Abstract
Stearic-9, 10-d2, stearic-9, 9, 10, 10-d4, oleic-9, 10-d2, decanoic-3, 3-d2, lauric-3, 3-d2, myristic-3, 3-d2, palmitic-3, 3-d2, and stearic-3, 3-d2 acids were synthesized, and 1H NMR spectra of the methyl esters of these deuterated acids were measured. The signals due to the protons which were substituted by deuterons disappeared on the 1H NMR spectra of the deuterated acid methyl esters. Estimation of the deuterium-labeled acid content in unlabeled acids was possible by measuring the relative decrease in the integrated areas of the signals for the corresponding methylene or olefinic protons which were replaced with deuterons in the deuterated acids. The shift reagents, Eu (fod) 3 and Pr (fod) 3, were effective for the NMR determination of deuterium-labeled fatty acids. Oleic-9, 10-d2 acid and saturated 3, 3-dideutero acids seem to be useful as nonradioactive tracers in the NMR analysis.
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