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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of Five Conjugated Linoleic Acid Isomers (9-Trans, 11-Cis; 9trans11-Trans-; 10-Trans, 12-Cis-; 10-Cis; 10-Trans, 12-Trans-18:2) Labeled Withfour Deuterium Atoms

Authors
item Adlof, Richard
item Walter, Erin

Submitted to: International Symposium on the Synthesis and Application of Isotopes
Publication Type: Abstract Only
Publication Acceptance Date: September 18, 1997
Publication Date: N/A

Technical Abstract: An 8-step synthesis was developed to prepare the methyl cis 9,trans-11- and the trans-9,trans-11-18:2-17,17,18,18-d4 (96% d4). 5-hexyn-1-ol was reduced D2 gas/ Wilkinson's catalyst to yield 1-hexanol-5,5,6,6-d4. The alcohol was converted to the iodide (phosphorous pentoxide/ phosphoric acid/ potassium iodide) and coupled with 2-propyn-1-ol (lithium amide in liquid ammonia) to yield 2-nonyn-1-ol-d4. The acetylenic alcohol was reduced with lithium metal in liquid ammonia to yield trans-2-nonen-1-ol-d4, converted to the bromide (via triphenylphos-phine dibromide) and then converted to the phosphonium salt. The isomer pair was obtained by coupling the phosphonium bromide (8,8,9,9-d4) and methyl 9-oxononanoate. A similar synthesis was used to prepare the trans-10-,cis-12 and cis-10,cis-12-18:2-15,15,16,16-d4 isomer pair (86% d4). 2-pentyn-1-ol was used as starting alcohol and the 7-carbon acetylenic intermediate was reduced to the cis olefin with H2 gas/ Lindlar catalyst. 10-oxodecanoate was used in the Wittig coupling reaction to yield the 10-trans,12-cis- and the 10-cis,12-cis-18:2 isomer pair. Isomer pairs (ca. 50/50) were readily separated by reversed-phase HPLC and silver resin chromatography (chemical purity >95%; overall yields ca. 20% for each isomer). cis-10,cis-12-18:2 was isomerized (p toluenesulfinic acid) to yield the trans-10, trans-12-18:2-d4 isomer in 75% yield.

Last Modified: 7/25/2014
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