Y. Fujita, J. Campbell, G. M. Mong
Sep 1, 2001
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Journal
International Journal of Environmental Analytical Chemistry
Abstract
Abstract An analytical approach combining chemical derivatization and degradation techniques with mass spectrometry (MS) was applied for the characterization of a bacterial metabolite of 2-bromooctylphenoxy acetic acid. The metabolite contains nitrogen and its proposed structure is 2-aminomethoxy-3-bromo-5-(1,1,3,3-tetrabutyl)phenol. Chemical ionization MS and high resolution MS provided the molecular weight and elemental composition, respectively, of the molecule, and chemical modifications provided evidence for the presence or absence of specific functional groups. In particular, methylation with diazomethane and acylation with acetic anhydride indicated the presence of a phenolic hydroxyl group, while the results of an attempt to propylate the compound with boron trifluoride/propanol indicated the absence of a carboxylic acid group. Treatment with hydrobromic acid suggested the presence of an ether functionality. Hydrogenation and dehalogenation with palladium catalyst provided little new structural information for this compound, but the results were consistent with those from the other analyses. MS/MS data supported the proposed structure as well. Approaches such as the one described here may be useful for the identification of other trace organic unknowns detected in the environment or in laboratory studies.