2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-one

• ChemBase ID: 154688
• Molecular Formular: C16H12O7
• Molecular Mass: 316.26228
• Monoisotopic Mass: 316.05830272
• SMILES: COc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O
• Canonical SMILES: COc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C16H12O7/c1-22-16-14(21)13-11(20)5-8(17)6-12(13)23-15(16)7-2-3-9(18)10(19)4-7/h2-6,17-20H,1H3
• InChIKey: WEPBGSIAWZTEJR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-one
• IUPAC Traditional name: quercetin 3-methyl ether
• Synonyms: 3-Methoxy-3',4',5,7-tetrahydroxyflavone; 3-Methylquercetin; 3-Methylquercetol; 3',4',5,7-Tetrahydroxy-3-methoxyflavone; 5,7,3',4'-Tetrahydroxy-3-methoxyflavone; NSC 154016; Quercetin 3-Methyl Ether; Quercetin-3-O-methyl Ether; 3-O-Methyl Quercetin; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-1-benzopyran-4-one; 5,7,3′ ,4′ -Tetrahydroxy-3-methoxyflavone; Quercetin 3-O-methyl ether; 3-O-Methylquercetin

Database IDs

• CAS Number: 1486-70-0
• MDL Number: MFCD00210588
• Beilstein Number: 324509
• PubChem SID: 162248826
• PubChem CID: 5280681

CALCULATED PROPERTIES

• Acid pKa: 6.3780603
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.2153401
• LogD (pH = 7.4): 1.1200694
• Log P: 2.269127
• Molar Refractivity: 81.6134 cm^3
• Polarizability: 30.312017 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310

Product Information

• Purity: ≥97% (HPLC); 98.5
• Empirical Formula (Hill Notation): C16H12O7

DETAILS

Toronto Research Chemicals - M326545

A metabolite of the flavanoid Quercetin (Q509500) with inhibitory activity on lipopolysaccharide-induced activation of macrophage U937 cells.

REFERENCES

• Okoko, T. et al.: Food Chem. Toxicol., 47, 809 (2009)
• Duenas, M. et al.: Eur. Food Res. Technol., 232, 103 (2009)
• Marzouk, M. et al.: Phytochem., 52, 943 (2009)