Mineral oil migration from paper-based packaging into food, investigated by means of food simulants and model substances

Fengler, Romy; Gruber, Ludwig

doi:10.1080/19440049.2020.1714750

Cited by 14 publications

(18 citation statements)

References 18 publications

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“…The PAHs present in food are typically unsubstituted as they are pyrogenic in nature, formed by incomplete heating or combustion of organic matter (EFSA 2008 ). However, contamination of food with petrogenic polycyclic aromatic hydrocarbons (PPAHs), which are typically alkylated, is an emerging health concern (EFSA 2012 ; Fengler and Gruber 2020 ; Grob 2018 ; Pirow et al 2019 ; Van Heyst et al 2018 ). In spite of the fact that petroleum-derived mineral oils are highly refined to eliminate undesirable substances such as mutagenic PAHs to make them compliant to EU regulations that forbid selling of carcinogenic substances to the general public (Carrillo et al 2019 ), concerns about potentially carcinogenic constituents have been raised.…”

Section: Introductionmentioning

confidence: 99%

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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Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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“…The hexane phase was removed for analysis after adding distilled water to the extract. In contrast to the original method, the extraction time was 24 h. The applicability of the procedure for these simulants was described in a previous publication 23 . This procedure causes Sorb‐Star to swell, avoids any potential disturbance from water desorbed from the donor and concentrates the substances in the final extract.…”

Section: Methodsmentioning

confidence: 99%

“…In order to be able to compare the migration behaviour of MOH surrogates with real MOH compounds as well as the data regarding food simulants, we conducted the experiments following the previous publication 23 . We used glass cells with an inner surface of 0.44 m 2 and a depth of the cell bottom of 55 mm to perform migration tests (Figure 2).…”

Section: Methodsmentioning

confidence: 99%

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Migration of mineral oil hydrocarbons from contaminated paperboard into the food simulants Tenax and Sorb‐Star—A comparison

Fengler

Gruber

2022

Packag Technol Sci

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A previous work dealt with surrogates and food simulants to evaluate mineral oil hydrocarbons (MOH) migration processes from paper-based food packaging. In this article, we compare this study with migration studies of real papers, contaminated with MOH. The focus was the applicability of food simulants in contact with MOH and the verification of surrogates. Tenax and Sorb-Star were chosen as food simulants, which were brought into contact with recycling paperboards. Kinetic studies were performed at 20 C, 40 C, and 60 C for up to 12 days. There were significantly lower migration rates for the more polar MOAH than for MOSH. There is nearly no migration of mineral oil aromatic hydrocarbons (MOAH) above C 25 . In general, Tenax in 'touching contact' showed the highest values, while Tenax tested with conditions that induce gas phase transport and Sorb-Star resulted in lower but similar migration rates. Sorb-Star in touching contact to the paperboard showed higher migration rates for non-volatile compounds compared to Tenax in gas phase transfer, depending on the test temperature used. Nevertheless, under comparable conditions, MOH migrate to a similar percentual extent for each type of paperboard used. It was shown that the migration behaviour of MOH can be depicted by the use of respective surrogates, which will help to ease the analytical tasks. Migration tests with these surrogates using Tenax and Sorb-Star as food simulants at 20 C and 40 C can cover a wide range of real-life migration processes from paper-based food packaging into foods, provided that appropriate conditions are chosen.

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“…The PAHs present in food are typically unsubstituted as they are pyrogenic in nature, formed by incomplete heating or combustion of organic matter . However, contamination of food with petrogenic polycyclic aromatic hydrocarbons (PPAHs), which are typically alkylated, is an emerging health concern Fengler and Gruber 2020;Van Heyst et al 2018). In spite of the fact that petroleum-derived mineral oils are highly refined to eliminate undesirable substances such as mutagenic PAHs to make them compliant to EU regulations that forbid selling of carcinogenic substances to the general public ), concerns about potentially carcinogenic constituents has been raised.…”

Section: Introductionmentioning

confidence: 99%

The effects of alkyl substitution on metabolism and resulting toxicities of Polycyclic Aromatic Hydrocarbons (PAHs) that may be present in mineral oils

Dan-lei¹

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PAH with a bay region which makes phenanthrene and its alkylated analogues interesting for studies of possible metabolic activation and mutagenicity. Therefore, phenanthrene, commercially available methyl-substituted phenanthrenes as well as custom-synthesized 1-n-hexyl and 1-ndodecyl substituted phenanthrenes were selected as model compounds (Table 3). B[a]P is a fivering PAH that has been extensively studied in the past decades and was prioritized by the SCF, the Grimmer institute and the EPA and was classified by IARC as a Group 1 carcinogen (Table 1).Bioactivation leading to mutagenicity, carcinogenicity and developmental toxicity have been reported in experimental animals as well as in in vitro bioassays and may also be relevant to human (Yang, McCourt et al. 1977, Gelboin 1980. B[a]P and twelve of its monomethyl substituted analogues showed positive mutagenic potential upon bioactivation in bacterial reverse mutation studies . To investigate the effect of methyl substitution that introduces artificial bay region(s) in B[a]P on its metabolism and mutagenic potential, four methyl substituted congeners of B[a]P, 3-, 6-, 7-and 8-methyl-B[a]P, were selected as model compounds (Table 3). In addition, custom synthesized 3-n-hexyl-and 3-n-dodecyl-B[a]P were included as model compounds to investigate the effect of chain length on the metabolic oxidation of alkylated PAHs (Table 3). Table 3. Non-substituted ('naked') and alkyl-substituted aromatic hydrocarbons selected as model compounds for the present thesis Chemical name and structure CAS number Boiling point Molecular weight Formula 2-ring non-substituted and alkyl-substituted aromatic hydrocarbons in Chapter 2 naphthalene 91-20-3 217.9°C 128.17g/mol C10H8 1-methyl-naphthalene 90-12-0 240-243°C 142.2 g/mol C11H10 2-methyl-naphthalene 91-57-6 241.1°C 142.2 g/mol C11H10 1-ethyl-naphthalene 1127-76-0 258.6 °C 156.22 g/mol C12H12 2-ethyl-naphthalene 939-27-5 258 °C 156.22 g/mol C12H12 1-n-hexyl-naphthalene 2876-53-1 322 °C 212.33 g/mol C16H20 1-n-dodecyl-naphthalene 38641-16-6 415°C 296.49 g/mol C22 H32 3-ring non-substituted and alkyl-substituted PAHs in Chapter 3 phenanthrene 85-01-8 340°C 178.23 g/mol C14H10 1-methyl-phenanthrene 832-69-9 354-355°C 192.26 g/mol C15H12 2-methyl-phenanthrene 2531-84-2 353°C 192.26 g/mol C15H12 3-methyl-phenanthrene 832-71-3 350°C 192.26 g/mol C15H12 9-methyl-phenanthrene 883-20-5 354°C 192.26 g/mol C15H12 2-ethyl-phenanthrene 2531-84-2 363°C 206.28 g/mol C16H14 9-ethyl-phenanthrene 3674-75-7 364°C 206.28 g/mol C16H14 9-ethyl-10-methylphenanthrene 17024-02-1 381°C 220.31 g/mol C17 H16 1-n-hexyl-phenanthrene -415°C 262.39 g/mol C20H22Chapter 2In vitro metabolism of naphthalene and its alkylated congeners by human and rat liver microsomes via alkyl side chain or aromatic oxidation

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Mineral oil migration from paper-based packaging into food, investigated by means of food simulants and model substances

Cited by 14 publications

References 18 publications

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

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

Migration of mineral oil hydrocarbons from contaminated paperboard into the food simulants Tenax and Sorb‐Star—A comparison

The effects of alkyl substitution on metabolism and resulting toxicities of Polycyclic Aromatic Hydrocarbons (PAHs) that may be present in mineral oils

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