Synthesis and Biological Testing of Blattellaquinone, the Sex Pheromone of the German Cockroach (Blattella germanica)

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 13 Issue 4 (2008) pp 231-233

Synthesis and Biological Testing of Blattellaquinone, the Sex Pheromone of the German Cockroach (Blattella germanica)

William H. Miles,* Evan M. Cohen, and Barbara J. Naimoli

Department of Chemistry, Lafayette College, Easton, PA 18042, milesw@lafayette.edu
Received September 20, 2007. Accepted July 18, 2008.

Published online: 24 July 2008

Abstract. This paper describes the synthesis and bioassay of blattellaquinone, the sex pheromone of the German cockroach (Blattella germanica). The first step in the synthesis is the titanium(IV) isopropoxide-catalyzed transesterification of methyl isovalerate with 2,5-dimethoxybenzyl alcohol to give (2,5-dimethoxyphenyl)methyl 3-methylbutanonate. In the second step of the synthesis, ceric ammonium nitrate oxidation of (2,5-dimethoxyphenyl)methyl 3-methylbutanonate gave blattellaquinone. Field testing of the synthetic pheromone with simple glue traps demonstrated the ability of blattellaquinone to act as an attractant for German cockroaches.

Key Words: Laboratories and Demonstrations; general chemistry

(*) Corresponding author. (E-mail: milesw@lafayette.edu)

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