title: Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.
abstract: Male-released sex pheromone constituents of the longhorn beetle Anaglyptus subfasciatus (Coleoptera: Cerambycidae) are identified by GC-MS and GC-Fourier transform infrared as a 7:1 molar mixture of 3-hydroxy-2-hexanone and 3-hydroxy-2-octanone. These two compounds undergo thermal isomerization during GC analyses to give the corresponding 2-hydroxy-3-alkanones. Comparison of GC retention times of the natural products with those of synthesized enantiomerically pure compounds revealed that both semiochemicals have (R)-stereochemistry. These absolute configurations were confirmed by comparisons of the (R)-methoxy(trifluoromethyl)phenylacetic acid esters of insect-derived and synthetic samples.
authors.affiliation: Department of Chemistry, Cornell University, Ithaca, NY 14853.
authors.forename: W S
authors.initials: WS
authors.lastname: Leal
authors.forename: X
authors.initials: X
authors.lastname: Shi
authors.forename: K
authors.initials: K
authors.lastname: Nakamuta
authors.forename: M
authors.initials: M
authors.lastname: Ono
authors.forename: J
authors.initials: J
authors.lastname: Meinwald
mesh_terms: D000818:Animals; D002849:Chromatography, Gas / Q000379:methods; D001517:Coleoptera / Q000737:chemistry*; D004563:Electrochemistry; D005260:Female; D005410:Flame Ionization; D006588:Hexanones / Q000737:chemistry*; D006358:Hot Temperature; D007536:Isomerism; D007659:Ketones / Q000737:chemistry*; D008297:Male; D015394:Molecular Structure; D012724:Sex Attractants / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C092072:3-hydroxy-2-hexanone; D006588:Hexanones; D007659:Ketones; D012724:Sex Attractants; C092071:3-hydroxy-2-octanone