In search of new cinnamic acid derived flavours and fragrances

In the search for new, non-cytotoxic substances for use as flavours and fragrances, isovanillin (1), vanillin (6), 3,4-dimethoxy-styrene (11) and veratraldehyde (14) were used as starting materials to access cyclopropanated analogues as well as analogues holding an additional oxirane or thiirane ring. The olfactory examination of the compounds showed that all compounds smell like cinnamon, but hold also an amber note; they are fruity and to some extend balsamic. It can safely be assumed that none of the substances has a major impact on cholinesterases, since their rate of inhibition for acetylcholinesterase (from Electrophorus electricus) and butyrylcholinesterase (from equine serum) and their cytotoxicity was far too low to have physiological effects to be expected.