• biological source: green tea
• Quality Level: 100
• 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)

Beschreibung

General description

(−)-Epicatechin gallate is one of the major polyphenols present in green tea.[1] 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.[2]

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[2]
• as an inhibitor in Human Salivary α-Amylase (HAS) and α-Glucosidase (AGH) in inhibition assays[3]
• may be used as a cancer chemopreventive polyphenol in two human colorectal cell lines HCT-116 and SW-480[4]
• as an inhibitor to in vitro collagenase and elastase enzymes[5]
• as a supplement in spermatozoa incubation to check its effectiveness against oxidative stress[6]

Biochem/physiol Actions

(−)-Epicatechin gallate (ECG), a potent free-radical scavenger[2] has an inhibitory effect on collagenase and elastase enzymes making it an anti-aging agent.[5] It displays antiproliferative effects on human colorectal cells and hence is a chemo-preventative agent.[4] It influences cell survival, preventing apoptosis or autophagy by promoting cell proliferation in oxygen-glucose deprived human brain microvascular endothelial cells.[2] 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.[7] ECG may contribute in preventing oxidative stress. It effectively inhibits secretory sphingomyelinase in many disease states[8] and provides protection for human spermatozoa in Assisted reproductive technology (ART).[6]

Sicherheitshinweise

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Lagerklasse: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)