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ERIC Number: EJ1159486
Record Type: Journal
Publication Date: 2017-Oct
Pages: 5
Abstractor: As Provided
ISSN: ISSN-0021-9584
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.
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:; Web site:
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