An Investigation of Chlorohydroxy Fatty Acids

People

Faculty
  John Kennish

Student Researchers
  Vanessa Bergstedt

Abstract

My proposed experiment is as follows:  Six biologically pertinent chlorohydroxy fatty acids will be synthesized, separated and run for structural analysis on GC, MS/MS, IR, and NMR.  The starting materials will be the cis isomers of tetradecenoic acid, hexadecenoic acid, and octadecenoic acid.  The 14, 16 and 18 carbon fatty acids were chosen because these are the most common in biological tissue. The cis isomers are the most common isomer.  Each of these compounds will be treated with N-chlorosuccinimide to produce the two chlorohydroxy regioisomers per compound.  The goal will be to learn more basic information about their structure and identification.  Without this fundamental information further research on the compounds cannot proceed.  There are several unanswered questions regarding chlorinated and chlorohydroxy fatty acids.  For example, chlorinated and chlorohydrosxy fatty acids disrupt the cell membrane.  They also have derogatory effects on the reproductive system of the organism.  However the cell gives no known indicator to register either of these compounds as toxic.  There is no current explanation for this.  Currently all chlorinated fatty acids are described together.  However having a hydroxyl group can greatly affect the chemistry of a compound.  Also the formation of a chlorohydroxy fatty acid requires different conditions than that of a dichloro fatty acid.  There have been speculations about the presence of chlorohydroxy fatty acids that differ from that of dichloro fatty acids.  Therefore I wish to increase the knowledge of chlorohydroxy fatty acids separately so that their individual role in these questions can become more apparent.

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