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

J Chem Ecol. 2015 Jul;41(7):670-7. doi: 10.1007/s10886-015-0603-9. Epub 2015 Jul 7.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Coleoptera / chemistry
  • Coleoptera / metabolism*
  • Female
  • Ketones / analysis
  • Ketones / chemical synthesis
  • Ketones / metabolism*
  • Male
  • Octanols / analysis
  • Octanols / chemical synthesis
  • Octanols / metabolism*
  • Sex Attractants / analysis
  • Sex Attractants / chemical synthesis
  • Sex Attractants / metabolism*
  • Volatile Organic Compounds / analysis
  • Volatile Organic Compounds / chemical synthesis
  • Volatile Organic Compounds / metabolism*

Substances

  • 2-hydroxyoct-4-en-3-one
  • Ketones
  • Octanols
  • Sex Attractants
  • Volatile Organic Compounds