Date of Award


Document Type

Open Access

Degree Name

Bachelor of Science



First Advisor

Joanne Kehlbeck




Insects, CHCs, structures, alkanes, species


Cuticular hydrocarbons (CHCs) have been studied extensively and their roles explored for various species of insects. However, only a single reported study has focused on the role of CHCs in Drosophila athabasca, a species of fruit fly native to North America. The work herein describes advances in identification, synthesis and quantification of biologically relevant CHCs present in this species. Identifying CHC profile differences among D. athabasca sub-races (Eastern A, Eastern B and WestNorthern) was performed using multiple analytical techniques. Synthesis of proposed structures confirmed their identity. External standard curves were used to quantify CHCs. GC-MS analysis of CHCs from several isofemale lines of D. Athabasca reveals multiple monoenes, dienes, and branched alkanes. Positions of unsaturation within CHCs were determined using dimethyl disulfide (DMDS) derivatization and branching locations were determined via bromination and subsequent elimination. Synthesis of mono- and di- unsaturated CHCs was accomplished through alkyl substitution, followed by cis-selective reduction. Branched alkanes were generated in a similar fashion or through coupled Grignard-elimination-reduction schemes. External standard curves, generated from synthesized compounds, can be used to produce synthetic profiles for continued exploration of CHC role within the D. athabasca system.

Included in

Chemistry Commons