The AOCS Lipid Library

Bibliography on Mass Spectrometry of Fatty Acids

Chemical-Ionization Mass spectrometry for Fatty Acid Identification

Atmospheric-pressure chemical-ionization (APCI) mass spectrometry is one of the mildest ionization techniques available, but is particularly effective linked to high-performance liquid chromatography, as it can tolerate relatively high solvent flow rates. In conjunction with tandem-MS techiques, it can give useful structural information on fatty acids. Another very promising technique involves acetonitrile-chemical-reaction tandem mass spectrometry in the gas phase for locating double bonds in fatty acid methyl esters (from the laboratory of Professor J.T. Brenna mainly). In the mass spectrometer, an ion (m/z = 54), formed by reaction of acetonitrile with itself, adds across the double bond in a cycloaddition reaction. When this nascent complex undergoes collision-induced dissociation, two diagnostic ions emerge. One of these results from loss of the hydrocarbon end of the FAME, and the other ion from loss of the methyl ester end, and together, these locate the positions of the double bonds in the FAME.

The following references were collected as part of our regular literature reviews for our own research purposes. We cannot claim to have covered the subject exhaustively, but we have done our best.  References are listed alphabetically by the first author of a paper, but not necessarily chronologically by that author. New references may be added at irregular intervals - check the bottom of the page for when it was last updated.

• Alves,S.P. and Bessa,R.J.B. Identification of cis-12,cis-15 octadecadienoic acid and other minor polyenoic fatty acids in ruminant fat. Eur. J. Lipid Sci. Technol., 109, 879-883 (2007).
• Bicalho,B., David,F., Rumplel,K., Kindt,E. and Sandra,P. Creating a fatty acid methyl ester database for lipid profiling in a single drop of human blood using high resolution capillary gas chromatography and mass spectrometry. J. Chromatogr. A, 1211, 120-128 (2008).
• Brenna,J.T. Double bond localization in fatty acid methyl esters by covalent adduct chemical ionization (CACI) tandem mass spectrometry. Lipid Technology, 17, 229-232 (2005).
• Brenna,J.T. Structural analysis of unsaturated fatty acid methyl ester isomers with acetonitrile covalent adduct chemical ionization. In: Lipid Analysis and Lipidomics: New Techniques and Applications. pp. 157-172 (ed: M.M. Mossoba, J.K.G. Kramer, J.T. Brenna and R.E. McDonald, AOCS Press, Champaign, USA) (2006)
• Gallon,A.A. and Pryor,W.A. The identification of the allylic nitrite and nitro derivatives of methyl linoleate and methyl linolenate by negative chemical ionization mass spectroscopy. Lipids, 28, 125-133 (1993).
• Goulitquer,S., Dreano,Y., Berthou,F., Corcos,L. and Lucas,D. Determination of epoxyeicosatrienoic acids in human red blood cells and plasma by GC/MS in the NICI mode. J. Chromatogr. B, 876, 83-88 (2008).
• Infante,J.P., Tschanz,C.L., Shaw,N., Michaud,A.L., Lawrence,P. and Brenna,J.T. Straight-chain acyl-CoA oxidase knockout mouse accumulates extremely long chain fatty acids from alpha-linolenic acid: Evidence for runaway carousel-type enzyme kinetics in peroxisomal beta-oxidation diseases. Mol. Genetics Metab., 75, 108-119 (2002).
• Lawrence,P. and Brenna,J.T. Acetonitrile covalent adduct chemical ionization mass spectrometry for double bond localization in non-methylene-interrupted polyene fatty acid methyl esters. Anal. Chem., 78, 1312-1317 (2006).
• Michaud,A.L, Lawrence,P., Adlof,R. and Brenna,J.T. On the formation of conjugated linoleic acid diagnostic ions with acetonitrile chemical ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom., 19, 363-368 (2005).
• Michaud,A.L, Yurawecz,M.P., Delmonte,P., Corl,B.A., Bauman,D.E. and Brenna,J.T. Identification and characterization of conjugated fatty acid methyl esters of mixed double bond geometry by acetonitrile chemical ionization tandem mass spectrometry. Anal. Chem., 75, 4925-4930 (2003).
• Michaud,A.L., Diau,G.Y., Abril,R. and Brenna,J.T. Double bond localization in minor homoallylic fatty acid methyl esters using acetonitrile chemical ionization tandem mass spectrometry. Anal. Biochem., 307, 348-360 (2002).
• Nichols,D.S. and Davies,N.W. Improved detection of polyunsaturated fatty acids as phenacyl esters using liquid chromatography-ion trap mass spectrometry. J. Microb. Methods, 50, 103-113 (2002).
• Oldham,N.J. and Svatos,A. Determination of the double bond position in functionalized monoenes by chemical ionization ion-trap mass spectrometry using acetonitrile as a reagent gas. Rapid Commun. Mass Spectrom., 13, 331-336 (1999).
• Park,W.J., Kothapalli,K.S.D., Lawrence,P., Tyburczy,C. and, Brenna,J.T. An alternate pathway to long-chain polyunsaturates: the FADS2 gene product Delta 8-desaturates 20:2n-6 and 20:3n-3. J. Lipid Res., 50, 1195-1202 (2009).
• Rezanka,T. Analysis of very long chain polyunsaturated fatty acids using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Biochem. System. Ecol., 28, 847-856 (2000).
• Rezanka,T. Analysis of polyunsaturated fatty acids using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J. High Resolut. Chromatogr., 23, 338-342 (2000).
• Rezanka,T. Identification of very long chain fatty acids by atmospheric pressure chemical ionization liquid chromatography-mass spectroscopy from green alga Chlorella kessleri. J. Sep. Sci., 25, 1332-1336 (2002).
• Rezanka,T. and Dembitsky,V.A. Tetratriacontanonaenoic acid, first natural acid with nine double bonds isolated from a crustacean Bathynella natans. Tetrahedron, 60, 4261-4264 (2004).
• Rezanka,T. and Sigler,K. Identification of very long chain unsaturated fatty acids from Ximenia oil by atmospheric pressure chemical ionization liquid chromatography-mass spectroscopy. Phytochemistry, 68, 925-934 (2007).
• Rezanka,T. and Votruba,J. Analysis of fatty acids by APCI-MS. In 'Modern Methods for Lipid Analysis by Liquid Chromatography/Mass Spectrometry and Related Techniques' (Ed. W.C. Byrdwell, AOCS Press, Champaign), pp. 242-275 (2005).
• Rezanka,T., Nedbalova,L. and Sigler,K. Identification of very-long-chain polyunsaturated fatty acids from Amphidinium carterae by atmospheric pressure chemical ionization liquid chromatography-mass spectroscopy. Phytochemistry, 69, 2391-2399 (2008).
• Rezanka,T., Nedbalova,L. and Sigler,K. Odd-numbered very-long-chain polyunsaturated fatty acids from the dinoflagellate Amphidinium carterae identified by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry. Phytochemistry, 69, 2849-2855 (2008).
• Ritter,A., Goulitquer,S., Salaun,J.P., Tonon,T., Correa,J.A. and Potin,P. Copper stress induces biosynthesis of octadecanoid and eicosanoid oxygenated derivatives in the brown algal kelp Laminaria digitata. New Phytologist, 180, 809-821 (2008).
• Saba,A., Mazzini,F., Raffaelli,A., Mattei,A. and Salvadori,P. Identification of 9(E),11(E)-18 : 2 fatty acid methyl ester at trace level in thermal stressed olive oils by GC coupled to acetonitrile CI-MS and CI-MS/MS, a possible marker for adulteration by addition of deodorized olive oil. J. Agric. Food Chem., 53, 4867-4872 (2005).
• Treschow,A.P., Hodges,L.D., Wright,P.F.A., Wynne,P.M., Kalafatis,N. and Macrides,T.A. Novel anti-inflammatory omega-3 PUFAs from the New Zealand green-lipped mussel, Perna canaliculus. Comp. Biochem. Physiol. B, 147, 645-656 (2007).
• Uenishi,Y., Takii,T., Yano,I. and Sunagawa,M. Separation and molecular characterization of mycolic acid from the cell wall skeleton of Mycobacterium bovis BCG Tokyo 172 (SMP-105) and BCG substrains by normal-phase high performance liquid chromatography and liquid chromatography/mass spectrometry. J. Microbiol. Methods, 77, 320-322 (2009).
• Valto, P., Knuutinen,J. and Alen,R. Resin and fatty-acid analysis by solid-phase extraction coupled to atmospheric pressure chemical ionization-mass spectrometry. Int. J. Environ. Anal. Chem., 87, 87-97 (2007).
• Van Pelt,C.K. and Brenna,J.T. Acetonitrile chemical ionization tandem mass spectrometry to locate double bonds in polyunsaturated fatty acid methyl esters. Anal. Chem., 71, 1981-1989 (1999).
• Van Pelt,C.K., Carpenter,B.K. and Brenna,J.T. Studies of structure and mechanism in acetonitrile chemical ionization tandem mass spectrometry of polyunsaturated fatty acid methyl esters. J. Am. Soc. Mass Spectrom., 10, 1253-1262 (1999).
• Van Pelt,C.K., Huang,M.C., Tschanz,C.L. and Brenna,J.T. An octaene fatty acid, 4,7,10,13,16,19,22,25-octacosaoctaenoic acid (28:8n-3), found in marine oils. J. Lipid Res., 40, 1501-1505 (1999).
• Wolyniak,C.J., Brenna,J.T., Murphy,K.J. and Sinclair,A.J. Gas chromatography-chemical ionization-mass spectrometric fatty acid analysis of a commercial supercritical carbon dioxide lipid extract from New Zealand green-lipped mussel (Perna canaliculus). Lipids, 40, 355-360 (2005).
• Xu,Y.H. and Brenna,J.T. Atmospheric pressure covalent adduct chemical ionization tandem mass spectrometry for double bond localization in monoene- and diene-containing triacylglycerols. Anal. Chem., 79, 2525-2536 (2007).
• Yin,H.Y. and Porter,N.A. New insights regarding the autoxidation of polyunsaturated fatty acids. Antiox. Redox Signaling, 7, 170-184 (2005).
• You,J., Zhao,X., Suo,Y., Li,Y., Wang,H. and Chen,G. Determination of long-chain fatty acids in bryophyte plants extracts by HPLC with fluorescence detection and identification with MS. J. Chromatogr. B, 848, 283-291 (2007).
• Zahardis,J., LaFranchi,B.W. and Petrucci,G.A. Photoelectron resonance capture ionization mass spectrometry of fatty acids in olive oil. Eur. J. Lipid Sci. Technol., 108, 925-935 (2006).

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