SCIENTIFIC OPINION. EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) 2, 3

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1 EFSA Journal 2014;12(10):3863 SCIENTIFIC OPINION Scientific Opinion on the safety assessment of the substance, 2,4,8,10- tetraoxaspiro[5.5]undecane-3,9-diethanol, β3,β3,β9,β9-tetramethyl-, CAS No , for use in food contact materials 1 EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) 2, 3 European Food Safety Authority (EFSA), Parma, Italy ABSTRACT This scientific opinion of the EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids deals with the safety assessment of the substance 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol, β3,β3,β9,β9-tetramethyl- (SPG), CAS No , FCM No 1052, for use as a co-monomer in polyesters. The polyesters are intended for contact with all food types for long-term storage at room temperature including hotfill/sterilisation conditions. Migration of the substance into 10 % ethanol was mg/kg food and no migration was detected (<0.003 mg/kg food) in 3 % acetic acid. No migration of the oligomers was detectable (< 0.2 mg/kg food). Based on three negative in vitro tests, the Panel considered that the substance does not raise a concern related to genotoxicity, while from a 90-day oral toxicity study in rats not providing a dose-response relationship of the incidental changes, it was concluded that the NOAEL is 2000 mg SPG/kg b.w. per day, the highest dose tested. The substance does not raise concern for accumulation in man. The Panel concluded that the use of the substance 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9-tetramethyl- (SPG) as a monomer in the production of polyesters, does not raise a safety concern for the consumer when the migration of the substance itself does not exceed 5 mg/kg food and the migration of the oligomers of less than 1000 Da does not exceed 50 µg/kg food (expressed as SPG). European Food Safety Authority, 2014 KEY WORDS 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9-tetramethyl-, CAS No , FCM substance No 1052, food contact materials, plastics, polyesters, safety assessment 1 On request from the Food Standards Agency, UK, Question No EFSA-Q , adopted on 24 September Panel members: Claudia Bolognesi, Laurence Castle, Jean-Pierre Cravedi, Karl-Heinz Engel, Paul Fowler, Roland Franz, Konrad Grob, Rainer Gürtler, Trine Husøy, Wim Mennes, Maria Rosaria Milana, André Penninks, Vittorio Silano, Andrew Smith, Maria de Fátima Tavares Poças, Christina Tlustos, Fidel Toldrá, Detlef Wölfle and Holger Zorn. One member of the Panel did not participate in the discussion on the subject referred to above because of potential conflicts of interest identified in accordance with the EFSA policy on declarations of interests. Correspondence: fip@efsa.europa.eu 3 Acknowledgement: The Panel wishes to thank the members of the Working Group on Food Contact Materials: Mona-Lise Binderup, Laurence Castle, Riccardo Crebelli, Alessandro Di Domenico, Roland Franz, Nathalie Gontard, Ragna Bogen Hetland, Martine Kolf-Clauw, Eugenia Lampi, Maria Rosaria Milana, Maria de Fátima Tavares Poças, Philippe Saillard, Kettil Svensson and Detlef Wölfle for the preparatory work on this scientific opinion. Suggested citation: EFSA CEF Panel (EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids), Scientific Opinion on the safety assessment of the substance, 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol, β3,β3,β9,β9-tetramethyl-, CAS No , for use in food contact materials. EFSA Journal 2014;12(10):3863, 8 pp. doi: /j.efsa Available online: European Food Safety Authority, 2014

2 SUMMARY Within the general task of evaluating substances intended for use in materials in contact with food according to Regulation (EC) No 1935/2004 of the European Parliament and of the Council of 27 October 2004 on materials and articles intended to come into contact with foodstuffs, the CEF Panel received a request from the Food Standards Agency, UK, for safety assessment of the substance 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9-tetramethyl- (SPG) following a corresponding application submitted on behalf of Mitsubishi Gas Chemical Company, Inc. The substance is intended for use as a co-monomer at a maximum content of 50 mole % of the diol component for manufacturing polyesters specifically in partial replacement of ethylene glycol in poly(ethylene terephthalate) (PET). The final articles are intended to be in contact with all types of foodstuffs for long-term storage at room temperature including hot-fill/sterilisation for up to 30 min at 100 C or for 2 hours at 70 C. Specific migration of the substance was determined using a modified PET and using test conditions simulating hot-fill followed by long-term storage. Migration into 10 % ethanol was mg/kg food whereas no migration was detected (< mg/kg food) into 3 % acetic acid. In the same tests, there was no detectable migration of oligomers (0.2 mg/kg food). Migration of both the substance itself and the oligomers was considerably higher into 50 % ethanol but it is considered that this simulant has too strong and unrepresentative interactions with polyesters of this type under the test conditions employed. Based on three in vitro tests, the Panel considered that SPG does not raise a concern related to genotoxicity. Following a 90-day oral toxicity study in rats that did not provide a dose-response relationship of the incidental changes, it was concluded that the no-observed-adverse-effect level (NOAEL) is 2000 mg/kg b.w. per day, the highest does tested. In consideration of the structure and the log P O/W value, the substance does not raise concern for accumulation in man, in addition the substance is acid-labile and will be decomposed in the stomach in highly hydrophilic components. The Panel concluded that the use of the substance SPG as a monomer in the production of polyesters, does not raise a safety concern for the consumer when the migration of the substance itself does not exceed 5 mg/kg food and the migration of the oligomers of less than 1000 Da does not exceed 50 µg/kg food (expressed as SPG). EFSA Journal 2014;12(10):3863 2

3 TABLE OF CONTENTS Abstract... 1 Summary... 2 Table of contents... 3 Background as provided by the legislation... 4 Terms of reference as provided by the legislation... 4 Assessment Introduction General information Data available in the dossier used for this evaluation Evaluation Non-toxicological data Toxicological data... 6 Conclusions... 7 Documentation provided to EFSA... 7 References... 7 Abbreviations... 8 EFSA Journal 2014;12(10):3863 3

4 BACKGROUND AS PROVIDED BY THE LEGISLATION Before a substance is authorised to be used in food contact materials and is included in a positive list EFSA s opinion on its safety is required. This procedure has been established in Articles 8 and 9 of Regulation (EC) No 1935/ of the European Parliament and of the Council of 27 October 2004 on materials and articles intended to come into contact with food. According to this procedure the industry submits applications to the Member States competent Authorities which transmit the applications to the EFSA for their evaluation. The application is supported by a technical dossier submitted by the industry following the Scientific Committee on Food (SCF) guidelines for the presentation of an application for safety assessment of a substance to be used in food contact materials prior to its authorisation (EC, 2001). In this case, EFSA received an application from the Food Standards Agency, UK requesting the evaluation of the monomer 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9- tetramethyl-, CAS No and FCM substance No TERMS OF REFERENCE AS PROVIDED BY THE LEGISLATION According to Regulation (EC) No 1935/2004 of the European Parliament and of the Council on materials and articles intended to come into contact with food, EFSA is asked to carry out an assessment of the risks related to the intended use of the substance and to deliver a scientific opinion. 4 Regulation (EC) No 1935/2004 of the European parliament and of the council of 27 October 2004 on materials and articles intended to come into contact with food and repealing Directives 80/590/EEC and 89/109/EEC. OJ L 338, , p EFSA Journal 2014;12(10):3863 4

5 ASSESSMENT 1. Introduction The European Food Safety Authority was asked by the Food Standards Agency, UK, to evaluate the safety of 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9-tetramethyl- (SPG), CAS No , and FCM substance No The request has been registered in the EFSA s register of questions under the number EFSA-Q The dossier was submitted on behalf of Mitsubishi Gas Chemical Company, Inc.. 2. General information According to the applicant, the substance 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9- diethanol,β3,β3,β9,β9-tetramethyl- (SPG) is intended to be used as a co-monomer at a maximum content of 50 mole % of the diol component for manufacturing polyesters, specifically in partial replacement of ethylene glycol units in PET. The final articles are intended to be used in contact with all types of foodstuffs for long-term storage at room temperature including a preceding hotfill/sterilisation of up to 30 min at 100 C or for up to 2 hours at 70 C. The substance has not been evaluated by the SCF or EFSA in the past. 3. Data available in the dossier used for this evaluation The studies submitted for evaluation followed the SCF guidelines for the presentation of an application for safety assessment of a substance to be used in food contact materials prior to its authorisation (EC, 2001). Non-toxicity data: Data on identity Data on physical and chemical properties Data on impurities Data on intended use and authorisation Data on migration of the substance Data on identification, quantification and migration of oligomers and other reaction products Toxicity data: 4. Evaluation Bacterial gene mutation test In vitro mammalian cell gene mutation test In vitro mammalian chromosome aberration test 90-day oral toxicity study in rats 4.1. Non-toxicological data Chemical formulae: C 15 H 28 O 6 Chemical structure: EFSA Journal 2014;12(10):3863 5

6 The substance (also known as spiroglycol, SPG) has a molecular weight of 304 Da and a melting point of 205 C. No evidence of chemical instability was gathered from thermo-analysis of SPG up to approximately 300 C, which is higher than the temperatures used to produce the polyesters and the finished FCM. At room temperature, SPG is poorly soluble in water (168 mg/l) and moderately soluble in organic solvents such as methanol and dimethylformamide. The log P O/W is The substance is obtained with a purity of 99.5 %. It contains several impurities which make up the remaining 0.5 % and consist largely of reactant residues from the manufacturing process and of compounds containing the SPG moiety. These impurities generally contain the hydroxyl functional group and are expected to react quantitatively with terephthalic acid during the polymerization reaction, thereby becoming incorporated into the polymer structure. Specific migration of the substance was determined using a modified PET in contact with food simulants 3 % acetic acid, 10 % ethanol and 50 % ethanol at test conditions of 70 C for 2 hours or 100 C for 30 min, followed by 30 C for 40 days. Migration into 3 % acetic acid and 10 % ethanol was < and mg/kg, respectively. Migration of the substance was considerably higher into 50 % ethanol but it is considered that this simulant has too strong and unrepresentative interactions with polyesters of this type under the test conditions employed. Overall migration into 3 % acetic acid and 10 % ethanol using the same test conditions as above was very low or not detectable. No migration of the oligomers was detectable at a detection limit of 0.2 mg/kg food. Based on the concentration of the impurities in the starting material and under the assumption that a 0.1 % fraction of impurities remained unreacted in the final food contact polymer, worst case migration assuming total mass transfer from a 250 µm thick material and at a 6dm 2 :kg ratio was estimated to be less than 0.05 mg/kg food for a modified PET with an SPG use level of 50 mole % of the total diol content. In fact, no migration at their respective limits of detection was observed neither for the impurities nor for possible breakdown products into 3 % acetic acid and 10 % ethanol at the same time/temperature test conditions. The observation that no significant difference was detected between the outcomes of migration tests with 3 % acetic acid and 10 % ethanol is taken as evidence that the acetal function of co-polymerized SPG is not unstable in acidic media Toxicological data The substance was tested in three in vitro genotoxicity tests with and without metabolic activation. The substance was neither mutagenic in bacteria (Salmonella typhimurium strains TA1537, TA1535, TA98, TA100 and in E. coli WP2 uvra) nor in mammalian cells (L5178Y TK +/- mouse lymphoma assay). The potential to induce structural chromosomal aberrations was tested in Chinese hamster CHL cells and the substance was not found to be clastogenic. In addition, no numerical chromosome aberrations were observed at any dose level in any experiment. Based on these three adequately performed in vitro tests, the Panel considered that the substance does not raise a concern related to genotoxicity. The substance was tested in a 90-day oral toxicity study in Sprague Dawley rats at dose levels of 500, 1000 and 2000 mg/kg bw/ day. Incidental chenges, in the absence of any dose-response relationship, were not considered treatment-related. Thus, it was concluded that the no-observed-adverse-effect level (NOAEL) for repeated-dose toxicity of the substance is 2000 mg/kg/day for males and females, the highest dose tested. EFSA Journal 2014;12(10):3863 6

7 Considering the structure and the Log Po/w value (1.63), the substance does not raise concern for accumulation in man in addition the substance is acid-labile and will be decomposed in the stomach in highly hydrophilic components. Based on the absence of genotoxicity of the starting monomers, the Panel considered that there is no concern on genotoxicity for the oligomeric species identified. Being simple esters of the substance itself with an already-evaluated monomer (terephthalic acid) it may be anticipated that the oligomers could be hydrolysed in vivo back to their starting substances. However no data were available to demonstrate this. Therefore the evaluation of the oligomers rests on the evaluation of genotoxicity of the starting substances. CONCLUSIONS Having considered the above-mentioned data, the CEF Panel concluded that the use of the substance 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9-tetramethyl- (SPG) as a monomer in the production of polyesters, does not raise a safety concern for the consumer when the migration of the substance itself does not exceed 5 mg/kg food and the migration of the oligomers of less than 1000 Da does not exceed 50 µg/kg food (expressed as SPG). DOCUMENTATION PROVIDED TO EFSA 1. Dossier 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9-tetramethyl-. June Submitted on behalf of Mitsubishi Gas Chemical Company, Inc. 2. Additional data for dossier 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diethanol,β3,β3,β9,β9- tetramethyl-. March Submitted on behalf of Mitsubishi Gas Chemical Company, Inc REFERENCES EC (European Commission), Guidelines of the Scientific Committee on Food for the presentation of an application for safety assessment of a substance to be used in food contact materials prior its authorization. EFSA Journal 2014;12(10):3863 7

8 ABBREVIATIONS CAS Chemical Abstracts Service CEF EC FCM EFSA NOAEL PET Po/w SCF SPG EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids European Commission Food Contact Materials European Food Safety Authority No Observed Adverse Effect Level Poly(ethylene terephthalate) Partition Coefficient octanol-water Scientific Committee on Food Spiroglycol EFSA Journal 2014;12(10):3863 8

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