Avj. Crone et al., SYNTHESIS, CHARACTERIZATION AND USE OF 2-TETRADECYLCYCLOBUTANONE TOGETHER WITH OTHER CYCLOBUTANONES AS MARKERS FOR IRRADIATED LIQUID WHOLE EGG, Journal of the Science of Food and Agriculture, 62(4), 1993, pp. 361-367
The synthesis and characterisation of 2-tetradecylcyclobutanone (TCB)
is described. Both 2-dodecylcyclobutanone and TCB were shown to be pre
sent in liquid whole egg irradiated at doses of 2.5 and 10.0 kGy. Thes
e compounds were absent from the unirradiated pasteurised samples. Usi
ng gas chromatography and infrared spectroscopy, there was also eviden
ce for the presence in irradiated egg of 2-tetradecenyl- and 2-tetrade
cadienylcyclobutanone which are formed from oleic and linoleic acids,
respectively. Authentic standards for these unsaturated cyclobutanones
were not available commercially but the presence of 2-tetradecenylcyc
lobutanone was substantiated by hydrogenating the egg extracts so conv
erting this unsaturated cyclobutanone to TCB. Saturated and unsaturate
d cyclobutanones appear to be specific products of irradiation and are
potential markers for detection of irradiated liquid egg and probably
other fat-containing foods.