Epigallocatechin | EGC | CAS#970-74-1

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

MedKoo CAT#: 600134

CAS#: 970-74-1

Description: (−)-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 ÂµM (−)-EGC can inhibit heregulin-β1-induced migration/invasion of MCF-7 human breast cancer cells. (Source: https://www.caymanchem.com).

Chemical Structure

Epigallocatechin

CAS# 970-74-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 600134
Name: Epigallocatechin
CAS#: 970-74-1
Chemical Formula: C15H14O7
Exact Mass: 306.07
Molecular Weight: 306.270
Elemental Analysis: C, 58.82; H, 4.61; O, 36.57

Price and Availability

Size	Price	Availability
10g	USD 650	2 weeks
50g	USD 1450	2 weeks
100g	USD 2450	2 weeks
500g	USD 4250	2 weeks
1kg	USD 5850	2 weeks
2kg	USD 9950	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 970-74-1 989-51-5,

Synonym: ()EGC; NSC 674039; epiGallocatechin

IUPAC/Chemical Name: [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate

InChi Key: WMBWREPUVVBILR-WIYYLYMNSA-N

InChi Code: 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

SMILES Code: O=C(O[C@H]1[C@@H](C2=CC(O)=C(O)C(O)=C2)OC3=C(C(O)=CC(O)=C3)C1)C4=CC(O)=C(O)C(O)=C4

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. 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

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.

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.

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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.

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