The selective determination of potentially carcinogenic polycyclic aromatic compounds in lubricant base oils by the DMSO extraction method IP346 and its correlation to mouse skin painting carcinogenicity assays

Carrillo, Juan-Carlos; Wiel, A. van der; Danneels, Dirk; Kral, Olaf; Boogaard, Peter J.

doi:10.1016/j.yrtph.2019.05.012

Cited by 24 publications

(26 citation statements)

References 29 publications

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“…Both mineral waxes and oils originate from the vacuum distillation columns of the lubricating oil manufacturing unit in a petroleum refinery. After crude oil is distilled at atmospheric pressure into light fractions the resulting residue is further refined to yield a non-carcinogenic "waxy raffinate", which is the common feedstock of mineral oils and waxes and comprises of normal, iso-and cyclo-alkanes and predominantly alkylated aromatics, as the little alkylated and naked ring 3-7 PAC have been extracted (Carrillo et al 2019). Before it is further processed under vacuum to yield a set of oil substances (base oils and white oils), the waxy raffinate must be dewaxed.…”

Section: Manufacturing Of Waxesmentioning

confidence: 99%

“…While "MOSH" and "MOAH" may have been intuitive for the context under which they were originally used, taken out of context introduced another layer of complexity (and confusion) in the interpretation of the data. For example, the MOAH fraction is a generic, unspecific analysis of a fraction containing aromatics (total content of aromatic compounds), thus it does not distinguish the harmless MOAH from the 3-7 ring polycyclic aromatic compounds (PAC) which are the species that are toxicologically relevant (Carrillo et al 2019). Further, it has been recognized that MOSH not only encompasses "mineral oil" fractions, but also structurally similar molecules like poly olefins (Biedermann et al 2015) and n-alkanes of natural origin (Cravedi et al 2017).…”

Section: Safety Evaluations Of Mineral Oils and Waxesmentioning

confidence: 99%

“…The consequence was that the focus shifted from the "toxicologically relevant" to a "catch all" method, which difficulties in interpretation and execution have been reviewed elsewhere (Weber et al 2018;Pirow et al 2019); but this is outside the scope of this paper. We will not address it further, because the issue of carcinogenicity of petroleum products has been recently addressed elsewhere (Carrillo et al 2019;Pirow et al 2019).…”

Section: Safety Evaluations Of Mineral Oils and Waxesmentioning

confidence: 99%

“…Animal studiesstrain and species differences While carcinogenicity assessment of mineral waxes and oils had been the key concern and was done using mouse skin painting studies discussed in detailed elsewhere (Doak et al 1983;McKee et al 1989;Chasey and McKee 1993;Carrillo et al 2019); the assessment of systemic effects after oral exposure was carried out in rats in sub-chronic and chronic feeding (dietary) studies for the purposes of sensitive applications such as food contact. These toxicological evaluations aimed at assessing a wide range of waxes and oils with different viscosities and manufacturing history (e.g.…”

Section: Toxicological Evaluations Of Hydrocarbon Waxesmentioning

confidence: 99%

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Relevance of animal studies in the toxicological assessment of oil and wax hydrocarbons. Solving the puzzle for a new outlook in risk assessment

Carrillo

Danneels

Woldhuis³

2021

Critical Reviews in Toxicology

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Paraffin waxes and white mineral oils are distinct petroleum products separated from a common feedstock by crystallization, where only n-alkanes, iso-and cyclo-alkanes with a linear backbone of $ 20 carbon atoms long, selectively crystalize out from the oil to form the wax, which is solid at room temperature, whereas oils remain liquid. Up until the 90's, these differences were reflected in separated regulatory assessments. A paradigm shift occurred when Fischer 344 rats (F-344) developed liver epithelioid granuloma following exposure to low and medium viscosity oils or waxes. This lesion was used as common denominator between these products to be jointly assessed under the common term "mineral hydrocarbons -MHC", obviating compositional differences. This regulatory paradigm dominated for the next 30 years, exacerbated by the EFSA 2012 evaluation using the analytical term "MOSH" (mineral oil saturated hydrocarbons) which encompassed these products under single chromatography fraction. The reconstruction of historical developments, together with recent EFSA-sponsored studies of toxicity and accumulation and supporting literature, has allowed us to understand the etiology of the F-344 rat hepatic epithelioid granuloma, which is presented in an adverse outcome pathway (AOP). Considering chemical composition, it clearly demonstrates that the hepatic effects in F-344 rats caused by linear alkanes of waxes are irrelevant for humans. Waxes are thus not MOSH and should thus be evaluated on their own merit. The term MOSH should not include n-alkanes and be exclusively used to mineral oil fractions when considering their chemical makeup for a relevant human hazard assessment.

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Section: Manufacturing Of Waxesmentioning

confidence: 99%

Section: Safety Evaluations Of Mineral Oils and Waxesmentioning

confidence: 99%

Section: Safety Evaluations Of Mineral Oils and Waxesmentioning

confidence: 99%

Section: Toxicological Evaluations Of Hydrocarbon Waxesmentioning

confidence: 99%

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Relevance of animal studies in the toxicological assessment of oil and wax hydrocarbons. Solving the puzzle for a new outlook in risk assessment

Carrillo

Danneels

Woldhuis³

2021

Critical Reviews in Toxicology

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“…Due to reactive intermediates (e.g., epoxides) formed along the oxidation route, they are classified as potentially mutagenic, referring in particular to three to seven ring compounds nonalkylated or poorly alkylated [8]. A high degree of alkylation is thought to reduce their metabolic activation, leading to the formation of nonmutagenic intermediates excreted via bile [36]. However, at present, a conclusive hazard characterization cannot be performed since either dose–response data or a toxicological reference point is not available.…”

Section: Evolution Of the European Framework On Mineral Oil And Statementioning

confidence: 99%

Evolution of hyphenated techniques for mineral oil analysis in food

Sdrigotti

Collard

Purcaro

2020

J of Separation Science

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The occurrence of mineral oil in food is known since the early 1990s, and it was discovered by chance in one of the first applications using the hyphenated LC–GC system. Since then, the relationship between hyphenated techniques and mineral oil analysis has been tightly interrelated and successful. This review aims to show and explain how this mutual interaction has driven the development of the hyphenated techniques on one side and has supported the increase of knowledge on the other, supporting the complex task of mineral oil determination in food. The paper presents the background of the mineral oil problem in food (a brief history of its finding, toxicology, and occurrence), moving then toward the analytical determination. The development of different hyphenated techniques in relation to mineral oil determination is discussed, focusing mainly on 2D techniques, such as LC–GC. The necessity of additional dimensions, such as LC–LC–GC and comprehensive approaches, such as GC × GC and LC × GC, is also discussed. Finally, the role of the hyphenation with MS is presented.

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The effect of alkyl substitution on the oxidative metabolism and mutagenicity of phenanthrene

et al. 2022

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Alkyl-substituted PAHs may be present in certain petroleum-derived products and in the environment and may eventually end up in consumer products, such as foodstuffs, cosmetics and pharmaceuticals. Safety concerns over possible exposure to alkylated PAHs have emerged. Bioactivation is a prerequisite for the mutagenicity and carcinogenicity of PAHs and has been extensively studied for non-substituted PAHs, while data on the bioactivation of alkyl-substituted PAHs are scarce. The present study investigated the effect of alkyl substitution on the CYP 450-mediated metabolism of phenanthrene and eight of its alkylated congeners by quantifying metabolite formation in rat and human liver microsomal incubations. Furthermore, the mutagenicity of four selected methylated phenanthrenes was compared to that of phenanthrene using the Ames test. The obtained results support the hypothesis that alkyl substitution shifts the oxidative metabolism from the aromatic ring to the alkyl side chain. Increasing the length of the alkyl chain reduced overall metabolism with metabolic conversion for 1-n-dodecyl-phenanthrene (C12) being negligible. 1- and 9-methyl-phenanthrene, in which the methyl group generates an additional bay region-like structural motif, showed mutagenicity toward Salmonella typhimurium TA98 and TA 100, whereas phenanthrene and also 2- and 3-methyl-phenanthrene, without such an additional bay region-like structural motif, tested negative. It is concluded that the position of the alkylation affects the metabolism and resulting mutagenicity of phenanthrene with the mutagenicity increasing in cases where the alkyl substituent creates an additional bay region-like structural motif, in spite of the extra possibilities for side chain oxidation.

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The selective determination of potentially carcinogenic polycyclic aromatic compounds in lubricant base oils by the DMSO extraction method IP346 and its correlation to mouse skin painting carcinogenicity assays

Cited by 24 publications

References 29 publications

Relevance of animal studies in the toxicological assessment of oil and wax hydrocarbons. Solving the puzzle for a new outlook in risk assessment

Relevance of animal studies in the toxicological assessment of oil and wax hydrocarbons. Solving the puzzle for a new outlook in risk assessment

Evolution of hyphenated techniques for mineral oil analysis in food

The effect of alkyl substitution on the oxidative metabolism and mutagenicity of phenanthrene

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