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Rapid Discrimination of Fatty Acid Composition in Fats and Oils by Electrospray Ionization Mass Spectrometry

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Rapid Discrimination of Fatty Acid Composition in Fats and Oils by Electrospray Ionization Mass Spectrometry ANALYTICAL SCIENCES DECEMBER 2005, VOL. 21 1457 2005 © The Japan Society for Analytical Chemistry Rapid Discrimination of Fatty Acid Composition in Fats and Oils by Electrospray Ionization Mass Spectrometry Shoji KURATA,*† Kazutaka YAMAGUCHI,* and Masatoshi NAGAI** *Criminal Investigation Laboratory, Metropolitan Police Department, 2-1-1, Kasumigaseki, Chiyoda-ku, Tokyo 100–8929, Japan **Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo 184–8588, Japan Fatty acids in 42 types of saponified vegetable and animal oils were analyzed by electrospray ionization mass spectrometry (ESI-MS) for the development of their rapid discrimination. The compositions were compared with those analyzed by gas chromatography–mass spectrometry (GC-MS), a more conventional method used in the discrimination of fats and oils. Fatty acids extracted with 2-propanol were detected as deprotonated molecular ions ([M–H]–) in the ESI-MS spectra of the negative-ion mode. The composition obtained by ESI-MS corresponded to the data of the total ion chromatograms by GC-MS. The ESI-MS analysis discriminated the fats and oils within only one minute after starting the measurement. The detection limit for the analysis was approximately 10–10 g as a sample amount analyzed for one minute. This result showed that the ESI-MS analysis discriminated the fats and oils much more rapidly and sensitively than the GC-MS analysis, which requires several tens of minutes and approximately 10–9 g. Accordingly, the ESI-MS analysis was found to be suitable for a screening procedure for the discrimination of fats and oils. (Received July 21, 2005; Accepted September 28, 2005) with organic solvent. This sample preparation is effective in Introduction removing impurities from polluted fats and oils. The analysis of the GC or GC-MS for fatty acid requires esterification or A variety of fats and oils are widely available for consumption transesterification, which is a laborious and time-consuming in the form of cooking oils, health products and food ingredients, exercise in the examination procedure. The measurement times as well as for the manufacture of cosmetics, soaps and surfactants. of GC and GC-MS analyses require at least a few tens of minutes These fats and oils primarily contain triacylglycerols (also for the elution and separation of the saponifiables of the fats and known as triglycerides), which are esters derived from the oils. Some fats and oils, particularly castor oil and fish oils, take reaction of the carboxylic functional groups of fatty acid with longer to analyze than others because they contain more types of each of the alcohol functional groups of glycerol. Fatty acid fatty acids. Recently, electrospray ionization mass spectrometry compositions vary among the various types of fats and oils. (ESI-MS) has been applied to the analysis of the fatty acid in Fatty acid compositions play an important role in forensic both the positive15–18 and negative19,20 ion modes. The saponifiables science, sometimes serving as evidence in criminal investigations of the fats and oils (fatty acids) transform relatively easily into into the causes of fires resulting from arson or spontaneous negative ions due to the compounds’ carboxyl group. The ESI- ignition.1–3 Discrimination between control oil samples, taken MS analysis of the fatty acids resulting from the saponification from a suspect or victim, and oil samples collected at crime is therefore expected to be suitable for a screening procedure for scenes is required, as is the identification of their types in certain the rapid discrimination of fats and oils. In this paper, we cases. When a control fat or oil is unknown, the fatty acid describe a new, faster, easier method that enables the analysis of composition (including the degree of unsaturation) and the a number of fat and oil samples by ESI-MS over a short period varying chain lengths are useful for establishing the distinction of time. The analysis of the saponifiables of 42 types of between liquid oils and solid fats; the classification into drying, vegetable and animal oils for the development of a screening semi-drying, and nondrying oils; and the discrimination of types procedure for the discrimination of fats and oils are reported in of fats and oils. Fatty acid composition is frequently analyzed this work. The sample preparation was reduced to only two by gas chromatography (GC)4–10 and gas chromatography–mass steps: saponification and extraction without esterification or spectrometry (GC-MS)1–3,11–14 of saponifiables1,2,4,5,11–13 for their transesterification. The GC-MS analysis of the saponifiables was classification, or for the discrimination of fats and oils. When also carried out to compare the analytical results. fats and oils are saponified, saponifiables are obtained in the form of fatty acid salts, such as potassium salts in an aqueous layer. They are acidified, and then extracted as free fatty acids Experimental † To whom correspondence should be addressed. Materials E-mail: [email protected] Fat and oil manufacturers in Japan supply 27 types of 1458 ANALYTICAL SCIENCES DECEMBER 2005, VOL. 21 Table 1 Fatty acid composition (%) of fats and oils by electrospray ionization mass spectrometry Vegetable oils No. 1 Fatty [M–H] Coconut Palm Palm Camellia Macadamia Bran Rapeseed Olive Tea seed Peanut acid (m/z) oil kernel oil oil oil nut oil oil oil oil oil oil C8:0 143 5.1 3.1 —— — ———— — C10:0 171 5.1 3.9 —— — ———— — C12:0 199 55.4 58.8 0.8 ——————— C14:0 227 19.6 15.5 1.0 trace 0.8 0.5 ——0.4 — C16:0 255 6.5 5.4 15.2 11.5 7.2 11.6 5.0 11.3 14.7 8.4 C16:1 253 ———0.9 27.7 0.5 0.4 1.0 0.5 — C18:0 283 2.2 1.6 1.0 1.1 0.9 trace 0.8 2.2 1.0 0.8 C18:1 281 4.3 10.1 63.4 69.9 58.6 45.7 58.9 78.2 63.5 48.0 C18:2 279 1.1 1.6 18.6 10.2 1.5 39.2 21.8 6.2 11.7 37.9 C18:3 277 ———0.9 — 1.8 8.5 —— 0.6 C20:0 311 ———— 0.8 — 0.5 —— 0.6 C20:1 309 ———0.9 2.3 0.6 1.5 — 1.2 0.6 C22:1 337 ——————0.5 —— — Other 0.7 trace trace 4.6 0.2 0.1 2.1 1.1 7.0 3.1 Total 100 100 100 100 100 100 100 100 100.0 100 Trace: < 0.1%, —: not detected. Vegetable oils No. 2 Fatty [M–H] Cocoa Tall Safflower Cotton Soybean Evening Corn Sesame Sunflower Grape acid (m/z) butter oil oil seed oil oil primrose oil oil oil oil seed oil C12:0 199 — 0.3 ——— — — ——— C14:0 227 — 0.4 — 1.2 —————— C16:0 255 10.3 3.0 6.8 14.1 7.3 4.8 9.2 6.0 4.5 6.2 C16:1 253 trace 0.5 — 0.8 ——0.3 0.5 —— C18:0 283 4.0 trace 0.8 0.4 1.0 0.8 0.9 2.0 1.7 2.2 C18:1 281 48.9 27.8 9.2 17.5 29.9 6.2 32.5 44.1 19.2 17.0 C18:2 279 4.6 20.2 80.5 62.9 53.3 66.3 53.6 46.5 69.1 67.3 C18:3 277 1.3 2.8 1.0 0.6 6.5 10.9 2.1 0.5 0.9 0.9 C20:0 311 ————— 0.9 0.3 0.3 trace 1.3 C20:1 309 — 0.3 ——— — 0.3 — trace trace C20:3 305 — 2.8a ——— — — ——— C20:5 301 — 30.6a ——— — — ——— C20:6 299 — 6.3a ——— — — ——— C24:1 365 2.5 —— — — — — ——— Other 28.4 5.0 1.7 2.5 2.0 10.1 0.8 0.1 14.6 5.1 Total 100 100 100 100 100 100 100 100 100 100 a. Resin acids. Vegetable oils No. 3 Fatty [M–H] Cayenne Perilla Egoma Linseed Jojoba Tung Castor Turkey red acid (m/z) oil oil seed oil oil oil oil oil oil [Cp–137]– 168 14.8 —— ———— — [DC–137]– 170 19.4 —— ———— — C10:0 171 2.8 —— ——trace —— C12:0 199 1.5 —— ———— — C14:0 227 2.7 —— ———— — C14:1 225 trace trace ———1.3 —— C15:0 241 2.5 —— ———— — C15:1 239 0.8 —— ———— — C16:0 255 6.1 4.7 7.5 6.1 1.3 5.0 0.5 1.0 C16:1 253 2.5 —— — 0.7 —— — C17:0 269 0.9 —— ———— — C18:0 283 0.6 1.3 1.1 1.8 — 2.9 0.4 0.5 C18:1 281 8.3 22.6 14.7 25.5 17.9 16.5 2.9 2.9 C18:2 279 17.1 16.8 12.3 14.6 trace 28.1 4.9 1.7 C18:3 277 6.5 47.1 59.4 46.7 — 30.9b 0.4 — C18:4 275 trace 1.2 0.8 1.5 — 0.8 —— Cp 304 2.7 —— ———— — DC 306 2.8 —— ———— — C20:0 311 trace —— ——6.2 —— C20:1 309 ————50.4 2.6 —— C22:1 337 ————11.3 —— — C24:1 365 ————1.3 —— — [RA–114]– 183 ——————14.8 6.8 [RA]– 297 ——————75.2 57.5 [RA+118]– 415 ———————23.7 Other 8.0 6.3 4.0 3.8 17.1 5.7 0.9 5.9 Total 100 100 100 100 100 100 100 100 b.
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