(-)-Epicatechin gallate

Bezeichnung:(-)-Epicatechin gallate

CAS-Nr1257-08-5

Englisch Name:(-)-Epicatechin gallate

CBNumberCB0738543

SummenformelC22H18O10

Molgewicht442.37

MOL-Datei1257-08-5.mol

(-)-Epicatechin gallate physikalisch-chemischer Eigenschaften

Schmelzpunkt	257-258°C
alpha	-182～-194°(D/20℃)(c=0.2,CH3OH)
Siedepunkt	861.7±65.0 °C(Predicted)
Dichte	1.80±0.1 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	Acetone (Sparingly), DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	7.75±0.25(Predicted)
Farbe	White to Off-White
Wasserlöslichkeit	Soluble in water, acetone, DMSO, methanol.
Stabilität	Light Sensitive
InChIKey	LSHVYAFMTMFKBA-TZIWHRDSSA-N
LogP	2.670 (est)
CAS Datenbank	1257-08-5(CAS DataBase Reference)

Sicherheit

S-Sätze:	24/25
WGK Germany	3
RTECS-Nr.	DH9030000
F	10-23
HS Code	29329990

Gefahreninformationscode (GHS)

(-)-Epicatechin gallate Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White powder
Verwenden
An antioxidant investigated as an adjunct treatment of some methyicillin resistant bacteria.
Verwenden
One of the catechin isomers and a potent antioxidant that can modulate a wide range of membrane proteins. Its bilayer-modifying potency was tested using gramicidin A (gA) channels as probes. All the c atechins alter gA channel function and modify bilayer properties, with a 500-fold range in potency. The gallate group causes current block, as evident by brief downward current transitions.
Verwenden
(-)-Epicatechin gallate is polyphenols which are abundant in green and black teas. (-)-Epicatechin gallate (ECG) is a natural catechin with a single galloyl group. The hydroxyl groups of ECG contribute to its potent antioxidant activity and facilitate the killing of methicillin-resistant strains of S. aureus.
Definition
ChEBI: A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.
Allgemeine Beschreibung
(?)-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.
Biologische Aktivität
(-)-epicatechin gallate is a major catechin component in green tea [1].(-)-epicatechin gallate (ecg) plays an important role in cell growth inhibition, apoptosis and membrane transport system [1].(-)-epicatechin gallate is a kind of catechin. in hct-116 cells, ecg activated transcription factor 3 (atf3), which played a critical role in pro-apoptosis. egr-1 was involved in ecg-induced atf3 expression. in hct-116 cells, ecg (50 μm) increased nag-1 and atf3 expression in time- and dose-dependent way [1]. in carcinoma hsc-2 cells, ecg (50 μm) exhibited cytotoxicity with midpoint cytotoxicity (nr50) value of 67 μm. however, in normal hgf-2 fibroblasts, ecg exhibited cytotoxicity at concentrations up to 25 μm with nr50 value of 100 μm. in carcinoma hsc-2 cells, ecg (250 μm) induced nucleosomal dna fragmentation and apoptosis. ecg (150 μm) significantly increased caspase-3 activity [2].in rats, there were five metabolites of ecg: (-)-epicatechin gallate, 3’,4’’-di-o-methyl-(-)-epicatechin gallate, 4’’-o-methyl-(-)-epicatechin gallate, 4’-o-methyl-(-)-epicatechin gallate and 3’-o-methyl-(-)-epicatechin gallate, which were excreted in rat urine [3].
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).
Einzelnachweise
[1]. cho kn, sukhthankar m, lee sh, et al. green tea catechin (-)-epicatechin gallate induces tumour suppressor protein atf3 via egr-1 activation. eur j cancer, 2007, 43(16): 2404-2412.
[2]. babich h, krupka me, nissim ha, et al. differential in vitro cytotoxicity of (-)-epicatechin gallate (ecg) to cancer and normal cells from the human oral cavity. toxicol in vitro, 2005, 19(2): 231-242.
[3]. kohri t, suzuki m, nanjo f. identification of metabolites of (-)-epicatechin gallate and their metabolic fate in the rat. j agric food chem, 2003, 51(18): 5561-5566.

(-)-Epicatechin gallate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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