A rapid microozonolysis-GLC procedure for locating unsaturation in olefinic acids, including trienes and tetraenes

TLDR: In this article, the Stein-Nicolaides procedure was used for the identification of unknown olefinic fatty acids by ozonolysis of monoenoic esters.

Abstract: Increased versatility has been achieved in the identification of unknown olefinic fatty acids by ozonolysis. The method has been applied to purified methyl esters containing up to four double bonds. Aldehydic fragments, obtained from esters by the Stein-Nicolaides procedure (2), were determined by GLC on two columns of different polarity. Equivalent chain lengths of each fragment on the two columns provide identification. For monoenoic esters the location of the double bond is clearly indicated by the aldehyde and aldehyde-ester fragments. Dienes are identified by the aldehyde and aldehyde-ester fragments when the original chain length of the ester is known; the dialdehyde fragment provides confirmatory evidence. Trienes and tetraenes are analyzed by interrupting the ozonolysis at various times, thereby producing unsaturated, as well as saturated, aldehydes and aldehyde-esters. Unsaturated fragments locate the central or interior double bonds.