Polyalkoxybenzenes from plant raw materials 1. Isolation of polyalkoxybenzenes from CO2 extracts of Umbelliferae plant seeds

Abstract

For the search for a domestic natural source of allylpolyalkoxybenzenes and development of an effective process for their isolation, CO2 extracts of several varieties of parsley, dill, celery, caraway, and nutmeg were analyzed systematically for the first time by GC/MS and GLC techniques. The varieties with high contents of myristicin, elemicin, allyltetramethoxybenzene, apiol, and dillapiol were identified. The conditions of CO2 extraction for obtaining concentrates with minimum contents of the distillation residues were selected. Using high performance fractional distillation, polyalkoxyallylbenzenes with 98–99% purity were isolated from the concentrates on a pilot unit. By isomerization of some allylbenzenes followed by ozonolysis under specially selected conditions, apiol-and dillapiolaldehydes were obtained in 75–80% yields.