Structure analysis of fatty acids by gas chromatography - Low resolution electron impact mass spectrometry of their 4,4-dimethyloxazoline derivatives - A review

Progress in Lipid Research

Volumn 35, Issue 4, 1996, Pages 387-408

  Spitzer, Volker ^a,b  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b NONE   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACID; OXAZOLINE DERIVATIVE;

ELECTRON MICROSCOPY; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; REVIEW; STRUCTURE ANALYSIS;

FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY;

EID: 0030402899     PISSN: 01637827     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7827(96)00011-2     Document Type: Review

References (48)

1. 1. Aitzetmüller K. An unusual fatty acid pattern in Eranthis seed oil. Lipids 31, 201-205 (1996).
2. 2. Andersson B. A. Mass spectrometry of fatty acid pyrrolidides. Prog. Chem. Fats Other Lipids 16, 279-308 (1978).
3. 3. Biemann K. Mass Spectrometry Organic Chemical Application. McGraw Hill Co. Inc., New York, 1962.
4. 4. Budzikiewicz H. Massenspektroskopische Analyse ungesättigter Fettsäuren. In Analytiker-Taschenbuch Band 5. pp. 135-158. Springer Verlag, Hamburg, 1985.
5. 5. Chardigny J.-M., Sebedio J.-L., Grandgirard A., Martine L., Bordeaux O. and Vatele J.-M. Identification of novel trans isomers of 20:5n-3 in liver lipids of rats fed a heated oil. Lipids 31, 165-168 (1996).
6. 6. Christie W. W. Mass spectrometry and fatty acids, ch. 7. In Gas Chromatography and Lipids. The Oily Press, Ayr, 1989.
7. 7. Christie W. W. Determination of fatty acid structure. Inform 4, 85-91 (1993).
8. 8. Classen E., Marx F. and Fabricius H. Mass spectra of 4,4-dimethyloxazoline derivatives of oxooctadecanoic acids. Fat Sci. Technol. 96, 331-332 (1994).
9. 9. Dobson G., Christie W. W., Brechany E. Y., Sebedio J.-L. and Le Quere J.-L. Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic dienoic acids formed in frying oils. Chem. Phys. Lipids 75, 171-182 (1995).
10. 10. Fay L. and Richli U. Location of double bonds in polyunsaturated fatty acids by gas chromatography-mass spectrometry after 4,4-dimethyloxazoline derivatization. J. Chromatogr. 541, 89-98 (1991).
11. 11. Garrido J. L. and Medina I. One-step conversion of fatty acids into their 2-alkenyl-4,4-dimethyloxazoline derivatives directly from total lipids. J. Chromatogr. 673, 101-105 (1994).
12. 12. Harvey D. J. Mass spectrometry of picolinyl and other nitrogen-containing derivatives of lipids, ch. 2. In Advances in Lipid Methodology - One. (W. W. Christie, ed.). The Oily Press, Dundee, 1992.
13. 13. Iversen S. A., Cawood P., Madigan M. J., Lawson A. M. and Dormandy T. L. Identification of a diene conjugated component of human lipis as octadeca-9,11-dienoic acid. FEBS 171, 320-324 (1984).
14. 14. Jensen N. J. and Gross M. L. Mass spectrometry methods for structural determination and analysis of fatty acids. Mass Spectrom. Rev. 6, 497-536 (1987).
15. 15. Lamberto M. and Ackman R. G. Confirmation by gas chromatography-mass spectrometry of two unusual trans-3-monoethylenic fatty acids from the Nova Scotian seaweeds Palmaria palmata and Chondrus crispus. Lipids 29, 441-444 (1994).
16. 16. Le Quéré J.-L. Gas chromatography-mass spectrometry and tandem mass spectrometry in the analysis of fatty acids, ch. 15. In New Trend in Lipid and Lipoproiein Analyses (J.-L. Sebedio and E. G. Perkins, eds). AOCS Press, Champaign, 1995.
17. 17. Liebich H. M., Schmieder N., Wahl H. G. and Wahl J. Separation and identification of unsaturated fatty acid isomers in blood serum and therapeutic oil preparations in the form of their oxazoline derivatives by GC-MS. J. High Resol. Chromatogr. 17, 519-521 (1994).
18. 18. Luthria D. L. and Sprecher H. 2-Alkenyl-4,4-dimethyloxazolines as derivatives for the structural elucidation of isomeric unsaturated fatty acids. Lipids 28, 561-564 (1993).
19. 19. Marx F. and Classer E. Analysis of epoxy fatty acids by GC-MS of their 4,4-dimethyloxazoline derivatives. Fat Sci. Technol. 96, 207-211 (1994).
20. 20. Minnikin D. E. Location of double bonds and cyclopropane rings in fatty acids by mass spectrometry. Chem. Phys. Lipids 21, 313-347 (1978).
21. 21. Mossoba M. M., Yurawecz M. P., Roach J. A. G., Lin H. S., McDonald R. E. and Flickinger B. D. Rapid determination of double bond configuration and position along the hydrocarbon chain in cyclic fatty acid monomers. Lipids 29, 893-896 (1994).
22. 22. Mossoba M. M., Yurawecz M. P., Roach J. A. G., Lin H. S., McDonald R. E., Flickinger B. D. and Perkins E. G. Elucidation of cyclic fatty acid monomer structures. Cyclic and bicyclic ring sizes and double bond position and configuration. J. Am. Oil Chem. Soc. 72, 721-727 (1995).
23. 23. Rezanka T. Polyunsaturated and unusual fatty acids from slime moulds. Phytochemistry 33, 1441-1444 (1993).
24. 24. Rezanka T., Zlatkin I. V., Viden I., Slabova O. I. and Nikitin D. I. Capillary gas chromatography-mass spectrometry of unusual and very long-chain fatty acids from soil oligotrophic bacteria. J. Chromatogr. 558, 215-221 (1991).
25. 25. Ryhage R. and Stenhagen E, Mass spectrometry in lipid research. J. Lipid Res. 1, 361-390 (1960).
26. 26. Schmitz B. and Klein R. A. Mass spectrometric localization of carbon-carbon double bonds: a critical review of recent methods. Chem. Phys. Lipids 39, 285-311 (1986).
27. 27. Spitzer V. GC-MS characterization (chemical ionization and electron impact modes) of the methyl esters and oxazoline derivatives of cyclopropenoid fatty acids. J Am. Oil Chem. Soc. 68, 963-969 (1991).
28. 28. Spitzer V. GLC-MS analysis of the fatty acids of the seed oil, triglycerides and cyanolipid of Paullinia elegans (Sapindaceae) - a rich source of cis-13-eicosenoic acid (paullinic acid). J. High Resol. Chromatogr. 18, 413-416 (1995).
29. 29. Spitzer V. The mass spectra of the 4,4-dimethyloxazoline derivatives of the methoxymethyl olefins of malvalic and sterculic acid. J. Am. Oil Chem. Soc. 72, 389-390 (1995).
30. 30. Spitzer V. The fatty acid composition of some seed oils of Sapindaceae. Phytochemistry 42, 1357-1360 (1996).
31. 31. Spitzer V. The mass spectra of the 4,4-dimethyloxazoline derivatives of some conjugated hydroxy eneyne C-17 and C-18 fatty acids. J. Am. Oil Chem. Soc. 73, 489-492 (1996).
32. 32. Spitzer V., Marx F., Maia J. G. S. and Pfeilsticker K. Occurrence of conjugated fatty acids in the seed oil of Couepia longipendula (Chrysobalanaceae). J. Am. Oil Chem. Soc. 68, 440-442 (1991).
33. 33. Spitzer V., Marx F., Maia J. G. S. and Pfeilsticker K. Curupira tefeensis II: occurrence of acetylenic fatty acids. Fat Sci. Technol. 93, 169-174 (1991).
34. 34. Spitzer V., Marx F., Maia J. G. S. and Pfeilsticker K. Occurrence of eleostearic acid in the seed oil of Parinari montana (Chrysobalanaceae). Fat Sci. Technol. 94, 58-60 (1992).
35. 35. Spitzer V., Marx F. and Pfeilsticker K. The electron impact mass spectra of the oxazoline derivatives of some conjugated diene and triene C-18 fatty acids. J. Am. Oil Chem. Soc. 71, 873-876 (1994).
36. 36. Spitzer V., Bordignon S. A. de L., Schenkel E. P. and Marx F. Identification of nine acetylenic fatty acids, 9-hydroxystearic acid and 9,10-epoxystearic acid in the seed oil of Jodina rhombifolia Hook et Arn. (Santalaceae). J. Am. Oil Chem. Soc. 71, 1343-1348 (1994).
37. 37. Spitzer V., Aitzetmüller K. and Vosman K. The seed oil of Bernardia pulchella (Euphorbiaceae) - a rich source of vernolic acid. J. Am. Oil Chem. Soc. 73, 1733-1735 (1986).
38. 38. Wahl H. G., Habel S.-Y., Schmieder N. and Liebich H. M. Identification of cis/trans isomers of methyl esters and oxazoline derivatives of unsaturated fatty acids using GC-FTIR-MS. J. High Resol. Chromatogr. 17, 543-548 (1994).
39. 39. Yu Q. T., Liu B. N., Zhang J. Y. and Huang Z. H. Location of methyl branchings in fatty acids: fatty acids in urpygial secretion of Shanghai duck by GC-MS of 4,4-dimethyloxazoline derivatives. Lipids 23, 804-810 (1988).
40. 40. Yu Q. T., Liu B. N., Zhang J. Y. and Huang Z. H. Location of double bonds in fatty acids of fish oil and rat testis lipids. Gas chromatography-mass spectrometry of the oxazoline derivatives. Lipids 24, 79-83 (1989).
41. 41. Yurawecz M. P., Molina A. A., Mossoba M. and Ku Y. Estimation of conjugated octadecatrienes in edible fats and oils. J. Am. Oil Chem. Soc. 70, 1093-1099 (1993).
42. 42. Yurawecz M. P., Hood J. K., Roach J. A. G., Mossoba M. M., Daniels D. H., Ku Y., Pariza M. W. and Chin S. F. Conversion of allylic hydroxy oleate to conjugated linoleic acid and methoxy oleate by acid-catalyzed methylation procedures. J. Am. Oil Chem. Soc. 71, 1149-1155 (1996).
43. 43. Zhang J. Y., Yu Q. T. and Huang Z. H. 2-Substituted 4,4-dimethyloxazolines as useful derivatives for the localization of cyclopropane rings in log-chain fatty acids. Shitzurjo Bunseki 35, 23-30 (1987).
44. 44. Zhang J. Y., Yu Q. T., Liu B. N. and Huang Z. H. Chemical modification in mass spectrometry IV: 2-alkenyl-4,4-dimethyloxazolines as derivatives for the double bond location of long-chain olefinic acids. Biomed. Environ. Mass Spectrom. 15, 33-44 (1988).
45. 45. Zhang J. Y., Yu Q. T., Yang Y. M. and Huang Z. H. Chemical modification in mass spectrometry 11. A study on the mass spectra of 4,4-dimethyloxazoline derivatives of hydroxy fatty acids. Chem. Scr. 28, 357-363 (1988).
46. 46. Zhang J. Y., Yu Q. T. and Huang Z. H. New keto acids from the kernel oil of Pseudobombax elliptica by GC-MS of the 4,4-dimethyloxazoline derivatives. Chem. Scr. 28, 353-356 (1988).
47. 47. Zhang J. Y., Yu X. J., Wang H. Y., Liu B. N., Yu Q. T. and Huang Z. H. Location of triple bonds in the fatty acids from the kernel oil of Pyrularia edulis by GC-MS of their 4,4-dimethyloxazoline derivatives. J. Am. Oil Chem. Soc. 66, 256-259 (1989).
48. 48. Zhang J. Y., Wang H. Y., Yu Q. T., Yu X. J., Liu B. N. and Huang Z. H. The structure of cyclopentenyl fatty acids in the seed oil of Flacourticaceae species by GC-MS of their 4,4-dimethyloxazoline derivatives. J. Am. Oil Chem. Soc. 66, 242-246 (1989).