Modeling the structure and infrared spectra of omega-3 fatty acid esters

被引:6
作者
Meng, Wenting [1 ]
Jiang, Yaoyukun [1 ]
Rothschild, Daniel [1 ]
Lipke, Mark [1 ]
Hall, Gene [1 ]
Wang, Lu [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
关键词
PARTICLE MESH EWALD; N-3; FATTY-ACIDS; MOLECULAR-DYNAMICS; FISH-OIL; ETHYL-ESTERS; ATR-FTIR; SPECTROSCOPY; WATER; BIOAVAILABILITY; QUANTITATION;
D O I
10.1063/5.0015402
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Omega-3 dietary supplements provide a rich source of the active moieties eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which exist in the form of triacylglycerols or ethyl esters. Infrared (IR) spectroscopy provides a rapid and quantitative tool to assess the quality of these products as specific normal modes, in particular the ester carbonyl stretch modes, exhibit characteristic spectral features for the two ester forms of omega-3 fatty acids. To uncover the origin of the observed spectra, in this work, we perform molecular dynamics simulations of EPA and DHA ethyl esters and triacylglycerols to characterize their conformation, packing, and dynamics in the liquid phase and use a mixed quantum/classical approach to calculate their IR absorption spectra in the ester carbonyl stretch region. We show that the ester liquids exhibit slow dynamics in spectral diffusion and translational and rotational motion, consistent with the diffusion ordered NMR spectroscopy measurements. We further demonstrate that the predicted IR spectra are in good agreement with experiments and reveal how a competition between intermolecular and intramolecular interactions gives rise to distinct absorption peaks for the fatty acid esters.
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页数:9
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