4-Vinylphenol excretion suggestive of arene oxide formation in workers occupationally exposed to styrene

Pfäffli, Pirkko; Hesso, A.; Vainio, Harri; Hyvönen, Martti

doi:10.1016/0041-008x(81)90138-1

Cited by 36 publications

(17 citation statements)

References 16 publications

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“…The former offers SO (2), reported as the primary metabolite of styrene, and the latter produces styrene-derived phenols. Urinary 4-VP (6) and its conjugates have been identified in rodents given styrene and in workers exposed to styrene (Bakke and Scheline, 1970;Pantarotto et al, 1978;Pfäffli et al, 1981;Manini et al, 2003). Based on the knowledge of general chemistry, we reasoned that aromatic hydroxylation of styrene would generate three isomers of styrene-derived phenols, i.e., 2-VP, 3-VP, and 4-VP (Scheme 1).…”

Section: Discussionmentioning

confidence: 99%

“…Urinary 4-vinylphenol (4-VP) and its glucuronide and sulfate conjugates were detected in urine of rats treated with styrene (Bakke and Scheline, 1970;Pantarotto et al, 1978). These metabolites were also detected in urine of workers in reinforced plastic plants (Pfäffli et al, 1981;Manini et al, 2003). 2-Vinylphenol (2-VP) and 3-vinylphenol (3-VP) have been proposed as aromatic hydroxylation products of styrene (Sumner and Fennell, 1994), but they have never been identified either in experimental animals or in humans exposed to styrene.…”

Section: Introductionmentioning

confidence: 99%

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Detection of Phenolic Metabolites of Styrene in Mouse Liver and Lung Microsomal Incubations

et al. 2010

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ABSTRACT:Metabolic activation is considered to be a critical step for styreneinduced pulmonary toxicity. Styrene-7,8-oxide is a primary oxidative metabolite generated by vinyl epoxidation of styrene. In addition, urinary 4-vinylphenol (4-VP), a phenolic metabolite formed by aromatic hydroxylation, has been detected in workers and experimental animals after exposure to styrene. In the present study, new oxidative metabolites of styrene, including 2-vinylphenol (2-VP), 3-vinylphenol

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Detection of Phenolic Metabolites of Styrene in Mouse Liver and Lung Microsomal Incubations

et al. 2010

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“…When animals of humans are exposed to styrene, 4-vinylphenol can be identified in the urine as glucuronic acid or sulphate conjugates (Bakke & Scheline, 1970;Pfäffli et al, 1981;Manini et al, 2003). In addition, after intraperitoneal injection of styrene in rats, p-hydroxymandelic acid, phydroxy-benzoic acid and p-hydroxyhippuric acid, which may be secondary metabolites of 4-vinylphenol after oxidation of the vinyl double bond, have been identified (Pantarotto et al, 1978).…”

Section: Ester Hydrolysismentioning

confidence: 99%

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring‐substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)

2007

EFS2

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The Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food is asked to advise the Commission on the implications for human health of chemically defined flavouring substances used in or on foodstuffs in the Member States. In particular, the Scientific Panel is asked to evaluate 23 flavouring substances in the Flavouring Group Evaluation FGE.22, using the procedure as referred to in the Commission Regulation EC No 1565/2000. These 23 flavouring substances belong to chemical groups 21 and 25, Annex I of the Commission Regulation EC No 1565/2000. The present Flavouring Group Evaluation deals with 23 ring-substituted phenolic substances. None of the 23 flavouring substances can exist as geometrical or optical isomers. Twenty of the flavouring substances are classified into structural class I and three are classified into structural class II.

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“…When animals or humans are exposed to styrene, 4-vinylphenol can be identified in the urine as glucuronic acid or sulphate conjugates (Bakke & Scheline, 1970;Pfäffli et al, 1981;Manini et al, 2003). In addition, after intraperitoneal injection of styrene in rats, p-hydroxymandelic acid, p-hydroxy-benzoic acid and phydroxyhippuric acid, which may be secondary metabolites of 4-vinylphenol after oxidation of the vinyl double bond, have been identified (Pantarotto et al, 1978).…”

Section: Vinyl-and Alkoxy-substituted Phenolmentioning

confidence: 99%

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring‐substituted phenolic substances from chemical groups 21 and 25

Flavourings¹

2011

EFS2

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The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the European Food Safety Authority was requested to evaluate 28 flavouring substances in the Flavouring Group Evaluation 22, Revision 1, using the Procedure in Commission Regulation (EC) No 1565/2000. The substance 3,4-methylenedioxyphenol [FL-no: 04.080] was reported to have a genotoxic potential in vitro, while in vivo studies were not available. Therefore, the Panel concluded that the Procedure could not be applied to this substance until adequate genotoxicity data become available. The remaining 27 substances were evaluated through a stepwise approach (the Procedure) that integrates information on structure-activity relationships, intake from current uses, toxicological threshold of concern, and available data on metabolism and toxicity. The Panel concluded that these 27 candidate substances do not give rise to safety concerns at their levels of dietary intake, estimated on the basis of the MSDI approach. Adequate specifications for the materials of commerce are available for all 27 flavouring substances evaluated through the Procedure.

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4-Vinylphenol excretion suggestive of arene oxide formation in workers occupationally exposed to styrene

Cited by 36 publications

References 16 publications

Detection of Phenolic Metabolites of Styrene in Mouse Liver and Lung Microsomal Incubations

Detection of Phenolic Metabolites of Styrene in Mouse Liver and Lung Microsomal Incubations

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring‐substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring‐substituted phenolic substances from chemical groups 21 and 25

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