ERIC Number: EJ1159486
Record Type: Journal
Publication Date: 2017-Oct
Pages: 5
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Isolation of Biliverdin Ixa, as Its Dimethyl Ester, from Emu Eggshells
Halepas, Steven; Hamchand, Randy; Lindeyer, Samuel E. D.; Bru¨ckner, Christian
Journal of Chemical Education, v94 n10 p1533-1537 Oct 2017
A laboratory experiment is described that extracts the tetrapyrrolic teal-colored biliverdin IXa, as its dimethyl ester, from commercially available emu eggshells. The extraction of ~10 mg samples of biliverdin is simple and requires two 3 h lab periods: A two-step acid digestion and liquid-liquid extraction, followed by short silica gel flash column chromatography. The deeply colored extract can be characterized by TLC, UV-vis, IR, [superscript 1]H NMR spectroscopy, ESI+ mass spectrometry, or its diagnostic chemical reduction to the yellow derivative bilirubin. A small-scale variant of this extraction requires only a single 3 h lab period, and the extracts can be analyzed by UV-vis spectroscopy, ESI[superscript +] MS, or HPLC. An introduction to the biological origin of biliverdin is provided. This pedagogically flexible project combines natural product isolation with the spectroscopic characterization of a multifunctional biomedically important compound and touches upon many aspects of chemistry and biology. The colorful experiment is appropriate for the introductory organic chemistry laboratory and possesses the prerequisites for a chemistry-biology interlaboratory approach.
Descriptors: Animals, Science Instruction, Laboratory Experiments, Chemistry, Spectroscopy, Organic Chemistry, Undergraduate Students, College Science, Laboratory Procedures, Science Experiments, Biology, Color, Science Activities, Molecular Structure
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: National Science Foundation (NSF)
Authoring Institution: N/A
Identifiers - Location: Connecticut
Grant or Contract Numbers: CHE1058846; CHE1465133; HRD1400382