title: Isolation, identification, and structure of a potent alkyl-peroxyl radical scavenger in crude canola oil, canolol.
abstract: Alkylhydroperoxides in oxidized oil are undesirable components because they become alkylperoxyl radicals (ROO*) in the presence of heme, hemoglobin, or myoglobin in red meat. ROO* are biochemically reactive and damage nucleic acids and proteins, thereby harming living cells. We isolated a component, a highly potent ROO* scavenger, from crude canola oil (rapeseed), which we designated canolol, and identified its chemical structure, 4-vinyl-2,6-dimethoxyphenol. The canolol content of crude canola oil greatly increased after the seed was roasted as compared with that from unroasted seed, but it decreased in highly purified oil. This anti-ROO* activity was highest in crude oil, deceased after each refining step, and was lowest in highly purified refined oil. Canolol was thus generated during roasting. As shown previously, canolol is one of the most potent anti-ROO* components in crude canola oil and its potency is much greater than that of well-known antioxidants, including alpha-tocopherol, vitamin C, beta-carotene, rutin, and quercetin.
authors.affiliation: Department of Materials and Life Science, Graduate School of Science and Technology, Kumamoto University, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Wakamatsu
authors.forename: Shigeru
authors.initials: S
authors.lastname: Morimura
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Sawa
authors.forename: Kenji
authors.initials: K
authors.lastname: Kida
authors.forename: Chiaki
authors.initials: C
authors.lastname: Nakai
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Maeda
mesh_terms: D002851:Chromatography, High Pressure Liquid; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010545:Peroxides / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014753:Vinyl Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D016166:Free Radical Scavengers; D010545:Peroxides; D010636:Phenols; D014753:Vinyl Compounds; C049375:perhydroxyl radical; C488411:4-vinyl-2,6-dimethoxyphenol