Analysis of hydroxy triacylglycerol as a lactone precursor in milk fat using liquid chromatography electrospray ionization tandem mass spectrometry

Food Chemistry

Volumn 274, Issue , 2019, Pages 298-304

  Yoshinaga, Kazuaki ^a   Obi, Junji ^b   Tago, Arisa ^b   Kato, Yasunari ^a   Nagai, Toshiharu ^a   Yoshida, Akihiko ^a   Gotoh, Naohiro ^b  

^a Tsukishima Foods Industry Co   (Japan)

^b TOKYO UNIVERSITY OF MARINE SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Hydroxy fatty acid; Lactone; Milk fat; Triacylglycerol

Indexed keywords

COLUMN CHROMATOGRAPHY; ESTERS; FATTY ACIDS; GLYCEROL; ISOMERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OILS AND FATS;

HEATING TESTS; HYDROXY FATTY ACIDS; LACTONE; LC-ESI-MS/MS; LIQUID CHROMATOGRAPHY ELECTROSPRAY; MILK FATS; TAG STANDARDS; TRIACYLGLYCEROLS;

ELECTROSPRAY IONIZATION;

HYDROXY FATTY ACID; LACTONE; MILK FAT; TRIACYLGLYCEROL; FATTY ACID;

ARTICLE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; GHEE; HEATING; ISOMER; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; ANIMAL; CHEMISTRY; ISOMERISM; LIQUID CHROMATOGRAPHY; MILK; PROCEDURES; TANDEM MASS SPECTROMETRY;

ANIMALS; CHROMATOGRAPHY, LIQUID; FATTY ACIDS; ISOMERISM; LACTONES; MILK; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; TRIGLYCERIDES;

EID: 85052973390     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2018.08.101     Document Type: Article

References (29)

1. Alewijn, M., Sliwinski, E.L., Wouters, J.T.M., A fast and simple method for quantitative determination of fat-derived medium and low-volatile compounds in cheese. International Dairy Journal 13 (2003), 733–741.
2. Alewijn, M., Sliwinski, E.L., Wouters, J.T.M., Production of fat-derived (flavour) compounds during the ripening of Gouda cheese. International Dairy Journal 15 (2005), 733–740.
3. Alewijn, M., Smit, B.A., Sliwinski, E.L., Wouters, J.T.M., The formation mechanism of lactones in Gouda cheese. International Dairy Journal 17 (2007), 59–66.
4. Boldingh, J., Taylor, R., Trace constituents of butterfat. Nature 194 (1962), 909–913.
5. Chance, D.L., Gerhardt, K.O., Mawhinney, T.P., Gas-liquid chromatography-mass spectrometry of hydroxy fatty acids as their methyl esters tert-butyldimethylsilyl esters. Journal of Chromatography A 793 (1998), 91–98.
6. Dimick, P.S., Harner, J.L., Effect of environmental factors on lactone potential in bovine milk fat. Journal of Dairy Science 51 (1968), 22–27.
7. Dimick, P.S., Patton, S., Kinsella, J.E., The prevalence of aliphatic delta-lactones or their precursors in animal fats. Lipids 1 (1966), 387–390.
8. Dolendo, A.L., Means, J.C., Tobias, J., Perkins, E.G., Synthesis and mass spectral properties of a triglyceride precursor of δ-dodecalactone. Journal of Dairy Science 52 (1969), 21–26.
9. Gimeno, R.E., Cao, J., Thematic review series: Glycerolipids. Mammalian glycerol-3-phosphate acyltransferases: New genes for an old activity. Journal of Lipid Research 49 (2008), 2079–2088.
10. Izco, J.M., Torre, P., Characterization of volatile flavor compounds in Roncal cheese extracted by the ‘purge and trap’ method and analyzed by GC-MS. Food Chemistry 70 (2000), 409–417.
11. Jurriens, G., Oele, J.M., Occurrence of esterified hydroxy fatty acids as precursors of lactones in butter. Nature 207 (1965), 864–865.
12. Keeny, P.G., Patton, S., The coconut like flavor defect of milk fat. I. Isolation of the flavor compound from butter oil and its identification as δ-decalactone. Journal of Dairy Science 39 (1956), 1104–1113.
13. Kinsella, J.E., Patton, S., Dimick, P.S., Chromatographic separation of lactone precursors and tentative identification of the γ-lactones of 4-hydroxy octanoic and 4-hydroxy nonanoic acids in butterfat. Journal of American Oil Chemists’ Society 44 (1967), 202–205.
14. Lísa, M., Holčapek, M., Characterization of triacylglycerol enantiomers using chiral HPLC/APCI-MS and synthesis of enantiomeric triacylglycerols. Analytical Chemistry 85 (2013), 1852–1859.
15. Mallia, S., Escher, F., Schlichtherle-Cerny, H., Aroma-active compounds of butter: A review. European Food Research and Technology 226 (2008), 315–325.
16. Mattick, L.R., Patton, S., Keeney, P.G., The coconut-like flavor defect from milk fat, III: Observations on the origin of δ-decalactone in fat-containing dairy products. Journal of Dairy Science 42 (1959), 791–798.
17. Obi, J., Yoshinaga, K., Tago, A., Nagai, T., Yoshida, A., Beppu, F., Gotoh, N., Simple quantification of lactones in milk fat by solvent extraction using gas chromatography-mass spectrometry. Journal of Oleo Science 67 (2018), 941–948.
18. Parliment, T.H., Nawer, W.W., Fagerson, I.S., Origin of delta-lactones in heated milk fat. Journal of Dairy Science 49 (1966), 1109–1112.
19. Povolo, M., Contarini, G., Comparison of solid-phase microextraction and purge-and-trap methods for the analysis of the volatile fraction of butter. Journal of Chromatography A 985 (2003), 117–125.
20. Schlutt, B., Moran, N., Schieberle, P., Hofmann, T., Sensory-directed identification of creaminess-enhancing volatiles and semivolatiles in full-fat cream. Journal of Agricultural and Food Chemistry 55 (2007), 9634–9645.
21. Siek, T.J., Albin, I.A., Sather, L.A., Lindsay, R.C., Comparison of flavor thresholds of aliphatic lactones with those of fatty acids, esters, aldehydes, alcohols, and ketones. Journal of Dairy Science 54 (1971), 1–4.
22. Tharp, B.W., Patton, S., Coconut-like flavor defect of milk fat. IV. Demonstration of δ-dodecalactone in the steam distillate from milk fat. Journal of Dairy Science 43 (1960), 475–479.
23. Urbach, G., Effect of feed on flavor in dairy foods. Journal of Dairy Science 73 (1990), 3639–3650.
24. Urbach, G., Stark, W., The effect of diet on the gamma- and delta-lactone and methyl ketone potentials of bovine butterfat. Journal of Dairy Research 45 (1978), 223–229.
25. Van der Ven, B., Detection of γ- and δ-keto acids in butterfat. Recueil des Travaux Chimiques des Pays-Bas 83 (1964), 976–982.
26. Vandeweghe, P., Reineccius, G.A., Comparison of flavor isolation techniques applied to Cheddar cheese. Journal of Agricultural and Food Chemistry 38 (1990), 1549–1552.
27. Villeneuve, M.P., Lebeuf, Y., Gervais, R., Tremblay, G.F., Vuillemard, J.C., Fortin, J., Chouinard, P.Y., Milk volatile organic compounds and fatty acid profile in cows fed timothy as hay, pasture, or silage. Journal of Dairy Science 96 (2013), 7181–7194.
28. Wong, N.P., Parks, O.W., Simple technique for extracting flavor compounds from fatty foods. Journal of Dairy Science 51 (1968), 1768–1769.
29. Wyatt, C.J., Pereira, R.L., Day, E.A., The lactone precursor in fresh milk fat: Identification of the hydroxy acids. Lipids 2 (1967), 208–211.