Determination of monounsaturated alkyl side chain 2-alkylcyclobutanones in irradiated foods

The 2-alkylcyclobutanones (2-ACBs) are formed from triglycerides by irradiation treatment and may be used as markers for this type of food processing. This paper describes a detection method for the analysis of monounsaturated alkyl side chain 2-ACBs, which is formed upon irradiation from monounsaturated fatty acids which frequently are the most abundant fatty acids in foods. The estimated radioproduction yields of the cis-2-(dodec-5'-enyl)-cyclobutanones (cis-2-dDeCB) and the cis-2-(tetradec-5'-enyl)-cyclobutanones (cis-2-tDeCB) were 1.0 +/- 0.5 and 0.9 +/- 0.2 nmol.mmol(-1) precursor fatty acid.kGy(-1), respectively, being similar to that of saturated 2-ACBs. The stability study of the s- and mu-2-ACBs in poultry meat samples irradiated at 10 kGy and stored for 3-4 weeks at 4 degrees C and 25 degrees C showed that these compounds undergo some transformation, their amounts being reduced by about 50%. These storage losses did not depend on the saturation state of the alkyl side chain. The EI-MS detection limit of 2-tDeCB is 3 times higher (0.6 pmol) than that of 2-dodecylcyclobutanone (0.2 pmol). Consequently, when the oleic acid content of the analyzed food exceeds the content of palmitic acid by a factor of 3, it would be of an advantage to apply 2-tDeCB as a marker for detection of the irradiation treatment.