Odour threshold concentrations, determined in agueous-ethanol solution, and odour qualities are reported for 18 enantiomeric and diastereomeric pairs of citronellyl derivatives [13 linear monoterpene compounds and five monocyclic α-damascone and α-ionone-related compounds (trans-2,2,6-trimethylcyclohexyl derivatives)] (98%ee). Fairly large differences in both odour strength and odour qualities were found between the monocyclic diastereomeric pairs. In four of the five cyclic compounds, the (1R, 6S)-form was found to be stronger and more sensorily active than the antipode. On the other hand, the linear enantiomeric pairs showed only small differences in both odour strength (half of them showed the same threshold values) and odour character. However, all the (3S)-forms showed milder, cleaner and a much preferable top note than the (3R)-forms except for citronellyl nitrile and the diester (citronellyl ethyl oxalate), whose (
Materials and SynthesesChiral (E)-3,7-dimethyl-1,6-octadienyldiethylamine
S)and ( R ) -[2-*H] lsopentenyl t pyrophosphates, which are useful precursors for stereochemical studies on the biosynthesis of isoprenoids, were chemically synthesized in five steps via (S)and ( R ) -3methyl-2,3-epoxybutan-l-ols starting with 3,3-dimethylallyl alcohol, in 18% and 15% overall yields, respectively.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.