(2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus

Yunfan Zou, Jocelyn G. Millar, J. Scott Blackwood, Ryan Van Duzor, Lawrence M. Hanks, Judith A. Mongold-Diers, Joseph C.H. Wong, Ann M. Ray

Research output: Contribution to journalArticle


We report the identification of a novel pheromone structure from males of the cerambycid beetle Tylonotus bimaculatus Haldeman (Cerambycinae: Hesperophanini), a species native to eastern North America. Volatiles collected from adult males contained (2S,4E)-2-hydroxyoct-4-en-3-one (71 %), (3R,4E)-3-hydroxyoct-4-en-2-one (15 %), (E)-4-octen-2,3-dione (13 %), and 2,3-octanedione (1.5 %). Four independent field bioassays with synthetic compounds confirmed that adults of both sexes were attracted by the racemate of the major component, (E)-2-hydroxyoct-4-en-3-one. No other cerambycid species were attracted in significant numbers. Attraction of both sexes is consistent with the male-produced pheromones of many other species in the subfamily Cerambycinae, but T. bimaculatus is unusual in having a pheromone chemistry that is so far unique among species in that subfamily.

Original languageEnglish (US)
Pages (from-to)670-677
Number of pages8
JournalJournal of Chemical Ecology
Issue number7
StatePublished - Jul 7 2015



  • 3-hydroxy-4-octen-2-one
  • Aggregation pheromone
  • Cerambycinae
  • Longhorned beetle
  • Semiochemical

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

Cite this

Zou, Y., Millar, J. G., Blackwood, J. S., Van Duzor, R., Hanks, L. M., Mongold-Diers, J. A., Wong, J. C. H., & Ray, A. M. (2015). (2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus. Journal of Chemical Ecology, 41(7), 670-677. https://doi.org/10.1007/s10886-015-0603-9