2, 4-Alkadienal trapping by phenolics. (15th October 2018)

• Record Type: Journal Article
• Authors: Hidalgo, Francisco J.; Zamora, Rosario
• Is Part Of: Food chemistry. Volume 263(2018)
• Page Start: 89
• Page End: 95
• Publication Date: 2018-10-15
• Subjects: (2E, 4E)-Deca-2, 4-dienal (PubChem ID: 5283349) -- 2-Methylresorcinol (PubChem ID: 11843) -- (2E, 4E)-Hepta-2, 4-dienal (PubChem ID: 5283321) -- (2E, 4E)-Hexa-2, 4-dienal (PubChem ID: 637564); Alka-2, 4-dienals -- Carbonyl-phenol reactions -- Lipid oxidation -- Maillard reaction -- Reactive carbonyls; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2018.04.121
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Phenolics rapidly trap alkadienals produced as a consequence of lipid oxidation. The reaction was characterized and adducts identified as a mixture of diastereomers. 4-(Alk-1-en-1-yl)-2, 7-dihydroxy-8-methylchromanes were the produced adducts. Diastereomers 2 R, 4 S plus 2 S, 4 R were formed to a higher extent than 2 R, 4 R plus 2 S, 4 S. The activation energies ( E a ) for adduct formation were ∼62 kJ·mol −1 . Abstract: Phenolics can trap lipid-derived reactive carbonyls as a protective function that diminishes the broadcasting of the lipid oxidative damage to food macromolecules. In an attempt to clarify the trapping of 2, 4-alkadienals by phenolics, this study analyzes the reactions of 2, 4-hexadienal, 2, 4-heptadienal, and 2, 4-decadienal with 2-methylresorcinol. These reactions produced ( E )-4-(alk-1-en-1-yl)-8-methyl-2, 7-bis(prop-1-en-2-yloxy)chromanes, which were isolated and characterized by 1D and 2D NMR and MS. Carbonyl-phenol adduct formation was favored at pH > 7 and moderate temperatures (25–80 °C). Adducts were quantified and shown to be produced as a mixture of diastereomers. Diastereomers 2 R, 4 S plus 2 S, 4 R were formed to a higher extent than diastereomers 2 R, 4 R plus 2 S, 4 S under the different conditions assayed, although activation energies ( E a ) for the formation of all of them was mostly the same (∼62 kJ·mol −1 ). These results show that phenolics can trap 2, 4-alkadienals and provide the basis for the later detection of the formed adducts in food pro[ducts.