Research Product

Isomeric fluorine-substituted phenols were used as analogues of phenol to investigate the transformation of phenol to benzoate by an anaerobic, phenol-degrading consortium derived from freshwater sediment. Transformation of 2-fluorophenol and 3-fluorophenol led to the accumulation of 3-fluorobenzoate and 2-fluorobenzoate, respectively, while 4-fluorophenol was not transformed (Figure 1). These data indicate that the carboxyl group was introduced para to the phenolic hydroxyl group in the fluorophenol isomers (Figure 2). Para-carboxylation was confirmed when the fluorinated analogue of para-hydroxybenzoate was dehydroxylated to 3-fluorobenzoate (Figure 3). By analogy, we presume that phenol is transformed to benzoate by a similar mechanism.