Isolating trans-Anethole from Anise Seeds and Elucidating Its Structure: A Project Utilizing One- and Two-Dimensional NMR Spectrometry

This three-week project involves isolating and purifying a natural product and determining its structure. trans-Anethole is isolated from anise seeds by steam distillation and liquid-liquid extraction. The crude product is analyzed by thin-layer chromatography and purified by flash chromatography. A...

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Bibliographic Details
Published in:Journal of chemical education 2000-03, Vol.77 (3), p.361
Main Author: LeFevre, Joseph W
Format: Article
Language:English
Subjects:
College students
Curricula
Experiments
Laboratory tests
Natural products
NMR
Nuclear magnetic resonance
Organic chemistry
Organic compounds
Science education
Spectrometry
Spectroscopy
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Summary:This three-week project involves isolating and purifying a natural product and determining its structure. trans-Anethole is isolated from anise seeds by steam distillation and liquid-liquid extraction. The crude product is analyzed by thin-layer chromatography and purified by flash chromatography. A variety of one- and two-dimensional NMR methods, along with infrared spectroscopy, are used to elucidate the structure. The one-dimensional NMR methods are proton homonuclear decoupling, Distortionless Enhancement by Polarization Transfer (DEPT), and Nuclear Overhauser Effect (NOE) difference spectroscopy. The two-dimensional NMR methods are proton-proton COrrelated SpectroscopY (COSY) and HETeronuclear CORrelated spectroscopy (HETCOR). Finally, the proton and carbon-13 NMR spectra are assigned.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed077p361