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

Vyssotski, Mikhail; Lagutin, Kirill; MacKenzie, Andrew; Itabashi, Yutaka

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

Vyssotski, Mikhail; Lagutin, Kirill; MacKenzie, Andrew et al.

Journal of the American Oil Chemists' Society, 2015, 92(3), 383-391

Permalink : https://hdl.handle.net/2115/64704

このアイテムのアクセス数:997件（2026-08-15 10:47 集計）

閲覧可能ファイル

ファイル	フォーマット	サイズ	閲覧回数	説明
gamma-stearidonic acid (for HUSCAP)-1	pdf	440 KB	914

論文情報

ファイル出力 EndNote Basic出力 Mendeley出力

アクセス権	open access
URI	https://hdl.handle.net/2115/64704
タイトル	Chemical Synthesis and Gas Chromatographic Behaviour of γ-Stearidonic (18:4n-6) Acid
著者	Vyssotski, Mikhail ; Lagutin, Kirill ; MacKenzie, Andrew ; Itabashi, Yutaka
著者名 Vyssotski, Mikhail
著者名 Lagutin, Kirill
著者名 MacKenzie, Andrew
e-Rad_Researcher 60142709 著者名 Itabashi, Yutaka
言語	英語
キーワード	Stearidonic
	Δ3 PUFA
	Octadecatetraenoic
	Octadecapentaenoic
	GC
	GC-MS
	NMR
発行日	2015-03
収録物名	Journal of the American Oil Chemists' Society
巻(号)	92(3)
ページ	383-391
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	The final publication is available at www.springer via http://dx.doi.org/10.1007/s11746-014-2588-x
PISSN	0003-021X
EISSN	1558-9331
NCID	AA00692919
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1007/s11746-014-2588-x