- Green Tea Extract
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- $10.00
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2026-10-13
- CAS:989-51-5
- Min. Order: 1kg
- Purity: 95.0% Polyphenols Test By UV
- Supply Ability: 10000
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| | (-)-Epigallocatechin gallate Basic information | | Uses |
| Product Name: | (-)-Epigallocatechin gallate | | Synonyms: | (-)-Epigallocatechin-3-O-gallate (20 mg);EGCG, (-)-Epigallocatechin gallate/Green Tea Extract;(-)-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;Epigallocatechin-3-Monogallate;L-Epigallocatechin Gallate;(-)-Epigallocatechin Gallate-d6;3-O-Galloyl-(-)-epigallocatechin-d6;EGCG-d6 | | CAS: | 989-51-5 | | MF: | C22H18O11 | | MW: | 458.37 | | EINECS: | 479-560-7 | | Product Categories: | Aromatics;Heterocycles;Natural Plant Extract;Standard extract;Amyloid beta-peptide and related;Inhibitors;Catechins & Tannins;All Inhibitors;Antioxidant;Biochemistry;Flavonoids;Pharmaceutical Raw Materials;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Plant extracts;Herb extract;Inhibitor;ProteasomeInhibitors;989-51-5 | | Mol File: | 989-51-5.mol |  |
| | (-)-Epigallocatechin gallate Chemical Properties |
| Melting point | 222-224°C | | alpha | D -185 ±2°(ethanol) | | refractive index | -175.5 ° (C=1, EtOH) | | storage temp. | 2-8°C | | solubility | H2O: ≥5mg/mL, clear | | Boiling point | 909.1±65.0 °C(Predicted) | | density | 1.90±0.1 g/cm3(Predicted) | | pKa | 7.75±0.25(Predicted) | | form | Solid | | color | White to Light Brown | | biological source | green tea | | Water Solubility | Soluble in ethanol, dimethyl formamide, water. | | Merck | 14,3526 | | Stability: | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. | | Major Application | metabolomics
vitamins, nutraceuticals, and natural products | | Cosmetics Ingredients Functions | ANTIOXIDANT | | 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 | | InChIKey | WMBWREPUVVBILR-WIYYLYMNSA-N | | SMILES | Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4cc(O)c(O)c(O)c4 | | LogP | 0.639 (est) | | CAS DataBase Reference | 989-51-5(CAS DataBase Reference) |
| Safety Statements | 24/25 | | WGK Germany | 2 | | RTECS | KB5200000 | | F | 10-23 | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Aquatic Chronic 2
Eye Irrit. 2
Skin Sens. 1 | | Toxicity | LD50 oral in mouse: 2170mg/kg |
| | (-)-Epigallocatechin gallate Usage And Synthesis |
| Uses | (-)-Epigallocatechin Gallate (egcg) is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-ß and amaloid plaques in mice. This compound has neuroprotective properties. | | Chemical Properties | solid | | Uses | telomerase inhibitor | | Uses | An inhibitor of Bcl-2 and NOS2 | | Uses | A tumor-inhibiting constituent of green tea. Alters the cleavage of amyloid precursor protein, decreasing production of amaloid- and amaloid plaques in mice | | Uses | (-)-Epigallocatechin Gallate (egcg) is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-β and amaloid plaques in mice. This compound has neuroprotective properties. | | Definition | ChEBI: (-)-epigallocatechin 3-gallate is a gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin. It has a role as an antineoplastic agent, an antioxidant, a Hsp90 inhibitor, a neuroprotective agent, a plant metabolite, a geroprotector and an apoptosis inducer. It is a gallate ester, a polyphenol and a member of flavans. It is functionally related to a (-)-epigallocatechin. | | General Description | Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Epigallocatechin gallate is a potent polyphenolic flavonoid which is found as a component of tea. It exhibits antioxidant, antimutagenic, antitumor and anti-inflammatory properties, thereby contributing to the health-beneficial actions. It finds potential use as a drug candidate in the pharmaceutical, cosmetic, and nutritional fields. | | Hazard | Moderately toxic by ingestion. | | Biological Activity | (-)-epigallocatechin gallate (egcg), the major catechin accounting for 59% of the total catechins in green tea, is a powerful antioxidant as well as an antiangiogenic and antitumor agent. egcg has been studied for its role in the chemoprevention of a wild range of cancers, including liver, stomach, skin, lung, mammary gland and colon cancers. study results show that egcg is able to induce apoptosis, promote cell growth arrest and block carcinogenesis by affecting signal transduction pathways. moreover, egcg exhibits inhibition against a variety of viruses, including hcv, hiv-1, hbv, hsv-1, hsv-2, ebv, adenovirus, influenza virus and enterovirus, as well as several enzymes, including dnmts, proteases and dhfr.singh bn, shankar s, srivastava rk. green tea catechin, epigallocatechin-3-gallate (egcg): mechanisms, perspectives and clinical applications. biochem pharmacol. 2011; 82(12):1807-1821.steinmann j, buer j, pietschmann t, steinmann e. anti-infective properties of epigallocatechin-3-gallate (egcg), a component of green tea. br j pharmacol. 2013; 168(5):1059-1073 | | 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. | | Anticancer Research | EGCG and EGC are the active polyphenol compounds found in green tea, found toinhibit p-glycoprotein transport activities in Chinese hamster ovary (p-gp+) cells.EGCG facilitates the retraction of MDR phenotype by reducing cellular drug effluxwhen given in combination with vinblastine or doxorubicin. Hesperetin, quercetin,daidzein, silymarin, naringenin, and resveratrol also inhibit the MRP1, MRP4, andMRP5 (Kawasaki et al. 2008). Curcumin increases the cellular accumulation ofanticancer agents like cisplatin, tamoxifen, daunorubicin, vincristine, anddoxorubicin and thereby effectively sensitizes the drug-resistant cancer cells. Areduction in MDR1B expression in L1210/Adr cells (mouse leukemic MDR cells)by curcumin is mediated by PI3K, Akt, and NF-κB pathways. It also inhibits theABCG2 transporter activity. In addition curcumin facilitates the accumulation ofmitoxantrone and doxorubicin in ABCG2-expressing HEK cells and hence reversesMDR (Kawasaki et al. 2008; Dandawate et al. 2013). | | Anticancer Research | EGCG is an ester of gallic acid and epigallocatechin and is a catechin compound(Murakami et al. 1996). It is found most abundantly in green tea. It can be used to treat brain, prostate, cervical, and bladder cancers (Wang et al. 2012). It suppressesthe ornithine decarboxylase action, an enzyme that leads to rapid proliferation andfurthermore circumvents apoptosis (Singh et al. 2016a). It suppresses nuclear factor(NF-κB) activation and expression of Bcl-2 (B-cell lymphoma 2) as well as COX-2(cyclooxygenase-2) in prostate cancer cells and causes induction of apoptosis. Ithamper the matrix metallopeptidase-9 (MMP-9) activation in bladder and lungcancer cells and suppresses the synthesis of VGEF (vascular endothelial growthfactor) in head and neck cancers. It prevents ERK (extracellular signal-regulatedkinase) phosphorylation and MMP-2 and MMP-9 activation and suppresses ERK,c-Jun N-terminal kinase (JNK), and MMP-9 expressions in gastric carcinoma cells(Singh et al. 2016a). It is binding and inhibits the antiapoptotic protein Bcl-xL,interferes with EGFR (epidermal growth factor receptor) signaling, and inhibitshepatocyte growth factor-induced cell proliferation and MAPK (mitogen-activatedprotein kinase), CDK (cyclin-dependent kinase), and cell signaling linked to growthfactors (Wang et al. 2012; Du et al. 2012).
Green tea constitutes the rich amount of EGCG which aids in cancer chemoprevention(Fujiki et al. 1998). EGCG improved the impacts of ginseng compoundin the restraint of colon tumor cell development, showing that green tea could bea successful synergist with an anticancer agent for malignancy chemoprevention.It obstructs the PDGF-initiated proliferation and migration of rodent pancreaticstellate cells (Masamune et al. 2005). The soluble and plasma membrane-integratedEGCG straightforwardly communicates with PDGF-BB and in this wayputs off precise receptor binding promoting the inhibitory impacts of EGCG onplatelet-derivedgrowth factor-incited cell signaling and mitogens (Weber et al.2004). | | Synthesis | Synthesis of (±)-epigallocatechin gallate (EGCG): starting from the dibenzyl-protected aldehyde 7b, aldol condensation with ketone 8b afforded enone 9b in quantitative yield; 9b was converted to α-hydroxyketone 6b in 55% overall yield over three steps by an established procedure; acylation of 6b with acid 13 (EDCI, DMAP) gave ester 2b in 98% yield; reductive cyclization of 2b under Et3SiH/(Ph3P)3RhCl directly formed the cis-3-acyloxy-2-arylbenzopyran scaffold via intramolecular reductive etherification (with neighboring-group participation of the C3 acyloxy group ensuring cis-stereoselectivity), and subsequent deprotection (TFA/Et3SiH, then H2/Pd(OH)2) furnished (±)-EGCG in 50% yield from 2b — a 25% overall yield over seven steps from 7b [1].
| | storage | Store at -20°C | | References |
[1]
Takahashi, T., Kitade, M., Ohno, Y., Tanaka, H. (2006). An Efficient Synthesis of (±)-Epigallocatechin Gallate by Reductive Intramolecular Etherification. Synlett, 2006(17), 2827–2829. https://doi.org/10.1055/s-2006-950283
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| | (-)-Epigallocatechin gallate Preparation Products And Raw materials |
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