All of these compounds were proposed as oxidation products from the β-carotene ozonolysis in solution during the present study, based on their tentative
identification DZNeP manufacturer through LC-MS. Secocarotenoids, such as 4,9,13,17,17-pentamethyl-16,21-dioxo-docos-2,4,6,8,10,12,14-heptaenal and 3,7,11,11-tetramethyl-10,15-dioxo-hexadec-2,4,6,8-tetra-enal, have not been assessed in the literature to date, since oxidation products originating from the breakdown of the ring’s double bond, producing a keto function, are not very common (Britton, 1995). The 5,6-seco-β-carotene-5,6-dione is a possible exception, although it has been identified as product of β-carotene oxidation in permanganate solutions (Chou and Labuza, 1984), thus in a different condition of this work. Other compounds observed, including β-cyclocitral, 15-apo-β-carotenal, 14´-apo-β-carotenal, 12´-apo-β-carotenal, 5,6-epoxy-12´-apo-β-carotenal and 5,6-epoxy-10´-apo-β-carotenal, had been identified previously by other researchers, although using different model systems, as, for instance,
exposure to UV light (Chou & Labuza, 1984), in combination with photo-sensitizers (Ojima et al., 1993 and Stratton et al., 1993), through autooxidation at 20 and 80 °C (Ojima, Sakamoto, Ishiguro &Terao, 1993) and in the presence of permanganate (Rodriguez et al., 2007), amongst other methods. It is generally accepted that the initial compounds Inositol oxygenase selleck compound formed, during the oxidation of β-carotene, are epoxides and apocarotenals. β-cyclocitral is frequently mentioned as a product of the reaction of the double bond between the C7–C8 carbons of β-carotene (Glória et al., 1993 and Sommerburg et al., 2003), since this bond has a high mobility index which favours its break-down and results in the formation
of this carbonyl compound. β-Ionone (9-apo-β-carotenone) has been mentioned in several studies (Glória et al., 1993 and Waché et al., 2002) as an oxidation product of β-carotene. However, this compound was not detected in our experiments. Since β-ionone still has double bonds in its structure which can react with ozone, this study proposes that β-ionone could have been completely oxidised during the experiments, giving rise to secondary oxidation products. As predicted, in our experiments the ozonolysis of β-ionone gave rise to three carbonilic compounds which had been also tentatively identified as products of β-carotene ozonolysis, namely methyglyoxal, β-cyclocitral and 6,6-dimethyl-undec-3-en-2,5,10-trione. It is worth to mention that methylglyoxal and β-cyclocitral had also been found previously in the gas-phase reactions between β-ionone and ozone in Teflon chambers (Forester, Ham & Wells, 2007). The oxidation of β-carotene, under different ozone concentrations, was found to follow a zero order kinetic model relative to β-carotene in the main region of the curves.