Critter Chemistry
November 22, 1999
Organohalogens Occur Naturally in Bird Eggs
Maureen Rouhi
Two organohalogen compounds that occur naturally in seabird eggs have been identified by Gordon W. Gribble, chemistry professor at Dartmouth College, and coworkers. They synthesized two hexahalogenated dimethylbipyrroles, determined their structures, and showed that they match the natural products [Chem. Commun., 1999, 2195]. The research team reports that one of the bipyrroles (shown) appears to be the major compound in a group of C10H6N2Br4Cl2 compounds previously identified in seabird eggs by Ross J. Norstrom of the Canadian Wildlife Service, Hull, Quebec, and coworkers [ Environ. Sci. Technol., 33, 26 (1999)]. The results provide evidence that organohalogens naturally produced by many types of marine bacteria, algae, and other marine organisms bioaccumulate in higher animals. Halogenated dimethylbipyrroles (HDBPs) are structurally similar to polychlorinated biphenyls and other anthropogenic halogenated compounds that are toxic to plants and animals. The charting of a synthetic route to HDBPs is important because it will allow sufficient quantities to be produced for toxicity testing as well as for identifying natural products, Norstrom tells C&EN.
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