(-)-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
Biologische Quelle	green tea
Wasserlöslichkeit	Soluble in water, acetone, DMSO, methanol.
Stabilität	Light Sensitive
Major Application	metabolomics vitamins, nutraceuticals, and natural products
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
InChIKey	LSHVYAFMTMFKBA-TZIWHRDSSA-N
SMILES	Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4ccc(O)c(O)c4
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
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

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

Chemische Eigenschaften
White powder
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
An antioxidant investigated as an adjunct treatment of some methyicillin resistant bacteria.
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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