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In addition, 2′-MeO-BDE 68 and 6MeO-BDE 47 were recently isolated from whale blubber and investigated by spectroscopic methods (Teuten et al. 2006). As seen from the structural code, 6-MeO-BDE 47 differs from BDE 47, a key compound in products used as brominated flame retardants (BFRs), only in the MeO-substituent in the ortho-position (Asplund et al. 1999). Reports on residues of BFRs in the environment have increased of late (de Boer et al. 2000), and it seems, for lack of plausible other sources, that the unknown brominated compounds detected in marine organisms may be metabolites of BFRs.

However, publications in this field are relatively scarce (Rimkus and Wolf 1991; Miyazaki et al. Marine Halogenated Natural Products OMe Br OMe OMe Br Br 35 Br Br Br Br 2,4,6-tribromoanisole 2,6-dibromoanisole 2,4-dibromoanisole (27) (28) (29) Fig. 13. Structures of the most prominent natural bromophenols. 2,4,6tribromoanisole (2,4,6-TBA or TBA, 27), 2,6-dibromoanisole (2,6-DBA, 28), and 2,4-dibromoanisole (2,4-DBA, 29). 1981; Watanabe et al. 1983; Whitfield et al. 1998; Vetter et al. 2001b; Vetter and Stoll 2002).

2005a). This structure is fulfilled for all known naturally produced MeOBDEs, but reductive debromination may lead to metabolites of natural MeO-BDE that do not contain any Br in the ortho-position (Melcher et al. 2005a). GC/EI-MS is less sensitive, but the molecular ion is abundant and provides a much higher selectivity for MeO-BDEs (Pettersson et al. 2004). GC/EI-MS was shown to distinguish ortho- (these form [M-94]+ fragment ions) from para- (these form [M-15]+ fragment ions) and from metasubstituted MeO-BDEs (these do not show the respective fragment ions observed in the EI-MS of the isomers) (Marsh et al.

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