Characterization of new thioacidolysis products of sinapyl aidehyde and coniferyl aidehyde

To elucidate the chemical structure of p-hydroxycinnamyl aldehyde moieties of abnormal angiosperm lignins of cinnamyl alcohol dehydrogenase down-regulated plants, sinapyl and coniferyl aldehydes were subjected to thioacidolysis, and the products were analyzed by gas chromatograph-mass spectrometer (GC-MS). The chromatograms indicated that two pairs of new isomeric compounds were released during thioacidolysis of sinapyl and coniferyl aldehydes, respectively, together with the previously found products. These products were also found in the thioacidolysis products of dehydrogenation polymer incorporating p-hydroxycinnamyl aldehydes. The new compounds had the novel indane structure in that the gamma position of the side chain was linked to an aromatic ring. In the case of sinapyl aldehyde, these isomer compounds were the main products, which indicated different reactivities of sinapyl and coniferyl aldehydes during thioacidolysis.