R. Adlof
1990
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0
Influential Citations
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Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
Methyl arachidonate (5c, 8c, 11c, 14c-20: 4) 17, 17, 18, 18-d4 was prepared for use in both in vivo and in vitro metabolism studies. The deuterium atoms were incorporated by deuterium gas and Wilkinson's catalyst. The tetraacetylenic acid precursor (5a, 8a, 11a, 14a-20: 4) 17, 17, 18, 18-d4 was synthesized by a series of Grignard coupling reactions and reduced by Lindlar catalyst and hydrogen gas to arachidonic acid-d4. The methyl ester was prepared by diazomethane and purified by a combination of reverse phase and silver resin chromatography. The deuterated methyl arachidonate was prepared in an overall yield of ca. 11% and with an isotopic purity of ≥91%. The deuterium-labelled tetracetylenic acid precursor and the methyl arachidonate-d4 were characterized by 13C-NMR.