(2,3,4,4-Tetramethylcyclopentyl)methyl acetate, a sex pheromone from the obscure mealybug: first example of a new structural class of monoterpenes.
The sex pheromone of the obscure mealybug, Pseudococcus viburni, consists of (1R*,2R*,3S*)-(2,3,4,4-tetramethylcyclopentyl)methyl acetate, the first example of a new monoterpenoid structural motif in which the two isoprene units forming the carbon skeleton are joined by 2'-2 and 3'-4 connections rather than the usual 1'-4, head-to-tail connections. This highly irregular terpenoid structure, and the irregular terpenoid structures of related mealybug species, suggest that these insects may have unique terpenoid biosynthetic pathways.
Millar
Jocelyn G
JG
Department of Entomology, University of California, Riverside, CA 92521, USA. millar@ucr.edu
Midland
Sharon L
SL
McElfresh
J Steven
JS
Daane
Kent M
KM
D000818:Animals; D002849:Chromatography, Gas; D005260:Female; D007313:Insecta / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D039821:Monoterpenes / Q000032:analysis*; D012724:Sex Attractants / Q000032:analysis*
C512831:(2,3,4,4-tetramethylcyclopentyl)methyl acetate; D039821:Monoterpenes; D012724:Sex Attractants