Determination of N-nitrosodiethanolamine in cosmetics by gas chromatography with electron capture detection

Rollmann, Bruno; Lombart, P.; Rondelet, J; Mercier, Michel

doi:10.1016/s0021-9673(00)82619-9

Cited by 20 publications

(5 citation statements)

References 8 publications

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“…It arises from di- and triethanolamine, and their various derivatives by inadvertent nitrosation processes that occur during product formulation. It has been found in cosmetics, shampoos, and personal care items ( − ), but most notably in metalworking fluids ( − ) where concentrations as high as 2−3% have been detected. To better estimate the human health hazards of this carcinogen, an understanding of its mechanism of activation is necessary.…”

Section: Introductionmentioning

confidence: 99%

Microsome-Mediated Oxidation of N-Nitrosodiethanolamine (NDELA), a Bident Carcinogen

Loeppky

Goelzer

2002

Chem. Res. Toxicol.

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N-Nitrosodiethanolamine (NDELA), an environmentally prevalent, potent carcinogen, undergoes competitive rat liver microsome-mediated oxidation at both the alpha (adjacent to N)- and beta-positions of the 2-hydroxyethyl chains. The former process, alpha-hydroxylation, is detected by the formation of glycolaldehyde (determined as its 2,4-dinitrophenylhydrazone DNP) that is assumed to arise from the decomposition of the corresponding alpha-hydroxynitrosamine, which is also the progenitor of the 2-hydroxyethyldiazonium ion. This finding refutes prior published work that states that the alpha-hydroxylation of NDELA does not occur. Competitive microsomal oxidation at the beta-position gives the hemiacetal N-nitroso-2-hydroxymorpholine (NHMOR) at a rate 1.5 times alpha-hydroxylation. Glycolaldehyde is oxidized in this system to glyoxal at a rate 39 times the conversion of NDELA to glycolaldehyde. The alpha-hydroxylation of NHMOR at either C-3 or C-5 to give glyoxal or glycolaldehyde, respectively, occurs at respective rates 3-6 times that of the alpha-hydroxylation of NDELA. Ethylene glycol, a hydrolysis product of the 2-hydroxyethyldiazonium ion is shown to undergo microsome mediate oxidation to glyoxal. Ethyl-2-hydroxyethylnitrosamine (NEELA) undergoes a similar set of microsome-mediated oxidations at alpha-position of the ethyl (fastest) and 2-hydroxyethyl groups, as well as beta-oxidation of the 2-hydroxyethyl group, a process which is slightly more rapid than alpha-hydroxylation of the same chain. Comparisons of oxidations rates of these substrates, as manipulated by preinducers, isoniazid, streptozocin, and phenobarbital, and enzyme inhibitors diethyldithiocarbamate and 4-methylpyrazole, with that of dimethylnitrosamine, a substrate for cytochrome P450 2E1, strongly suggest that this isozyme is also responsible for the oxidations reported here. alpha-Deuteration of NDELA practically eliminates its alpha-hydroxylation by microsomes from isoniazid induced rats, but doubles beta-oxidation, while beta-deuteration of this substrate significantly reduces beta-oxidation and enhances alpha-hydroxylation. Since both glyoxal-guanine and 2-hydroxyethyl-DNA base adducts are known to arise from the in vivo administration of NDELA and because this work demonstrates that these two fragments can come from the microsomal oxidation of a single nitrosamine molecule containing the 2-hydroxyethyl group, NDELA and related nitrosamines are bident (two-toothed) carcinogens, a process which is likely to enhance their carcinogenic potency.

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Section: Introductionmentioning

confidence: 99%

Microsome-Mediated Oxidation of N-Nitrosodiethanolamine (NDELA), a Bident Carcinogen

Loeppky

Goelzer

2002

Chem. Res. Toxicol.

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“… The first involves extraction of NDELA from the sample matrix, followed by derivatization. The extracted NDELA is derivatizated, the separation of the analyte from matrix components is achieved by gas chromatography then the derivatizated NDELA is detected by using a range of detectors [electron capture, electrolytic conductivity, mass spectrometry or thermal energy analyser (TEA)] [7–9]. The second approach involves the extraction of NDELA from the sample matrix, followed by separation by liquid chromatography (LC) and detection using a TEA [10].…”

Section: Methodsmentioning

confidence: 99%

A method for the determination of N‐nitrosodiethanolamine in personal care products – collaboratively evaluated by the CTPA Nitrosamines Working Group

Flower¹,

Carter²,

Earls³

et al. 2006

Intern J of Cosmetic Sci

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A procedure for the determination of N-nitrosodiethanolamine (NDELA) in personal care products was evaluated in collaborative studies by member organizations of the United Kingdom's Cosmetic Toiletry and Perfumery Association (CTPA) and LGC Limited, formerly known as the Laboratory of the Government Chemist (LGC). Samples were prepared depending on the matrix of the cosmetic product: aqueous samples were prepared by diluting in water followed by solid-phase extraction; emulsions, oils and solid materials were dissolved in dichloromethane and extracted with water. NDELA was separated from the sample matrix using reverse-phase liquid chromatography. The N-nitroso bond was cleaved by photolysis to give nitrite, which was colorimetrically quantified. The nitrite functional group reacted with sulphanilamide in an acid medium to form a diazonium ion which was then coupled with N-(1-naphthyl)ethylenediamine dihydrochloride according to the Griess reaction to give a purple-coloured azo dye that absorbed at 540 nm. Compared with other published methods for NDELA, the method described here is quick and easy to use. It has the required sensitivity and specificity, and can accurately and reliably quantify NDELA in a wide range of personal care product matrices.

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“…LC is the most chosen analytical technique, either coupled with thermal energy analyzer (TEA) , UV–Vis , MS/MS , or differential pulse polarography . Besides, GC either coupled with TEA , MS , electrolytic conductivity detector , or electron capture detector has also been employed for its determination. CEC has been also occasionally used .…”

Section: Introductionmentioning

confidence: 99%

Determination of N‐nitrosamines in cosmetic products by vortex‐assisted reversed‐phase dispersive liquid–liquid microextraction and liquid chromatography with mass spectrometry

Miralles

Chisvert

Salvador

2018

J of Separation Science

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A new analytical method for the simultaneous determination of trace levels of seven prohibited N-nitrosamines (N-nitrosodimethylamine, N-nitrosoethylmethylamine, N-nitrosopyrrolidine, N-nitrosodiethylamine, N-nitrosopiperidine, N-nitrosomorpholine, and N-nitrosodiethanolamine) in cosmetic products has been developed. The method is based on vortex-assisted reversed-phase dispersive liquid-liquid microextraction, which allows the extraction of highly polar compounds, followed by liquid chromatography with mass spectrometry. The variables involved in the extraction process were studied to obtain the highest enrichment factor. Under the selected conditions, 75 μL of water as extraction solvent was added to 5 mL of n-hexane sample solution and assisted by vortex mixing during 30 s to form the cloudy solution. The method was successfully validated showing good linearity (0.5-50 ng/mL), enrichment factors up to 65 depending on the target compound, limits of detection values of 1.8-50 ng/g, and good repeatability (RSD < 9.8%). Finally, the proposed method was applied to different cosmetic samples. Quantitative relative recovery values (80-113%) were obtained, thus showing that matrix effects were negligible. The achieved analytical features of the proposed method, besides of its simplicity and affordability, make it useful to perform the quality control of cosmetic products to ensure the safety of consumers.

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Determination of N-nitrosodiethanolamine in cosmetics by gas chromatography with electron capture detection

Cited by 20 publications

References 8 publications

Microsome-Mediated Oxidation of N-Nitrosodiethanolamine (NDELA), a Bident Carcinogen

Microsome-Mediated Oxidation of N-Nitrosodiethanolamine (NDELA), a Bident Carcinogen

A method for the determination of N‐nitrosodiethanolamine in personal care products – collaboratively evaluated by the CTPA Nitrosamines Working Group

Determination of N‐nitrosamines in cosmetic products by vortex‐assisted reversed‐phase dispersive liquid–liquid microextraction and liquid chromatography with mass spectrometry

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