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E4143

Sigma-Aldrich

(−)-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:
989-51-5
Molecular Weight:
458.37
MDL number:
MFCD00075940
UNSPSC Code:
12352205
PubChem Substance ID:
57654158
NACRES:
NA.25

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)

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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.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H317,H319,H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
(-)-Epigallocatechin-3-gallate stimulates myogenic differentiation through TAZ activation
Kim AR, et al.
Biochemical and Biophysical Research Communications, 486(2), 378-384 (2017)
Epigallocatechin-3-gallate induces cell death in acute myeloid leukaemia cells and supports all-trans retinoic acid-induced neutrophil differentiation via death-associated protein kinase 2
Britschgi A, et al.
British Journal of Haematology, 149(1), 55-64 (2010)
Prostate carcinoma and green tea:(-) epigallocatechin-3-gallate inhibits inflammation-triggered MMP-2 activation and invasion in murine TRAMP model
Sartor L, et al.
International Journal of Cancer. Journal International Du Cancer, 112(5), 823-829 (2004)
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