Monoepoxy octadecadienoates and monoepoxy octadecatrienoates 1: NMR spectral characterization
Monoepoxy octadecadienoates and monoepoxy octadecatrienoates 1: NMR spectral characterization
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DOI：
10.1016/j.chemphyslip.2008.02.003
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发表时间：
2008-04-01
影响因子：
3.4
通讯作者：
Duke, Colin C.
中科院分区：
文献类型：
--
作者：
Cui, Pei H.;Duke, Rujee K.;Duke, Colin C.
用间氯过苯甲酸对γ-亚麻酸、α-亚麻酸和十八碳四烯酸甲酯进行环氧化，得到9种顺式单环氧-C18脂肪酸甲酯（FAME），包括新的十八碳四烯酸的顺式单环氧甲基衍生物和γ-亚麻酸的顺式-6，7-环氧衍生物。这9个单环氧FAME通过正相HPLC纯化，通过LC-MS，H-1和C-13 NMR鉴定，并通过质谱和NMR光谱表征。本研究的重点是这些C18单环氧FAME的结构表征使用NMR光谱技术，包括H-1，C-13，H-1-H-1相关光谱（COSY）和H-1-C-13杂原子相关（HETCOR）。的质子和碳NMR化学位移的环氧化物，双键，和中断的亚甲基分配。还讨论了这些单环氧化合物的H-1和C-13 NMR谱的解释，包括环氧化物形成所导致的相邻双键上的烯碳的C-13共振的变化。(c)2008爱思唯尔爱尔兰有限公司保留所有权利。
Methyl esters of gamma-linolenic acid, alpha-linolenic acid and stearidonic acid were epoxidised using m-chloroperbenzoic acid to achieve nine cis-monoepoxy-C18 fatty acid methyl esters (FAMEs), including novel methyl cis-monoepoxy derivatives of stearidonic acid and a cis-6,7-epoxy derivative of gamma-linolenic acid. These nine monoepoxy FAMEs were purified by normal-phase HPLC, identified by LC-MS, H-1 and C-13 NMR, and characterized by mass spectrometry and NMR spectroscopy. This study is focused on structural characterization of these C18 monoepoxy FAMEs using techniques in NMR spectroscopy including H-1, C-13, H-1-H-1 correlated spectroscopy (COSY) and H-1-C-13 heteronuclear correlation (HETCOR). The proton and carbon NMR chemical shifts of the epoxide, the double bonds, and the interrupted methylenes are assigned. Also discussed is an interpretation of the H-1 and C-13 NMR spectra of these monoepoxides including the changes in the C-13 resonance of the olefinic carbons on the neighboring double bonds resulting from epoxide formation. (c) 2008 Elsevier Ireland Ltd. All rights reserved.