ABSTRACT: The triacylglycerol fraction of three samples of margarine, namely “Flora” (Holland), “Kaliakra” (Bulgaria), and “Corona”
(Holland), were studied by13C nuclear magnetic resonance spectroscopy. By examining the various carbon chemical shifts of the saturated and unsaturated
carbon nuclei, “Flora” margarine was shown to contain a mixture of hydrogenated and unhydrogenated vegetable oils. This technique
allowed all major acyl groups (saturated, oleate, linoleate, and linolenate) and minor acyl components [different positional
isomers of long-chain (E)- and (Z)-monoenoic moieties, arising as by-products during catalytic hydrogenation] to be identified. The amount of each fatty acid
present in the margarine was also estimated from the relative intensities of the corresponding signals. “Kaliakra” margarine
consisted of a blend of unhydrogenated natural fats and oils that contained saturated fatty acids, oleate, and linoleate.
There were no signs in the spectrum of “Kaliakra” of any (E)-isomers, nor signals associated with positional unsaturated acyl groups (other than oleate and linoleate). The sample of
“Corona” margarine consisted of a mixture of hydrogenated and unhydrogenated vegetable oils and butter (1.3%). The presence
of butter in this sample was identified by the characteristic carbon shifts of the C-1 to C-4 carbon atoms of butyrate. The
distribution of the fatty acids on the glycerol “backbone” also was estimated by this technique.
Journal of Oil & Fat Industries 01/1996; 73(8):1011-1017. · 1.77 Impact Factor
ABSTRACT: 13C nuclear magnetic resonance (NMR) spectroscopic analysis of the whole oil (triacylglycerols) ofBiota orientalis seeds confirms the presence of oleate [18:1(9Z)], linoleate [18:2(9Z, 12Z)], linolenate [18:3((9Z, 12Z, 15Z)], 20:3 (5Z,
11Z, 14Z), 20:4(5Z, 11Z, 14Z, 17Z), and saturated fatty acids in the acyl groups by comparing the observed carbon shifts with
previously established shift data for model triacylglycerols. This technique shows that the saturated, 20:3 and 20:4 fatty
acids are distributed mainly in the α-acyl positions, whereas oleate, linoleate, and linolenate are randomly acylated to the
α- and β-positions of the glycerol “backbone”. Stereospecific hydrolysis of theBiota oil with pancreatic lipase, followed by chromatographic analysis of fatty esters, reveals the presence of trace amounts of 16:0(0.7%),
18:0(0.5%), 20:3 (0.4%), and 20:4 (1.3%) in the β-position of the glycerol “backbone”, which are undetectable by13C NMR technique on the whole oil. Semiquantitative assessment of the13C NMR signal intensities gives the relative percentages of the fatty acid distribution as: saturated 16:0, 18:0 (12.0% α-acyl),
oleate (7.7% α-acyl 8.7% β-acyl), total linoleate and linolenate (31.7% α-acyl; 24.2% βacyl), total 20:3 and 20:4 (15.7% α-acyl).
The13C NMR spectroscopic analysis of carrot seed oil identifies the presence of saturated (18:0), 18:1(6Z), 18:1(9Z), and 18:2(9Z,
12Z). The saturated fatty acid is found in the α-acyl positions. Semi-quantitative assessment of the signal intensities gives
the relative percentages of the fatty acids as: 18:0 (4.5% α-acyl), 18:1(6Z) (49.6% α-acyl; 19.7% β-acyl), oleate (6.5% α-acyl;
8.6% β-acyl) and linoleate (5.2% α-acyl; 6.9% β-acyl).
Journal of Oil & Fat Industries 01/1996; 73(5):557-562. · 1.77 Impact Factor
ABSTRACT: The 1H-NMR spectroscopic properties of 15 synthetic homologous saturated triacylglycerols of type AAA and 16 mixed saturated triacylglycerols of type ABA and AAB have been studied. Triacylglycerols containing short-chain fatty acids (2:0–6:0) are readily identified. Triacylglycerols containing medium- and long-chain fatty acid components are not differentiated. From the analysis of 19 acetylenic triacylglycerols of type AAA, ABA and AAB (containing positional isomers of acetylenic fatty acids), it is only possible to characterize triacylglycerols with acyl groups containing the acetylenic bond at the Δ2−Δ5 position. 1H-NMR analysis could not confirm the positions (α- or β-acyl) of the acetylenic acids in mixed triacylglycerols. In the study of 22 ethylenic triacylglycerols of type AAA containing positional isomers of (Z)- or (E)-ethylenic acids, molecules containing an ethylenic bond in the Δ2 position of the acyl chains were readily characterized, as the ethylenic protons in the α- and β-acyl chains were fully resolved. Triacylglycerols containing an unsaturated center at the position were characterized by the shifts of the 2-H protons. The spectra of the remaining triacylglycerol molecules were very similar and the position of the ethylenic system could not be determined by this technique.
Chemistry and Physics of Lipids.