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Merck

E4143

(−)-Epigallocatechin gallate

≥95%

동의어(들):

(−)-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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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):
C22H18O11
CAS 번호:
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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Hazard Classifications

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

저장 등급

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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문서

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.

Sigma article discusses tumor cell metabolic pathways, focusing on aerobic glycolysis and mitochondrial activity.

Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer.

모든 기사 보기

(-)-Epigallocatechin-3-gallate stimulates myogenic differentiation through TAZ activation
Kim AR, et al.
Biochemical and Biophysical Research Communications, 486(2), 378-384 (2017)
Takuya Miyagawa et al.
Pharmaceutics, 12(5) (2020-05-02)
Neovascularization (NV) of the cornea disrupts vision which leads to blindness. Investigation of antiangiogenic, slow-release and biocompatible approaches for treating corneal NV is of great importance. We designed an eye drop formulation containing gelatin/epigallocatechin-3-gallate (EGCG) nanoparticles (NPs) for targeted therapy
(-)-Epigallocatechin gallate inhibition of osteoclastic differentiation via NF-kappaB
Lin RW, et al.
Biochemical and Biophysical Research Communications, 379(4), 1033-1037 (2009)