Preparation of the addition products of alpha-tocopherol with cholesteryl linoleate-peroxyl radicals.
a-Tocopherol was reacted with cholesteryl linoleate hydroperoxides (Ch18:2-OOH) in the presence of an iron-chelate, Fe(III) acetylacetonate, at 37 degrees C in benzene. The reaction products were isolated and identified as four positional isomers of cholesteryl (8a-dioxy-alpha-tocopherone)-epoxyoctadecenoates and two positional isomers of cholesteryl (8a-dioxy-alpha-tocopherone)-octadecadienoates. The result indicates that the peroxyl radicals from Ch18:2-OOH react with the 8a-carbon radical of alpha-tocopherol to form the addition products.
Yamauchi
Ryo
R
Department of Bioprocessing, Faculty of Agriculture, Gifu University, Japan. yamautir@cc.gifu-u.ac.jp
Kamatani
Toshifumi
T
Shimoyamada
Makoto
M
Kato
Koji
K
D000975:Antioxidants / Q000138:chemical synthesis*; D002788:Cholesterol Esters / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005609:Free Radicals / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006885:Hydroxybutyrates / Q000737:chemistry; D007502:Iron Chelating Agents / Q000737:chemistry; D007536:Isomerism; D015227:Lipid Peroxidation; D010422:Pentanones / Q000737:chemistry; D010545:Peroxides / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000975:Antioxidants; D002788:Cholesterol Esters; D005609:Free Radicals; D006885:Hydroxybutyrates; D007502:Iron Chelating Agents; D010422:Pentanones; D010545:Peroxides; D014810:Vitamin E; C049529:acetyl acetonate; C021976:cholesteryl linoleate