5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 175004
• Molecular Formular: C15H12O5
• Molecular Mass: 272.25278
• Monoisotopic Mass: 272.06847348
• SMILES: c1c(cc(c2c1OC(CC2=O)c1ccc(cc1)O)O)O
• Canonical SMILES: Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2O)O
• InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2
• InChIKey: FTVWIRXFELQLPI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: asahina
• Synonyms: 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; (R,S)-Naringenin; (+/-)-5,7,4'-Trihydroxyflavanone; 5,7,4'-Trihydroxyflavanone; rac Naringenin

Database IDs

• CAS Number: 480-41-1
• PubChem SID: 164230914
• PubChem CID: 932

CALCULATED PROPERTIES

• Acid pKa: 7.9097586
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.8334327
• LogD (pH = 7.4): 2.7181597
• Log P: 2.835108
• Molar Refractivity: 71.2898 cm^3
• Polarizability: 27.291258 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 247-249°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N378950

The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions.

REFERENCES

• Lomovskaya, N., et al.: J. Bacteriol., 181, 305 (1999)
• Chung, L., et al.: J. Antibiot., 54, 250 (1999)
• Kim, D., et al.: Biochemistry, 43, 981 (1999)
• Kumar, S., et al.: J. Biol. Chem., 280, 19569 (1999)