5,7-dihydroxy-2-[3-hydroxy-4-(2H3)methoxyphenyl]-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 169886
• Molecular Formular: C16H14O6
• Molecular Mass: 302.27876
• Monoisotopic Mass: 302.07903817
• SMILES: c1(cc(c2c(c1)OC(CC2=O)c1cc(c(cc1)OC)O)O)O
• Canonical SMILES: COc1ccc(cc1O)C1CC(=O)c2c(O1)cc(cc2O)O
• InChI: InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3
• InChIKey: AIONOLUJZLIMTK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-[3-hydroxy-4-(^2H₃)methoxyphenyl]-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: 5,7-dihydroxy-2-[3-hydroxy-4-(^2H₃)methoxyphenyl]-2,3-dihydro-1-benzopyran-4-one
• Synonyms: 2,3-Dihydro-5,7-dihydroxy-2-[3-hydroxy-4-(methoxy-d3)phenyl)-4H-1-benzopyran-4-one; 3',5,7-Trihydroxy-4'-(methoxy-d3)flavanone; Eriodictyol-d3 4'-Monomethyl Ether; 4’-(Methoxy-d3)-3’,5,7-trihydroxyflavanone; NSC 57654-d3; rac-Hesperetin-d3

Database IDs

• PubChem SID: 162264018
• PubChem CID: 71317210

CALCULATED PROPERTIES

• Acid pKa: 7.916038
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.6757855
• LogD (pH = 7.4): 2.5623946
• Log P: 2.6774368
• Molar Refractivity: 77.753 cm^3
• Polarizability: 29.837467 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 227-229°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H289502

Labelled Hesperetin (H289500). The aglucon of Hesperidin (H281185), a flavanone found in citrus fruits.

REFERENCES

• Tsujimoto, M., et al.: Biol. Pharm. Bull., 32, 671 (2009)
• Wang, H., et al.: J. Pharm. Biomed. Anal., 49, 1157 (2009)
• Lee, S,. et al.: Bioorg. Med. Chem. Lett., 19, 2116 (2009)