Analytical methods for determination of trans fatty acid content in food

European Journal of Lipid Science and Technology

Volumn 109, Issue 9, 2007, Pages 901-917

  Juanéda, Pierre ^a   Ledoux, Martial ^b   Sébédio, Jean Louis ^c  

^a CENTRE DES SCIENCES DU GOÛT ET DE L ALIMENTATION   (France)

^b Healthy Pigs Production and Experimentation Section   (France)

^c UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Analytical methodology; Attenuated total reflection; Conjugated linoleic acid; Fourier transform infrared spectroscopy; Gas chromatography; Official methods; Trans fatty acids

Indexed keywords

EID: 34948853178     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.200600277     Document Type: Review

References (93)

1. W. W. Christie: Preparation of ester derivatives of fatty acids for chromatographic analysis. In: Advances in Lipid Methodology. Ed. W. W. Christie, The Oily Press, Dundee (UK) 1993, pp. 69-110.
2. O. Berdeaux, R Juanéda, J.-L. Sébédio: Analyse des acides gras conjugués et trans après dérivation. Analusis Magazine 1998, 26, M45-M51.
3. W. M. N. Ratnayake, G. Pelletier: Positional and geometrical isomers of linoleic acid in partially hydrogenated oils. J Am Oil Chem Soc. 1992, 69, 95-105.
4. O. Berdeaux, J.-L. Sébédio, J.-M. Chardigny, J.-P. Blond, T. Mairot, J.-M. Vatèle, D. Poullain, J.-P. Noël: Effects of trans n-6 fatty acids on the fatty acid profile of tissues and liver microsomal desaturation in the rat. Grasas Aceites. 1996, 47, 86-99.
5. J.-L. Sébédio, P. Juanéda, G. Dobson, I. Ramilison, J.-C. Martin, J.-M. Chardigny, W. W. Christie: Metabolites of conjugated linoleic acid in the rat. Biochim Biophys Acta. 1997, 1345, 5-10.
6. G. Dobson: Identification of conjugated fatty acids by gas chromatography-mass spectrometry of 4-methyl-1,2,4-triazoline-3, 5-dione adducts.J Am Oil Chem Soc. 1998, 75, 137-142.
7. O. Berdeaux, W. W. Christie, F. D. Gunstone, J.-L. Sébédio: Large-scale synthesis of methyl cis-9, trans-11 octadecadienoate from methyl ricinoleate. J Am Oil Chem Soc. 1997, 74, 1011-1015.
8. M. P. Yurawecz, J. K. Hood, J. A. G. Roach, M. M. Mossoba, D. H. Daniels, Y. Ku, M. W. Pariza, S. F. Chin: Conversion of allylic hydroxy oleate to conjugated linoleic acid and methoxy oleate by acid-catalyzed methylation procedures. J Am Oil Chem Soc. 1994, 71, 1149-1155.
9. M. Yamasaki, K. Kishihara, I. Ikeda, M. Sugano, K. Yamada: A recommended esterification method for gas chromatographic measurement of conjugated linoleic acid. J Am Oil Chem Soc. 1999, 76, 933-938.
10. N. C. Shantha, E. A. Decker, B. Henning: Comparison of methylation methods for the quantitation of conjugated linoleic acid isomers. J AOAC Int. 1993, 76, 644-649.
11. S. A. Werner, L. O. Luedecke, T. D. Shultz: Determination of conjugated linoleic acid content and isomer distribution in three cheddar-type cheeses: Effects of cheese cultures, processing and aging. J Agric Food Chem. 1992, 40, 1817-1821.
12. J. K. G. Kramer, J. Zhou: Conjugated linoleic acid and octadecenoic acids: Extraction and isolation of lipids. Eur J Lipid Sci Technol. 2001, 103, 594-600.
13. Y. Park, K. J. Albright, Z. U. Cai, M. W. Pariza: Comparison of methylation procedures for conjugated linoleic acid and artifact formation by commercial (trimethylsilyl)diazomethane. J Agric Food Chem. 2001, 49, 1158-1164.
14. J. K. G. Kramer, V. Fellner, M. E. R. Dugan, F. D. Sauer, M. M. Mossoba, M. P. Yurawecz: Evaluating acid and base catalysts in the methylation of milk and rumen fatty acids with a special emphasis on conjugated dienes and total trans fatty acids. Lipids. 1997, 32, 1219-1228.
15. W. W. Christie, J.-L. Sébédio, P. Juanéda: A practical guide to analysis of conjugated linoleic acid. Inform. 2001, 12, 147-152.
16. S. W. Christopherson, R. L. Glass: Preparation of milk fat methyl esters by alcoholysis in an essentially nonalcoholic solution. J Dairy Sci. 1969, 52, 1289-1290.
17. D. Precht, J. Molkentin: Trans-geometrical and positional isomers of linoleic acid including conjugated linoleic acid (CLA) in German milk and vegetable fats. Fett/Lipid. 1997, 99, 319-326.
18. F. E. Luddy, R. A. Barford, S. F. Herb, P. Magidman: Rapid and quantitative procedure for the preparation of methyl esters of butter oil and other fats. J Am Oil Chem Soc. 1968, 45, 549-552.
19. R. L. Wolff, C. C. Bayard, R. J. Fabien: Evaluation of sequential methods for the determination of butterfat fatty acid composition with emphasis on trans-18:1 acids. Application to the study of seasonal variations in French butter. J Am Oil Chem Soc. 1995, 72, 1471-1483.
20. C. Cruz-Hernandez, Z. Deng, J. Zhou, A. R. Hill, M. P. Yurawecz, P. Delmonte, M. M. Mossoba, M. E. R. Dugan, J. K. G. Kramer: Methods for analysis of conjugated linoleic acids and trans-18:1 isomers in dairy fats by using a combination of gas chromatography, silver-ion thin-layer chromatography/gas chromatography, and silver-ion liquid chromatography. J AOAC Int. 2004, 87, 545-562.
21. D. Firestone, A. Sheppard: Determination of trans fatty acids. In: Advance in Lipid Methodology. Ed. W. W. Christie, The Oily Press, Ayr (UK) 1992, pp. 273-322.
22. M. M. Mossoba, J. K. G. Kramer, P. Delmonte, M. P. Yurawecz, J. I. Rader: Official Methods for the Determination of Trans Fat. AOCS Press, Champaign, IL (USA) 2003.
23. F. Ulberth, H. J. Haider: Determination of low level trans unsaturation in fats by Fourier transform infrared spectroscopy. J Food Sci. 1992, 57, 1444-1447.
24. W. M. N. Ratnayake: Analysis of trans fatty acids. In: Trans Fatty Acids in Human Nutrition. Eds. J.-L. Sébédio, W. W. Christie, The Oily Press, Dundee (UK) 1988, pp. 115-161.
25. P. S. Belton, R. H. Wilson, H. Sadeghi-Jorabchi, K. E. Peers: A rapid method for the estimation of isolated trans double bonds in oils and fats using FTIR combined with ATR. Lebensm Wiss Technol. 1988, 21, 153-157.
26. A. C. Lanser, E. A. Emken: Comparison of FTIR and capillary gas chromatographic methods for quantitation of trans unsaturation of fatty acid methyl esters. J Am Oil Chem Soc. 1988, 65, 1483-1487.
27. R. T. Sleeter, R. G. Matlock: Automated quantitative analysis of isolated (non conjugated) trans isomers using Fourier transform infrared spectroscopy incorporating improvements in the procedure. J Am Oil Chem Soc. 1989, 66, 121-127.
28. M. M. Mossoba, M. P. Yurawecz, P. Delmonte, J. K. G. Kramer: Overview of infrared methodologies for trans fat determination. J AOAC Int. 2004, 87, 540-544.
29. M. M. Mossoba, M. P. Yurawecz, R. E. McDonald: Rapid determination of the total trans content of neat hydrogenated oils by attenuated total reflection spectroscopy. J Am Oil Chem Soc. 1996, 73, 1003-1009.
30. J. Fritsche, H. Steinhart, M. M. Mossoba, M. P. Yurawecz, N. Senat, Y. Ku: Rapid determination of trans-fatty acids in human adipose tissue. Comparison of attenuated total reflection infared spectroscopy and gas chromatography. J Chromatogr B 1998, 705, 177-182.
31. L. H. Ali, G. Angyal, C. M. Weaver, J. J. Rader, M. M. Mossoba: Determination of total trans fatty acids in foods: Comparison of capillary-column gas chromatography and single-bounce horizontal attenuated total reflection infrared spectroscopy. J Am Oil Chem Soc. 1996, 73, 1699-1705.
32. T. G. Toschi, C. Holt, W. W. Christie: A comparison of silver ion HPLC plus GC with Fourier-transform IR spectroscopy for the determination of trans double bonds in unsaturated fatty acids. J Sci Food Agric. 1993, 61, 261-266.
33. J. Sedman, F. R. van de Voort, A. A. Ismail, P. Maes: Industrial validation of Fourier transform infrared trans and iodine value analyses of fats and oils. J Am Oil Chem Soc. 1998, 75, 33-39.
34. H. J. Dutton: Analysis and monitoring of trans-isomerization by IR ATR spectrophotometry. J Am Oil Chem Soc. 1974, 51, 406-409.
35. M. Adam, M. M. Mossoba, T. Dawson, M. Chew, S. Wasserman: Comparison of attenuated total reflection infrared spectroscopy to capillary gas chromatography for trans fatty acid determination. J Am Oil Chem Soc. 1999, 76, 375-378.
36. M. Adam, M. Chew, S. Wasserman, A. McCollum, R. E. McDonald, M. M. Mossoba: Determination of trans fatty acids in hydrogenated vegetable oils by attenuated total reflection infrared spectroscopy: Two limited collaborative studies. J Am Oil Chem Soc. 1998, 75, 353-358.
37. M. Adam, M. M. Mossoba, T. Lee: Rapid determination of total trans fat content by attenuated total reflection infrared spectroscopy: An international collaborative study. J Am Oil Chem Soc. 2000, 77, 457-462.
38. M. M. Mossoba, M. Adam, T. Lee: Rapid determination of total trans fat content - An attenuated total reflection infrared spectroscopy international collaborative study. J AOAC Int. 2001, 84, 1144-1150.
39. M. M. Mossoba, J. K. G. Kramer, J. Fritsche, M. P. Yurawecz, K. Eulitz, Y. Ku, J. I. Rader: Application of standard addition to eliminate conjugated linoleic acid and other interferences in the determination of total trans fatty acids in selected food products by infrared spectroscopy. J Am Oil Chem Soc. 2001, 78, 631-634.
40. J.-L. le Quéré, E. Sémon: Le couplage chromatographie en phase gazeuse/spectrométrie infrarouge à transformée de Fourier (CPG/IRTF) dans l'analyse des acides gras d'orgine biologique. Analusis 1998, 26, M40-M44.
41. W. M. N. Ratnayake, J. L. Beare-Rogers: Problems of analysing C18 cis- and trans-fatty acids of margarine on the SP-2340 capillary column. J Chromatogr Sci. 1990, 28, 633-639.
42. Z.-Y. Chen, G. Pelletier, R. Hollywood, W. M. N. Ratnayake: Trans fatty acid isomers in Canadian human milk. Lipids. 1995, 30, 15-21.
43. W. M. N. Ratnayake: Overview of methods for the determination of trans fatty acids by gas chromatography, silver-ion thin-layer chromatography, silver-ion liquid chromatography, and gas chromatography/mass spectrometry. J AOAC Int. 2004, 87, 523-539.
44. R. L. Wolff: Recent applications of capillary gas-liquid chromatography to some difficult separations of unsaturated fatty acids. In: New Trends in Lipid and Lipoprotein Analysis. Ed. J.-L Sébédio, E. G. Perkins, AOCS Press, Champaign, IL(USA) 1995, pp. 147-180.
45. D. Precht, J. Molkentin: Trans fatty acids: Implications for health, analytical methods, incidence fats and intake. Nahrung. 1995, 39, 343-374.
46. D. Precht, J. Molkentin: C18:1, C18;2 and C18:3 trans and cis fatty acid isomers including conjugated cis9, trans11 linoleic acid (CLA) as well as total fat composition of German human milk lipids. Nahrung. 1999, 43, 233-244.
47. J. Molkentin, D. Precht: Occurrence of trans-C16:1 acids in bovine milkfats and partially hydrogenated edible fats. Milchwissenschaft. 1997, 52, 380-385.
48. M. LeDoux, A. Rouzeau, P. Bas, D. Sauvant: Occurrence of trans-C18:1 fatty acid isomers in goat milk: Effect of two dietary regimens. J Dairy Sci. 2002, 85, 190-197.
49. J. K. G. Kramer, C. B. Blackadar, J. Zhou: Evaluation of two columns (60-m SUPELCOWAX 10 and 100-m CP Sil 88) for analysis of milkfat with emphasis on CLA, 18:1, 18:2 and 18:3 isomers, and short- and long-chain FA. Lipids 2002, 37, 823-835.
50. G. S. M. J. E. Duchateau, H. J. van Oosten, M. A. Vasconcellos: Analysis of cis-and trans-fatty acid isomers in hydrogenated and refined vegetable oils by capillary gas-liquid chromatography. J Am Oil Chem Soc. 1996, 73, 275-282.
51. R. L. Wolff, C. C. Bayard: Improvement in the resolution of individual trans-18:1 isomers by capillary gas-liquid chromatography: Use of a 100-m CP-Sil 88 column. J Am Oil Chem Soc. 1995, 70, 1197-1201.
52. J. K. G. Kramer, C. Cruz-Hernandez, J. Zhou: Conjugated linoleic acids and octadecenoic acids: Analysis by GC. Eur J Lipid Sci Technol. 2001, 103, 600-609.
53. D. Precht, J. Molkentin: Rapid analysis of the isomers of trans-octadecenoic acid in milk. Int Dairy J. 1996, 6, 791-809.
54. P. Y. Chouinard, L. Corneau, D. M. Barbano, L. E. Metzger, D. E. Bauman: Conjugated linoleic acids alter milk fatty acid composition and inhibit milk fat secretion in dairy cows. J Nutr. 1999, 129, 1579-1584.
55. M. Collomb, T. Bülher: Analyse de la composition en acides gras de la graisse de lait. Mitt Lebensm Hyg. 2000, 91, 306-332.
56. R. J. Baer, J. Ryali, D. J. Schingoethe, K. M. Kasperson, D. C. Donovan, A. R. Hippen, S. T. Franklin: Composition and properties of milk and butter from cows fed fish oil. J Dairy Sci. 2001, 84, 345-353.
57. R. L. Wolff, N. A. Combe, D. Precht, J. Molkentin, W. M. N. Ratnayake: Accurate determination of trans-18:1 isomers by capillary gas-liquid chromatography on cyanoalkyl polysiloxane stationary phases. OCL 1998, 5, 295-300.
58. F. Ulberth, M. Henninger: Quantitation of trans fatty acids in milk fat using spectroscopic and chromatographic methods. J Dairy Sci. 1994, 61, 517-527.
59. D. Precht, J. Molkentin: Analysis and seasonal variation of conjugated linoleic acid and further cis-/trans-isomers of C18:1 and C18:2 in bovine milk fat. Kieler Milchwirtsch Forsch Ber. 1999, 51, 63-78.
60. D. Precht, J. Molkentin: Identification and quantitation of cis/trans C16:1 and C17:1 fatty acid positional isomers in German human milk lipids by thin-layer chromatography and gas chromatography/mass spectrometry. Eur J Lipid Sci Technol. 2000, 102, 102-113.
61. F. Destaillats, R. L. Wolff, D. Precht, J. Molkentin: Study of individual trans- and cis-16:1 isomers in cow, goat, and ewe cheese fat by gas-liquid chromatography with emphasis on the trans-Δ3 isomer. Lipids. 2000, 35, 1027-1032.
62. R. L. Wolff: Further studies on artificial geometrical isomers of alpha-linolenic acid in edible linolenic acid-containing oils. J Am Oil Chem Soc. 1993, 70, 219-224.
63. R. L. Wolff: Heat-induced geometrical isomerization of linoleic acid: Effect of temperature and heating time on the appearance of individual isomers. J Am Oil Chem Soc. 1993, 70, 425-430.
64. W. M. N. Ratnayake, L. J. Plouffe, E. Pasquier, C. Gagnon: Temperature-sensitive resolution of cis- and trans-fatty acid isomers of partially hydrogenated vegetable oils on SP-2560 and CP-Sil 88 capillary columns. J AOAC Int. 2002, 85, 1112-1118.
65. R. L. Wolff: Contribution of trans-18:1 acids from dairy fat to European diets. J Am Oil Chem Soc. 1994, 71, 277-283.
66. P. Juanéda: Utilisation of reversed-phase high-performance liquid chromatography as an alternative to silver-ion chromatography for the separation of cis- and trans-C18:1 fatty acid isomers. J Chromatogr A. 2002, 954, 285-289.
67. B. Nikolova-Damyanova: Silver-ion chromatography and lipids. In: Advances in Lipid Methodology. Ed. W. W. Christie, The Oily Press, Ayr (UK) 1992, pp. 181-237.
68. W. W. Christie, G. H. McBreckenridge: Separation of cis and trans isomers of unsaturated fatty acids by HPLC in the silver ion mode. J Chromatogr. 1989, 469, 261-269.
69. W. W. Christie: A stable silver-loaded column for the separation of lipids by high-performance liquid chromatography. J High Resol Chromatogr Chromatogr Comm. 1987, 10, 148-150.
70. R. O. Adlof, L. C. Copes, E. A. Emken: Analysis of the monoenoic fatty acid distribution in hydrogenated vegetable oils by silver-ion high-performance liquid chromatography. J Am Oil Chem Soc. 1995, 72, 571-574.
71. R. O. Adlof: Separation of cis and trans unsaturated fatty acid methyl esters by silver ion high-performance liquid chromatography. J Chromatogr A. 1994, 659, 95-99.
72. R. O. Adlof, T. Lamm: Fractionation of cis- and trans-oleic, linoleic, and conjugated linoleic fatty acid methyl esters by silver ion high-performance liquid chromatography. J Chromatogr A. 1998, 799, 329-332.
73. P. Juanéda, J.-L. Sébédio: Complete separation of the geometrical isomers of linolenic acid by high performance liquid chromatography with a silver ion column. J High Resol Chromatogr. 1994, 17, 321-324.
74. B. Nikolova-Damyanova, S. Momchilova, W. W. Christie: Silver ion high-performance liquid chromatograpic separation of conjugated linoleic acid isomers, and other fatty acids, after conversion to p-methoxyphenacyl derivatives. J High Resol Chromatogr. 2000, 23, 348-352.
75. J. K. G. Kramer, N. Sehat, M. E. R. Dugan, M. M. Mossoba, M. P. Yurawecz, J. A. G. Roach, K. Eulitz, J. L. Aalhus, A. L. Schaefer, Y. Ku: Distribution of conjugated linoleic acid (CLA) isomers in tissue lipid class of pigs fed a commercial CLA mixture determined by gas chromatography and silver ion-high performance liquid chromatography. Lipids. 1998, 33, 549-558.
76. M. P. Yurawecz, J. A. G. Roach, N. Sehat, M. M. Mossoba, J. K. G. Kramer, J. Fritsche, H. Steinhart, Y. Ku: A new conjugated linoleic acid isomer, 7-trans, 9-cis octadecadienoic acid, in cow milk, cheese, beef and human milk and adipose tissue. Lipids. 1998, 33, 803-809.
77. N. Sehat, R. Rickert, M. M. Mossoba, J. K. G. Kramer, M. P. Yurawecz, J. A. G. Roach, R. O. Adlof, K. M. Morehouse, J. Fritsche, K. Eulitz, H. Steinhart, Y. Ku: Improved separation of conjugated fatty acid methyl esters by silver ion-high performance liquid chromatography. Lipids. 1999, 34, 407-413.
78. N. Sehat, M. P. Yurawecz, J. A. G. Roach, M. M. Mossoba, J. K. G. Kramer, Y. Ku: Silver ion high performance liquid chromatography separation and identification of conjugated linoleic acid isomers. Lipids. 1998, 33, 217-221.
79. R. Rickert, H. Steinhart, J. Fritsche, N. Sehat, M. P. Yurawecz, M. M. Mossoba, J. A. G. Roach, K. Eulitz, Y. Ku, J. K. G. Kramer: Enhanced resolution of conjugated linoleic acid isomers by tandem-column silver-ion high performance liquid chromatography. J High Resol Chromatogr. 1999, 22, 144-148.
80. K. Eulitz, M. P. Yurawecz, N. Sehat, J. Fritsche, J. A. G. Roach, M. M. Mossoba, J. K. G. Kramer, R. O. Adlof, Y. Ku: Preparation, separation, and confirmation of eight geometrical cis/trans conjugated linoleic acid isomers 8, 10-through 11, 13-18:2. Lipids. 1999, 34, 873-877.
81. W. W. Christie: Silver ion chromatography using solid-phase extraction columns packed with a bonded-sulfonic acid phase. J Lipid Res. 1989, 30, 1471-1473.
82. W. W. Christie, J. H. Moore: Structures of triglycerides isolated from various sheep tissues. J Sci Food Agric. 1971, 22, 120-124.
83. M. LeDoux, L. Laloux, R. L. Wolff: Analytical methods for determination of trans-C18 fatty acid isomers in milk fat. A review. Analusis. 2000, 28, 402-412.
84. D. Precht, J. Molkentin: Vergleich der Fettsäuren und der Isomerenverteilung der trans-C18:1 -Fettsäuren von Milchfett, Margarine, Back- und Diätfetten. Kieler Milchwirtsch Forsch Ber. 1997, 49, 17-34.
85. R. L. Wolff: Resolution of linolenic acid geometrical isomers by gas-liquid chromatography on the capillary column coated with a 100% cyanopropyl polysiloxane film (CPTMSil 88). J Chromatogr Sci. 1992, 30, 17-22.
86. M. Buchgraber, F. Ulberth: Determination of trans octadecenoic acids by silver-ion chromatography-gas liquid chromatography: An intercomparison of methods. J AOAC Int. 2001, 84, 1490-1498.
87. N. Sehat, J. K. G. Kramer, M. M. Mossoba, M. P. Yurawecz, J. A. G. Roach, K. Eulitz, K. M. Morehouse, Y. Ku: Identification of conjugated linoleic acid isomers in cheese by gas liquid chromatography, silver ion high performance liquid chromatography and mass spectral reconstructed ion profiles. Comparison of chromatographic elution sequences. Lipids. 1998, 33, 963-971.
88. P. Delmonte, M. P. Yurawecz, M. M. Mossoba, C. Cruz-Hernandez, J. K. G. Kramer: Improved identification of conjugated linoleic acid isomers using silver-ion HPLC separations. J AOAC Int. 2004, 87, 563-568.
89. P. Juanéda, J.-L. Sébédio: Combined silver-ion and reversed-phase high-performance liquid chromatography for the separation of C20 metabolites of conjugated linoleic acid isomers in rat liver lipids. J Chromatogr B. 1999, 724, 213-219.
90. P.-A. Golay, F. Dionisi, B. Hug, F. Giuffrida, F. Destaillats: Direct quantification of fatty acids in dairy powders with special emphasis on trans fatty acid content. Food Chem. 2006, 101, 1115-1120.
91. FDA Department of Health and Human Services: Food labeling: Trans fatty acids in nutrition labeling; consumer research to consider nutrient content and health claims and possible footnote or disclosure statements; final rule and proposed rule. 21 CFR Part 101, 41434-41506.
92. M. LeDoux, L. Laloux: Evolution des teneurs en acide ruménique du lait au beurre: Variations saisonnières et régionales. Sci Alim. 2006, 26, 123-141.
93. P. Juanéda, S. Brac de la Pérrière, J.-L. Sébédio, S. Grégoire: Influence of heat and refining on formation of CLA isomers in sunflower oil. J Am Oil Chem Soc. 2003, 80, 937-940.