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E4143 Sigma-Aldrich

(−)-Epigallocatechin gallate

≥95%

Synonym: (−)-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

  • CAS Number 989-51-5

  • Empirical Formula (Hill Notation) C22H18O11

  • Molecular Weight 458.37

  •  MDL number MFCD00075940

  •  PubChem Substance ID 57654158

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Description

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

Packaging

50 mg in poly bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
KB5200000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Frequently Asked Questions

How does the storage temperature relate to shipping conditions?
The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.
Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
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What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
Is (-)-Epigallocatechin gallate (Product No. E4143) sterile and tested for endotoxins?
Product No. E4143 ((-)-Epigallocatechin gallate) is not prepared under sterile conditions and has not been tested for endotoxins.
Is (-)-Epigallocatechin gallate (Product No. E4143) for human use
No. Product No. E4143 ((-)-Epigallocatechin gallate) is for laboratory research use only, not for human use.
What is the solubility of (-)-Epigallocatechin gallate (E4143)?
We have tested the solubility of (-)-Epigallocatechin gallate at 5 mg/mL in water.
What is the solution stability of (-)-Epigallocatechin gallate (E4143)?
A solution of (-)-Epigallocatechin gallate in water at a concentration of 0.3 mg/mL was found to have significantly decreased in purity (from 99.6% to 81.7%) after 2.5 hours at room temperature. A similar solution of (-)-Epigallocatechin gallate in water at a concentration of 0.3 mg/mL was found to have decreased in purity only slightly (from 99.5% to 99.3%) after 2.0 hours at 4°C.
Can (-)-Epigallocatechin gallate be determined in plasma and urine?
The determination of (-)-Epigallocatechin gallate in plasma and urine by HPLC has been reported in Cancer Epidemiol. Biomark. Prev., 4, 393 (1995).
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Protocols & Articles

Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete. The expansion of the carcinogenesi...
Vicki Caligur
BioFiles 2008, 3.5, 18.
Keywords: Acetylations, Adhesion, Alkylations, Apoptosis, Biofiles, Cancer, Carcinogens, Cell division, Cell proliferation, Cell signaling, DNA microarrays, Drug discovery, Environmental, Epigenetics, Events, Gene expression, Genetic, Hormones, Metabolism, Methylations, Microarray Analysis, Mutagens, PAGE, Recombination, Reductions, Sequences, Transcription, Type, transformation

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.1 During the oxi...
Biofiles Volume 2 Article 2
Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

Fatty Acid Synthesis and Metabolism in Cancer Cells

Proliferatively active cells require fatty acids for functions such as membrane generation, protein modification, and bioenergetic requirements. These fatty acids are derived either from dietary sour...
BioFiles v7 n4
Keywords: Apoptosis, Cancer, Carboxylations, Catalysis, Citric Acid Cycle, Gene expression, Glycolysis, Metabolism, Oxidations, Phosphorylations

Glutamine Metabolism is Dysregulated in Many Cancer Cells

Proliferatively active cells require both a source of carbon and of nitrogen for the synthesis of macromolecules. Although a large proportion of tumor cells utilize aerobic glycolysis and shunt metab...
BioFiles v7 n4
Keywords: Aerobic, Cancer, Citric Acid Cycle, Gene expression, Glycolysis, Metabolism, Metabolites, Phosphorylations, Transcription

LC/MS Analysis of Green Tea Components on Chromolith® FastGradient RP-18 endcapped

From our library of Articles, Sigma-Aldrich presents LC/MS Analysis of Green Tea Components on Chromolith® FastGradient RP-18 endcapped
Keywords: Chromatography, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry

Modulators and Proteins for Methylation

DNA methyltransferases are a family of enzymes that catalyze the transfer of a methyl group to DNA. There are five related DNA cytosine-5-methyltransferases (DNMTs) that transfer a methyl group from ...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 7–9
Keywords: Gene expression, Methylations

NF-κB and Inflammation

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. Oxidative cellular ...
BioFiles 2007, 2.4, 14.
Keywords: Acetylations, Adhesion, Angiogenesis, Apoptosis, Cancer, Carcinogens, Catalysis, Cell culture, Cell proliferation, Cell signaling, Cellular processes, Degradations, Diabetes, Diseases, Environmental, Gene expression, Glycosylations, High performance liquid chromatography, Inflammation, PAGE, Phosphorylations, Thin layer chromatography, Transcription, transformation

Peer-Reviewed Papers
15

References

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