Long-chain alkanediols, ketoaldehydes, ketoalcohols and ketoalkyl esters in the cuticular waxes of Osmunda regalis fronds

In the frond waxes of Osmunda regalis four homologous series of previously unknown compounds were detected. In order to assign their structures various derivatives were prepared and analyzed by GC-MS. The wax components were identified as C-28 to C-32 alkanediols, C-26 to C-36 ketoalcohols, C-28 to C-36 ketoaldehydes and long-chain fatty acid esters of C-28 to C-36 ketoalcohols. All fractions showed strong prevalence of even numbered homologues with a maximum for C-30. Isomer distributions were in all cases dominated by 1,9, 1,11-, 1,13- and 1,15-compounds, their relative abundances shifting towards the latter with increasing homologue chain length. A total of 77 (69 novel) compounds were identified, partially as minor components in unresolved isomer mixtures. (C) 1999 Elsevier Science Ltd. All rights reserved.