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

• ChemBase ID: 155918
• Molecular Formular: C20H18O11
• Molecular Mass: 434.35032
• Monoisotopic Mass: 434.0849114
• SMILES: c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)OC1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)OC1OC[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15+,17-,20?/m1/s1
• InChIKey: PZZRDJXEMZMZFD-DUYPVGENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-4-one
• Synonyms: Reinutrin; Reynoutrin; Quercetin-3-D-xyloside

Database IDs

• CAS Number: 549-32-6
• MDL Number: MFCD00210590
• Beilstein Number: 6023007
• PubChem SID: 162250056; 24888116
• PubChem CID: 5320863

CALCULATED PROPERTIES

• H Donor: 7
• LogD (pH = 5.5): 0.43799454
• LogD (pH = 7.4): -0.5303556
• Log P: 0.48549965
• Molar Refractivity: 103.313 cm^3
• Polarizability: 39.68719 Å^3
• Polar Surface Area: 186.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false
• Acid pKa: 6.433963
• H Acceptors: 11

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C20H18O11

DETAILS

Sigma Aldrich - 83390

Other Notes
Flavonol glycoside present in quince, pear, and apple1,2 and cranberry. Shows potent free-radical scavenging and antioxidant activity in vivo.3