Kinetic Study of the Quenching Reaction of Singlet Oxygen by Eight Vegetable Oils in Solution. 2019

Kazuo Mukai, and Ayaka Ohara, and Junya Ito, and Masayuki Hirata, and Eri Kobayashi, and Kiyotaka Nakagawa, and Shin-Ichi Nagaoka
Department of Chemistry, Faculty of Science, Ehime University.

A kinetic study of the reaction of singlet oxygen (1O2) with eight vegetable oils 1-8 containing different concentrations of tocopherols (Tocs) and tocotrienols (Toc-3s) was performed. The second-order rate constants (kQ) for the reaction of 1O2 with vegetable oils 1-8 (rice bran, perilla, rape seed, safflower, grape seed, sesame, extra virgin olive, and olive oils) were measured in ethanol/chloroform/D2O (50:50:1, v/v/v) solution at 35°C using UV-vis spectrophotometry. Furthermore, comparisons of kQ values determined for the above oils 1-8 with the sum of the product {∑kQAO-i [AO-i]/105} of the kQAO-i values obtained for each antioxidant (AO-i) and concentration (in mg/100 g) ([AO-i]/105) of AO-i (Tocs and Toc-3s) contained in the oils 1-8 were performed. The observed kQ values were not reproduced by the kQ values calculated using only the concentrations of the four Tocs and Toc-3s. These results suggest that the contribution of fatty acids contained in the oils 1-8 is also necessary to fully explain the kQ values. Recently, the second-order rate constants (kS) for the reaction of aroxyl radical (ArO・) with the same vegetable oils 1-8 were measured in the same solvent at 25℃ using stopped-flow spectrophotometry (Ref. 23). The kS values obtained could be well explained as the sum of the product {Σ kSAO-i [AO-i]/105} of the kSAO-i and the [AO-i]/105 of AO-i (Tocs and Toc-3s) contained in the vegetable oils.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D010938 Plant Oils Oils derived from plants or plant products. Oils, Plant,Oils, Vegetable,Plant Oil,Vegetable Oil,Vegetable Oils,Oil, Plant,Oil, Vegetable
D005227 Fatty Acids Organic, monobasic acids derived from hydrocarbons by the equivalent of oxidation of a methyl group to an alcohol, aldehyde, and then acid. Fatty acids are saturated and unsaturated (FATTY ACIDS, UNSATURATED). (Grant & Hackh's Chemical Dictionary, 5th ed) Aliphatic Acid,Esterified Fatty Acid,Fatty Acid,Fatty Acids, Esterified,Fatty Acids, Saturated,Saturated Fatty Acid,Aliphatic Acids,Acid, Aliphatic,Acid, Esterified Fatty,Acid, Saturated Fatty,Esterified Fatty Acids,Fatty Acid, Esterified,Fatty Acid, Saturated,Saturated Fatty Acids
D012275 Oryza A genus of grass family (Poaceae) that include several rice species. Oryza sativa,Rice,Rices
D024505 Tocopherols A collective name for a group of closely related lipids that contain substitutions on the 2H-1-benzopyran-6-ol nucleus and a long hydrocarbon chain of isoprenoid units. They are antioxidants by virtue of the phenolic hydrogen. Tocopherols react with the most reactive form of oxygen and protect unsaturated fatty acids from oxidation. Tocopherol,Abortosan,Antioxidans E-Hevert,Aquasol E,Auxina E,Bio E,Biopto-E,Biosan,Bioweyxin,Dal-E,Davitamon,Dermorelle,Detulin,E Vitamin E,E-Mulsin,E-Vicotrat,E-Vitamin-Ratiopharm,E-ferol,EUNOVA Vitamin E,Ecoro,Elex Verla,Embial,Ephynal,Eplonat,Equivit E,Eusovit,Evion,Hydrovit E,Lasar,Malton E,Micorvit E,Mowivit Vitamin E,Puncto E,Richtavit E,Sanavitan S,Snow-E Muscle, Energy & Feritility,Spondyvit,Tocolion,Tocopa,Tocopharm,Tocopherol Bayer,Tocovital,Togasan Vitamin E,Unique E,Uno-Vit,Vibolex,Vit E hydrosol,Vit. E Stada,Vita-E,Vita-Plus E,Vitagutt Vitamin E,Vitamin E AL,Vitamin E Natur,Vitamin E Sanum,Vitamin E Suspension,Vitamin E-mp,Vitamin-E Dragees,Vitamin-E EVI-MIRALE,Vitamine E GNR,Vitazell,Dal E,E Mulsin,E Vicotrat,Uno Vit,UnoVit,Vita E,Vita Plus E,VitaE,VitaPlus E,Vitamin E Dragees,Vitamin E EVI MIRALE,Vitamin E mp,Vitamin E, Mowivit,Vitamin E, Togasan,Vitamin E, Vitagutt,Vitamin Emp,VitaminE EVIMIRALE
D024508 Tocotrienols Natural analogs of TOCOPHEROLS exhibiting antioxidant activity. These tocol derivatives and isomers contain a benzopyran ring and an unsaturated isoprenoid side chain. Tocotrienol
D026082 Singlet Oxygen An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages. Singlet Dioxygen,Dioxygen, Singlet,Oxygen, Singlet
D027843 Vitis A plant genus in the family Vitaceae. It is a woody vine cultivated worldwide. It is best known for grapes, the edible fruit and used to make WINE and raisins. Grapes,Raisins,Vitis vinifera,Grape,Raisin
D029741 Brassica rapa A subspecies of Brassica that includes rape mustard. It is cultivated for the seed and used as animal feed. Field Mustard,Wild Rutabaga,Wild Turnip,Field Mustards,Mustard, Field,Mustards, Field,Rutabaga, Wild,Rutabagas, Wild,Turnip, Wild,Turnips, Wild,Wild Rutabagas,Wild Turnips
D031187 Carthamus tinctorius A plant genus of the family ASTERACEAE. Oil from the seed (SAFFLOWER OIL) is an important food oil of commerce. Safflower,Safflowers

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