Antioxidant activity of 5-alkoxymethyl-6-chromanols.
The 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanols (II) are excellent antioxidants against autoxidising safflower oil (ASO), although not as good as 2,2,5,7,8-pentamethyl-6-chromanol (I), the model compound of alpha-tocopherol. The aim of this work was to determine whether the rate of reaction of (II) with the radicals diphenylpicrylhydrazyl (DPP*) and galvinoxyl (ArO*) was directly proportional to their antioxidant activity against ASO. Compounds (II) reacted faster with DPP* than with ArO* but, in each case, slower than compound (I). The rates of reaction of I and II with both radicals followed the order I > II (R = H) > II (R = CH3) > II (R = other alkyls) and were directly proportional to their antioxidant activity against ASO.
Chen
M
M
School of Chemistry, University of New South Wales, Sydney, Australia.
Kohar
I
I
Southwell-Keely
P T
PT
D000478:Alkylation; D000975:Antioxidants / Q000494:pharmacology*; D001559:Benzhydryl Compounds / Q000378:metabolism; D015764:Bepridil / Q000031:analogs & derivatives* / Q000378:metabolism; D001713:Biphenyl Compounds; D002839:Chromans / Q000737:chemistry / Q000494:pharmacology*; D005609:Free Radicals; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010851:Picrates; D012450:Safflower Oil / Q000378:metabolism; D013329:Structure-Activity Relationship
D000975:Antioxidants; D001559:Benzhydryl Compounds; D001713:Biphenyl Compounds; D002839:Chromans; D005609:Free Radicals; D010851:Picrates; D015764:Bepridil; D012450:Safflower Oil; C029141:2,2,5,7,8-pentamethyl-1-hydroxychroman; C004931:1,1-diphenyl-2-picrylhydrazyl; C020338:galvinoxyl