Absolute configuration of a new mosquito repellent, (+)-eucamalol and the repellent activity of its epimer.
(+)-Eucamalol (1) and (-)-1-epi-eucamalol (2) were synthesized from (S)-(-)-perillaldehyde to determine the absolute configuration of 1, the structure of natural (+)-eucamalol being determined to be (1R,6R)-(+)-3-formyl-6-isopropyl-2-cyclohexen-1-ol. (+)-Eucamolol (1) and its 1-epimer (2) exhibited significant repellent activity against Aedes albopictus, and inhibited its feeding as well as DEET.
Satoh
A
A
Department of Bioscience and Technology, School of Engineering, Hokkaido Tokai University, Sapporo, Japan.
Utamura
H
H
Nakade
T
T
Nishimura
H
H
D000330:Aedes; D000818:Animals; D007302:Insect Repellents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013729:Terpenes / Q000737:chemistry*
D007302:Insect Repellents; D013729:Terpenes; C094690:eucamalol