2024-03-29T02:31:11Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/156772019-02-13T10:51:07Zcom_10261_5063com_10261_5com_10261_105com_10261_1col_10261_5066col_10261_358
2009-08-05T07:50:20Z
urn:hdl:10261/15677
On the generation and outcome of 3-(N-phenylamino)propane-1,2-diol derivatives in deodorized model oils related to toxic oil syndrome
Morató, Anna
Escabrós, Jordi
Manich, Albert M.
Reig, Natalia
Castaño, Yolanda
Abián, Joaquín
Messeguer Peypoch, Ángel
Toxic Oil Syndrome
Deodorized Model Oils
PAP
Anilides
Deodorization process
10 pages, 5 figures, 5 schemes, 5 tables.-- PMID: 15833026 [PubMed].-- Printed version published Apr 2005.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/tx0497595
Toxic Oil Syndrome (TOS) was a massive food-born intoxication that occurred in Spain in 1981 and affected more than 20 000 people. TOS was attributed to the ingestion of rapeseed oil that had been adulterated with aniline, illegally refined, and delivered for human consumption. Two chemical species derived from aniline have been identified in oil batches: fatty acid anilides, qualified as biomarkers of the adulterated oil, and fatty acid esters of 3-(N-phenylamino)propane-1,2-diol (PAP), considered toxic oil biomarkers. These esters were generated by chemical processes during oil refining, specifically in the deodorization step, which involves treatment of the oil at high temperatures under vacuum to remove volatile contaminants. Since PAP derivatives are strongly associated with TOS, their formation and putative interconversion in a toxic oil model has been studied. The main results obtained are (i) only triglycerides and aniline are required to produce PAP esters, thus eliminating the possibility that unknown activators present in the deodorization tank were required for toxification of the oil; (ii) PAP and PAP mono- and diesters are chemically interrelated, as are anilides and PAP esters to an even higher degree. In addition to the reaction of aniline with triglycerides, anilides can be also formed via attack of PAP esters by aniline. However, the most important source of anilides during deodorization seems to be the thermal decomposition of PAP esters. Overall, these results suggest that the generation and outcome of PAP derivatives during deodorization is a complex scenario whereby PAP esters are not only generated from different reactions but decompose to produce anilides, among other compounds. In addition to providing a rapeseed oil model that reproduces the composition of case oils with respect to anilides and PAP derivatives, the results presented herein further support the hypothesis imputing PAP diesters or their metabolites for the intoxication episode.
2009-08-05T07:50:20Z
2009-08-05T07:50:20Z
2005-03-24
artículo
Chemical Research in Toxicology 18(4): 665-674 (2005)
0893-228X
http://hdl.handle.net/10261/15677
10.1021/tx0497595
1520-5010
eng
http://dx.doi.org/10.1021/tx0497595
closedAccess
American Chemical Society