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E4268

Sigma-Aldrich

(−)-Epigallocatechin gallate

≥80% (HPLC), from green tea

Sinonimo/i:

(−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxy-flavane-3-gallate, EGCG

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About This Item

Formula empirica (notazione di Hill):
C22H18O11
Numero CAS:
989-51-5
Peso molecolare:
458.37
Numero MDL:
MFCD00075940
Codice UNSPSC:
12352205
ID PubChem:
57654159
NACRES:
NA.79

Origine biologica

green tea

Livello qualitativo

200

Saggio

≥80% (HPLC)

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

2-8°C

Stringa SMILE

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4cc(O)c(O)c(O)c4

InChI

1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
WMBWREPUVVBILR-WIYYLYMNSA-N

Informazioni sul gene

human ... CYP1A2(1544)

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Categorie correlate

Descrizione generale

(−)-Epigallocatechin gallate, is a bioactive component of green tea accounting for 50-80% of the total catechin content.

Applicazioni

(−)-Epigallocatechin gallate has been used as:
  • a potential neuroprotective agent to test its protective effect against spinal cord injury and blood-spinal cord barrier (BSCB) leakage
  • an effective antioxidant against light-induced photoreceptor degeneration in mice retina
  • an antioxidant in retinitis pigmentosa (RP) and reduces oxidative damage and changes circadian rhythms in pigmented heterozygous P23H rat
  • to test its reversal effect on Diastolic dysfunction in restrictive cardiomyopathy (RCM) mice
  • an anti-cancer agent in colorectal cancer in mice

Azioni biochim/fisiol

(−)-Epigallocatechin gallate (EGCG) comprises eight -hydroxyl (OH) groups that determine its high antioxidant property. Other than being an efficient free oxygen radical scavenger, it also acts as a good chelating agent and a modulator of important transcription factors, namely nuclear factor-kappa β (NF-kβ). EGEC is proven to be an efficient anti-obesity agent by increasing energy expenditure, fat oxidation, and lowering appetite in humans. EGCG also acts as an anti-inflammatory and neuroprotective agent in the initial stages of ischemia and spinal cord injury. It reduces caveolin-1 expression, maintaining blood-brain barrier integrity and downregulating pro-inflammatory cytokines.

Pittogrammi

Exclamation markEnvironment
GHS07,GHS09

Avvertenze

Warning

Indicazioni di pericolo

H302 - H317 - H319 - H411

Classi di pericolo

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Shounan Qi et al.
Molecular vision, 23, 171-178 (2017-05-02)
(-)-epigallocatechin-3-gallate (EGCG), a major catechin component of green tea, is reported to delay or prevent certain forms of cancer, arthritis, cardiovascular disease, and neurodegenerative disorders. In this study, we determined if systemically administered EGCG could protect the retina against light
Tea polyphenols-their antioxidant properties and biological activity-a review
Gramza A, et al.,
Polish Journal of Food and Nutrition Sciences, 14(3), 219-219 (2005)
Yoichi Kakuta et al.
Transplant international : official journal of the European Society for Organ Transplantation, 24(5), 514-522 (2011-02-05)
Epigallocatechin-3-gallate (EGCG) shows diverse chemical and biological activities. We investigated the effects of EGCG in a rat renal ischemia reperfusion (I/R) injury model. Sprague-Dawley rats received intraperitoneal injection of 50 mg/kg EGCG 48 h, 24 h, and 30 min prior
Xin Wang et al.
World journal of gastroenterology, 23(46), 8128-8139 (2018-01-02)
To investigate the effect of epigallocatechin gallate (EGCG) on structural changes of gut microbiota in colorectal carcinogenesis. An azoxymethane (AOM)/dextran sodium sulfate (DSS)-induced colitis mouse model was established. Forty-two female FVB/N mice were randomly divided into the following three groups:
Kosuke Dodo et al.
Bioorganic & medicinal chemistry, 16(17), 7975-7982 (2008-08-12)
Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity.
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Articoli

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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