Skip to Content
Merck
CN
All Photos(2)

Documents

E4143

Sigma-Aldrich

(−)-Epigallocatechin gallate

≥95%

Sign Into View Organizational & Contract Pricing
All Photos(2)
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
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

Quality Level

200

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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

  1. 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.

  2. 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.

  3. 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.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. 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. 

  6. 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.

  7. 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.

  8. What is the solubility of (-)-Epigallocatechin gallate (E4143)?

    We have tested the solubility of (-)-Epigallocatechin gallate at 5 mg/mL in water.

  9. 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.

  10. 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).

  11. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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-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)
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)
Bing Fu et al.
Oxidative medicine and cellular longevity, 2019, 7824684-7824684 (2019-04-10)
Green tea is one of the most beverages with antioxidants and nutrients. As one of the major components of green tea, (-)-epicatechin gallate (ECG) was evaluated for its antioxidative properties in the present study. Cell proliferation assay, tube formation, cell
View All Related Papers

Articles

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.

Glutamine Metabolism in Cancer Cells

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

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.

Fatty Acid Synthesis in Cancer Cells

Fatty acid synthesis supports cancer cell proliferation, essential for membrane generation, protein modification, and bioenergetics.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service