IDENTIFICATION OF 5-(2-OXOALKYL) RESORCINOLS AND 5-(2-OXOALKENYL) RESORCINOLS IN WHEAT AND RYE GRAINS

Several homologs of 5-(2-oxoalkyl)- and 5-(2-oxoalkenyl)resorcinols were identified in extracts of wheat and rye grains. Homologs of the 5-(2-oxoalkyl)resorcinols included 5-(2-oxononadecyl)-, 5-(2-oxoheneicosanyl)-, 5-(2-oxotricosanyl)-, and 5-(2-oxopentacosanyl)resorcinol, with the heneicosanyl and tricosanyl homologs being predominant. The homologs of 5-(2-oxoalkenyl)resorcinols consisted of 5-(2-oxoheneicosenyl)- and 5-(2-oxotricosenyl)resorcinol. The major alkyl and alkenyl homologs were isolated by thin-layer (TLC) and high-performance liquid chromatography (HPLC) and then identified by TLC, HPLC, gas chromatography coupled with infrared and mass spectroscopy, and proton magnetic resonance spectroscopy. Abundances of the "oxo" components are minor compared to the 5-n-alkyl-resorcinols and, apparently, have been overlooked in previous studies of resorcinols in wheat and rye grains.