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

• ChemBase ID: 155545
• Molecular Formular: C22H18O10
• Molecular Mass: 442.37232
• Monoisotopic Mass: 442.08999678
• SMILES: c1cc(c(cc1[C@H]1[C@@H](Cc2c(cc(cc2O1)O)O)OC(=O)c1cc(c(c(c1)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)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-CTNGQTDRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• IUPAC Traditional name: ent-catechin 3-O-gallate
• Synonyms: 3,4,5-Trihydroxybenzoic Acid (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl Ester; (-)-Catechin Gallate; (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate); (-)-Catechin gallate

Database IDs

• CAS Number: 130405-40-2
• MDL Number: MFCD00214258
• PubChem SID: 162249683; 24892268
• PubChem CID: 6419835

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

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... BACE1(23621)

Product Information

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

DETAILS

Sigma Aldrich - C0692

Biochem/physiol Actions
Antioxidant constituent of green tea. At μM concentrations, it inhibits VEGF-induced tyrosine phosphorylation. It also inhibits aromatase activity, an enzyme that converts androgens to estrogen and is thought to play a role in the etiology of breast cancer.

Toronto Research Chemicals - C217510

A major component of green tea, is a dual phosphoinositide-3-kinase/mTOR inhibitor.

REFERENCES

• Van Aller, G., et al.: Biochem. Biophys. Res. Commun., 406, 194 (2011)