Identification of 4-Hydroxycumyl Alcohol As the Major MnO2-Mediated Bisphenol A Transformation Product and Evaluation of Its Environmental Fate

Environ Sci Technol. 2015 May 19;49(10):6214-21. doi: 10.1021/acs.est.5b00372. Epub 2015 May 6.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Benzhydryl Compounds / chemistry*
  • Biodegradation, Environmental
  • Biotransformation
  • Buffers
  • Fresh Water
  • Hydrogen-Ion Concentration
  • Kinetics
  • Manganese Compounds / chemistry*
  • Microbiota
  • Minerals / chemistry
  • Oxides / chemistry*
  • Phenols / chemistry*


  • Alcohols
  • Benzhydryl Compounds
  • Buffers
  • Manganese Compounds
  • Minerals
  • Oxides
  • Phenols
  • bisphenol A
  • manganese dioxide