Applications of liquid chromatographic and spectroscopic methods for the characterisation of fatty acid anilides in contaminated cooking oils

Wheals, B.B.; Whitehouse, Martin J.; Curry, C.J.

doi:10.1016/s0021-9673(00)82727-2

Cited by 18 publications

(4 citation statements)

References 3 publications

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“…Initial methods were based on the production of aniline from anilide using thermal or alkaline decomposition. − These methods were not able to distinguish between the different anilides present in oils. More specific analyses were carried out using HPLC-UV with a previous purification of the analyte. − These methods allowed the characterization of oleic, linoleic, linolenic, and stearic anilides. Meanwhile, Blackey et al, using gas chromatography, demonstrated that oleyl anilide was the major anilide component of the toxic oils .…”

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confidence: 99%

Determination of Aniline Derivatives in Oils Related to the Toxic Oil Syndrome by Atmospheric Pressure Ionization-Tandem Mass Spectrometry

et al. 2001

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In 1981, an unknown disease appeared in Spain, the Spanish Toxic Oil Syndrome. Nowadays and despite all efforts, the etiological agent is still unknown. Early studies showed a link between this illness and the consumption of denatured rapeseed oil fraudulently processed and marketed as edible oil. Two families of aniline derivatives present in these oils (fatty acid anilides and acylated phenyl amino propanediol derivatives or PAPs) were found to be good chemical markers of toxic oils. In this work, a new method has been developed to analyze these aniline derivatives in oil samples by HPLC-MS and HPLC-MS/MS with an API source. For their quantification, three different internal standards were used, one for anilides and two for PAPs. Quantification limits were 8 ppm for anilides and 0.2 ppm for PAPs. Anilides and PAPs were found in marker-positive samples at levels up to 50,000 and 330 ppm, respectively. The relative abundance of the different fatty acid anilides and PAPs correlates with the fatty acid composition of the oils. More than 2,600 different samples were analyzed by this method in the most exhaustive screening of suspected toxic oils carried out to date.

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confidence: 99%

Determination of Aniline Derivatives in Oils Related to the Toxic Oil Syndrome by Atmospheric Pressure Ionization-Tandem Mass Spectrometry

et al. 2001

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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: 99%

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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“…Fatty acid anilides in the oils were measured by HPLC using a modification of the method of Wheals et al (1982). An aliquot of 17:0-AN was added as an internal standard to a known weight (ca 50 mg) of the oil, which was extracted with 750 FL of methanol.…”

Section: Fatty Acid Anilidesmentioning

confidence: 99%

Compositional Analysis of Oil Samples Implicated in the Spanish Toxic Oil Syndrome

Bernert¹,

Kilbourne²,

Akins³

et al. 1987

Journal of Food Science

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A selected group of 195 oils from the Spanish "Toxic Oil" Syndrome (TOS) epidemic including 29 high-probability "case" and 64 "control" oils were examined to investigate the relationship between oil composition and the risk of TOS. As indicated by fatty acid and sterol patterns, the presence of rapeseed oil was significantly more prevalent in the case than in the control oils, but fatty acid anilides were the most useful markers of case-related samples. Anilides were detected in 62% of case oils and at lower concentrations in 23% of the control samples. The ratios of individual anilides were quite constant in these oils and most consistent with their formation in the original (undiluted) rapeseed oil.

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Applications of liquid chromatographic and spectroscopic methods for the characterisation of fatty acid anilides in contaminated cooking oils

Cited by 18 publications

References 3 publications

Determination of Aniline Derivatives in Oils Related to the Toxic Oil Syndrome by Atmospheric Pressure Ionization-Tandem Mass Spectrometry

Determination of Aniline Derivatives in Oils Related to the Toxic Oil Syndrome by Atmospheric Pressure Ionization-Tandem Mass Spectrometry

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

Compositional Analysis of Oil Samples Implicated in the Spanish Toxic Oil Syndrome

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