GC/MS analysis of the oxidation products of fatty acids methyl esters of sunflower oil
Keywords:
gas chromatography/mass spectrometry, fatty acids methyl esters of sunflower oil, oxidation, epoxidation.
Abstract
Oxidation of sunflower oil FAMEs with hydrogen peroxide in the presence of formic acid may be
used in the development of new technologies for production of valuable compounds from the renewable plant
raw materials.
A mixture of the derivatives of the fatty acids methyl esters have been investigated by the GC/MS
method using a capillary column. It has been revealed the presence of large numbers of compounds, with a
prevalence of at least 24 components. 14 oxidation products have been identified by fragmentation from their
individual mass spectra. The main components of the mixture of oxidation FAMEs were methyl 9,10-
epoxyoctadecanoate and methyl 9,10-dihydroxyoctadecanoate.
In summary, the proposed method has proved to be an excellent step to approach the quantitative
analysis of oxidized fatty acids methyl esters of sunflower oil.
Downloads
Download data is not yet available.
References
1. Gan L. H., Ooi K. S., Gan L. M. et al.
Effects of epoxidation on the thermal oxidative
stabilities of fatty acid esters derived from palm
olein, JAOCS, 1995, Vol. 72, No 4, pp. 439-442.
2. Litz J.T. in: Encyclopedia of Chemical
Technology, Wallace, J.G. (Ed.), 3rd ed., John
Wiley: New York, 1978, pp. 251-261.
3. Pignitter M., Somoza V. Critical Evaluation
of Methods for the Measurement of Oxidative
Rancidity in Vegetable Oils, Journal of Food
and Drug Analysis, 2012, Vol. 20, No 4,
pp. 772-777.
4. Dobarganes C., Marquez-Ruiz G. Oxidized
fats in foods, Curr. Opin. Clin. Nutr. Metab.
Care, 2003, Vol. 6,. pp. 157-163.
5. Salimon J., Saliha N., Yousif E. Chemically
modified biolubricant basestocks from
epoxidized oleic acid: Improved low
temperature properties and oxidative stability,
Journal of Saudi Chemical Society, 2011,
Vol. 15, pp. 195-201.
6. Gunstone D. The study of natural epoxy oils
and epoxidized vegetable oils by13C nuclear
magnetic resonance spectroscopy, JAOCS,
1993, Vol. 70, No 11, pp.1139-1144.
7. Akintayo E.T. Ziegler T., Onipede A.
Сhromatographic and spectroscopic analysis of
epoxidised canola oil, Bull. Chem. Soc. Ethiop,
2006, Vol. 20, pp. 75-81.
8. Campanella A., Fontanini C., Baltanás M.A.
High yield epoxidation of fatty acid methyl
esters with performic acid generated in situ //
Chemical Engineering Journal, 2008, Vol. 144,
pp. 466-475.
9. Kleiman R., Spencer G.F. Gas
Chromatography-Mass Spectrometry of Methyl
Esters of Unsaturated Oxygenated Fatty Acids,
JAOCS, 1973, Vol. 50, pp. 31-38.
10. LaScala J., Wool R.P. Effect of FA
Composition on Epoxidation Kinetics of TAG,
JAOCS, 2002, Vol. 79, pp. 373-377.
11. Marmesat S., Velasco J., Dobarganes M.C.
Quantitative determination of epoxy acids, keto
acids and hydroxy acids formed in fats and oils
at frying temperatures, Journal of
Chromatography A, 2008, Vol. 1211,
pp. 129-134.
12. Hasanov V.V., Ryzhova G.L., Dychko
K.A. et al. Sostav zhirnyh kislot i steroidov
rastitel'nyh masel, Himija rastitel'nogo syr'ja,
2006, No 3, pp. 27-31.
13. Falaleev A.V., Voronjuk I.V., Kruzhilin
A.A. et al. GH-MS analiz N,Ndimetilaminopropilamidov
zhir-nyh kislot
rastitel'nyh masel, Sorbcionnye i
hromatograficheskie processy, 2014, Vol. 14,
No 3. pp. 494-501.
14. Plattner R.D., Gardner H.W. Mass
Spectrometry of Isomeric Fatty Acid
Hydroperoxides by Chemical Ionization via
Direct Exposure Probe, Lipids, 1985, Vol. 20,
No 2, pp. 126-131.
15. Mochida Y., Yokoyama Yu., Kawai T. et
al. Liquid Ionization Mass Spectrometry of
Methyl Hydroperoxyoleates and Their Related
Леденева и др. / Сорбционные и хроматографические процессы. 2015. Т. 15. Вып. 2
287
Compounds, J. Mass Spectrom. Soc. Jpn, 1994,
Vol. 42, No 3, pp. 207-215.
16. Sharma B.K., Doll K.M., Erhana S.Z.
Oxidation, friction reducing, and low
temperature properties of epoxy fatty acid
methyl esters, Green Chem, 2007, Vol. 9,
pp. 469-474.
17. Wilson R., Lyall K. Simultaneous
Determination by GC-MS of Epoxy and
Hydroxy FA as Their Methoxy Derivatives,
Lipids, 2002, Vol. 37, No 9, pp. 917-924.
18. Newman J. W., Hammock B. D.
Optimized thiol derivatizing reagent for the
mass spectral analysis of disubstituted epoxy
fatty acids, Journal of Chromatography A, 2001,
Vol. 925, pp. 223-240.
19. Halarnkar P.P., Nourooz-Zadeh J.,
Kuwano E. et al. Formation of Cyclic Products
from the Diepoxide of Long-Chain Fatty Esters
by Cytosolic Epoxide Hydrolase, Archives of
Biochemistry and Biophysics, 1992, Vol. 294,
No 2, pp. 586-593.
Effects of epoxidation on the thermal oxidative
stabilities of fatty acid esters derived from palm
olein, JAOCS, 1995, Vol. 72, No 4, pp. 439-442.
2. Litz J.T. in: Encyclopedia of Chemical
Technology, Wallace, J.G. (Ed.), 3rd ed., John
Wiley: New York, 1978, pp. 251-261.
3. Pignitter M., Somoza V. Critical Evaluation
of Methods for the Measurement of Oxidative
Rancidity in Vegetable Oils, Journal of Food
and Drug Analysis, 2012, Vol. 20, No 4,
pp. 772-777.
4. Dobarganes C., Marquez-Ruiz G. Oxidized
fats in foods, Curr. Opin. Clin. Nutr. Metab.
Care, 2003, Vol. 6,. pp. 157-163.
5. Salimon J., Saliha N., Yousif E. Chemically
modified biolubricant basestocks from
epoxidized oleic acid: Improved low
temperature properties and oxidative stability,
Journal of Saudi Chemical Society, 2011,
Vol. 15, pp. 195-201.
6. Gunstone D. The study of natural epoxy oils
and epoxidized vegetable oils by13C nuclear
magnetic resonance spectroscopy, JAOCS,
1993, Vol. 70, No 11, pp.1139-1144.
7. Akintayo E.T. Ziegler T., Onipede A.
Сhromatographic and spectroscopic analysis of
epoxidised canola oil, Bull. Chem. Soc. Ethiop,
2006, Vol. 20, pp. 75-81.
8. Campanella A., Fontanini C., Baltanás M.A.
High yield epoxidation of fatty acid methyl
esters with performic acid generated in situ //
Chemical Engineering Journal, 2008, Vol. 144,
pp. 466-475.
9. Kleiman R., Spencer G.F. Gas
Chromatography-Mass Spectrometry of Methyl
Esters of Unsaturated Oxygenated Fatty Acids,
JAOCS, 1973, Vol. 50, pp. 31-38.
10. LaScala J., Wool R.P. Effect of FA
Composition on Epoxidation Kinetics of TAG,
JAOCS, 2002, Vol. 79, pp. 373-377.
11. Marmesat S., Velasco J., Dobarganes M.C.
Quantitative determination of epoxy acids, keto
acids and hydroxy acids formed in fats and oils
at frying temperatures, Journal of
Chromatography A, 2008, Vol. 1211,
pp. 129-134.
12. Hasanov V.V., Ryzhova G.L., Dychko
K.A. et al. Sostav zhirnyh kislot i steroidov
rastitel'nyh masel, Himija rastitel'nogo syr'ja,
2006, No 3, pp. 27-31.
13. Falaleev A.V., Voronjuk I.V., Kruzhilin
A.A. et al. GH-MS analiz N,Ndimetilaminopropilamidov
zhir-nyh kislot
rastitel'nyh masel, Sorbcionnye i
hromatograficheskie processy, 2014, Vol. 14,
No 3. pp. 494-501.
14. Plattner R.D., Gardner H.W. Mass
Spectrometry of Isomeric Fatty Acid
Hydroperoxides by Chemical Ionization via
Direct Exposure Probe, Lipids, 1985, Vol. 20,
No 2, pp. 126-131.
15. Mochida Y., Yokoyama Yu., Kawai T. et
al. Liquid Ionization Mass Spectrometry of
Methyl Hydroperoxyoleates and Their Related
Леденева и др. / Сорбционные и хроматографические процессы. 2015. Т. 15. Вып. 2
287
Compounds, J. Mass Spectrom. Soc. Jpn, 1994,
Vol. 42, No 3, pp. 207-215.
16. Sharma B.K., Doll K.M., Erhana S.Z.
Oxidation, friction reducing, and low
temperature properties of epoxy fatty acid
methyl esters, Green Chem, 2007, Vol. 9,
pp. 469-474.
17. Wilson R., Lyall K. Simultaneous
Determination by GC-MS of Epoxy and
Hydroxy FA as Their Methoxy Derivatives,
Lipids, 2002, Vol. 37, No 9, pp. 917-924.
18. Newman J. W., Hammock B. D.
Optimized thiol derivatizing reagent for the
mass spectral analysis of disubstituted epoxy
fatty acids, Journal of Chromatography A, 2001,
Vol. 925, pp. 223-240.
19. Halarnkar P.P., Nourooz-Zadeh J.,
Kuwano E. et al. Formation of Cyclic Products
from the Diepoxide of Long-Chain Fatty Esters
by Cytosolic Epoxide Hydrolase, Archives of
Biochemistry and Biophysics, 1992, Vol. 294,
No 2, pp. 586-593.
Published
2018-02-19
How to Cite
Фалалеев, А. В., Леденева, И. В., Картавцев, П. А., Перелыгина, И. Э., & Ляпун, Д. В. (2018). GC/MS analysis of the oxidation products of fatty acids methyl esters of sunflower oil. Sorbtsionnye I Khromatograficheskie Protsessy, 15(2), 280-287. https://doi.org/10.17308/sorpchrom.2015.15/276
Section
Статьи
