New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils

Abstract

Abstract New β‐ and γ‐cyclodextrin derivatives, selectively substituted with n ‐pentyl and methyl groups, e.g. heptakis(2,6‐di‐ O ‐methyl‐3‐ O ‐pentyl)‐β‐cyclodextrin, octakis(2‐ O ‐methyl‐3,6‐di‐ O ‐pentyl)‐γ‐cyclodextrin, and octakis(2,6‐di‐ O ‐methyl‐3‐ O ‐pentyl)‐γ‐cyclodextrin, have been prepared from specifically protected intermediates. The new cyclodextrin derivatives exhibit unique enantioselectivity towards important chiral constituents of essential oils. The enantiomers of lavandulol, α‐bisabolol, nerolidol, and other terpenoid alcohols could be resolved and their presence in different essential oils could be proved. Methyl jasmonate and epi ‐methyl jasmonate could, in addition, be detected in jasmine concrete by two‐dimensional gas chromatography. The enantiomers of the macrocyclic ketone muscone have been separated for the first time.