Identification of fatty acid anilides in adulterated Spanish cooking oils

Diachenko, Gregory W.; Yurawecz, M. P.; Puma, Bartholomew J; Dreifuss, Peter A.; Chen, J. T.; Egry, Ivan J.; Carver, Ruth B

doi:10.1007/bf01606155

Cited by 14 publications

(7 citation statements)

References 4 publications

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“…Due to the clean methanolic extracts of the oils injected, the precolumn maintained its performance for long time, but it was found convenient to replace the stationary phase every 40-50 samples. Despite the general greater sensitivity of detectors used in GC over UV detection in HPLC, and the higher resolution of the GLC capillary columns, only one published method had take advantage of these facts for the analysis of anilides (Bailey et al 1983), while other three used less resolutive GLC packed columns (Diachenko et al 1982;Vázquez Roncero et al 1983;Artigas et al 1983). However, the non-polar silicone stationary phase used by Balley et al (1983) is unable to separate the interesting group of polyunsaturated FAAs, which could be resolved on a more polar stationary phase, such as the 70% cyanopropyl column.…”

Section: Resultsmentioning

confidence: 99%

“…Four gas chromatographic methods have been published for the analysis of FAAs in oils (Diachenko et al 1982;Vázquez Roncero et al 1983;Artigas et al 1983;Balley et al 1983). The chemical similarity with the methyl esters of fatty acids makes gas-liquid chromatography (GLC) the method of choice for the analysis of FAAs, although their higher molecular weights limited up to now the use of the more resolutive polar stationary phases.…”

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confidence: 99%

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Improved Analysis of Fatty Acid Anilides: Application to Toxic and to Aniline and Citric Acid-Containing Oils

Guitart

Guerrero

Mateo

1996

Bulletin of Environmental Contamination and Toxicology

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Improved Analysis of Fatty Acid Anilides: Application to Toxic and to Aniline and Citric Acid-Containing Oils

Guitart

Guerrero

Mateo

1996

Bulletin of Environmental Contamination and Toxicology

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“…The occurrence of fatty acid anilides has been observed in a number of studies related to the toxic oil syndrome. These anilides are believe to be the result of reaction of the aniline used to denature the rapeseed oil with the fatty acids are part of the triglyceride structure of rapeseed oil (Diachenko et al, 1982;Wheals et al, 1982;Kaphalia and Ansari, 1991;Ferrer et al, 1993). A representative MS/MS spectrum of a fatty acid anilide is shown in Fig.…”

Section: Ms/ms Data Analysismentioning

confidence: 98%

On‐Line HPLC‐UV‐mass spectrometry and tandem mass spectrometry for the rapid delineation and characterization of differences in complex mixtures: a case study using toxic oil variants

Crow

Cragun

Johnson

et al. 2002

Biomedical Chromatography

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An integrated differential approach to the characterization of complex mixtures is presented which includes the targeting of liquid chromatography (LC) peaks for identification using characteristic UV adsorption of the LC peak, subsequent molecular weight and formula determination using accurate mass LC mass spectrometry (MS), and structure characterization using accurate mass LC-tandem mass spectrometry. The use of differential UV adsorption aids in narrowing the scope of the study to only specific peaks of interest. Accurate mass measurement of the molecular ion species provides molecular weight information as well as atomic composition information. The tandem MS (MS/MS) spectra provide fragmentation information which allows for structural characterization of each component. Accurate mass assignment of each of the fragment ions in the MS/MS spectrum provides atomic composition for each of the fragment ions and thus further aids in the structural characterization. These experiments are facilitated through the use of on-line LC-MS and LC-MS/MS with in-line UV detection. A synthetic toxic oil (STO) related to Toxic Oil Syndrome is studied with a focus on possible contaminants resulting from the interaction of aniline, used as a denaturant, with the normal components of the oil. A differential analysis between the STO and a control oil is performed. LC peaks were targeted using UV absorbance to indicate the possible presence of the aniline moiety. Further differential analysis was performed through the determination of the MS signals associated with each component separated on the LC. Finally, the MS/MS data was also used to determine if the fragmentation of the targeted components indicated the presence of aniline. The MS/MS and accurate mass data were used to assign the structures for the targeted components.

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“…Anilides of fatty acids have been identified as contaminants of cooking oil associated with the outbreak of poisoning in Spain in 1981 (Tabuenca 1981;Pestana and Munoz 1982;Diachenko et al 1982;Wheals et al 1982;Dabrio 1982). The anilides were probably formed during a refining process from a reaction between free fatty acids and aniline which had originally been added to the oil as a denaturing agent.…”

Section: Introductionmentioning

confidence: 98%

Hydrolysis of oleylanilide in the rat

1983

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The fate of oleylanilide, administered as a single intragastric dose in rape oil, has been studied in Porton Wistar rats. Following a dose of oleyl[U-14C]anilide approximately 60% of the label was recovered in the faeces over a 3 day period, and identified principally as unchanged anilide. Most of the remainder of the dose was recovered in urine as hydrophilic metabolites. p-hydroxyacetanilide, which is a major metabolite of aniline in the rat was identified in the hydrolysed samples of urine from anilide treated rats. Following administration of [9,10(n)-3H]oleyl[U-14C]-anilide to rats which had been fitted with a cannula in the thoracic lymph duct the [3H] label which was absorbed was recovered principally in triglycerides showing that extensive hydrolysis of the anilide occurs prior to or during uptake from the gut. Oleylanilide was identified in lymph by gas chromatography but amounted to less than 6% of the dose.

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Identification of fatty acid anilides in adulterated Spanish cooking oils

Cited by 14 publications

References 4 publications

Improved Analysis of Fatty Acid Anilides: Application to Toxic and to Aniline and Citric Acid-Containing Oils

Improved Analysis of Fatty Acid Anilides: Application to Toxic and to Aniline and Citric Acid-Containing Oils

On‐Line HPLC‐UV‐mass spectrometry and tandem mass spectrometry for the rapid delineation and characterization of differences in complex mixtures: a case study using toxic oil variants

Hydrolysis of oleylanilide in the rat

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