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Formation of Toxic α,β‐Unsaturated 4‐Hydroxy‐Aldehydes in Thermally Oxidized Fatty Acid Methyl Esters
Author(s) -
Han In Hwa,
Csallany A. Saari
Publication year - 2009
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-008-1343-6
Subject(s) - chemistry , linolenic acid , stearate , stearic acid , oleic acid , unsaturated fatty acid , linoleic acid , fatty acid , medicinal chemistry , nuclear chemistry , organic chemistry , biochemistry
To investigate the heat induced formation of α,β‐unsaturated 4‐hydroxy‐aldehydes (4‐hydroxy‐2‐ trans ‐hexenal (HHE), 4‐hydroxy‐2‐ trans ‐octenal (HOE), 4‐hydroxy‐2‐ trans ‐nonenal (HNE) and 4‐hydroxy‐2‐ trans ‐decenal (HDE)) fatty acid methyl esters (FAMEs) of stearic, oleic, linoleic and linolenic acids were heated separately at 185°C for 0 to 6 hrs. The formation of 2,4‐decadienal, a suspected intermediate in HNE formation, was also measured in these FAMEs. As expected methyl stearate (MS) and methyl oleate (MO) did not produce any of the α,β‐unsaturated 4‐hydroxy‐aldehydes as a consequence of thermally induced lipid peroxidation. The formation of HHE was detected in both methyl linoleate (ML) and methyl linolenate (MLN), with concentration higher in MLN than in ML. The maximum HHE concentration was 3.99 μg HHE/g ML after 2 h and 50.78 μg HHE/g MLN after 4 h of heat treatment. HOE was detected in both ML and MLN, and the maximum concentration was 102.50 μg HOE/g ML after 6 h and 90.56 μg HOE/g MLN after 2 h of heating. HNE was found only in ML and its highest concentration was 84.82 μg HNE/g ML after 3 h of heating. HDE was not detected in any of the four heat treated FAMEs. 2,4‐Decadienal was not found to be an intermediate in the formation of HNE in thermally induced oxidation of FAMEs.