Determination of the absolute configuration of quercivorol, (1S,4R)-p-menth-2-en-1-ol, an aggregation pheromone of the ambrosia beetle Platypus quercivorus (Coleoptera: Platypodidae)

Abstract

A pair of enantiomers of trans-p-menth-2-en-1-ol, an aggregation pheromone of Platypus quercivorus, was synthesized from (S)- and (R)-limonene. The retention time of the aggregation pheromone from the insect coincided with that of (1S,4R)-p-menth-2-en-1-ol synthesized from (S)-limonene from GC analyses with a chiral column, enabling the absolute configuration of the aggregation pheromone to be determined as (1S,4R).