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Research with Dr. Dan Blanchard

Synthesis of a Known Insect Pheromone: trans-Conophthorin

Robert Hachtman, Jaclyn Berg, Christopher DiJiacomo, and Dr. Dan Blanchard 

Cone BeetlePheromones are chemicals that are secreted by insects to communicate location of food sources, presence of danger, and to attract mates. One of the pheromones secreted by cone beetles (Conophthorus banksianae, C. resinosae, and C. coniperda) is trans-conophthorin.

The goal of this project is to synthesize this natural pheromone from readily available starting materials so that it can be used in biological studies with cone beetles.

We developed a six-step synthesis that would start with materials we could purchase inexpensively, and would hopefully end at our target compound, trans-conophthorin. Pheromone Synthesis

Pheromone NMRAfter each step in the synthesis, we characterized the intermediate products using one or more of the following techniques: thin-layer chromatography, IR spectroscopy, GC-MS, and NMR. We have successfully completed all steps in the synthesis, except the last one. The NMR spectrum of the second to the last product summarizes our success up to this point.

Investigation of Amino Acid Derivatives as Low Molecular Mass Gelators

Sandra Zimmerman and Dr. Dan Blanchard

Low molecular mass gelators are molecules whose heated solutions are homogeneous, but when cooled to room temperature, form a gel. The test tubes below contain ethyl acetate with a low concentration of a gelator

.Gelator Solutions

 
Gelator Structure

We were interested in synthesizing several gelators to investigate what structural properties influenced the ability of molecule to make a good gelator.

We have chemically attached a long hydrocarbon chain to various amino acid derivatives (of isoleucine*, phenylalanine, leucine and threonine), and tested their ability to act as gelators. The reaction on the right summarizes the preparation of the gelators.

Derivatives of isoleucine and phenylalanine produced the best gelators, while derivatives of leucine and threonine did not cause gelation.

*Hanabusa, Kenji; Hiratsuka, K; Kimura, M; and Shirai, H. "Easy Preparation and Useful Character of Organogel Electrolytes Based on Low Molecular Weight Gelator." Chem. Mater. (1999), Volume 11, pages 649-655.