Identification, Quantification, and Synthesis of a Novel Dimethoxylated Polybrominated Biphenyl in Marine Mammals Caught Off the Coast of Japan

• Published in: Environmental science & technology 2005-11, Vol.39 (22), p.8684-8690
• Main Authors: Marsh, GÖran, Athanasiadou, Maria, Athanassiadis, Ioannis, Bergman, Åke, Endo, Tetsuya, Haraguchi, Koichi
• Format: Article
• Language: English
• Subjects: Animal, plant and microbial ecology; Animals; Animals, Wild - metabolism; Applied ecology; Biological and medical sciences; Bottle-Nosed Dolphin; Chromatography, Gas; Dolphins & porpoises; Ecotoxicology, biological effects of pollution; Effects of pollution and side effects of pesticides on vertebrates; Environmental Pollution - analysis; Fundamental and applied biological sciences. Psychology; Halogenated Diphenyl Ethers; Hydrocarbons, Brominated - analysis; Hydrocarbons, Brominated - metabolism; Japan; Mammalia; Mammals - metabolism; Marine mammals; Mass Spectrometry; Minke Whale; Natural products; Organic contaminants; Phenyl Ethers - analysis; Phenyl Ethers - metabolism; Polybrominated Biphenyls - analysis; Polybrominated Biphenyls - chemistry; Polybrominated Biphenyls - metabolism; Polybrominated diphenyl ethers; Stenella; Whales; Whales & whaling
• ISSN: 0013-936X; 1520-5851
• DOI: 10.1021/es051153v

Bioaccumulation of persistent organic compounds can eventually lead to concentrations in wildlife and humans that are deleterious to health. The present paper documents the identification, quantification, and synthesis of a novel compound, 2,2‘-dimethoxy-3,3‘,5,5‘-tetrabromobiphenyl (2,2‘-diMeO-BB80), present in the marine mammals Striped dolphin (Stenella coeruleoalba), Bottlenose dolphin (Tursiops truncatus), Minke whale (Balaenoptera acutorostrata), and Baird's beaked whale (Berardius bairdii) caught in the Pacific Ocean. Identification was based on comparison of the relative retention times of the compound on two gas chromatographic columns of different polarities to those of an authentic standard. Furthermore, this identification was also supported by comparison of the full scan mass spectrometric data collected employing electron ionization (EI), positive ion chemical ionization (PICI), and electron capture negative ionization (ECNI). The concentrations of 2,2‘-diMeO-BB80 in the samples ranged from 12 to 800 ng/g lipid, making this consistently one of the most abundant compounds among those analyzed, including polybrominated diphenyl ethers (PBDEs), hexabromocyclododecane (HBCDD), and methoxylated PBDEs. The known occurrence of 3,3‘,5,5‘-tetrabromo-2,2‘-biphenyldiol (2,2‘-diOH-BB80) in the marine environment as a natural product suggests that its methylated derivative, 2,2‘-diMeO-BB80, is also of natural origin. To obtain the necessary authentic standards, synthesis was performed of 2,2‘-diMeO-BB80 and the known natural product 2‘,6-dimethoxy-2,3‘,4,5‘-tetrabromodiphenyl ether (2‘,6-diMeO-BDE68).