SATURATED BICYCLIC FATTY-ACIDS FORMED IN HEATED SUNFLOWER OILS

On the basis of the mass spectra of the dimethyloxazoline (DMOX) deriv atives and picolinyl esters, several C-18 bicyclic fatty acids, belong ing to four basic structural types, have been characterized from heate d sunflower oil. There were fatty acids with six-membered rings either from C-10 to C-15 or from C-7 to C-12 of the parent C-18 fatty acid, and acids with five-membered rings either from C-10 to C-14 or from C- 8 to C-12. Ln every case, a bond across the ring gave the bicyclic str ucture but the position of the bond could not be determined. It is lik ely that the bicyclic acids are derived from linoleic acid by free rad ical mechanisms via cyclohexenyl and cyclopentenyl intermediates. (C) 1997 Elsevier Science Ireland Ltd.