Trioleoylglycerol was oxidized in the dark at 60 degrees C under oxyge
n. The composition of trioleoylglycerol oxidation products was analyze
d by reversed phase HPLC, and the products were characterized intact b
y chemical ionization mass spectrometry, proton and carbon nuclear mag
netic resonance spectrometry and by capillary gas chromatography after
conversion to methyl esters. Trioleoylglycerol autoxidation proceeded
with mono-hydroperoxide as the only oxidation product formed initiall
y, the bis-hydroperoxide was detected by 84 days, and the tris-hydrope
roxide detected by 91 days. After 105 days, a peroxide value of 55 Meg
/kg was obtained. The oxidation mixture at this point consisted of mon
o-hydroperoxide (47%), bis-hydroperoxide (50%) and tris-hydroperoxide
(3%). The trioleoylglycerol autoxidation is thus sequential with the m
ono-hydroperoxide formed first, followed by the bis- and tris-hydroper
oxides, respectively.