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Characterization of the Polyphenolics Related to the Colour of Western Red Cedar (Thuja plicata Donn) Heartwood

Summary Three quarters of the western red cedar's heartwood colour is due to a polymeric material easily isolated by methanol extraction. The nature of this polymer has not been fully investigated and published information is contradictory. Our initial examination of the coloured polymer by pyrolysis-gas chromatography, combined with mass spectrometry, indicated that the polymer was guaiacyl in nature and thus similar to softwood lignin. However, analysis by infrared spectroscopy indicated the presence of both lignin and lignan like moieties. To clarify this issue a more detailed analysis was conducted using nuclear magnetic resonance spectroscopy (1H NMR, 31P NMR, 13C NMR). Analysis of the spectra and comparison with the spectra of plicatic acid and a product from mild acid treatment of plicatic acid, indicated that the polymeric fraction was derived almost entirely from lignans. During polymer formation, the highly reactive pyrocatechol moiety in the plicatic acid is destroyed, leaving a guaiacyl-like polymer. The reaction mechanism appears to proceed via an ortho-quinone intermediate followed by polymerization.