PRODUCTS OF ANILINE AND TRIGLYCERIDES IN OIL SAMPLES ASSOCIATED WITH THE TOXIC OIL SYNDROME

The toxic oil syndrome (TOS) was a devastating disease that occurred i n Spain in 1981. The disease was associated with the consumption of an iline-denatured and refined rapeseed oil that had been illegally sold as olive oil. Many aniline-derived oil components have been identified in the oils; however, no etiological agent has ever been identified f or this disease. We have continued the study of the TOS problem by app lying new technology in the form of liquid chromatography interfaced v ia atmospheric pressure ionization with tandem mass spectrometry. Usin g liquid chromatography tandem mass spectrometry, we studied diluted T OS-associated oils by direct analysis without prior sample treatment; Using this technology, we found new classes of compounds that are asso ciated with disease-related oils, The compounds that have been identif ied are esters and ester amides of 3-(N-phenylamino)-1,2-propanediol a nd are products of aniline and triglycerides. Because of the varied fa tty acid (oleic acid, etc.) content of the oils, many variations of th e above compounds are possible. We now report the identities of more t han 20 compounds not previously identified. These compounds are strong ly associated with oils that caused the toxic oil syndrome. We believe these compounds should be considered for future animal studies.