Synthesis and Occurrence of Oxoaldehydes in Used Frying Oils

Takeoka, Gary R.; Buttery, Ron G.; Perrino, Charles T. Jr.

doi:10.1021/jf00049a006

Cited by 12 publications

(8 citation statements)

References 7 publications

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“…5 that the aldehydes generated in the different oils submitted to this degradation process, also shown in Tab. 4, are: trans-2-alkenals (doublet (a) at 9.480 and 9.500 ppm) and trans,trans-2,4-alkadienals (doublet (b) at 9.507 and 9.527 ppm); 4,5-epoxy-trans-2-alkenals (doublet signal (c) at 9.535 and 9.555 ppm); 4-hydroxy-trans-2-alkenals (doublet signal (d) at 9.562 and 9.582 ppm); moreover, in oils with a significant level of polyunsaturated acyl groups (such as corn, sunflower, soybean and linseed oils), cis,trans-2,4-alkadienals (doublet signal (f) at 9.586 and 9.606 ppm) whose assignment was made using as standard a mixture of trans,trans-2,4-decadienal and cis,trans-2,4-decadienal, and in addition in agreement with data provided by other authors [17,18,37]; n-alkanals (with wellknown triplet signal (g) centered at 9.748 ppm); other unidentified aldehydes which could be either saturated aldehydes having a small number of carbon atoms or oxo-alkanals (triplet signal (h) at 9.778 ppm) in agreement with different data from the literature [38].…”

Section: Resultssupporting

confidence: 92%

Monitoring of heat‐induced degradation of edible oils by proton NMR

Guillén¹,

Ruiz²

2008

Euro J Lipid Sci & Tech

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The degradation process of edible oils of very different nature, submitted to 190 7C with aeration, is studied by means of 1 H nuclear magnetic resonance (NMR). In this study, no primary oxidation products, such as hydroperoxides, are detected, the signals of aldehydes being the first to be observed in the 1 H NMR spectra. Differences between this degradation process and those occurring at 70 7C with aeration or under microwave action are discussed, not only in relation to the degradation rate of the different acyl groups, but also in relation to the nature and proportions of some of the degradation products generated. Oils rich in oleic acyl groups are not only more resistant to degradation than oils rich in linoleic and linolenic acyl groups, but also produce lower proportions of toxic aldehydes.

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Section: Resultssupporting

confidence: 92%

Monitoring of heat‐induced degradation of edible oils by proton NMR

Guillén¹,

Ruiz²

2008

Euro J Lipid Sci & Tech

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“…Two kinds of compounds were detected from among the oxygenated saturated aldehydes: 2,3‐epoxyalkanals and 4‐oxoalkanals. The former were identified by their mass spectra, in agreement with previous studies , and have also been detected before in the headspace of extra virgin olive, sunflower and virgin linseed oils submitted to frying temperature ; 4‐oxoalkanals were also previously detected among the volatile compounds of frying oils . The most abundant oxygenated saturated aldehydes detected, 2,3‐epoxyoctanal and 4‐oxononanal, are derived mainly from linoleic acyl groups .…”

Section: Resultssupporting

confidence: 88%

Volatile compounds generated in corn oil stored at room temperature. Presence of toxic compounds

Goicoechea

Guillén

2014

Euro J Lipid Sci & Tech

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Solid Phase Microextraction (SPME) followed by GC/MS was employed to study the headspace composition of corn oil (maize oil) samples stored at room temperature in closed receptacles with limited amounts of air for different periods of time. Samples with a high oxidation level showed the presence of typical secondary volatile oxidation compounds such as alkanals, 2-alkenals, 2,4-alkadienals, acids, alcohols, ketones, alkylfurans, and lactones. Aldehydes were the most numerous group; however, acids, which were fewer in number, showed the highest abundances. The high number of lactones detected is also noteworthy. In agreement with corn oil composition, those volatiles derived from linoleic acyl groups appeared in the highest abundances. The detection of two groups of toxic compounds, whose rise in concentration corresponded with the oxidation level of the samples, was remarkable. There were, on the one hand, alkylbenzenes and mono-and poly-cyclic aromatic hydrocarbons (PAHs) of low molecular weight, such as toluene, naphthalene, and fluorene. On the other hand, there were oxygenated a,b-unsaturated aldehydes like 4-hydroxy-2-nonenal, 4-oxo-2-nonenal, and 4,5-epoxy-2-decenal brought about by the oxidation of omega-6 polyunsaturated acyl groups (linoleic), and, in much lower proportions, 4-hydroxy-2-hexenal and 4,5-epoxy-2-heptenal coming from omega-3 ones (linolenic).Practical applications: The identification and quantification of such a great number of volatile compounds coming from corn oil can be very helpful for other researchers who study the degradation of this vegetable oil or other kinds with similar proportions of acyl groups.

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“…However, in oils rich in polyunsaturated groups, in addition to n‐alkanals and ( E )‐2‐alkenals, significant proportions of ( E,E )‐2,4‐alkadienals are also formed, as well as 4‐hydroxy‐( E )‐2‐alkenals, those tentatively identified as ( Z,E )‐2,4‐alkadienals, and also small proportions of 4,5‐epoxy‐2‐alkenals. In all the oils, 4‐oxo‐alkanals, a kind of aldehyde typical of frying temperatures, were tentatively identified (Takeoka and others ). In none of the oils were 4‐hydroperoxy‐( E )‐2‐alkenals detected.…”

Section: H Nmr As a Tool For The Study Of Food Lipid Thermo‐oxidatiomentioning

confidence: 99%

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

Martínez‐Yusta

Goicoechea

Guillén

2014

Comp Rev Food Sci Food Safe

143

153

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This review summarizes present-day knowledge provided by proton nuclear magnetic resonance ( 1 H NMR) concerning food lipid thermo-oxidative degradation. The food lipids considered include edible oils and fats of animal and vegetable origin. The thermo-oxidation processes of food lipids of very different composition, occurring at low, intermediate, or high temperatures, with different food lipid surfaces exposed to oxygen, are reviewed. Mention is made of the influence of both food lipid nature and degradative conditions on the thermo-oxidation process. Interest is focused not only on the evolution of the compounds that degrade, but also on the intermediate or primary oxidation compounds formed, as well as on the secondary ones, from both qualitative and quantitative points of view. Very valuable qualitative and quantitative information is provided by 1 H NMR, which can be useful for metabolomic and lipidomic studies. The chemical shift assignments of spectral signals of protons of primary (hydroperoxides and hydroxides associated with conjugated dienes) and secondary, or further (aldehydes, epoxides, among which 9,10-epoxy-12-octadecenoate [leukotoxin] can be cited, alcohols, ketones) oxidation compounds is summarized. It is worth noting the ability of 1 H NMR to detect toxic oxygenated α,β-unsaturated aldehydes, like 4-hydroperoxy-, 4,5-epoxy-, and 4-hydroxy-2-alkenals, which can be generated in the degradation of food lipids having omega-3 and omega-6 polyunsaturated groups in both biological systems and foodstuffs. They are considered as genotoxic and cytotoxic, and are potential causative agents of cancer, atherosclerosis, and Parkinson's and Alzheimer's diseases.

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Synthesis and Occurrence of Oxoaldehydes in Used Frying Oils

Cited by 12 publications

References 7 publications

Monitoring of heat‐induced degradation of edible oils by proton NMR

Monitoring of heat‐induced degradation of edible oils by proton NMR

Volatile compounds generated in corn oil stored at room temperature. Presence of toxic compounds

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

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Synthesis and Occurrence of Oxoaldehydes in Used Frying Oils

Cited by 12 publications

References 7 publications

Monitoring of heat‐induced degradation of edible oils by proton NMR

Monitoring of heat‐induced degradation of edible oils by proton NMR

Volatile compounds generated in corn oil stored at room temperature. Presence of toxic compounds

A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by 1H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature

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A Review of Thermo‐Oxidative Degradation of Food Lipids Studied by ¹H NMR Spectroscopy: Influence of Degradative Conditions and Food Lipid Nature