New oxidation products of 2,2,5,7,8-pentamethyl-6-chromanol

Oxidation of the α-tocopherol model compound 2,2,5,7,8-pentamethyl-6-chromanol (1) byt-butyl hydroperoxide in chloroform, to which an alcohol has been added, produces 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanol as the major product. In the present study,1 was oxidized byt-butyl hydroperoxide in water-saturated chloroform to determine whether water would influence product formation in the same way as alcohols. In addition to the usual products of oxidation such as 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethyl-1,4-benzoquinone (9), 5-formyl-2,2,7,8-tetramethyl-6-chromanol (11), the spirodimer and spirotrimer of1, three new products have been identified−2,2,7,8-tetramethyl-5-(2,2,5,7,8-pentamethyl-6-chromanoxy)methyl-6-chromanol (4), 5-hydroxymethyl-2,2,7,8-tetramethyl-6-chromanol (5) and 3-hydroxymethyl-2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-1,4-benzoquinone (7).