Synthesis and characterization of [1‐13C]‐and d8‐arachidonic acid

Abstract
Methyld 8- and [1-13C] 5,8,11,14-eicosatetraenoate (arachidonate) were prepared from a common synthetic precursor, 4,7,10,13-nonadecatetrayn-1-ol. The purified products were characterized by gas chromatography-mass spectrometry. Mass spectra oft-butyldimethylsilyl esters ofd 8-and [1-13C]-arachidonic acid showed a most intense [M-57]+ peak at high mass. The isotopic purity of methyl [1-13C] arachidonate was 99% and that of methyld 8-arachidonate was 56%. Whend 8-arachidonic acid was prepared by direct deuteration of 5,8,11,14-eicosatetraynoic acid, the isotopic purity of the sample was 86%.