Scientific Opinion on Brominated Flame Retardants (BFRs) in Food: Brominated Phenols and their Derivatives 1

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1 EFSA Journal 2012;10(4):2634 SCIENTIFIC OPINION Scientific Opinion on ominated Flame Retardants (BFRs) in Food: ominated Phenols and their Derivatives 1 ABSTRACT EFSA Panel on Contaminants in the Food Chain (CONTAM) 2, 3 European Food Safety Authority (EFSA), Parma, Italy EFSA was asked by the European Commission to deliver a scientific opinion on brominated phenols and their derivatives, other than tetrabromobisphenol A (TBBPA) or its derivatives, in food. ominated phenols and their derivatives comprise a complex group of brominated flame retardants, used as reactive as well as additive flame retardants in a large range of resins and polyester polymers. A call for data was issued by EFSA in December No data on brominated phenols or their derivatives were submitted to EFSA. A limited number of occurrence data, covering the food group Fish and other seafood, was identified in the literature. Data from European sampling showed that 2,4,6-tribromophenol (2,4,6-TBP) predominates over the other brominated phenols. Toxicity studies are scarce and mostly relates to 2,4,6-TBP. The main targets are liver and kidneys. In a limited repeated dose oral toxicity study a no-observed-adverse-effect level (NOAEL) for 2,4,6-TBP of 100 mg/kg b.w. per day was identified. 2,4,6-TBP was not genotoxic in bacterial tests in vitro, and not in vivo, but induced chromosomal aberrations in mammalian cells in vitro. No long-term toxicity or carcinogenicity studies with 2,4,6-TBP were identified. The CONTAM Panel concluded that due to the limitations and uncertainties in the current database, the establishment of a health based guidance value for 2,4,6-TBP was not appropriate. Therefore, the Panel derived a margin of exposure to assess the level of possible health concern for high consumers of fish, molluscs and crustaceans. The CONTAM Panel concluded that it is unlikely that current dietary exposure to 2,4,6-TBP in the European Union would raise a health concern. Also exposure of infants to 2,4,6-TBP via breast feeding is unlikely to raise a health concern. Due to lack of data a risk assessment of the other brominated phenols or their derivatives is not possible. European Food Safety Authority, 2012 KEY WORDS ominated phenols, tribromophenol, pentabromophenol, occurrence, food, toxicity, human exposure, risk assessment 1 On request from the European Commission, Question No EFSA-Q , adopted on 21 March Panel members: Jan Alexander, Diane Benford, Alan Boobis, Sandra Ceccatelli, uce Cottrill, Jean-Pierre Cravedi, Alessandro Di Domenico, Daniel Doerge, Eugenia Dogliotti, Lutz Edler, Peter Farmer, Metka Filipič, Johanna Fink- Gremmels, Peter Fürst, Thierry Guerin, Helle Katrine Knutsen, Miroslav Machala, Antonio Mutti, Martin Rose, Josef Schlatter and Rolaf van Leeuwen. Correspondence: 3 Acknowledgement: The Panel wishes to thank the members of the Working Group on ominated Flame Retardants in Food: Åke Bergman, Alan Boobis, Sandra Ceccatelli, Jean-Pierre Cravedi, Metka Filipič, Peter Fürst, Niklas Johansson, Helle Knutsen, Miroslav Machala, Franco Merletti, Olaf Päpke, Dieter Schrenk, Rolaf Van Leeuwen and Stefan Van Leeuwen for the preparatory work on this scientific opinion and EFSA staff: Davide Arcella, Alessandro Carletti, Gina Cioacata and Luisa Ramos Bordajandi for the support provided to this scientific opinion. Suggested citation: EFSA Panel on Contaminants in the Food Chain (CONTAM); Scientific Opinion on ominated Flame Retardants (BFRs) in Food: ominated Phenols and their Derivatives. EFSA Journal 2012;10(4):2634. [42 pp.] doi: /j.efsa Available online: European Food Safety Authority, 2012

2 SUMMARY Following a request from the European Commission, the Panel on Contaminants in the Food Chain (CONTAM Panel) was asked to deliver a scientific opinion on brominated phenols and their derivatives in food. The present opinion will focus on brominated phenolic compounds and their derivatives, other than tetrabromobisphenol A (TBBPA) or TBBPA derivatives, since the latter have been dealt with separately in a previous opinion by the CONTAM Panel. ominated phenols and their derivatives comprise a complex group of brominated flame retardants (BFRs). ominated phenols that have been identified as flame retardants include 2,4-dibromophenol (2,4-DBP), 2,4,6-tribromophenol (2,4,6-TBP), pentabromophenol (PBP), and tetrabrominated bisphenol S (TBBPS). 2,4,6-TBP, PBP and TBBPS are precursors of four non-phenolic derivatives also being applied as BFRs, i.e. TBP allyl ether (TBP-AE), PBP allyl ether (PBP-AE), TBP 2,3-dibromopropyl ether (TBP-DBPE) and TBBPS bis(2,3-dibromopropyl ether) (TBBPS-BDBPE). These brominated phenols and their derivatives are used as reactive as well as additive flame retardants in a large range of resins and polyester polymers. Several of the commercially produced brominated phenols also occur as natural products in the marine environment. A call for data on BFRs including brominated phenols was issued by the European Food Safety Authority (EFSA) in December No data on brominated phenols or their derivatives considered in this opinion were submitted to EFSA. A limited number of occurrence data was identified in the literature. Data from European sampling showed that 2,4,6-TBP predominates over the other brominated phenols. Levels of 2,4,6-TBP in fish meat of perch and Arctic char from < 0.03 to 3.5 ng/g wet weight (w.w.) were reported. Higher levels were reported for blue mussels (3.2 to 13 ng/g w.w.) and cod liver (86 ng/g w.w.). These data cover one food group only, Fish and other seafood, and therefore a meaningful exposure assessment for the general population is not possible. In order to provide some indication of whether there could be a possible health concern with respect to dietary exposure to 2,4,6-TBP, the CONTAM Panel made a tentative exposure estimate for the specific group of adult high consumers of fish, molluscs and crustaceans. The worst case exposure estimate for this population group was 40 ng/kg body weight (b.w.) per day. Data on levels of brominated phenols in human milk are too limited to perform a meaningful risk assessment for breast-fed infants. In order to obtain a rough idea about the magnitude of exposure via human milk, the data on 2,4,6-TBP in one pooled sample of Norwegian human milk were used for a tentative exposure estimate. For 3 months old breast-fed infants with an average human milk consumption (800 ml per day) the concentration of 2,4,6-TBP human milk would result in a daily exposure of 3 ng/kg b.w. For infants with high human milk consumption (1 200 ml per day) the daily exposure would be 4 ng/kg b.w. The limited toxicokinetics data suggest that, following oral administration to rats, 2,4,6-TBP is rapidly absorbed, distributed in different tissues such as kidney, lung and liver and eliminated, mainly via urine, within 48 hours. No information was found on metabolic pathways of 2,4,6-TBP. No data on the other brominated phenols considered in this opinion were identified. Data on the toxicity of brominated phenols are generally lacking and most of the sparse information available relates to 2,4,6-TBP. In a few short-term oral toxicity studies in rats, liver and kidneys were the main targets. In a repeated dose oral toxicity study, which was combined with a reproduction/developmental toxicity screening test, a no-observed-adverse-effect level (NOAEL) for 2,4,6-TBP of 100 mg/kg b.w. per day was identified. In the reproduction/developmental phase of this study, reduced neonatal viability and reduced neonatal body weights were observed at a dose of mg/kg b.w. per day. The NOAEL for developmental toxicity was 300 mg/kg b.w. 2,4,6-TBP did not induce gene mutations in bacterial cells, but induced chromosomal aberrations in mammalian cells. In vivo, no increase in micronuclei formation in bone marrow of mice was found. No long-term toxicity or carcinogenicity studies with 2,4,6-TBP were identified. EFSA Journal 2012;10(4):2634 2

3 The CONTAM Panel concluded that due to the limitations and uncertainties in the current database, the establishment of a health based guidance value for 2,4,6-TBP was not appropriate. Therefore, the Panel derived a margin of exposure to assess the level of possible health concern. Comparison of the NOAEL for 2,4,6-TBP of 100 mg/kg b.w. with the worst case dietary exposure estimate of 40 ng/kg b.w. per day for high consumers of fish, molluscs and crustaceans, results in an estimated margin of exposure of about six orders of magnitude. This margin of exposure is, however, so large that the CONTAM Panel concluded that it is unlikely that current dietary exposure to 2,4,6-TBP in Europe would raise a health concern. For breast-fed infants with average or high human milk consumption a margin of exposure of about seven orders of magnitude was estimated. Although the exposure estimate was only based on one pooled sample of Norwegian human milk, this margin is so large, that the CONTAM Panel concluded that it is unlikely that exposure to 2,4,6-TBP via breast feeding in Europe would raise a health concern. Due to lack of data a risk assessment of the other brominated phenols or their derivatives is not possible. The CONTAM Panel recommended that information on production rates and use of brominated phenols should be obtained, and that data on occurrence in food, especially of marine origin, should be generated. EFSA Journal 2012;10(4):2634 3

4 TABLE OF CONTENTS Abstract... 1 Summary... 2 Table of contents... 4 Background as provided by the European Commission... 6 Terms of reference as provided by the European Commission... 6 Assessment Introduction General information Previous risk assessments Chemical characteristics Legislation Sampling and methods of analysis Sampling Methods of analysis Sources, use and environmental fate Formation and production Use ominated phenols in the environment including natural formation Air Water, sediment, soil and plants Occurrence and bioaccumulation in wildlife Combustion Occurrence of brominated phenols and their derivatives in food Current occurrence of brominated phenols and their derivatives in food: call for data Previously reported literature data on occurrence of brominated phenols and their derivatives Occurrence in Food Effects of processing Occurrence in human milk Food consumption EFSA s Comprehensive European Food Consumption Database High consumers of fish, crustaceans and molluscs east-fed infants Human exposure assessment Dietary exposure to specific sub-groups of the population east-fed infants Previously reported data on dietary intake of brominated phenols and their derivatives Non-dietary exposure Hazard identification Toxicokinetics Biomarkers of exposure Toxicity Single and repeated dose toxicity studies ,4-DBP ,4,6-TBP PBP Developmental and reproductive toxicity Genotoxicity Carcinogenicity Biochemical effects and molecular mechanisms Observation in humans Consideration of critical effects and possibilities for derivation of a health based guidance value EFSA Journal 2012;10(4):2634 4

5 9. Risk characterization Uncertainty Assessment objectives Exposure scenarios/exposure model Other uncertainties Summary of uncertainties Conclusions and recommendations References Abbreviations EFSA Journal 2012;10(4):2634 5

6 BACKGROUND AS PROVIDED BY THE EUROPEAN COMMISSION ominated flame retardants (BFRs) are anthropogenic chemicals that are added to a wide variety of consumer/commercial products in order to improve their fire resistance. There are 5 major classes of BFRs: brominated bisphenols, diphenyl ethers, cyclododecanes, phenols and phthalic acid derivatives. Concern has been raised because of the occurrence of several chemical compounds from the group of BFRs in the environment, including feed and food, and in human biota. This has led to bans on the production and use of certain formulations of polybrominated diphenyl ethers (PBDEs). EFSA concluded in its advice on a request from the Commission related to relevant chemical compounds in the group of brominated flame retardants for monitoring in feed and food of 24 February 2004 that the available occurrence data on brominated flame retardants in feed and food did not allow a comprehensive assessment of contamination in all feeds and foods and identified the following compounds as the most important ones to be monitored based on the analytical feasibility to measure the chemical compounds routinely in accredited laboratories, the production volumes, the occurrence of the chemical compounds in food and feed, their persistence in the environment and their toxicity: - polybrominated diphenyl ethers (PBDEs): BDE congeners #28, 47, 99, 100, 153, 154, 183 and hexabromocyclododecane (HBCD): total amount (isomer specific analysis of a limited number of samples and/or pools in case of significantly elevated levels or increasing trends). - polybrominated biphenyls (PBBs): BB congener #153. Optionally, the following brominated flame retardants were recommended to be monitored: - TBBP-A and other phenols - decabromodiphenyl ethane - hexabromobenzene - bis(2,4,6-tribromophenoxy)ethane Subsequently EU-wide monitoring of these compounds was organised as of October Monitoring results will be made available to EFSA. In order to assess the need for regulatory measures as regards BFR in food, EFSA is requested to assess the risks related to the presence of BFR in food. TERMS OF REFERENCE AS PROVIDED BY THE EUROPEAN COMMISSION In accordance with Art 29 (1) of Regulation (EC) No 178/2002, the European Commission asks the European Food Safety Authority for a scientific opinion on the risks to human health related to the presence of brominated phenols and their derivatives in food. In particular, the opinion should - evaluate the toxicity of brominated phenols and their derivatives for humans considering all relevant toxicological information available; - carry out an exposure assessment on the basis of the occurrence data obtained in the monitoring exercise and other occurrence data that may be available; EFSA Journal 2012;10(4):2634 6

7 - consider the exposure situation for specific groups of the population (e.g. infants and children, people following specific diets, etc.) and indicate the relative importance from other nondietary sources; - take into account, if available, biomonitoring data when assessing the exposure and compare the results with the calculated exposure; - explore whether individual compounds can be used as markers for dietary exposure to these BFRs; - identify potential data gaps for these BFRs, EFSA Journal 2012;10(4):2634 7

8 ASSESSMENT 1. Introduction 1.1. General information Flame retardants include a broad and diverse group of compounds used to prevent fires or at least to slow down the development of a fire. There are three main categories of chemical flame retardants: halogenated hydrocarbons, organophosphorous compounds and inorganic products often based on metallic hydroxides (Vos et al., 2003). Within the halogenated hydrocarbons, the group of the brominated flame retardants (BFRs) consists of a number of chemicals with different physicochemical properties and uses. The main BFRs are the polybrominated (i) neutral aromatic, (ii) neutral cycloaliphatic, (iii) phenolic, including neutral derivatives, (iv) aromatic carboxylic acid esters and (v) trisalkyl phosphate compounds (WHO/IPCS, 1997; Andersson et al., 2009; Harju et al., 2009; de Wit et al., 2011). The major BFRs within these five classes are, respectively, polybrominated diphenyl ethers (PBDEs), hexabromocyclododecanes (HBCDDs 4 ), tetrabromobisphenol A (TBBPA), 2,4,6-tribromophenol-bis(2-ethylhexyl) tetrabromophthalate (BEHTBP) and tris[3-bromo- 2,2-bis(bromomethyl)propyl] phosphate (TTBNPP). The present opinion will focus on brominated phenolic compounds and their derivatives, other than TBBPA or TBBPA derivatives. The latter have been dealt with separately in a previous opinion by the Panel on Contaminants in the Food Chain (CONTAM Panel). The compounds considered in this opinion are listed together with their abbreviations in Tables 1 and 2. Numerous brominated phenols occur as natural products, including some di- and tribromophenols (Whitfield et al., 1999; Gribble, 2000, 2010). Hence, some of the brominated phenols are both natural products and manmade commercial chemicals for application as BFRs Previous risk assessments The World Health Organisation (WHO, 2005) evaluated the available toxicological information on 2,4,6-tribromophenol (2,4,6-TBP) and other simple brominated phenols. No short-, medium-, or long-term toxicity data were identified for the lower brominated phenols or for pentabromophenol (PBP). A few toxicity studies with 2,4,6-TBP were identified. In a repeated-dose toxicity study combined with a reproduction/developmental toxicity screening test by Tanaka et al. (1999), Sprague- Dawley rats were administered doses of 0, 100, 300 or mg/kg body weight (b.w.) per day by gavage. No reproductive or developmental effects were seen at a dose of 300 mg/kg b.w. per day, but at that dose salivation was observed in both sexes, and a significant increase in creatinine in blood was found in males. The WHO concluded that the no-observed-adverse-effect level (NOAEL) for repeated dose oral toxicity was 100 mg/kg b.w. per day for both sexes, and that exposure of the general population to 2,4,6-TBP was through drinking water and the consumption of seafood, and that the brominated phenols in seafood were of natural origin. Since the only reported short-term toxicity study by the oral route was a screening test, and no biochemical or histopathological observations were performed with females, the WHO could not establish a reliable tolerable daily intake for 2,4,6-TBP for drinking water or food (WHO, 2005) Chemical characteristics The brominated phenols that are used as BFRs include, apart from TBBPA and its derivatives, three brominated phenols, an alkyl-substituted tribromophenol and tetrabrominated bisphenol S (TBBPS), i.e. a compound with a sulfone group between the phenol groups. The structure of 2,4-dibromophenol (2,4-DBP), 2,4,6-TBP and PBP and their derivatives are presented in Figure 1. TBP allyl ether 4 HBCDDs is used as the abbreviation for hexabromocyclododecanes (1,2,5,6,9,10-hexabromocyclododecane, CAS No ) instead of HBCD in this document, to avoid misunderstandings. HBCD is occasionally used as an abbreviation of hexabromocyclodecane (CAS No ). EFSA Journal 2012;10(4):2634 8

9 (TBP-AE) is pre-registered by the European Chemicals Agency (ECHA) under the name: 2-(allyloxy)- 1,3,5-tribromobenzene. Some of their physico-chemical characteristics are given in Table 1. ominated phenols are slightly acidic compounds with pk a values between 4 and 8 (Scifinder, 2012). Tribromophenol-2,3-dibromopropyl ether (TBP-DBPE) has a chiral center, leading to the occurance of two enantiomers which both have been synthesized and characterized (von der Recke and Vetter, 2007). OH 2,4-DBP 2,4,6-TBP PBP TBPD-TBP O O O TBP-AE PBP-AE TBP-DBPE Figure 1: Chemical structures of 2,4-dibromophenol (2,4-DBP), 2,4,6-tribromophenol (2,4,6-TBP), pentabromophenol (PBP) and 3-(tetrabromopentadecyl)-2,4,6-tribromophenol (TBPD-TBP) are presented in the upper row. In the second row the structures of the 2,4,6-TBP allyl ether (TBP-AE) (left) and PBP allyl ether (PBP-AE) (middle) are presented, as well as that of TBP 2,3-dibromopropyl ether (TBP-DBPE) (far right). ominated phenols are technically produced by bromination of phenol to contain 2, 3 or 5 bromine substituents. Polybrominated dibenzo-p-dioxins and dibenzofurans are known by-products from polybromophenol production and transformation products thereof (WHO/IPCS, 1998). Table 1: Physico-chemical characteristics of 2,4-dibromophenol (2,4-DBP), 2,4,6-tribromophenol (2,4,6-TBP), pentrabromophenol (PBP) and their derivatives (Scifinder, 2012). CAS number MW Log k ow pk a Vapour pressure (Torr) 2,4-DBP ,4,6-TBP PBP TBPD-TBP n.a. n.a. n.a. TBP-AE PBP-AE TBP-DBPE n.a.: not available. EFSA Journal 2012;10(4):2634 9

10 The structures of TBBPS and its two derivatives (tetrabromobisphenol S bismethyl ether (TBBPS- BME) and tetrabromobisphenol S bis(2,3-dibromopropyl ether) (TBBPS-BDBPE)) are presented in Figure 2. Some of their physico-chemical characteristics are given in Table 2. TBBPS is prepared by bromination of bisphenol S, and it is characterized by its potential for ionization and its acidic character, more than TBBPA, due to the sulfone bridge between the two phenol rings. Only one pk a has hitherto been reported for TBBPS (Scifinder, 2011), but as for TBBPA, two pk a values are to be expected. The low pk a value (3.5) for TBBPS will cause the compound to be entirely ionized at neutral or physiological ph. The byproducts present in TBBPS are not yet known. Based on the manufacturing procedure it is likely that TBBPS has traces of isomers and lower brominated congeners, similar to TBBPA. Each of the TBBPS derivatives (Figure 2) is produced individually, not as a mixture. Still, the purity of the compounds is a matter of the technical quality of the parent product which means that there may be small amounts/traces of by-products present in the commercial products. To the best of our knowledge TBBPS and its derivatives have not been tested in relation to their inheritant chemical reactivity in the environment or in biota. HO OH O O O O S O 2 S O 2 S O 2 TBBPS TBBPS-BME TBBPS-BDBPE Figure 2: Chemical structure of tetrabromobisphenol S (TBBPS) and its derivatives tetrabromobisphenol S bismethyl ether (TBBPS-BME) and tetrabromobisphenol S bis(2,3- dibromopropyl ether) (TBBPS-BDBPE). Table 2: Physico-chemical characteristics of TBBPS and its derivatives (TBBPS-BME and TBBPS-DBPE) (Scifinder, 2011). CAS number MW Log K ow pk a Vapour pressure (Torr) TBBPS (a) TBPPS-BME TBBPS-BDBPE (a): Only one pk a value found due to its origin as a modelled value. 2. Legislation In order to protect public health, Article 2 of Council Regulation (EEC) No 315/93 5 of 8 February 1993 laying down Community procedures for contaminants in food stipulates that, where necessary, maximum tolerances for specific contaminants shall be established. Thus, a number of maximum tolerances are currently laid down in Commission Regulation (EC) No. 1881/ of 19 December 2006 setting maximum levels for certain contaminants, e.g. dioxins, dioxin-like and non dioxin-like polychlorinated biphenyls (PCBs) and several polycyclic aromatic hydrocarbons in foodstuffs. ominated phenols are not regulated so far under this Regulation or under any other specific European Union (EU) regulation for food. 5 Council Regulation (EEC) No 315/93 of 8 February 1993 laying down Community procedures for contaminants in food. OJ L 37, , p Commission Regulation (EC) No 1881/2006 of 19 December 2006 setting maximum levels for certain contaminants in foodstuffs. OJ L 364, , p EFSA Journal 2012;10(4):

11 According to WHO (2005), 2,4,6-TBP is registered as a wood preservative in South America. For example, the pesticide register for Chile reveals that three products based on the sodium tribromophenol salt are approved for use as a fungicide treatment (two manufacturers in Chile and one in azil). However, it is not registered as a pesticide in the EU and is not known to be registered in other parts of the world (WHO, 2005). If a pesticide is not registered in the EU and thus not included in any of the Annexes of Regulation (EC) No. 396/2005, 7 according to Art. 18 (1b) of this Regulation a default maximum residue level (MRL) of 0.01 mg/kg applies. Council Directive 2002/32/EC 8 regulates undesirable substances in animal feed. While maximum levels are set for a number of inorganic and organic contaminants in various feed materials, no brominated phenols are so far regulated by either the European Commission (EC) under this Directive or under the Stockholm or Long-Range Transboundary Air Pollution (LRTAP) conventions. Amongst the brominated phenols considered in this opinion (Table 1 and 2), 2,4,6-TBP is a registered substance under the Regulation, Evaluation and Authorisation of Chemicals (REACH) regulation, 9 while according to the information provided on the ECHA website 10 the remaining brominated phenols are pre-registered substances, except for TBPD-TBP and TBBPS-BME. 3. Sampling and methods of analysis 3.1. Sampling There are no specific guidelines for the sampling of foods to be analysed for their 2,4-DBP, 2,4,6-TBP or PBP (and derivatives) and TBBPS (and derivatives) content. Therefore, basic rules for sampling of organic contaminants or pesticides should be followed. Respective requirements are for example laid down in Commission Regulation (EC) No 1883/ of 19 December 2006 for methods of sampling and analysis for the official control of dioxins and dioxin-like PCBs in certain foodstuffs. This Regulation contains inter alia a number of provisions concerning methods of sampling depending on the size of the lot, packaging, transport, storage, sealing and labelling. The primary objective is to obtain a representative and homogeneous laboratory sample with no secondary contamination Methods of analysis The analytical method starts with the isolation of the target analytes from the sample matrix. ominated phenols are rather volatile analytes when substituted with one or two bromine atoms, otherwise they can be regarded as semi-volatile. Volatile brominated phenols are flavour components in seafood and from that perspective, several methods release the analytes from the matrix by volatilisation. Steam distillation extraction (SDE) with a pentane-diethylether (DEE) mixture was applied by Mota da Silva et al. (2005) for extraction of several brominated phenols from fish. Whitfield et al. (1997) performed SDE (with pentane/dee) for extraction of several brominated phenols in prawn samples and Fuller et al. (2008) also used SDE followed by acetylation and solid phase microextraction (SPME). Generally no clean-up is employed with these methods. Acidification (e.g. to ph = 1) improves extraction efficiency by keeping the brominated phenols protonated. The ph should be at least two units lower than the pk a value of the polybromophenol. In none of these studies, were PBP nor polybromophenol derivatives analysed as they are not flavour components. 7 Regulation /EC) No 396/2006 of the European Parliament and of the Council of 23 February 2005 on maximum residue levels in or in food and feed of plant and animal origin and amending Council Directive 91/414/EEC. OJ L 70, , p Directive 2002/32/EC of the European Parliament and of the Council of 7 May 2002 on undesirable substances in animal feed. OJ L 140, , p a1a-84f4-94ee329f3519_DISS-9c79e4eb-ef e f67d249.html#section_1.1 (accessed on ) 10 (accessed on ) 11 Commission Regulation (EC) No 1883/2006 of 19 December 2006 laying down methods of sampling and analysis for the official control of levels of dioxin and dioxin-like PCBs in certain foodstuffs. OJ L 364, , p EFSA Journal 2012;10(4):

12 In other studies, the brominated phenols and their derivatives were analysed from an environmental contamination perspective. In these studies, similar approaches were used as for e.g. PBDEs and HBCDs. Papachlimitzou et al. (2011) reviewed the analysis of brominated phenols and derivatives. Extraction of these analytes from biota samples is carried out using microwave assisted extraction (MAE), Soxhlet extraction and pressurised liquid extraction (PLE) (Papachlimitzou et al., 2011). Column extraction has also been employed (Klif, 2010). In most cases, medium-polar solvents or solvent mixtures were used (e.g. cyclohexane/acetone and dichloromethane/n-hexane) for efficient extraction. Clean-up and fractionation of biota samples is mostly performed, as with other BFRs, in a two-step process. According to the review by Papachlimitzou et al. (2011), several studies used gel permeation chromatography (GPC), followed by adsorption chromatography (e.g. aluminaoxide, silica, acidified silica or Florisil) for further clean-up and fractionation. Concerning liquid samples, PBP and 2,4,6-TBP were extracted from blood using solid phase extraction (SPE) (Thomsen et al., 2001a). A similar approach was taken for the extraction of human milk (Thomsen et al., 2002a). Clean-up was performed by sulphuric acid directly on the SPE column or on a sulphuric acid coated silica column. Instrumental analysis, i.e. chromatographic separation and detection, of brominated phenols is mostly performed with gas chromatography (GC) equipped with a capillary column and coupled to mass spectrometry (MS). For the chromatographic separation, mostly apolar or slightly polar stationary phases are used (Papachlimitzou et al., 2011). Column lengths of 10 up to 50 m have been used. Vetter et al. (2010) separated enantiomers of TBP-DBPE on an enantioselective GC column. Derivatisation of the brominated phenols may be applied for improving chromatography and detector responses. Thomsen et al. (2001a) used diazomethane derivatisation combined with electron capture negative ionisation (ECNI) MS (methane as reagent gas). This resulted in very low limits of detection (LOD), below 1 pg/g plasma. Other derivatising agents include bis-(trimethylsilyl)-trifluoroacetamide and acetic anhydride (Papachlimitzou et al., 2011). Rosenfelder and Vetter (2009) tried nitrogen as reagent gas for ECNI-MS detection of 2,4,6-TBP, but without satisfactory results. Whitfield et al. (1997) used a 5 m uncoated deactivated retention gap preceding the capillary GC column in order to protect the column from co-extracted fatty acids. They used electron impact ionisation (EI) MS and achieved LODs of 10 pg/g product in prawn samples. Detection is mostly done using ECNI-MS and monitoring of the bromine ions (m/z 79 and 81). This is a very sensitive technique, and sensitivity increases with an increasing number of bromines in the molecule. EI-MS has also been used for detection of brominated phenols without (Chung et al., 2003a) or after derivatisation (Thomsen et al., 2001a; Papachlimitzou et al., 2012). A benefit of derivatisation is that it may improve the specificity of the detection, as compared to the less specific GC-ECNI-MS approach. Care should be taken as brominated phenols and derivatives may co-elute with PBDEs, which may also be present in the extract. This may lead to false positive results when using non-specific detection methods (e.g. GC-ECNI-MS). Separation and detection of 2,4-, 2,6-DBP and 2,4,6-TBP is also achieved using high performance liquid chromatography (HPLC) coupled with ultraviolet (UV) detection (wavelength 286 nm) (Mota da Silva et al., 2005). This method is fairly simple, but at the cost of higher detection limits compared to the GC approaches. Zhou et al. (2010) and Letcher and Chu (2010) developed an HPLC approach with atmospheric pressure photoionisation (APPI)-MS/MS detection for TBBPS-BDBPE, TBP-AE and TBP-DBPE. Low limits of queantification (LOQs) were achieved (mostly < 1 ng/g w.w.). Chromatography is usually performed on reversed phase (C18 phase) columns. Vetter et al. (2010) separated the two enantiomers of TBP-DBPE using an enantioselective LC column. Quality control (QC) and quality assurance (QA) The analysis of brominated phenols is laborious and complex and involves several critical steps. Errors are easily made in extraction, cleanup, GC determination and quantification. A number of EFSA Journal 2012;10(4):

13 factors determine the final accuracy and precision (i.e. the quality) of the results reported. Although the studies cited above did not report specific precautions, caution should be taken when analysing these compounds, just as with other BFRs (e.g. PBDEs and HBCDDs) and trace analysis of micropollutants in general. For BFRs in general, exposure to UV radiation should be avoided as it may lead to degradation, and all analytical work should be carried out in such a manner that UV light is excluded. Exposure to high temperatures should most likely also be avoided, to prevent degradation. Problems with blanks can be minimised by avoiding contact with dust particles at every stage of sampling, pretreatment and analysis. Commercial standards for instrument calibration are available for the brominated phenols and several derivatives (except e.g. the TBBPS derivatives). Isotope labelled internal standards for polybromophenols and derivatives are lacking. Interlaboratory studies and certified reference materials (CRMs) So far, no interlaboratory studies have been reported on the analysis of brominated phenols (and derivatives) and TBBPS (and derivatives). Standard or Certified Reference Materials (SRM, CRM) are important tools for laboratory performance evaluation against external references. However, such reference materials are lacking. 4. Sources, use and environmental fate A large number of brominated aromatic compounds including brominated phenols are found in marine organisms as naturally occurring metabolites. This makes it difficult to assess the relative contribution of anthropogenic brominated phenols in relation to the corresponding natural products in food of marine origin. The situation is even more complex since, in addition to the application as BFR, there could be other technical applications for some of these polybrominated phenols Formation and production 2,4-DBP is produced as a flame retardant but also as an intermediate for other flame retardants (US EPA, 1987). It has not been possible to identify any reliable information on production sites or volumes. Both 2,4- and 2,6-DBP are naturally produced in the marine environment (Whitfield et al., 1999; Gribble, 2000, 2010). This is discussed further in Section 4.3. Covaci et al. (2011) indicated that 2,4,6-TBP is, or has been, produced in China, in Japan (3 600 tonnes in 2003), and in the US (4 500 to tonnes in 2006) and that it is considered a High Production Volume Chemical (HPVC) in the EU, i.e. a substance produced or imported in quantities in excess of tonnes per year. 2,4,6-TBP has also been shown to be formed when drinking water containing phenol and bromine is chlorinated (Sweetman and Simmons, 1980). Formation of chlorinated/brominated phenols, above all 2,4,6-TBP, has also been demonstrated from the chlorination of wastewater from a sewage plant (Watanabe et al., 1984). This could be a source of environmental contamination with 2,4,6-TBP in certain areas. 2,4,6-TBP can also be formed as a metabolite from certain PBDEs (Qiu et al., 2009) and it has been identified as an impurity in commercial BTBPE products (Suzuki et al., 2008). 2,4,6-TBP is also naturally produced in the marine environment (Whitfield et al., 1999; Gribble, 2000, 2010). This is discussed further in Section 4.3. Trade names and synonyms identified for 2,4,6-TBP are 1,3,5-Tribromo-2-hydroxybenzene, omkal Pur 3, omol, Flammex 3BP, NSC 2136, PH 73, PH-73FF and FR-613, TBP. PBP is produced as a BFR but the quantities are not known. A total of 55 sources, among which some are for authentic reference purposes only, are identified by Scifinder (2012). The primary commercial sources are located in the USA and China. Trade names and synonyms identified for PBP are Pentabromophenol, omophenasic acid, Flammex 5BP, NSC 5717 and Perbromophenol. TBPD-TBP is not a preregistered chemical within REACH and it has no known trade name(s). It is a patented BFR (Indian (2004), IN A ) described in some detail by Menon et al. (1995). However, there is as yet no bulk production of this BFR (Scifinder, 2012). EFSA Journal 2012;10(4):

14 TBP-AE is produced as a reactive, as well as an additive, flame retardant in polystyrene. The US production in 2006 was 227 tonnes (US EPA, 2006). Only two commercial sources are listed for this BFR by Scifinder (2012). Also a limited number of bibliographic references (54) are indicated. It has been shown that TBP-AE can be formed as a transformation product of 2,4,6-tribromophenyl 2,3- dibromopropyl ether (von de Recke and Vetter, 2007). Trade names for TBP-AE are NSC 35767, Pyroguard FR 100, omkal 64-3AE and PHE-65. TBP-DBPE was manufactured in Germany and sold as omkal 73-5PE until the mid 1980s, and it is still available as a commercial product from the USA under this trade name (Scifinder, 2012). PBP-AE is known under the trade name Flammex 5AE. Data on current production and use as a flame retardant are not known (Scifinder, 2012). TBBPS is commercially available from ca. 60 suppliers globally. It is known under trade names as EB 400S, FG 400S, Flame Cut 160R, NFPP and Tetrabromobisphenol S. TBBPS-BME is not a pre-registered chemical within REACH and no trade names have been identified. There does not appear to be any bulk production of this BFR. It is available as an authentic reference standard for chemical analysis. TBBPS-BDBPE is available from more than 40 commercial suppliers around the world. It is, or has been offered on the market under trade names such as Flame Cut 161R, Nonnen 52, Nonnen PR 2 and PR Use The two compounds, TBPD-TBP and TBBPS-BME, with no known commercial production as BFRs are not further discussed in this opinion. Although the phenolic, non-tbbpa, BFRs and their derivatives have trade names, indicating their commercial uses, it is not fully clear to what extent they are used as flame retardants. 2,4-DBP, 2,4,6-TBP and PBP are used as reactive flame retardants in epoxy resins, phenolic resins, polyester resins, polyolefins (WHO/IPCS, 1997; Weil and Levchik, 2009) and vinyl-aromatic polymers (Scifinder, 2012). 2,4,6-TBP is also used as a fungicide, e.g. for the treatment of wood (see Section 2). Moreover, 2,4,6-TBP is a common precursor for other BFRs, such as TBP-AE, TBP- DBPE, 1,2-bis(2,4,6-tribromophenoxy)ethane and 2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine. PBP is a precursor for PBP-AE. TBP-AE is used as a reactive as well as an additive flame retardant in e.g. expandable polystyrene (EPS) and foam. It may also be used as a synergist for aromatic BFRs in applications where maximum process temperatures do not exceed 150 C. TBP-DBPE has at least been suggested for use in polypropylene, thermostabilized styrene polymers, polyurethane foams, but it has not been possible to obtain any firm data. As there is only one commercial supplier of the compound, its use may be limited. TBBPS may be used as a reactive BFR but also as an additive, similar to TBBPA, but no firm information on this has been identified TBBPS is used in thermal recording materials, in polypropylene, polyolefin and polyester polymers TBBPS-BDBPE is reported to be an additive flame retardant with use in electronic equipment (TV sets) (Dettmer et al. 1999). It has been reported to be used in polystyrene foam (Andersson et al., 2006), polypropylene, polyethylene, polyolefin, polyester materials and in thermoplastic resins (Scifinder, 2012). EFSA Journal 2012;10(4):

15 4.3. ominated phenols in the environment including natural formation Emerging brominated flame retardants, e.g. 1,4-bis(pentabromophenoxy)tetrabromobenzene and 2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine and others might degrade into more bioavailable compounds such as PBP and 2,4,6-TBP. It should therefore be noted that brominated phenols found in the environment could, in part, result from degradation processes. Furthermore, it has been shown by many authors that numerous brominated aromatic compounds, e.g. 2- and 4- bromophenol, 2,4- and 2,6-DBP and 2,4,6-TBP, are found naturally in a number of different marine organisms, e.g. algae and polychaetans (Anthoni et al., 1990; Whitfield et al., 1999; Flodin and Whitfield, 2000; Fielman et al., 2001; Chung et al., 2003a,b). The compounds are common marine secondary metabolites, and biosynthesized in the presence of bromoperoxidases, hydrogen peroxide, and bromide. ominated phenols have also been found in other marine organisms such as algae, sponges, hemichordates, ascidians and polychaetes. Thus, brominated phenols of natural origin can reach crustaceans and fish via ecological food chains. There are multiple sources that may explain their presence in various environmental compartments. Its presence in marine water (Vetter et al., 2009), sediments (Sim et al., 2009), invertebrates (Löfstrand et al., 2010), and fish (Chung et al., 2003a,b; Wan et al., 2009) seems to be mainly the result of natural production. The ecological function of brominated phenols is not yet clear, but some may play a role in chemical defence and deterrence. Many brominated compounds are also found in terrestrial ecosystems in bacteria, fungi, plants, insects but also in higher animals but no information on the formation of phenols is available from terrestrial or limnic ecosystems (Gribble, 2000, 2010). The presence of 2,4,6-TBP in vegetation collected in the vicinity of sawmills in Chile is probably related to its use as a fungicide on wood and products thereof (Mardones et al., 2003). The presence of naturally occurring brominated phenols in food has been shown to cause an unpleasant taste in a number of types of marine seafood, such as crustaceans and fish. The flavour threshold concentration for 2,6-DBP, 2-BP and 2,4,6-TBP has been estimated to be , 0.03 and 0.6 ng/g, respectively (Whitfield et al., 1998) Air 2,4-DBP concentrations from background (i.e. remote from known point sources) and urban areas in Denmark, Norway and Sweden are reported in the range of < pg/m 3 (Nordic Council of Ministers, 2011). In the same study, concentrations recorded in indoor air were always below the LOQ of 60 pg/m 3. The CONTAM Panel noted that differences in sampling procedures for outdoor and indoor air may be the reason for the apparent differences in LOQs. In flue gas from a hazardous waste incinerator, Öberg et al. (1987) found concentrations between and < pg/m 3 for 2,4-DBP and 2,6-DBP, respectively. 2,4,6-TBP concentrations from the same background and urban areas as for 2,4-DBP (see above) are reported in the range of < pg/m 3, whereas the levels measured in indoor air were always below the LOQ of 20 pg/m 3 (Nordic Council of Ministers, 2011). Saito et al. (2007) reported concentrations in indoor air from 18 Japanese homes in the range of < pg/m 3. The levels in 14 Japanese offices were < pg/m 3. The CONTAM Panel noted that the LOQ of this study was pg/m 3. In flue gas from a hazardous waste incinerator concentrations up to pg/m 3 were found (Öberg et al., 1987). For PBP, there are very few data, but concentrations from Norwegian sites classified as background locations and in urban areas are reported to be in the range of < 0.5 pg/m 3 and < pg/m 3, respectively, whereas the levels recorded in indoor air were always below the LOQ (100 pg/m 3 ) (Nordic Council of Ministers, 2011). Saito et al. (2007) reported concentrations in indoor air from 14 Japanese offices ranging from <1 100 to pg/m 3. TBP-DBPE has been identified in indoor air at levels approximately between pg/m 3, in background outdoor air between pg/m 3, and in urban air up to 3.2 pg/m 3 (Nordic Council of Ministers, 2011). EFSA Journal 2012;10(4):

16 Water, sediment, soil and plants 2,4-DBP has been analysed in brackish water (Baltic proper) at levels between < 5 and 35 ng/l (Remberger et al., 2002). Considerably higher concentrations were reported from an Indian river, ranging from 540 to ng/l (Nomani et al., 1996). 2,4-DBP has also been analysed in soil and sediment in Sweden by Remberger et al. (2002). Sediment from the Baltic proper show concentrations between < 5 and 13 ng/g dry weight and soil from a background area was reported to contain < 3-15 ng/g dry weight. The same authors also reported concentrations in sewage sludge between < 0.04 and 40 ng/g dry weight, while Fielman et al. (2001) reported 2 ng/g dry weight in marine sediments from a background area. In the report of the Nordic Council of Ministers (2011) concentrations in sediments from <0.03 (LOD) to 2.9 ng/g dry weight were reported, with the highest concentration reported from the Faroe Islands. For 2,4,6-TBP, in the German Bight concentrations up to 6 ng/l have been reported for water according to Møskeland (2010). Fielman et al. (2001) reported concentrations in marine sediments of 4-30 ng/g dry weight. In the report of the Nordic Council of Ministers (2011) concentrations in sediments are reported to be between LOD and 7.8 ng/g dry weight, and the highest concentration was reported from the Faroe Islands. Sauer et al. (1997, as referred by von der Recke and Vetter (2007)) reported levels in German sewage sludge up to ng/g dry weight. In sewage sludge from the Nordic countries concentrations ranged between < 0.01 and 100 ng/g dry weight (Nordic Council of Ministers, 2011). In plants, brominated phenols have only been analysed in a small number of samples. On the Faroe Islands, 2,4-DBP and 2,4,6-TBP were found in concentrations of 0.53 and 0.46 ng/g dry weight, respectively in moss samples (Nordic Council of Ministers, 2011). As these were moss samples, these levels rather reflect deposition from air rather than uptake from soil or other substrates. TBP-DBPE was found in one Norwegian sediment sample from Åsefjorden showing a concentration of 0.5 ng/g dry weight (Nordic Council of Ministers, 2011) Occurrence and bioaccumulation in wildlife Only a few studies have been indentified reporting the concentrations of brominated phenols in wildlife. The results reported in the Nordic Council of Ministers (2011) study are for fish based on 6-20 individuals, for eggs homogenates of 5-10 eggs, and for mussels only two composite samples from two different sites. 2,4-DBP was found in liver from Atlantic cod (Gadus morhua) from Norway at approximately ng/g w.w. and from the Faroe Islands at approximately 7 ng/g w.w. In fish muscle, lower concentrations were recorded (approximately ng/g w.w.). In Blue mussels (Mytilus edulis) from Norway, the concentrations were in the range of ng/g w.w. (Nordic Council of Ministers, 2011). Eggs from Black Guillemot (Ceppus grille) from the Faroe Islands contained 2,4,6-TBP at around 1-2 ng/g w.w. whereas Guillemot (Uria aagle) eggs from the Baltic proper contained less than 1 ng/g w.w. (Nordic Council of Ministers, 2011). According to the same author, liver from Atlantic cod from Norway contained between 3-21 ng/g w.w. and from the Faroe Islands 86 ng/g w.w. In fish muscle, lower concentrations were recorded (approximately ng/g w.w.). In Blue mussels from Norway and Iceland the concentations were between 3-13 ng/g w.w. (Nordic Council of Ministers, 2011). 2,4,6-TBP has also been found in marine birds and polar bears at low concentrations, with possible origins from metabolism of PBDEs and/or as a result of natural production from marine organisms (Wan et al., 2009). EFSA Journal 2012;10(4):

17 PBP was found in Guillemot eggs from the Baltic proper at around 0.4 ng/g w.w. and in Black Guillemot (Ceppus grille) from the Faroe Islands the concentrations were ng/g w.w. (Nordic Council of Ministers, 2011). In Blue mussels from Norway and Iceland the concentrations of TBP-DBPE were up to 0.05 ng/g w.w. (Nordic Council of Ministers, 2011). It was found in harp seals (Phoca groenlandica) from the Barents and Greenland Seas in concentrations ranging from 322 to 470 and from 130 to 340 ng/g w.w. in blubber and brain, respectively (von der Recke and Vetter, 2007). The enantiomeric fraction (EF) of TBP-DBPE in blubber samples from Hooded seals (Cystophora cristata) and Harp seals was determined by Vetter et al. (2010). They found that the EF in samples from the Barents Sea ranged from to 0.527, and samples from the Greenland Sea showed EFs ranging from to 0.492, whereas EF in the standard TBP-DBPE was The authors concluded that as most EFs were close to racemic conditions this indicates that TBP-DBPE in seal blubber is predominantly transformed by non-enantioselective processes. TBP-AE has been detected in blubber ( ng/g w.w.) and brain ( ng/g w.w.) of harp seals from the Barents and Greenland Seas (von der Recke and Vetter, 2007). The co-occurrence in the same samples, of TBP-DBPE (see above) and 2-bromoallyl-2,4,6-tribromophenyl ether (BATE), suggests that both TBP-AE and BATE could be metabolites of TBP-DBPE. TBBPS-DBPE was determined in Herring Gull eggs from the Great Lakes by Gauthier et al. (2009). The concentrations were however below the LOQ (0.3 ng/g w.w.). Letcher and Chu (2010) analysed 11 samples of Herring Gull eggs but could not find TBBPS-DBPE above the LOD (1.28 ng/g w.w.). ominated phenols are not generally readily biodegradable and will persist in the environment for a longer or shorter time depending on the conditions. However, adapted communities of microorganisms and specialist communities (such as anaerobic or sulfidogenic) may degrade the compounds. Log K ow values for the brominated phenols would give rise to estimates for bioaccumulation potential that increase with increasing bromination. Predicted bioconcentration factors (BCFs) of 24, 120 and for 2,4-DBP, 2,4,6-TBP and PBP have been calculated (WHO, 2005). Measured BCFs for 2,4,6- TBP are similar to the predicted value (WHO, 2005) Combustion As indicated in Section ,4-DBP and 2,6-DBP have been found in flue gas from a hazardous waste incinerator. The combustion of domestic products containing BFRs such as brominated phenols including TBBPS and its derivatives may lead to formation and release of polybrominated dibenzo-pdioxins and dibenzofurans (PBDD/Fs). It has been shown by e.g. Söderström and Marklund (1999) and Swedish Environmental Protection Agency (EPA) (2011), that brominated and mixed chlorobromo dibenzo-p-dioxins and dibenzofurans can be formed in accidental fires where BFRs are present. Similar information on the formation of PBDD/Fs has also been reported by Thoma et al. (1986) and Thoma and Hutzinger (1989). 5. Occurrence of brominated phenols and their derivatives in food 5.1. Current occurrence of brominated phenols and their derivatives in food: call for data A call for data on BFRs 12 from the Dietary and Chemical Monitoring Unit (DCM) (former Data Collection and Exposure Unit, DATEX) was issued by EFSA in December 2009, with different deadlines according to the chemicals to be collected. The closing date for data submissions on TBBPA and other brominated phenols was December No data on brominated phenols or their derivatives were submitted to EFSA. 12 EFSA Journal 2012;10(4):

18 5.2. Previously reported literature data on occurrence of brominated phenols and their derivatives Occurrence in Food Occurrence data in the open literature on brominated phenols and their derivatives in food samples are scarce and were identified only for fish, molluscs and crustaceans. Occurrence of brominated phenols in fish, shellfish and crustaceans has been studied because they impart a typical marine, briny or iodine flavour to the products (e.g. Whitfield et al., 1997; Fuller et al., 2008). The data in Table 3 originate partly from such studies, particularly carried out in Australia and Asia. ominated phenols and their derivatives have also been studied as environmental contaminants (e.g. Löfstrand et al., 2010; Nordic Council of Ministers, 2011). ominated phenols such as 2,4- and 2,6-DBP and 2,4,6-TBP are also produced by algae and may accumulate in aquatic organisms. The levels in Table 3 may originate (partly) from natural sources. A natural or anthropogenic origin of the bromophenols cannot be distinguished in these studies. Several brominated phenols have been detected in fish and shellfish from Europe. The CONTAM Panel noted, however, that in a number of cases it was unclear whether the results were expressed on a wet weight, lipid weight or dry weight basis. 2,4,6-TBP predominates, with levels in fish meat ranging from < ng/g w.w. in capelin, a fish not commonly consumed, up to 3.5 ng/g w.w. in perch. A level of 86 ng/g w.w. was reported for cod liver from the Faroe Islands. 2,4,6-TBP levels in blue mussels were reported to range from 3.2 to 13 ng/g w.w. Levels of 2,4-DBP and 2,6-DBP were lower. PBP was analysed in a range of North-European fish and bivalve samples but was never detected (< LOQ). Some studies analysed the bromophenol derivatives in fish and bivalves from Scandinavia, but in most cases, they were not detected (< 0.13 ng/g w.w. or lower). In blue mussel from Norway, traces of TBP-AE and TBP-DBPE were detected. In blue mussels from Iceland traces of TBP-DBPE and its likely metabolite 2-bromoallyl-2,4,6-tribromophenyl ether were detected (Table 3). No occurrence data of TBP-DBPE enantiomers in fish, bivalves or crustaceans were identified in the literature. Levels in non-european fish and shellfish ranged from < LOQ to 299 ng/g w.w. in snapper from azil and ng/g dry weight (408 ng/g w.w.) in clams from Hong Kong (Table 3b). In these samples, 2,4,6-TBP often predominates over the other brominated phenols as well, but exceptions exist, and 2,4,6-TBP levels in crustaceans and molluscs are generally higher than in fish. Whitfield et al. (1997) found considerably higher levels for 2,4-DBP, 2,6-DBP and 2,4,6-TBP in wild caught prawns compared to farmed prawns. It was suggested by the authors that polychaetes (marine worms) and algae producing brominated phenols were the origin of the high levels in wild prawns (Whitfield et al., 1997). Fuller et al. (2008) compared farmed and wild caught barramundi, but differences were rather small. Chung et al. (2003b) studied seasonal distribution of brominated phenols in fish and shellfish from Hong Kong. They found that seasonal variations in levels coincided with the seasonal growth cycle of the brominated phenol synthesizing seaweeds (e.g. brown algae). The seasonal variations of 2,4,6-TBP varied amongst the species, from 3 fold in shrimps to 50 fold in crab. Occurrence data on TBBPS and its derivatives have not been identified in fish or shellfish Effects of processing There are no data available on effects of processing on the levels of brominated phenols and their derivatives in food Occurrence in human milk In Japan, Ohta et al. (2004) reported the concentrations of tribromophenols and other BFRs in human milk from primiparae and multiparae women. Individual samples were pooled to analyse 4 pools for primipare women, and 5 pools for multiparae women. The concentrations of tribromophenols (predominantly 2,4,6-TBP and some 2,4,5-TBP) were pg/g fat and pg/g fat EFSA Journal 2012;10(4):

19 for primiparae and multiparae, respectively. The sample with the highest concentration of pg/g fat differed considerably from the other pools, as the major contribution came from other tribromophenols which are not further specified. Excluding the contribution of these other TBPs, the sum for 2,4,6-TBP and 2,4,5-TBP in this sample amounts to approximately pg/g fat. Thomsen et al. (2002a) developed a method for the determination of several halogenated flame retardants including 2,4,6-TBP and PBP in human milk using solid phase extraction. The analysis of a pooled human milk sample from about 20 Norwegian mothers sampled in 2001 revealed a concentration of 627 pg/g fat for 2,4,6-TBP. PBP could not be detected at the reported LOD of 0.3 pg/g whole milk (Thomsen et al., 2002a). EFSA Journal 2012;10(4):

20 Table 3a: Occurrence data from Europe of brominated phenols from the literature. Country Location Year N Species 2,4-DBP 2,6-DBP 2,4,6-TBP PBP TBP-AE TBP-DBPE Units Reference Faraoe Nordic Council of Mylingsgrunurin P Cod (liver) < 0.2 < < 0.13 ng/g w.w. Islands Ministers, 2011 Faraoe Nordic Council of Myrarnar P Arctic char < < 0.03 < < ng/g d.w. Islands Ministers, 2011 Finland Helsinki P Perch < 0.02 < < ng/g w.w. Nordic Council of Ministers, 2011 Finland Tampere P Perch < < 0.03 < < ng/g w.w. Nordic Council of Ministers, 2011 Iceland West Iceland P Cod, liver < 0.3 < < ng/g w.w. Nordic Council of Ministers, 2011 Iceland West Iceland P Blue mussel (a) < < 0.03 < ng/g w.w. Nordic Council of Ministers, 2011 Norway Åse P Blue Mussel (a) < 0.03 < Nordic Council of ng/g w.w Ministers, 2011 Norway Åsefjorden P Cod, liver < 0.04 < < ng/g w.w. Nordic Council of Ministers, 2011 Sweden Riddarfjärden/Stora Nordic Council of P Perch < 0.03 < < 0.03 < < ng/g ww Essingen Ministers, 2011 Sweden West coast P Blue Mussels (a) ng/g EOM (b) Löfstrand et al., Iceland NS NS NS Haddock ND ng/g (c) Boyle et al., 1992 Europe NS NS NS ine cured herring ND ND 13.5 ng/g (c) Boyle et al., 1992 Norway Svalbard Capelin (whole fish) <0.013 <0.001 <0.006 ng/g w.w. Klif, 2010 N: number of samples; NS: not specified; F: farmed; P: each sample consisted of several pooled individuals. The numerical values indicated with < refer to the LOD or LOQ reported in the respective study. (a): Not mentioned whether the mussels were depurated prior to analysis and may have therefore contained contaminated suspended particulate matter. (b): Extractable Organic Matter, basically lipids and some other co-extracted material, see Löfstrand et al. (2010). (c): not specified on what basis result is expressed (e.g. wet weight, lipid weight, dry weight). EFSA Journal 2012;10(4):

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