Synthesis and Olfactory Characterization of Sila-Methyl Pamplemousse and Related Odorants with a 2,2,5-Trimethyl-2-silahex-4-ene Skeleton
摘要:
The synthetic grapefruit odorant methyl pamplemousse (1a) has lately become an important trend odorant, and the related 2,2,5-trimethylhex-4-enes 2a-4a also possess interesting olfactory properties of fresh hesperidic and fruity-agrestic character. On the basis of the carbon/silicon switch strategy, the silicon-containing analogues silamethyl pamplemousse (1b) and 2b-4b were synthesized and studied for their olfactory properties (olfactory evaluation of the C/Si pairs 1a/1b-4a/4b). Si la substitution (C/Si exchange) was demonstrated to affect the olfactory properties substantially. The C/Si analogues la and 1b were found to be genuine grapefruit odorants, with the silicon compound 1b showing additional agrestic facets. As a proof of principle, it Was demonstrated that C/Si analogues can display a different mechanism and rate of degradation (degradation studies with la and 1b under acidic conditions).
The synthetic grapefruit odorant methyl pamplemousse (1a) has lately become an important trend odorant, and the related 2,2,5-trimethylhex-4-enes 2a-4a also possess interesting olfactory properties of fresh hesperidic and fruity-agrestic character. On the basis of the carbon/silicon switch strategy, the silicon-containing analogues silamethyl pamplemousse (1b) and 2b-4b were synthesized and studied for their olfactory properties (olfactory evaluation of the C/Si pairs 1a/1b-4a/4b). Si la substitution (C/Si exchange) was demonstrated to affect the olfactory properties substantially. The C/Si analogues la and 1b were found to be genuine grapefruit odorants, with the silicon compound 1b showing additional agrestic facets. As a proof of principle, it Was demonstrated that C/Si analogues can display a different mechanism and rate of degradation (degradation studies with la and 1b under acidic conditions).