(2R,3S)-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

• ChemBase ID: 173454
• Molecular Formular: C16H16O6
• Molecular Mass: 304.29464
• Monoisotopic Mass: 304.09468823
• SMILES: c1(cc(c2c(c1)O[C@@H]([C@H](C2)O)c1ccc(c(c1)O)OC)O)O
• Canonical SMILES: COc1ccc(cc1O)[C@H]1Oc2cc(O)cc(c2C[C@@H]1O)O
• InChI: InChI=1S/C16H16O6/c1-21-14-3-2-8(4-12(14)19)16-13(20)7-10-11(18)5-9(17)6-15(10)22-16/h2-6,13,16-20H,7H2,1H3/t13-,16+/m0/s1
• InChIKey: ZHDMPVIDHWJGTN-XJKSGUPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: catechin 4'-methyl ether
• Synonyms: (2R,3S)-3,4-Dihydro-2-(3-hydroxy-4-methoxyphenyl)-2H-1-benzopyran-3,5,7-triol; (2R-trans)-3,4-Dihydro-2-(3-hydroxy-4-methoxyphenyl)-2H-1-benzopyran-3,5,7-triol; 4'-O-Methyl-(+)-catechin; 4'-O-Methylcatechin

Database IDs

• CAS Number: 69912-75-0
• PubChem SID: 164229364
• PubChem CID: 9995184

CALCULATED PROPERTIES

• Acid pKa: 9.273445
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.9409283
• LogD (pH = 7.4): 1.9352465
• Log P: 1.941001
• Molar Refractivity: 78.482 cm^3
• Polarizability: 30.318836 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M294480

A metabolite of (+)-Catechin, a major polyphenol in many fruits and vegetables.

REFERENCES

• Heptinstall, S., et al.: J. Cardiovas. Pharmacol., 47, S197 (2006)
• Gonzalez-Manzano, S., et al.: J. Agric. Food Chem., 57, 1231 (2006)
• Frank, J., et al.: J. Nut., 139, 58 (2006)