2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 171477
• Molecular Formular: C21H20O12
• Molecular Mass: 464.3763
• Monoisotopic Mass: 464.09547608
• SMILES: c1(cc(c2c(c1)oc(c(c2=O)O[C@H]1OC([C@H](C([C@@H]1O)O)O)CO)c1ccc(c(c1)O)O)O)O
• Canonical SMILES: OCC1O[C@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13?,15-,17?,18-,21-/m1/s1
• InChIKey: OVSQVDMCBVZWGM-HHJZGNMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
• Synonyms: 2-(3,4-Dihydroxyphenyl)-3-(β-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one; 3,3',4',5,7-Pentahydroxyflavone 3-O-β-D-galactopyranoside; Quercetin 3-O-β-D-galactoside; Hyperoside

Database IDs

• CAS Number: 482-36-0
• PubChem SID: 164227387
• PubChem CID: 46781931

CALCULATED PROPERTIES

• Acid pKa: 6.433962
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -0.19234054
• LogD (pH = 7.4): -1.1606922
• Log P: -0.1448353
• Molar Refractivity: 109.2755 cm^3
• Polarizability: 42.19499 Å^3
• Polar Surface Area: 206.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: >260°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H998200

A major flavonoid in apple peels; a bioactive constituent of apple peels with potent antioxidant and antiproliferative activities.

REFERENCES

• Willett, W., et al.: Science, 264, 532 (1994)
• Eberhardt, M., et al.: Nature, 405, 903 (1994)
• Sun, J., et al.: J. Agric. Food Chem., 50, 7449 (1994)
• Liu, R., et al.: J. Nutr., 134, 3479 (1994)
• Sun, J., et al.: Cancer Lett., 241, 124 (1994)