Microbial O-Methylation of the Flame Retardant Tetrabromobisphenol-A

Abstract

We demonstrated the O-methylation of tetrabromobisphenol-A (TBBPA) [4,4'-isopropylidenebis (2,6-dibromophenol)] to its mono- and dimethyl ether derivatives by microorganisms present in different sediments. A most probable number assay of a marsh sediment suggested that up to 10% of the total aerobic heterotrophs may be capable of O-methylation. Although TBBPA dimethyl ether is not produced in industry, it has been detected in terrestrial and aquatic sediments. Our study supports the hypothesis that TBBPA dimethyl ether is a product of microbial O-methylation. The O-methylation of TBBPA, as well as its analog, tetrachlorobisphenol-A (TCBPA), was also demonstrated in cultures of two chlorophenol-metabolizing bacteria, Mycobacterium fortuitum CG-2 and Mycobacterium chlorophenolicum PCP-1. These strains also mediated the O-methylation of 2,6-dibromophenol and 2,6-dichlorophenol, analogs of TBBPA and TCBPA, to their corresponding anisoles, but 2,6-fluorophenol was not transformed. Due to the addition of hydrophobic methyl groups, O-methylated derivatives are more lipophilic, increasing the probability of bioaccumulation in the food chain. Future research regarding the toxicological effects of the O-methylated derivatives of TBBPA is recommended and will further elucidate potential risks to environmental and human health.