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Chemical Synthesis and Gas Chromatographic Behaviour of γ-Stearidonic (18:4n-6) Acid
| Title: | Chemical Synthesis and Gas Chromatographic Behaviour of γ-Stearidonic (18:4n-6) Acid |
| Authors: | Vyssotski, Mikhail Browse this author | | Lagutin, Kirill Browse this author | | MacKenzie, Andrew Browse this author | | Itabashi, Yutaka Browse this author →KAKEN DB |
| Keywords: | Stearidonic | | Δ3 PUFA | | Octadecatetraenoic | | Octadecapentaenoic | | GC | | GC-MS | | NMR |
| Issue Date: | Mar-2015 |
| Journal Title: | Journal of the American Oil Chemists' Society |
| Volume: | 92 |
| Issue: | 3 |
| Start Page: | 383 |
| End Page: | 391 |
| Publisher DOI: | 10.1007/s11746-014-2588-x |
| Abstract: | γ-Stearidonic acid, 18:4n-6, a potential product of β-oxidation of arachidonic acid (20:4n-6), was only recently positively identified in a living organism—a thermophilic cyanobacterium Tolypothrix sp., albeit at low levels, whilst some indirect evidence suggests its wider presence, e.g. in a unicellular marine alga. We have prepared 18:4n-6 using an iodolactonisation chain-shortening approach from 22:5n-6 and obtained its 1H-, 13C-, COSY- and HSQC NMR spectra, with 18:5n-3 spectra also recorded for a comparison. The GC and GC-MS behaviour of its methyl ester was also studied. Like another Δ3 polyunsaturated acid, octadecapentaenoic (18:5n-3), 18:4n-6 rapidly yields 2-trans isomer upon formation of dimethyloxazoline derivative. On a polar ionic liquid phase (SLB-IL100, 200 °C) the methyl ester could be mistaken for 18:3n-3, while on methylsilicone phase (BP1, 210 °C) it eluted ahead of 18:3n-6 and 18:4n-3, suggesting that when present it may be easily misidentified during GC analysis of fatty acids. |
| Rights: | The final publication is available at www.springer via http://dx.doi.org/10.1007/s11746-014-2588-x |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/64704 |
| Appears in Collections: | 水産科学院・水産科学研究院 (Graduate School of Fisheries Sciences / Faculty of Fisheries Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 板橋 豊
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