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GC Separation of cis-Eicosenoic Acid Positional Isomers on an Ionic Liquid SLB-IL100 Stationary Phase

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Journal of the American Oil Chemists' Society

Abstract

Gas chromatography (GC) of cis-eicosenoic acid (20:1) positional isomers has been investigated on a capillary column of ionic liquid 1,9-di(3-vinyl-imidazolium)nonane bis(trifluoromethyl)sulfonylimidate stationary phase (SLB-IL100). A test mixture of isomeric 20:1 methyl esters was prepared from flathead flounder flesh lipids. On a 60-m column operated at 150–180 °C, six peaks appeared in the elution order of 20:ln-15 → 20:ln-13 → 20:ln-11 → 20:ln-9 → 20:ln-7 → 20:ln-5. These peaks were baseline resolved within 20 min at 180 °C. The 20:ln-13 and 20:ln-11 isomers, poorly resolved on conventional polar polysiloxane stationary phases, were completely separated from each other with separation factor α = 1.02 and peak resolution (Rs) ≥ 1.57. When equivalent chain length (ECL) values were compared between the SLB-IL100 and CP-Sil 88 (biscyanopropyl polysiloxane), those of 20:ln-15 and 20:ln-13 exceptionally tended to be lower on the SLB-IL100. The excellent separation of 20:1 isomers seems due to less retention of 20:ln-15 and 20:ln-13 on SLB-IL100 rather than simply due to its high polarity. Analysis of herring oil 20:1 revealed the occurrence of 20:ln-13 in the Pacific herring but not in the Atlantic herring. The ionic liquid stationary phase, SLB-IL100, is effective for analyzing 20:1 isomers occurring in fish and other natural oils.

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Acknowledgments

The authors wish to thank Ms. Seiko Oka, Instrumental Analysis Division, Equipment Management Center, Creative Research Institution, Hokkaido University, for the GC–MS analyses.

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Authors and Affiliations

  1. Division of Marine Life Sciences, Faculty of Fisheries Science, Hokkaido University, 3-1-1 Minato-cho, Hakodate, Hokkaido, 041-8611, Japan

    Yasuhiro Ando & Tsubasa Sasaki

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  1. Yasuhiro Ando
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  2. Tsubasa Sasaki
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Correspondence to Yasuhiro Ando.

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Ando, Y., Sasaki, T. GC Separation of cis-Eicosenoic Acid Positional Isomers on an Ionic Liquid SLB-IL100 Stationary Phase. J Am Oil Chem Soc 88, 743–748 (2011). https://doi.org/10.1007/s11746-010-1733-4

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  • DOI: https://doi.org/10.1007/s11746-010-1733-4

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