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E3768

Sigma-Aldrich

(−)-Epigallocatechin

≥95% (HPLC), from green tea

Synonyme(s) :

(−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxyflavane

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About This Item

Formule empirique (notation de Hill) :
C15H14O7
Numéro CAS:
970-74-1
Poids moléculaire :
306.27
Numéro MDL:
MFCD00075939
Code UNSPSC :
12352205
ID de substance PubChem :
24894529
Nomenclature NACRES :
NA.21

Source biologique

green tea

Niveau de qualité

200

Essai

≥95% (HPLC)

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne SMILES 

O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3cc(O)c(O)c(O)c3

InChI

1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1

Clé InChI

XMOCLSLCDHWDHP-IUODEOHRSA-N

Informations sur le gène

human ... CYP1A2(1544)

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Description générale

(−)-Epigallocatechin is one of the main catechin compounds found in green tea and the most abundant one (~20%), with antioxidant properties.

Application

(−)-Epigallocatechin (EGC) has been used:
  • as a reference standard in high-performance liquid chromatography (HPLC) analysis
  • to analyze its inhibitory effect on α-amylase and α-glucosidase activity to control postprandial hyperglycemia in Diabetes mellitus
  • in cell viability assays to check its efficacy and protection against ferroptosis and iron toxicity in murine pancreatic β-cells
  • to evaluate its potential anti-inflammatory effects on long-term acute and chronic Pristen-induced arthritis
  • to treat pregnant and nursing mice, on in vitro angiogenesis, proliferation, and movement of endothelial cells
  • to evaluate its effect on pregnant and nursing mice spleen based on the number and localization of CD4+ (cluster of differentiation 4) and CD8+ cluster of differentiation 8) cells

Actions biochimiques/physiologiques

(−)-Epigallocatechin (EGC) has proven to be an anti-cancer agent by its inhibitory effects on heregulin-b1 (HRG)-induced migration/invasion in MCF-7 human breast carcinoma cells. It has also shown strong antiviral activity against the herpes simplex virus.
Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
SLCL5281
SLCG2781
SLCB1171
SLBW7003
SLBR6704V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

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Yukihiro Kushima et al.
Biological & pharmaceutical bulletin, 32(5), 899-904 (2009-05-08)
Migration/invasion is involved in the multiple steps of metastasis, resulting in a poor prognosis of breast cancer. (-)-Epigallocatechin-3-gallate (EGCG) in green tea inhibits the metastasis of some cancer cell lines. Cell migration/invasion assays using Boyden chambers demonstrated that (-)-epigallocatechin (EGC)
Sławomir Lewicki et al.
Central-European journal of immunology, 42(1), 10-16 (2017-07-07)
Rhodiola kirilowii, a member of Crassulaceae family, grows wildly in Asiatic mountains and is also cultivated in some European countries. Its underground parts traditionally are used for enhance physical and mental performance of the body. In our previous papers we
Tugba Kose et al.
Pharmaceuticals (Basel, Switzerland), 12(1) (2019-02-10)
Ferroptosis is a form of programmed cell death that is characterized by lipid peroxidation and is inducible by iron and the accumulation of reactive oxygen species (ROS). It is triggered by erastin but inhibited by antioxidants such as -tocopherol, -carotene
Wanda C Reygaert
BioMed research international, 2018, 9105261-9105261 (2018-08-15)
Green tea is one of the most popular drinks consumed worldwide. Produced mainly in Asian countries from the leaves of the Camellia sinensis plant, the potential health benefits have been widely studied. Recently, researchers have studied the ability of green
Katarzyna Naparlo et al.
Molecules (Basel, Switzerland), 25(6) (2020-03-28)
The aim of this study was to characterize the interaction of chosen catechins ((+)-catechin, (-)-epigallocatechin (EGC), and (-)-epigallocatechin gallate (EGCG)) with human erythrocytes and their protective effects against oxidative damage of erythrocytes. Uptake of the catechins by erythrocytes was studied
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