title: 2-Alkenal-scavenging ability of m-diphenols.
abstract: The reaction between m-diphenols (resorcinol, 2-methylresorcinol, 2,5-dimethylresorcinol, 3-methylphenol, orcinol, and phloroglucinol) and 2-alkenals (2-pentenal and 2-octenal) was studied in an attempt to understand the chemical pathways involved in the scavenging ability of m-diphenols for the 2-alkenals produced as a consequence of lipid oxidation. Phenols reacted chemically with 2-alkenals producing a number of 2H-chromenols, chromandiols, chromanols, and dihydropyrano[3,2-g]chromenes, which were isolated and identified by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). The identification of all these compounds resulted in the construction of a general pathway for these reactions. These results confirm that the 2-alkenal-scavenging ability of m-diphenols is a consequence of their structure. This is a complex reaction in which many different products are formed. The most stable products were the chromandiols. However, the main reaction products were the 2H-chromenols. These products were unstable and disappeared as a consequence of polymerisation and browning reactions.
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avenida Padre García Tejero 4, 41012 Seville, Spain.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Hidalgo
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avenida Padre García Tejero 4, 41012 Seville, Spain. Electronic address: rzamora@ig.csic.es.
authors.forename: Rosario
authors.initials: R
authors.lastname: Zamora
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D012118:Resorcinols / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D012118:Resorcinols; C057348:2-octenal; C049083:2-methylresorcinol; C005282:orcinol; C064599:2-pentenal; C031389:resorcinol
keywords: 2-Alkenals; Carbonyl–phenol adducts; Carbonyl–phenol reactions; Lipid oxidation; Orcinol; Phloroglucinol; Resorcinol