Identification of 4-Hydroxycumyl Alcohol As the Major MnO2-Mediated Bisphenol A Transformation Product and Evaluation of Its Environmental Fate.
Bisphenol A (BPA), an environmental contaminant with weak estrogenic activity, resists microbial degradation under anoxic conditions but is susceptible to abiotic transformation by manganese dioxide (MnO2). BPA degradation followed pseudo-first-order kinetics with a rate constant of 0.96 (±0.03) min(-1) in the presence of 2 mM MnO2 (0.017% w/w) at pH 7.2. 4-hydroxycumyl alcohol (HCA) was the major transformation product, and, on a molar basis, up to 64% of the initial amount of BPA was recovered as HCA. MnO2 was also reactive toward HCA, albeit at 5-fold lower rates, and CO2 evolution (i.e., mineralization) occurred. In microcosms established with freshwater sediment, HCA was rapidly biodegraded under oxic, but not anoxic conditions. With a measured octanol-water partition coefficient (Log K(ow)) of 0.76 and an aqueous solubility of 2.65 g L(-1), HCA is more mobile in saturated media than BPA (Log K(ow) = 2.76; aqueous solubility = 0.31 g L(-1)), and therefore more likely to encounter oxic zones and undergo aerobic biodegradation. These findings corroborate that BPA is not inert under anoxic conditions and suggest that MnO2-mediated coupled abiotic-biotic processes may be relevant for controlling the fate and longevity of BPA in sediments and aquifers.
†Department of Microbiology, University of Tennessee, Knoxville, Tennessee 37996, United States.|‡Center for Environmental Biotechnology, University of Tennessee, Knoxville, Tennessee 37996, United States.
Jeongdae
J
Im
§Department of Chemistry, University of Tennessee, Knoxville, Tennessee 37996, United States.
Carson W
CW
Prevatte
§Department of Chemistry, University of Tennessee, Knoxville, Tennessee 37996, United States.
Shawn R
SR
Campagna
†Department of Microbiology, University of Tennessee, Knoxville, Tennessee 37996, United States.|‡Center for Environmental Biotechnology, University of Tennessee, Knoxville, Tennessee 37996, United States.|∥Department of Civil and Environmental Engineering, University of Tennessee, Knoxville, Tennessee 37996, United States.|⊥University of Tennessee and Oak RidgeNational Laboratory (UT-ORNL) Joint Institute for Biological Sciences (JIBS) and Biosciences Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37831, United States.
Frank E
FE
Löffler
D000438:Alcohols / Q000737:chemistry*; D001559:Benzhydryl Compounds / Q000737:chemistry*; D001673:Biodegradation, Environmental; D001711:Biotransformation; D002021:Buffers; D005618:Fresh Water; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D017895:Manganese Compounds / Q000737:chemistry*; D064307:Microbiota; D008903:Minerals / Q000737:chemistry; D010087:Oxides / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D000098826:Bisphenol A Compounds
D000438:Alcohols; D001559:Benzhydryl Compounds; D002021:Buffers; D017895:Manganese Compounds; D008903:Minerals; D010087:Oxides; D010636:Phenols; C006780:bisphenol A; D000098826:Bisphenol A Compounds; C016552:manganese dioxide