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Fatty acids of Thespesia populnea: Mass spectrometry of picolinyl esters of cyclopropene fatty acids†
Article first published online: 18 MAY 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
European Journal of Lipid Science and Technology
Volume 113, Issue 8, pages 980–984, August 2011
How to Cite
Knothe, G., Rashid, U., Yusup, S. and Anwar, F. (2011), Fatty acids of Thespesia populnea: Mass spectrometry of picolinyl esters of cyclopropene fatty acids. Eur. J. Lipid Sci. Technol., 113: 980–984. doi: 10.1002/ejlt.201100004
- Issue published online: 15 AUG 2011
- Article first published online: 18 MAY 2011
- Accepted manuscript online: 14 APR 2011 07:10AM EST
- Manuscript Accepted: 12 APR 2011
- Manuscript Revised: 24 MAR 2011
- Manuscript Received: 4 JAN 2011
- Nuclear magnetic resonance;
- Thespesia populnea
Thespesia populnea belongs to the plant family of Malvaceae which contain cyclopropane and cyclopropene fatty acids. However, previous literature reports vary regarding the content of these compounds in Thespesia populnea seed oil. In this work, the content of malvalic acid (8,9-methylene-9-heptadecenoic acid) in the fatty acid profile of Thespesia populnea seed oil was approximately 7% by GC. Two cyclopropane fatty acids were identified, including dihydrosterculic acid. The methyl and picolinyl esters of Thespesia populnea seed oil were also prepared. The mass spectrum of picolinyl malvalate was more closely investigated, especially an ion at m/e 279, which does not fit the typical series of ions observed in picolinyl esters. It is shown that this ion is caused by cleavage at the picolinyl moiety and contains the fatty acid chain without the picolinyl moiety. This type of cleavage has previously not been observed prominently in picolinyl esters and may therefore be diagnostic for picolinyl esters of cyclopropene fatty acids. The NMR spectra of Thespesia populnea methyl esters are also discussed.
Practical applications: The work reports the fatty acid composition of Thespesia seed oil whose derivatives have not yet been extensively utilized for industrial purposes, for example, biodiesel. Knowing this composition is essential for understanding potential uses and, for example, in case of biodiesel the fuel properties. Besides this issue, some data (mass spectrometry and NMR) crucial for obtaining the composition information are analyzed in detail. The biodiesel properties of methyl esters of Thespesia populnea will be reported separately.