Fatty acid conjugates of chlorinated phenols and their high-performance liquid chromatographic analysis

Fatty acid (C₁₆ and C₁₈) conjugates of pentachlorophenol and four other commonly used chlorinated phenols (2,4-di-, 2,4,5- and 2,4,6-tri-, and 2,3,4,6-tetra-chlorophenols) were systhesized and their structures were established by proton nuclear magnetic resonance spectroscopy and chenmical ionization mass spctrometry. The high-performance liquid chromatographic (HPLC) separation was achieved on reversed-phase (C-18) column using methanol-water (39:1, v/v) at a flow-rate of 1 ml/min. Palmitoyl- and oleoyl-2,4-dichlorophenols (19.6 min), palmitoyl- and oleoyl-2,4,5-trichlorophenols and stearoyl-2,4-dichlorophenols (28.0 min), oleoyl-2,4,6-trichlorophenol and linoleoyl-2,3,4,6-tetrachlorophenol (30.8 min), palmitoyl- and oleoyl-2,3,4,6-tetrachlorophenols and stearoyl-2,4,5-trichlorophenol (43.2 min) and palmitoyl- and oleoyl-petachlorophenols (72.0 min) were co-eluted under the HPLC conditions described above. Therefore, reversed-phase HPLC separation of a mixture of the five chlorinated phenol conjugates of each fatty acid was achieved.