title: (2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus.
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.
authors.affiliation: Department of Entomology, University of California, Riverside, CA, 92521, USA.
authors.forename: Yunfan
authors.initials: Y
authors.lastname: Zou
authors.forename: Jocelyn G
authors.initials: JG
authors.lastname: Millar
authors.forename: J Scott
authors.initials: JS
authors.lastname: Blackwood
authors.forename: Ryan
authors.initials: R
authors.lastname: Van Duzor
authors.forename: Lawrence M
authors.initials: LM
authors.lastname: Hanks
authors.forename: Judith A
authors.initials: JA
authors.lastname: Mongold-Diers
authors.forename: Joseph C H
authors.initials: JC
authors.lastname: Wong
authors.forename: Ann M
authors.initials: AM
authors.lastname: Ray
mesh_terms: D000818:Animals; D001517:Coleoptera / Q000737:chemistry / Q000378:metabolism*; D005260:Female; D007659:Ketones / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism*; D008297:Male; D000442:Octanols / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism*; D012724:Sex Attractants / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism*; D055549:Volatile Organic Compounds / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism*
chemical_list: C000607505:2-hydroxyoct-4-en-3-one; D007659:Ketones; D000442:Octanols; D012724:Sex Attractants; D055549:Volatile Organic Compounds