Migration of cyclo-diBA from coatings into canned food: method of analysis, concentration determined in a survey and in silico hazard profiling

Food Chem Toxicol. 2013 Aug:58:107-15. doi: 10.1016/j.fct.2013.04.004. Epub 2013 Apr 19.


Cyclo-diBA, the cyclic product formed from bisphenol A and bisphenol A diglycidyl ether during production of epoxy resins, was measured in canned food using reversed phase HPLC with fluorescence detection. Half (9 of 17) of the samples of canned fish in oil collected in April 2010 contained cyclo-diBA with an average concentration of 1025 μg/kg and a maximum of 1980 μg/kg. In September 2012, cyclo-diBA was detectable (>25 μg/kg) in merely 13 from 44 such products; the average concentration in these was 807 μg/kg and the maximum now reached 2640 μg/kg. Fish in brine contained far less cyclo-diBA. The majority of the canned meat products contained cyclo-diBA at a mean concentration of 477 μg/kg and a maximum of 1050 μg/kg. All prepared meals, such as ravioli or soups, contained cyclo-diBA, with a mean at 287 μg/kg. In canned tomatoes, peas and other vegetables in water or fruits in syrup, no cyclo-diBA was detected (<25 μg/kg). Since no experimental toxicity data are available except for its cytotoxicity, an in silico hazard profiling was performed. Cyclo-diBA seems to be stable and of low reactivity. There is indication for considerable oral bioavailability and for the potential to accumulate in the human body. Cyclo-diBA can be metabolized into cyclic and acyclic compounds. Based on SAR assessment for cyclo-diBA and read-across from BADGE to linear cyclo-diBA metabolites, genotoxic effects are improbable. Specific binding of cyclo-diBA to nuclear receptors, such as ERβ, can be predicted, indicating a potential endocrine-disrupting potency. The limit by the EFSA guidelines of 50 μg/person/d for compounds shown not to be genotoxic as well as the TTC-based Cramer structural class III value of 90 μg/person/d could be exceeded several fold by high consumers of canned fish in oil with high brand loyalty. As a consequence, risk reduction measures were taken.

Keywords: Canned fish in oil; Epoxy can coatings; Exposure estimation; Prediction of oral bioavailability; Structure-activity relationship (SAR).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzhydryl Compounds / analysis*
  • Benzhydryl Compounds / pharmacokinetics
  • Benzhydryl Compounds / toxicity
  • Biological Availability
  • Chromatography, High Pressure Liquid
  • Chromatography, Reverse-Phase
  • Computer Simulation
  • Food Analysis / methods*
  • Food Contamination*
  • Food, Preserved*
  • Hep G2 Cells
  • Humans
  • Limit of Detection
  • Phenols / analysis*
  • Phenols / pharmacokinetics
  • Phenols / toxicity
  • Spectrometry, Fluorescence
  • Structure-Activity Relationship


  • Benzhydryl Compounds
  • Phenols
  • bisphenol A