title: The relationship between the physicochemical properties of antioxidants and their ability to inhibit lipid oxidation in bulk oil and oil-in-water emulsions.
abstract: Chain-breaking antioxidants differ in their effectiveness at inhibiting lipid oxidation because of their chemical properties and physical location within a food. Our objective was how the physicochemical properties of four structurally related lipid-soluble antioxidants were related to their antioxidant activity. Antioxidants differed in the number of methyl (alpha-tocopherol and delta-tocopherol) or hydroxyl (butylated hydroxytoluene (BHT) and 4-hydroxymethyl-2,6-ditertiarybutylphenol) groups. Surface activity of the antioxidants was in the order of delta-tocopherol > alpha-tocopherol approximately 4-hydroxymethyl-2,6-ditertiarybutylphenol > BHT. Free-radical scavenging activity was similar between alpha-tocopherol and delta-tocopherol as well as BHT and 4-hydroxymethyl-2,6-ditertiarybutylphenol. In bulk menhaden oil, BHT was a more effective antioxidant than 4-hydroxymethyl-2,6-ditertiarybutylphenol while alpha-tocopherol was more effective than delta-tocopherol. In menhaden oil-in-water emulsions, BHT was a more effective antioxidant than 4-hydroxymethyl-2,6-ditertiarybutylphenol while delta-tocopherol was more effective than alpha-tocopherol. These results indicate that the surface activity and polarity of lipid-soluble antioxidants were not the only determinants of their antioxidant effectiveness in food lipids.
authors.affiliation: Department of Food Science, University of Massachusetts, Amherst, Massachusetts 01003, USA.
authors.forename: Wilailuk
authors.initials: W
authors.lastname: Chaiyasit
authors.forename: D Julian
authors.initials: DJ
authors.lastname: McClements
authors.forename: Eric A
authors.initials: EA
authors.lastname: Decker
mesh_terms: D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D002084:Butylated Hydroxytoluene / Q000737:chemistry / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004655:Emulsions / Q000737:chemistry*; D005395:Fish Oils / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D015227:Lipid Peroxidation / Q000187:drug effects*; D012995:Solubility
chemical_list: D000975:Antioxidants; D004655:Emulsions; D005395:Fish Oils; D016166:Free Radical Scavengers; C033266:Menhaden oil; D002084:Butylated Hydroxytoluene