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1 H– 13 C HMBC NMR experiments as a structural and analytical tool for the characterization of elusive trans/cis hydroperoxide isomers from oxidized unsaturated fatty acids in solution
Author(s) -
Ahmed Raheel,
Siddiqui Hina,
Choudhary Muhammad Iqbal,
Gerothanassis Ioannis P.
Publication year - 2019
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4844
Subject(s) - chemistry , cis–trans isomerism , structural isomer , stereochemistry , methyl oleate , nuclear magnetic resonance spectroscopy , carbon 13 nmr , proton nmr , organic chemistry , catalysis
Abstract The radical‐dependent oxidation of unsaturated fatty acids is a fundamental reaction in lipid chemistry, biochemistry, and technology. We report herein the first successful application of 1 H– 13 C HMBC NMR experiment for the identification and quantification of complex and minor (3.9% to 0.85%) components of cis and trans primary hydroperoxide isomers of oxidized oleate and linoleate methyl esters in solution, without the need of laborious isolation of the individual components.