E3893

(−)-Epicatechin gallate

≥98% (HPLC), from green tea

• Sinônimo(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
• Fórmula empírica (Notação de Hill): C₂₂H₁₈O₁₀
• Número CAS: 1257-08-5
• Peso molecular: 442.37
• Número MDL: MFCD00075936
• Código UNSPSC: 12352205
• ID de substância PubChem: 24894531
• NACRES: NA.21

Propriedades

• fonte biológica: green tea
• Nível de qualidade: 100
• Ensaio: ≥98% (HPLC)
• aplicação(ões): metabolomics; vitamins, nutraceuticals, and natural products
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: 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
• chave InChI: LSHVYAFMTMFKBA-TZIWHRDSSA-N
• Informações sobre genes: human ... CYP1A2(1544)

Descrição

Descrição geral

(−)-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.

Aplicação

(−)-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

Ações bioquímicas/fisiológicas

(−)-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).

Informações de segurança

• Pictogramas: GHS07
• Palavra indicadora: Warning
• Frases de perigo: H315,H319,H335
• Declarações de precaução: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classificações de perigo: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Órgãos-alvo: Respiratory system
• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Gloves, type N95 (US)