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

• ChemBase ID: 127266
• Molecular Formular: C22H18O10
• Molecular Mass: 442.37232
• Monoisotopic Mass: 442.08999678
• SMILES: O=C(O[C@@H]1Cc2c(O[C@@H]1c1ccc(O)c(O)c1)cc(O)cc2O)c1cc(O)c(O)c(O)c1
• Canonical SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
• InChIKey: LSHVYAFMTMFKBA-TZIWHRDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• IUPAC Traditional name: (-)-epicatechin 3-O-gallate
• Synonyms: ECG; Epicatechin 3-gallate; (-)-Epicatechin-3-O-gallate; Epicatechin gallate; 3,4,5-Trihydroxybenzoic Acid (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl Ester; (-)-epi-Catechin 3-O-gallate; 3-Galloyl-(-)-epicatechin; 3-Galloyl-(2R,3R)-(-)-Epicatechin; (-)-Epicatechin Gallate; (-)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate; (-)-cis-3,3′,4′,5,7-Pentahydroxyflavane 3-gallate; (-)-Epicatechin gallate; (-)-表儿茶素没食子酸酯

Database IDs

• CAS Number: 1257-08-5
• MDL Number: MFCD00075936
• PubChem SID: 24894531; 162221587
• PubChem CID: 107905
• CHEMBL: 36327
• Chemspider ID: 97034
• Wikipedia Title: Epicatechin_gallate

CALCULATED PROPERTIES

• Acid pKa: 8.03228
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 3.3784473
• LogD (pH = 7.4): 3.2868483
• Log P: 3.379711
• Molar Refractivity: 109.7644 cm^3
• Polarizability: 41.964565 Å^3
• Polar Surface Area: 177.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: DH9030000
• German water hazard class: 3
• 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)

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (HPLC)
• Grade: purum
• Biological Source: from green tea
• Empirical Formula (Hill Notation): C22H18O10

DETAILS

Sigma Aldrich - E3893

Biochem/physiol Actions
抗氧化剂

Toronto Research Chemicals - E582265

One of the catechin isomers and a potent antioxidant that can modulate a wide range of membrane proteins. Its bilayer-modifying potency was tested using gramicidin A (gA) channels as probes. All the catechins alter gA channel function and modify bilayer p

REFERENCES

• Ingolfsson, H., et al.: FEBS Lett., 585, 3101 (2011)