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MedKoo Cat#: 600134 | Name: Epigallocatechin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

(−)-Epigallocatechin ((−)-EGC) is a major green tea polyphenol with antioxidant, anti-inflammatory, and anticancer activities. It has been shown to scavenge DPPH radicals with an EC50 value of 0.01 mM and to prevent the growth of several different AML cell lines at micromolar concentrations. Furthermore, at 30 µM (−)-EGC can inhibit heregulin-β1-induced migration/invasion of MCF-7 human breast cancer cells. (Source: https://www.caymanchem.com).

Chemical Structure

Epigallocatechin
Epigallocatechin
CAS#970-74-1

Theoretical Analysis

MedKoo Cat#: 600134

Name: Epigallocatechin

CAS#: 970-74-1

Chemical Formula: C15H14O7

Exact Mass: 306.0740

Molecular Weight: 306.27

Elemental Analysis: C, 58.82; H, 4.61; O, 36.57

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
2g USD 350.00 2 Weeks
5g USD 650.00 2 Weeks
10g USD 950.00 2 Weeks
25g USD 1,450.00 2 Weeks
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Related CAS #
970-74-1 989-51-5 (gallate)
Synonym
(-)-Epigallocatechin; Epigallocatechin; Epigallocatechol; L-Epigallocatechin; epi-Gallocatechin; (-)-EGC; NSC 674039; NSC674039; NSC-674039;
IUPAC/Chemical Name
(2R,3R)-3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
InChi Key
XMOCLSLCDHWDHP-IUODEOHRSA-N
InChi Code
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
SMILES Code
O[C@H]1[C@@H](C2=CC(O)=C(O)C(O)=C2)OC3=C(C(O)=CC(O)=C3)C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
(-)-Epigallocatechin (Epigallocatechin) is the most abundant flavonoid in green tea, can bind to unfolded native polypeptides and prevent conversion to amyloid fibrils.
In vitro activity:
Caffeine and EGCG significantly increased F-actin level by 46.5% and 92.7%, respectively (Fig. 2B). In addition to immunofluorescence staining, Western blotting demonstrated the increased level of β-actin in caffeine-treated and EGCG-treated ECs when compared with the control cells (Fig. 2C). In consistent, quantitative data revealed that β-actin level was significantly enhanced by 53.4% and 76.0% by caffeine and EGCG, respectively (Fig. 2D). Thus, EGCG had greater effects to induce actin crosslinking activity in the EA.hy926 cells. Reference: Biomed Pharmacother. 2021 Jun 24;141:111837. https://pubmed.ncbi.nlm.nih.gov/34175818/
In vivo activity:
Western blot analysis showed increased iNOS and COX-2 expressions in tissues from vehicle treated rats 24 h, and three and five days after surgery, as compared to sham animals. EGCG administration reduced both expressions at all timepoints (Figure 7A,B). Additionally, PGE2 levels were significantly increased 24 h, and three and five days after surgery and EGCG administration reduced its levels (Figure 7C). Reference: Int J Mol Sci. 2021 Jul; 22(13): 6879. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8268037/
Solvent mg/mL mM
Solubility
DMSO 75.3 245.96
DMF 25.0 81.63
Ethanol 5.0 16.33
PBS (pH 7.2) 1.0 3.27
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 306.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Gallemit PEM, Yoodee S, Malaitad T, Thongboonkerd V. Epigallocatechin-3-gallate plays more predominant roles than caffeine for inducing actin-crosslinking, ubiquitin/proteasome activity and glycolysis, and suppressing angiogenesis features of human endothelial cells. Biomed Pharmacother. 2021 Jun 24;141:111837. doi: 10.1016/j.biopha.2021.111837. Epub ahead of print. PMID: 34175818. 2. Panji M, Behmard V, Zare Z, Malekpour M, Nejadbiglari H, Yavari S, Nayerpour Dizaj T, Safaeian A, Maleki N, Abbasi M, Abazari O, Shabanzadeh M, Khanicheragh P. Suppressing effects of green tea extract and Epigallocatechin-3-gallate (EGCG) on TGF-β- induced Epithelial-to-mesenchymal transition via ROS/Smad signaling in human cervical cancer cells. Gene. 2021 Aug 20;794:145774. doi: 10.1016/j.gene.2021.145774. Epub 2021 Jun 11. PMID: 34126197. 3. Siracusa R, Monaco F, D'Amico R, Genovese T, Cordaro M, Interdonato L, Gugliandolo E, Peritore AF, Crupi R, Cuzzocrea S, Impellizzeri D, Fusco R, Di Paola R. Epigallocatechin-3-Gallate Modulates Postoperative Pain by Regulating Biochemical and Molecular Pathways. Int J Mol Sci. 2021 Jun 26;22(13):6879. doi: 10.3390/ijms22136879. PMID: 34206850; PMCID: PMC8268037. 4. Zhang SL, Chen ZH, Lin DT, Yan Q, Gao F, Lin H. Epigallocatechin gallate regulates inflammatory responses and new bone formation through Wnt/β-Catenin/COX-2 pathway in spondyloarthritis. Int Immunopharmacol. 2021 Jun 18;98:107869. doi: 10.1016/j.intimp.2021.107869. Epub ahead of print. PMID: 34153673.
In vitro protocol:
1. Gallemit PEM, Yoodee S, Malaitad T, Thongboonkerd V. Epigallocatechin-3-gallate plays more predominant roles than caffeine for inducing actin-crosslinking, ubiquitin/proteasome activity and glycolysis, and suppressing angiogenesis features of human endothelial cells. Biomed Pharmacother. 2021 Jun 24;141:111837. doi: 10.1016/j.biopha.2021.111837. Epub ahead of print. PMID: 34175818. 2. Panji M, Behmard V, Zare Z, Malekpour M, Nejadbiglari H, Yavari S, Nayerpour Dizaj T, Safaeian A, Maleki N, Abbasi M, Abazari O, Shabanzadeh M, Khanicheragh P. Suppressing effects of green tea extract and Epigallocatechin-3-gallate (EGCG) on TGF-β- induced Epithelial-to-mesenchymal transition via ROS/Smad signaling in human cervical cancer cells. Gene. 2021 Aug 20;794:145774. doi: 10.1016/j.gene.2021.145774. Epub 2021 Jun 11. PMID: 34126197.
In vivo protocol:
1. Siracusa R, Monaco F, D'Amico R, Genovese T, Cordaro M, Interdonato L, Gugliandolo E, Peritore AF, Crupi R, Cuzzocrea S, Impellizzeri D, Fusco R, Di Paola R. Epigallocatechin-3-Gallate Modulates Postoperative Pain by Regulating Biochemical and Molecular Pathways. Int J Mol Sci. 2021 Jun 26;22(13):6879. doi: 10.3390/ijms22136879. PMID: 34206850; PMCID: PMC8268037. 2. Zhang SL, Chen ZH, Lin DT, Yan Q, Gao F, Lin H. Epigallocatechin gallate regulates inflammatory responses and new bone formation through Wnt/β-Catenin/COX-2 pathway in spondyloarthritis. Int Immunopharmacol. 2021 Jun 18;98:107869. doi: 10.1016/j.intimp.2021.107869. Epub ahead of print. PMID: 34153673.
1: Xicota L, Rodríguez-Morató J, Dierssen M, de la Torre R. Potential Role of (-)-epigallocatechin-3-gallate (EGCG) in the Secondary Prevention of Alzheimer Disease. Curr Drug Targets. 2015 Aug 25. [Epub ahead of print] PubMed PMID: 26302801. 2: Santamarina AB, Carvalho-Silva M, Gomes LM, Okuda MH, Santana AA, Streck EL, Seelaender M, Oller do Nascimento CM, Ribeiro EB, Lira FS, Oyama LM. Decaffeinated green tea extract rich in epigallocatechin-3-gallate prevents fatty liver disease by increased activities of mitochondrial respiratory chain complexes in diet-induced obesity mice. J Nutr Biochem. 2015 Jul 26. pii: S0955-2863(15)00158-8. doi: 10.1016/j.jnutbio.2015.07.002. [Epub ahead of print] PubMed PMID: 26300331. 3: Lee JH, Shin YC, Yang WJ, Park JC, Hyon SH, Han DW. Epigallocatechin-3-O-Gallate-Loaded Poly(lactic-co-glycolic acid) Fibrous Sheets as Anti-Adhesion Barriers. J Biomed Nanotechnol. 2015 Aug;11(8):1461-71. PubMed PMID: 26295146. 4: Papi A, Govoni M, Ciavarella C, Spisni E, Orlandi M, Farabegoli F. Epigallocatechin-3-gallate increases RXRg-mediated pro-apoptotic and anti-invasive effects in gastrointestinal cancer cell lines. Curr Cancer Drug Targets. 2015 Aug 17. [Epub ahead of print] PubMed PMID: 26278714. 5: Cai Y, He SQ, Hong HQ, Cai YP, Zhao L, Zhang M. High doses of (-)-epigallocatechin-3-gallate from green tea induces cardiac fibrosis in mice. Biotechnol Lett. 2015 Aug 14. [Epub ahead of print] PubMed PMID: 26272391. 6: Betts JW, Sharili AS, Phee LM, Wareham DW. In Vitro Activity of Epigallocatechin Gallate and Quercetin Alone and in Combination versus Clinical Isolates of Methicillin-Resistant Staphylococcus aureus. J Nat Prod. 2015 Aug 12. [Epub ahead of print] PubMed PMID: 26267658. 7: Yao HT, Yang YC, Chang CH, Yang HT, Yin MC. Protective effects of (-)-epigallocatechin-3-gallate against acetaminophen-induced liver injury in rats). Biomedicine (Taipei). 2015 Sep;5(3):15. doi: 10.7603/s40681-015-0015-8. Epub 2015 Aug 12. PubMed PMID: 26264479; PubMed Central PMCID: PMC4531855. 8: Ning Y, Ling J, Wu CD. Synergistic effects of tea catechin epigallocatechin gallate and antimycotics against oral Candida species. Arch Oral Biol. 2015 Jul 13;60(10):1565-1570. doi: 10.1016/j.archoralbio.2015.07.001. [Epub ahead of print] PubMed PMID: 26263544. 9: Lu QY, Zhang L, Yee JK, Go VW, Lee WN. Metabolic Consequences of LDHA inhibition by Epigallocatechin Gallate and Oxamate in MIA PaCa-2 Pancreatic Cancer Cells. Metabolomics. 2015 Feb;11(1):71-80. PubMed PMID: 26246802; PubMed Central PMCID: PMC4523095. 10: Wubetu GY, Shimada M, Morine Y, Ikemoto T, Ishikawa D, Iwahashi S, Yamada S, Saito Y, Arakawa Y, Imura S. Epigallocatechin gallate hinders human hepatoma and colon cancer sphere formation. J Gastroenterol Hepatol. 2015 Aug 4. doi: 10.1111/jgh.13069. [Epub ahead of print] PubMed PMID: 26241688.