Abstract
To complement studies on monoethylenic fatty acids produced from the major polyunsaturated fatty acid (20:5A5,8,11,14,17) during hydrogenation of a menhaden oil of iodine value (IV) 159, the C10 dienoic and trienoic fatty acid isomers of partially hydro-genated menhaden oils (PHMO) of IV 131.5, 96.5 and 85.5 were isolated by a combination of preparative gas liquid chromatography (GLC), mercuric adduct fractionation, and silver nitrate thin layer chromatography (AgNO3-TLC). The 20:2 fatty acid methyl esters of the three PHMO samples were transformed to the corresponding alcohols and ozonized in BF3-MeOH, followed by GLC analysis of the ozonolysis fragments. During the hydrogenation process, re-sidual ethylenic bonds in the 20:2 isomers tend to migrate both towards the carboxyl group and towards the methyl end of the molecule. The hydrazine reaction results revealed that thetrans ethylenic bonds in the 20:2 and 20:3 isomers were distributed all along the the carbon chain, but thecis ethylenic bonds were more localized in the Δ11,Δ14 and Δ17 positions of the preexisting major menhaden oil component 20:5Δ5,8,11,14,17. Iatroscan analyses on AgNO3-chromarods revealed that, as a result of the hydrogenation process, almost half of the 20:2 isomers were non-methylene-interruptedcis, trans/trans, cis structures.
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Presented in part at the 73rd annual AOCS meeting, Toronto, 1982.
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Sebedio, J.L., Ackmam, R.G. Hydrogenation of a menhaden oil: II. Formation and evolution of the C20 dienoic and trienoic fatty acids as a function of the degree of hydrogenation. J Am Oil Chem Soc 60, 1992–1996 (1983). https://doi.org/10.1007/BF02669971
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DOI: https://doi.org/10.1007/BF02669971