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Merck
CN

E4143

(−)-Epigallocatechin gallate

≥95%

Synonym(s):

(−)-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

Empirical Formula (Hill Notation):
C22H18O11
CAS Number:
Molecular Weight:
458.37
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
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Quality Level

assay

≥95%

solubility

H2O: ≥5 mg/mL, clear

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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

InChI key

WMBWREPUVVBILR-WIYYLYMNSA-N

Gene Information

human ... CYP1A2(1544)

General description

(−)-Epigallocatechin gallate from green tea is the prime bioactive component, accounting for 50-80% of the total catechin content. It comprises a chemical structure similar to that of epicatechin gallate (ECG), an ester of gallic acid and epigallocatechin.

Application

(-)-Epigallocatechin gallate has been used:
  • as an anti-tumor agent on murine TRAMP metastatic prostate cell line by cell proliferation assay, apoptosis detection and modified Boyden-chamber assay
  • induces cell death in acute myeloid leukaemia through death associated protein kinase-2 pathway analyzed through cell viability, cell cycle and apoptosis assay
  • as an inhibitor of osteoclast differentiation in murine preosteoclast cell line RAW264.7
  • to promote myogenic differentiation

Biochem/physiol Actions

(-)-Epigallocatechin gallate (EGCG), an antioxidant polyphenol flavonoid exerts anti-tumor properties by inhibiting telomerase and DNA methyltransferase activity. EGCG inhibits the expression of matrix metalloproteinase-2 (MMP-2), MMP-9 and reduces the invasiveness. EGCG blocks the activation of epidermal growth factor (EGF) receptors and human epidermal growth factor receptor-2 (HER-2). EGCG increases bone mineral density and reduces bone resorption. EGCG inhibits osteoclastogenesis by inhibiting receptor activator of nuclear factor κ-B ligand (RANKL) induced nuclear factor κ B (NF-κB) transcriptional activity. EGCG reduces skeletal muscle atrophy. EGCG has anti-aging property and increases myogenic differentiation. EGCG inhibits fatty acid synthase and glutamate dehydrogenase activity.


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Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Articles

抗氧化剂可保护生物系统免受含氧自由基和氧化还原过渡金属离子(如铁、铜和镉)引起的氧化损伤。

本文介绍了增殖活性细胞为何需要碳源和氮源合成大分子。尽管大部分肿瘤细胞利用有氧糖酵解途径并分流线粒体氧化磷酸化代谢物,但许多肿瘤细胞表现出线粒体活性增加。

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.

View All Articles

(-)-Epigallocatechin-3-gallate stimulates myogenic differentiation through TAZ activation
Kim AR, et al.
Biochemical and Biophysical Research Communications, 486(2), 378-384 (2017)
(-)-Epigallocatechin gallate inhibition of osteoclastic differentiation via NF-kappaB
Lin RW, et al.
Biochemical and Biophysical Research Communications, 379(4), 1033-1037 (2009)
Proposed mechanisms of (-)-epigallocatechin-3-gallate for anti-obesity
Moon HS, et al.
Chemico-Biological Interactions, 167(2), 85-98 (2007)



Global Trade Item Number

SKUGTIN
E4143-50MG04061835544455