Zhang, A.J., Amalin, D., Shirali, S., Serrano, M.S., Franqui, R.A., Oliver, J.E., Klun, J.A, Aldrich, J.R., Meyerdirk, D.E., & Lapointe, S.L. 2004 Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene.. Proceedings of the National Academy of Sciences of the United States of America 101(26): 9601-9606.
Notes: [www.pnas.org/cgi/doi/10.1073/pnas.0401298101] Two compounds that together constitute the female sex pheromone of the pink hibiscus mealybug (PHM), Maconellicoccus hirsutus, were isolated, identified, and synthesized. They are (R)-2-isopropenyl-5-methyl-4-hexenyl (S)-2-methylbutanoate [common name is (R)-lavandulyl (S)-2-methylbutanoate] and [(R)-2,2-dimethyl-3-(l-methylethylidene)cyclobutyl]methyl (S)-2-methylbutanoate [which we refer to as (R)-maconelliyl (S)-2-methylbutanoate]. Maconelliol is an unusual monoterpene, and its structure has been established by enantioselective synthesis from precursors of known structure and configuration. A 1:5 synthetic mixture of the two RS esters (11 mug per rubber septum) proved to be a potent attractant of males in field bioassays. The pheromone component, maconelliyl 2-methylbutanoate, represents a heretofore undescribed natural product.