(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

• ChemBase ID: 72911
• Molecular Formular: C22H18O11
• Molecular Mass: 458.37172
• Monoisotopic Mass: 458.0849114
• SMILES: c1(c(c(cc(c1)C(=O)O[C@H]1[C@H](Oc2c(C1)c(cc(c2)O)O)c1cc(c(c(c1)O)O)O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• IUPAC Traditional name: (-)-epigallocatechin gallate; (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• Synonyms: (-)-Epigallocatechin gallate; (-)-Epigallocatechin gallate; Epigallocatechin gallate; (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate; EGCG; (-)-Epigallocatechin gallate; 3-O-(4-Hydroxybenzoyl)epigallocatechin; EGCG (Epigallocatechin gallate ); Teavigo; epi-Gallocatechin 3-O-Gallate; epi-Gallocatechin Gallate; Epigallocatechin-3-monogallate; L-Epigallocatechin Gallate; 3-O-Galloyl-(-)-epigallocatechin; (-)-cis-3,3′,4′,5,5′,7-Hexahydroxy-flavane-3-gallate; (-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate; (-)-顺式-2-(3,4,5-三羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7--三醇 3-没食子酸酯; (-)-顺式-3,3′,4′,5,5′,7-六羟基-黄烷-3-没食子酸酯; (-)-表没食子儿茶素没食子酸酯

Database IDs

• CAS Number: 989-51-5
• MDL Number: MFCD00075940
• PubChem SID: 24873355; 24894544; 24894548; 162037831
• PubChem CID: 65064
• CHEBI ID: 4806
• CHEMBL: 297453
• Chemspider ID: 58575
• MeSH Name: Epigallocatechin+gallate
• Wikipedia Title: Epigallocatechin_gallate

CALCULATED PROPERTIES

• Acid pKa: 7.9929934
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): 3.0747623
• LogD (pH = 7.4): 2.9740098
• Log P: 3.0761456
• Molar Refractivity: 111.7453 cm^3
• Polarizability: 42.63128 Å^3
• Polar Surface Area: 197.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; soluble in ethanol, DMSO, dimethyl formamide at about 20 g/l; soluble in water
• Apperance: ''; Light Pink Solid
• Melting Point: 216-218°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: KB5200000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)
• Mechanism of Action: Shows anti-HIV activity. Tumour promotion inhibitor, putative cancer chemopreventive agent. Implicated in occup. asthma in green tea factories

Product Information

• Purity: ≥80% (HPLC); ≥95%; ≥97.0% (HPLC); ≥98.0% (HPLC)
• Grade: analytical standard; purum
• Salt Data: Free Base
• Biological Source: from green tea; Green Tea
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antioxidant
• Empirical Formula (Hill Notation): C22H18O11

DETAILS

Selleck Chemicals - S2250

Research Area: Infection
Biological Activity:
(-)-Epigallocatechin gallate is a potent anti-oxidant polyphenol flavonoid isolated from green tea. It is the ester of epigallocatechin and gallic acid, and is a type of catechin. Its possible benefit as a nutritional chemopreventive agent for cancer, atherosclerosis, and neurodegenerative diseases is generating increased scientific interest. EGCG has demonstrated chemopreventive and chemotherapeutic actions in cellular and animal models of cancer. [1][2]

Sigma Aldrich - E4268

Biochem/physiol Actions
Catechins are a plant derived polyphenolic anti-oxidants with phytotoxic properties. Racemic catechin may be used in studies on seed germination and plant invasiveness. Catechin and Epigallocatechin gallate (EGCG) may be used with other polyphenol flavonoids to study their effects in oxidation and peroxidation-related processes.

Sigma Aldrich - E4143

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Antioxidant polyphenol flavonoid that inhibits telomerase and DNA methyltransferase. EGCG blocks the activation of EGF receptors and HER-2 receptors. ECGG inhibits fatty acid synthase and glutamate dehydrogenase activity.

Toronto Research Chemicals - E588500

(-)-Epigallocatechin Gallate 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.

REFERENCES

• Katiyar S et al. J Nutr Biochem. 2007 May;18(5):287-96.
• Yamane, T. et al.: Cancer Res., 55, 2081 (1995)
• Tan, J. et al.: J. Neurosci. 25, 8807 (1995)
• Nakane, H., Biochemistry, 1990, 29, 2841, (anti-HIV activity)
• Lee, M.W. et al., Phytochemistry, 1992, 31, 2117, (gallates)
• Fujiki, H. et al., Prev. Med., 1992, 21, 503, (gallate, pharmacol, rev)