Eggciting! The isolation of porphyrins from brown egg shells and their detection by luminescence

CHED 104

Michelle L. Dean, michelle.dean@uconn.edu, Tyson A. Miller, tyson.miller@uconn.edu, and Christian Brückner, c.bruckner@uconn.edu. Department of Chemistry, University of Connecticut, Unit 3060, Storrs, CT 06269
What is more appealing than to extract a natural product from familiar materials and to detect minute quantities by a chemiluminescence reaction that lights up the entire test tube with a bright red glow? Described here is such an engaging natural product isolation sequence. Protoporphyrin IX is extracted from brown hen's egg shells using a variety of methods. The extracted porphyrin diacid can be esterified, chromatographed using TLC, detected by UV-vis or fluorescence spectroscopy, or by ESI(+) mass spectrometry. Using a number of procedures initially presented by Brandl, the porphyrin solutions are susceptible to detection using a chemiluminescence reaction. Thus, the common brown hen's egg serves a pedagogical tool discuss a number of topics: The chemistry of the extraction and esterification, the optical properties of the extended π-systems of porphyrins, the relationship between UV-vis and fluorescence spectra, the structure and biological significance of porphyrins, and the mechanism of the chemiluminescence reaction.
 

General Posters
7:30 PM-9:30 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Chemical Education

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007