Structure elucidation of some minor components of the polybromobiphenyl mixture, Firemaster

Donna L. Orti, Robert H. Hill, Donald G. Patterson, Larry L. Needham, Renate D. Kimbrough, Cynthia C. Alley, Hsing Chung J. Lee

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Abstract

The polybrominated biphenyl known as "Firemaster" is a flame retardant that accidentally became mixed with cattle feed in Michigan in 1973. The resulting toxicosis to animals and humans prompted extensive study to determine Firemaster's toxic components. Although 4 of 12 major Chromatographic peaks of Firemaster produce mixed enzyme induction, they do not account for the total toxicity. By capillary gas chromatography, it was observed that Firemaster FF-1, lot FH 7042, consisted of at least 60 compounds. We have isolated or otherwise determined the structure for 10 minor components of Firemaster: 3,3′,4,4′-tetra-,2,2′,3,5′, 6-penta-,2,2′,4,4′,5-penta-,3,3′, 4,4′,5-penta-,2,3,3′, 4,4′, 5-hexa-,2,3,3′,4,4′,5′-hexa-, 3,3′,4,4′,5,5′-hexa-, 2,2′, 3,3′,4,5,5′- hepta-,2,3,3′,4,4′,5,5′- hepta-and 2,2′,3,3′,4,5,6′- hepta-bromobiphenyl. All of these polybromobiphenyl congeners except 2,2′,4,4′,5-pentabromobiphenyl are in the latest eluting (most polar) fraction by normal-phase high-performance liquid chromatography of Firemaster. This fraction exhibits biological activity. Hyperkeratosis induction tests were carried out on rabbit ears with 3,3′,4,4′-tetra-,2,2′,3,5′, 6-penta-, 2,3,3′,4,4′,5-hexa-, 3,3′,4,4′,5,5′-hexa-, and 2,2′,3,3′,4,5,6′-heptabromobiphenyl, but only 3,3′,4,4′-tetra- and 3,3′,4,4′,5,5′-hexabromobiphenyl gave positive responses. Apparently, these two compounds and 3,3′,4,4′,5-pentabromobiphenyl are significant contributors to the hyperkeratotic activity of Firemaster.

Original languageEnglish (US)
Pages (from-to)603-614
Number of pages12
JournalArchives of Environmental Contamination and Toxicology
Volume12
Issue number6
DOIs
Publication statusPublished - Nov 1 1983

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All Science Journal Classification (ASJC) codes

  • Toxicology
  • Pollution
  • Health, Toxicology and Mutagenesis

Cite this

Orti, D. L., Hill, R. H., Patterson, D. G., Needham, L. L., Kimbrough, R. D., Alley, C. C., & Lee, H. C. J. (1983). Structure elucidation of some minor components of the polybromobiphenyl mixture, Firemaster. Archives of Environmental Contamination and Toxicology, 12(6), 603-614. https://doi.org/10.1007/BF01060741