Synthesis and Characterization of 3-Hydroxy-2-(5'-Hydroxypentyl)-4H-Pyran-4-one and Study of Its Complexation with Iron(III)

Iron(III) complexing ability of new ligands based on natural γ-pyrone maltol

“…1 H-NMR (400MHz, D2O): δ (ppm) 2.40 (s, 3H, 2-CH3), 4.89 (s, 1H, H2), 6.42 (d,1H, J = 5.6 Hz, H5), 7.92 (d, 1H, J = 5.6 Hz, H6). 13 C-NMR (100MHz, D2O): δ (ppm) 14.98, 114.95, 116.58, 142.80, 156.02, 163.47, 174.30, 176.76. ESI-MS: m/z 227(M+H), 249(M+Na).…”

“…75-76 °C 1 H-NMR (400MHz, CDCl3): δ (ppm) 1.19 (t, 6H, J = 7.2 Hz, OCH2CH3), 3.28 (d, 2H, J = 8.0 Hz, CH2), 3.80 (t, 1H, J = 8.0 Hz, CH), 4.08-4.20 (m, 4H, OCH2CH3), 6.38 (d,1H, J = 5.4 Hz, H5), 7.67 (d,1H, J = 5.4 Hz, H6). 13…”

“…1 H-NMR (400MHz,D2O): δ (ppm) 3.06 (d, 2H, J = 7.6 Hz, CH2), 3.37 (t, 1H, J = 7.6 Hz, CH), 6.29 (d,1H, J = 5.2 Hz, H5), 7.74 (d,1H J = 5.2 Hz, H6). 13 C-NMR (100MHz, D2O): δ (ppm) 29.29, 38.26, 151.55, 153.19, 153.47, 154.82, 178.74, 180.80. ESI-MS: m/z 227(M+H).…”

“…Melting point was measured with a Kofler apparatus and was uncorrected. The 1 H and 13 C NMR spectra were recorded at 400.13 MHz and 100.13 MHz on a Bruker Advance DPX400 instrument. Chemical shifts were reported relative to tetramethylsilane at 0.00 ppm.…”

“…Maltol (3hydroxy-2-methyl-4-pyrones), presented in Scheme 1 above, is readily available from natural sources and is widely used in food and cosmetics additives, as well as in many derivatives design for medical applications [5], [8], [9], [10]. The advantages of using maltol for clinical purposes are its strong metal binding affinity (good iron chelator), high bioavailability and a low toxicity profile [11], [12], [13], [14]. Furthermore, maltol prevents the iron-catalyzed formation of free radicals and free radical cascades by binding this metal ion and render it redox inactive.…”