The PMR analysis of non-conjugated alkenoic and alkynoic acids and esters.

Chemistry and Physics of Lipids
D J Frost, F D Gunstone

Abstract

The 220 MHz PMR spectra of 143 non-conjugated alkenoic and alkynoic acids and esters are correlated so as to provide a method for the structural analysis of such compounds in general. The spectral data are explained in terms of long-range deshielding of the double bonds, triple bonds, acid and ester groups in the molecules, and parameters are derived to quantify the influence of these groups on the chemical shifts of methyl and methylene protons up to six carbon atoms distant along an alkyl chain. It is shown that, by the application of these parameters, 220 MHz PMR spectroscopy can be used to determine both the stereochemistry and position of double bonds, and the position of triple bonds, in the majority of fatty acids and esters. The 2- to 9- and 13- to 17-cis- and trans-isomers of octadecenoic acid may be readily idenfited in this way, whilst for the octadecynoic acids all positional isomers may be characterized. Examples are also given of the structural analysis of several polyenoic compounds, including methyl cis-5, cis-8, cis-11, cis-14, cis-5, cis-8, cis-11, trans-14, and trans-5, cis-8, cis-11, cis-14-eicosatetraenoates, and methyl trans-5, cis-9, cis-12-octadecatrienoate.

References


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Citations

Oct 1, 1974·Chemistry and Physics of Lipids·D J Frost, I Sies
Mar 28, 1997·Chemistry and Physics of Lipids·S G Batrakov, O N Tolkachev
Mar 27, 2009·Journal of Natural Products·Vanessa V HomannAlison Butler
Nov 11, 2008·Evidence-based Complementary and Alternative Medicine : ECAM·Anna AielloWerner E G Müller
Dec 19, 2006·Chemistry and Physics of Lipids·Lauro M de SouzaGuilherme L Sassaki
Oct 31, 2015·Organic Letters·Christian NilewskiErick M Carreira
Nov 29, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Tamim A DarwishMichael James
Oct 18, 2015·Lipids·Elena A SantalovaPavel S Dmitrenok
Jan 1, 1978·Progress in the Chemistry of Fats and Other Lipids·G R Khan, F Scheinmann
Oct 6, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eleni AlexandriIoannis P Gerothanassis
Jun 18, 2003·The Journal of Biological Chemistry·Nicolas W J SchröderRalf R Schumann
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Mar 6, 2019·International Journal of Molecular Sciences·Seindé TouréVéronique Eparvier
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Jul 26, 1996·Biochimica Et Biophysica Acta·S G Batrakov, D I Nikitin
Aug 12, 1983·Biochemical and Biophysical Research Communications·M O Funk, A W Alteneder

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