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ERIC Number: EJ940781
Record Type: Journal
Publication Date: 2011-Jun
Pages: 3
Abstractor: As Provided
Reference Count: 10
ISBN: N/A
ISSN: ISSN-0021-9584
Isolation and Structure Elucidation of the Terpene "[beta]"-Thujone from Cedar Leaf Oil
French, Larry G.
Journal of Chemical Education, v88 n6 p829-831 Jun 2011
Western red cedar leaf affords an essential oil characterized by high thujone content. Students in an advanced organic chemistry lab course isolate a single thujone diastereoisomer from commercially available cedar leaf oil. Treatment of crude oil, containing roughly 70% thujone, predominately as [alpha]-thujone (6.5:1), with ethanolic sodium hydroxide leads to epimerization at the chiral [alpha]-carbon. Equilibration thus inverts the diastereoisomeric ratio in favor (roughly 2:1) of the [beta]-thujone epimer. Selective formation of the bisulfite addition product from the [beta]-isomer allows for a simple purification via filtration. Release of the free ketone upon treatment with Na[subscript 2]CO[subscript 3] yields highly pure [beta]-thujone, which is characterized and identified using IR, MS, and NMR spectroscopy. (Contains 1 figure and 1 scheme.)
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: N/A
Authoring Institution: N/A