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Chemical Synthesis and Gas Chromatographic Behaviour of γ-Stearidonic (18:4n-6) Acid

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/64704

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)

Submitter: 板橋 豊

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