Synthesis of octadecynoic acids and [1-14C] labeled isomers of octadecenoic acids |
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Authors: | A. J. Valicenti F. J. Pusch R. T. Holman |
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Affiliation: | (1) The Hormel Institute, University of Minnesota, 55912 Austin, MN;(2) Travenol Laboratories Inc. 1435, Lake Cook Rd, 60015 Deerfield, IL;(3) Present address: Nutrition/Metabolism Laboratory, Harvard Medical School, 194 Pilgrim Rd., 02215 Boston, MA |
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Abstract: | Geometric and positional isomers of [1-14C] octadecenoic acids have been synthesized by modifications of published procedures. Positional isomers of octadecynoic acids also have been synthesized to obtain the geometric and positional isomers of the unlabeled octadecenoic acid analogs. The syntheses were accomplished by coupling a haloalkyl compound with a substituted acetylene using n-butyl lithium in hexamethylphosphoramide. The coupled product, either a 17-or 18-carbon acetylenic alcohol, could be semihydrogenated and chain extended to afford a carboxy labeled derivative, could be partially hydrogenated and chain extended to afford a carboxyl labeledcis-ortrans-octadecenoic acid in the former case. In the latter case, octadecynoic,cis-octadecenoic ortrans-octadecenoic acids could be obtained by the appropriate reactions. The methods used in this study enabled the synthesis of14C-labeled fatty acids in generally higher yields and by simpler reactions than were previously possible. |
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