Synthesis and Characterization of Blattellaquinone and Analogues for Their Evaluation as Cockroach Sex Pheromones

Presenter

Thomas Francesco Adler-Mandile

Campus

Fitchburg State University

Sponsor

Mathangi Krishnamurthy, Department of Biology and Chemistry, Fitchburg State University

Schedule

Session 4, 2:30 PM - 3:15 PM [Schedule by Time][Poster Grid for Time/Location]

Location

Poster Board A58, Campus Center Auditorium, Row 3 (A41-A60) [Poster Location Map]

Abstract

Insect pheromones are important for the study of insect behavior, as well as for pest control. The sex pheromone of the German cockroach, blattellaquinone, is unique in that it contains a quinone moiety as well as a more typical ester group. In this paper, we describe the synthesis of blattellaquinone itself and three analogues produced by altering the acid portion of the ester group. The compounds were synthesized in two steps starting with the esterification of 2,5-dimethoxybenzyl alcohol, followed by oxidation with ceric ammonium nitrate to generate the quinone. The compounds produced as such were analyzed with proton NMR and IR spectroscopy and the results reported. Improved synthetic procedures were developed by variation of methods found in the literature, resulting in an increased yield. The utility of the synthetic methods used and possible improvements are discussed herein. The activity of these compounds as pheromones was evaluated using Madagascar hissing cockroaches.

Keywords

Organic synthesis, Insect behavior, Optimization, Structure activity relationship, Spectroscopy

Research Area

Chemistry and Materials Science

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