Selective synthesis of octadeuterated (+/-)-5-HETE for use in GC-MS quantitation of 5-HETE

5(S)-hydroxy-6 trans-8,11,14 cis-eicosatetraenoic acid (5-HETE) is the major product of arachidonic acid metabolism via the 5-lipoxygenase pathway. A limiting factor in the quantitation of 5-HETE by GC-MS analysis is the availability of a stable isotope analog for use as an internal standard. In this report, we detail procedures for selective chemical synthesis of multimilligram quantities of octadeuterated (+/-)-5-HETE from octadeuterated arachidonic acid. The octadeuterated (+/-)-5-HETE is suitable for use as an internal standard for GC-MS quantitation of 5-HETE. Preparation of the octadeuterated analog of 5-HETE can be readily performed in most laboratory settings.