Chemistry of Fatty Acids
Charlie Scrimgeour
The James Hutton Institute, Dundee, Scotland
Search for more papers by this authorYue Gao
Memorial University of Newfoundland, St. John's, Newfoundland, Canada
Search for more papers by this authorWon Young Oh
Memorial University of Newfoundland, St. John's, Newfoundland, Canada
Search for more papers by this authorFereidoon Shahidi
Memorial University of Newfoundland, St. John's, Newfoundland, Canada
Search for more papers by this authorCharlie Scrimgeour
The James Hutton Institute, Dundee, Scotland
Search for more papers by this authorYue Gao
Memorial University of Newfoundland, St. John's, Newfoundland, Canada
Search for more papers by this authorWon Young Oh
Memorial University of Newfoundland, St. John's, Newfoundland, Canada
Search for more papers by this authorFereidoon Shahidi
Memorial University of Newfoundland, St. John's, Newfoundland, Canada
Search for more papers by this authorAbstract
Oils and fats consist of triacylglycerols containing a range of fatty acids. Commodity oils are predominant sources of C16–C18 fatty acids (corn, cottonseed, groundnut, linseed, olive, palm, rape, sesame, soybean, sunflower), whereas some contain short- and medium-chain fatty acids (butter, coconut, palm kernel) or long-chain fatty acids (fish, other seafoods, algal, and fungal) in various proportions. Fatty acid and triacylglycerol compositions determine the physical, chemical, and nutritional properties of oils and fats and their uses in both food and nonfood, such as oleochemical manufacture. Fatty acids generally contain only two types of reactive functional groups, the terminal carboxyl and a number of carbon–carbon double bonds. Reaction at, or modification of, these groups is central to their industrial use. Oxidation (particularly oxidative degradation of edible fats), reduction (particularly partial hydrogenation), and reactions used to produce surfactants and oleochemicals (epoxidation, ozonolysis, metathesis, sulfonation, production of nitrogen-containing derivatives) are described. A current concern is the environmental impact of industrial chemistry and new processes that use less solvent, milder conditions, and renewable resources, and that produce less waste are required. Oils and fats are a major renewable resource, and environmental concerns may be met “through the use of enzymes and improved chemical catalysts as alternatives to current technologies.” Novel chemistry of oils, fats, and fatty acid derivatives with potential industrial application is highlighted, particularly by introducing new functionality to the alkyl chain.
References
- 1Akoh, C.C. (2017). Food Lipids: Chemistry, Nutrition, and Biotechnology, 4e. Boca Raton, FL: CRC Press Taylor & Francis Group.
10.1201/9781315151854 Google Scholar
- 2Gunstone, F.D. (2001). Eur. J. Lipid Sci. Technol. 103: 307–314.
- 3 F.D. Gunstone and R.J. Hamilton (ed.) (2001). Oleochemical Manufacture and Applications. Sheffield, UK: Sheffield Academic Press.
- 4Biermann, U., Friedt, W., Lang, S. et al. (2000). Angew. Chem. Int. Ed. 39: 2206–2224.
10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar
- 5 G. Knothe and J.T.P. Derksen (ed.) (1999). Recent Developments in the Synthesis of Fatty Acid Derivatives. Champaign, IL: AOCS Press.
10.1201/9781439832073.ch14 Google Scholar
- 6 F.D. Gunstone and F.B. Padley (ed.) (1997). Lipid Technologies and Applications. New York: Marcel Dekker, Inc.
- 7 A. Karleskind (ed.) (1996). Oils and Fats Manual. Vols. 1 and 2. Andover, UK: Intercept Ltd.
- 8Gunstone, F.D. (1996). Fatty Acid and Lipid Chemistry. London, UK: Blackie Academic and Professional.
10.1007/978-1-4615-4131-8 Google Scholar
- 9 F.D. Gunstone, J.L. Harwood, and F.B. Padley (ed.) (1994). The Lipid Handbook, 2e. London, UK: Chapman and Hall.
- 10Baumann, H., Bühler, M., Fochem, H. et al. (1988). Angew. Chem. Int. Ed. 27: 41–62.
- 11Pfleger, B.F., Gossing, M., and Nielsen, J. (2015). Metab. Eng. 29: 1–11.
- 12Yanty, N., Marikkar, J., and Che Man, Y. (2013). J. Therm. Anal. Calorim. 111: 2203–2209.
- 13 American Oil Chemists' Society (1997). Official Methods and Recommended Practices of the American Oil Chemists' Society, Section I. Champaign, IL: American Oil Chemists' Society.
- 14Ucciani, E. (1995). Dictionnaire des Huiles Végétales. Paris: Lavoisier Publishing.
- 15Vingering, N., Oseredczuk, M., du Chaffaut, L. et al. (2010). OCL 17: 185–192.
10.1051/ocl.2010.0309 Google Scholar
- 16Godard, A., de Caro, P., Vedrenne, E. et al. (2016). OCL 23: D510.
10.1051/ocl/2016037 Google Scholar
- 17Celenk, V.U., Gumus, Z.P., Argon, Z.U. et al. (2018). J. Turk. Chem. Soc. Section A 5: 1–18.
- 18Parnham, M.J. (1996). Inform 7: 1168–1175.
- 19 American Oil Chemists' Society (1998). Official Methods and Recommended Practices of the American Oil Chemists' Society, Fifth Edition, Sections Cd 1 and Cd 3. Champaign, IL: American Oil Chemists' Society.
- 20Li, H., van de Voort, F.R., Ismail, A.A. et al. (2000). J. Am. Oil Chem. Soc. 77: 29–36.
- 21Li, H., van de Voort, F.R., Sedman, J., and Ismail, A.A. (1999). J. Am. Oil Chem. Soc. 76: 491–497.
- 22Oterhals, Å. and Marc, M.H.G. (2010). J. Agric. Food Chem. 58: 12250–12259.
- 23Gordon, M.H. (2002). In: Oils and Fats Authentication (ed. M. Jee), 143–155. Oxford: Blackwell.
- 24Kiss, A.A. and Ignat, R.M. (2012). Appl. Energy 99: 146–153.
- 25Christie, W.W. (2002). Lipid Analysis, 3e. Bridgwater, UK: The Oily Press.
- 26Sonntag, N.O.V. (1988). In: Fatty Acids in Industry (ed. R.W. Johnson and E. Fritz), 23–72. New York: Marcel Dekker, Inc.
- 27Kodali, D.R. (1987). J. Lipid Res. 28: 464–469.
- 28Gunstone, F.D. (1999). In: Lipid Synthesis and Manufacture (ed. F.D. Gunstone), 321–346. Sheffield, UK: Sheffield Academic Press.
- 29Christie, W.W. (2002, April 29). The lipid library. http://www.lipid.co.uk/infores/select.html.
- 30Choo, Y.M., Ma, A.N., and Ong, A.S.H. (1997). In: Lipid Technologies and Applications (ed. F.D. Gunstone and F.B. Padley), 771–773. New York: Marcel Dekker, Inc.
- 31Knothe, G. and Dunn, R.O. (2001). In: Oleochemical Manufacture and Applications (ed. F.D. Gunstone and R.J. Hamilton), 128–132. Sheffield, UK: Sheffield Academic Press.
- 32Lee, K.-L., Foglia, T.A., and Chang, Y.-S. (2002). J. Am. Oil Chem. Soc. 79: 191–195.
- 33Watanabe, Y., Shimada, Y., Sugihara, A., and Tominga, Y. (2001). J. Am. Oil Chem. Soc. 78: 703–707.
- 34Rozendaal, A. and Macrae, A.R. (1997). In: Lipid Technologies and Applications (ed. F.D. Gunstone and F.B. Padley), 223–245. New York: Marcel Dekker, Inc.
- 35Rousseau, D. and Marangoni, A.G. (2002). In: Food Lipids: Chemistry, Nutrition, and Biotechnology, 2e (ed. C.C. Akoh and D.B. Min), 301–333. New York: Marcel Dekker, Inc.
- 36Gunstone, F.D. (1999). J. Sci. Food Agric. 79: 1535–1549.
10.1002/(SICI)1097-0010(199909)79:12<1535::AID-JSFA430>3.0.CO;2-7 CAS Web of Science® Google Scholar
- 37Xu, X. (2000). Eur. J. Lipid Sci.Technol. 102: 287–303.
- 38Torres, C.F., Barrios, E., and Hill, C.G. (2002). J. Am. Oil Chem. Soc. 79: 457–466.
- 39Akoh, C.C. and Xu, X. (2002). In: Lipid Biotechnology (ed. T.M. Kuo and H.W. Gardner), 461–469. New York: Marcel Dekker, Inc.
- 40Christensen, M.W., Andersen, L., Kirk, O., and Holm, H.C. (2001). Lipid Technol. Newslett. 7: 33–37.
- 41Nielsen, P.M. (2002). Oils and Fats International, 18: (4) 18–19. Redhill: International Trade Publications.
- 42Shimada, Y., Fukushima, N., Fujita, H. et al. (1998). J. Am. Oil Chem. Soc. 75: 1581–1586.
- 43Shimada, Y., Sugihara, A., Shibahiraki, M. et al. (1997). J. Am. Oil Chem. Soc. 74: 1465–1470.
- 44Ju, Y.-H. and Chen, T.-C. (2002). J. Am. Oil Chem. Soc. 79: 29–32.
- 45Shimada, Y., Maruyama, K., Sugihara, A. et al. (1998). J. Am. Oil Chem. Soc. 75: 1565–1571.
- 46Spurvey, S.A., Senanayake, S.P.J.N., and Shahidi, F. (2001). J. Am. Oil Chem. Soc. 78: 1105–1112.
- 47Chiplunkar, P.P., Zhao, X., Tomke, P.D. et al. (2018). Ultra. Sonochem. A 40: 587–593.
- 48Frankel, E.N. (1998). Lipid Oxidation. Dundee, UK: The Oily Press.
- 49Frankel, E.N. (1998). Lipid Oxidation. Dundee, UK: The Oily Press, 19 and 43–54.
- 50Frankel, E.N. (2001). J. Oleo Sci. 50: 387–391.
- 51Miyashita, K. (2002). Lipid Technol. Newslett. 8: 35–41.
- 52Hämäläinen, T.I., Sundberg, S., Hase, T., and Hopia, A. (2002). Lipids 37: 533–540.
- 53Bodin, A., Linnerborg, M., Nilsson, J.L.G., and Karlberg, A.T. (2002). J. Surfactant Deterg. 5: 107–110.
- 54Rawls, H.R. and Van Santen, P.J. (1970). J. Am. Oil Chem. Soc. 47: 121–125.
- 55Doleiden, F.H., Farenholtz, S.R., Lamola, A.A., and Trozzolo, A.M. (1974). Photochem. Photobiol. 20: 519–521.
- 56Min, D.B. (1998). In: Food Lipids: Chemistry, Nutrition and Biotechnology (ed. C.C. Akoh and D.B. Min), 289–292. New York: Marcel Dekker, Inc.
- 57Macfarlane, N., Salt, J., Birkin, R., and Kendrick, A. (2001). Inform 12: 244–249.
- 58Schuler, P. (1999). In: Food Antioxidants (ed. B.J.F. Hudson), 138–141. London, UK: Elsevier.
- 59Misharina, T.A., Alinkina, E.S., Fatkulina, L.D. et al. (2012). Appl. Biochem. Microbiol. 48: 102–107.
- 60Decker, E.A. and McClements, D.J. (2001). Inform 12: 251–256.
- 61Bartlett, P.D. (1950). Rec. Chem. Prog. 11: 47–51.
- 62Chang, S.-P. (1979). J. Am. Oil Chem. Soc. 56: 855–856.
- 63Karlson, K.D., Kleiman, R., and Bagby, M.O. (1994). J. Am. Oil Chem. Soc. 71: 175–182.
- 64Warwel, S. and Rüsch gen. Klass, M. (1995). J. Mol. Catal. B 1: 29–35.
- 65Rüsch gen. Klass, M. and Warwel, S. (1996). J. Am. Oil Chem. Soc. 73: 1453–1457.
- 66Rudolph, J., Reddy, K.L., Chiang, J.P., and Sharpless, K.B. (1997). J. Am. Chem. Soc. 119: 6189–6190.
- 67Refvik, M.D. and Larock, R.C. (1999). J. Am. Oil Chem. Soc. 76: 99–102.
- 68Rüsch gen. Klass, M. and Warwel, S. (1999). In: Recent Developments in the Synthesis of Fatty Acid Derivatives (ed. G. Knothe and J.T.P. Derksen), 157–167. Champaign, IL: AOCS Press.
10.1201/9781439832073.ch10 Google Scholar
- 69Piazza, G.J. (1999). In: Recent Developments in the Synthesis of Fatty Acid Derivatives (ed. G. Knothe and J.T.P. Derksen), 182–195. Champaign, IL: AOCS Press.
- 70Brown, H.C. and Mandal, A.K. (1980). Synthesis 153–155.
- 71Wilson, R., Smith, R., Wilson, P. et al. (1997). Anal. Biochem. 248: 76–85.
- 72Brinksma, J., Schmieder, L., van Vliet, G. et al. (2002). Tetrahedron Lett. 43: 2619–2622.
- 73Hou, C.T., Kuo, T.M., and Lanser, A.C. (2002). Inform 13: 307–316.
- 74Furniss, B.S., Hannaford, A.J., Smith, P.W.G., and Tatchell, A.R. (1989). Vogel's Textbook of Practical Organic Chemistry, 492–494. Harlow, UK: Longman.
- 75Rebrovic, L. (1992). J. Am. Oil Chem. Soc. 69: 159–165.
- 76Rebrovic, L. and Gunstone, F.D. (1996). Lipid Technol. 8: 135–137.
- 77Klein, H.-P. (1984). J. Am. Oil Chem. Soc. 61: 306–312.
- 78Warwel, S. and Rüsch gen. Klass, M. (1997). Lipid Technol. 9: 10–14.
- 79Rüsch gen. Klass, M. and Warwel, S. (1999). In: Recent Developments in the Synthesis of Fatty Acid Derivatives (ed. G. Knothe and J.T.P. Derksen), 167–173. Champaign, IL: AOCS Press.
- 80Dickens, B.F., Ramesha, C.S., and Thompson, G.A. (1982). Anal. Biochem. 127: 37–48.
- 81Sébédio, J.L., Juanéda, P., Grégoire, S. et al. (1999). Lipids 34: 1319–1325.
- 82Studentschnig, A.F.H., Schober, S., and Mittelbach, M. (2015). Energy Fuel 29: 3776–3779.
- 83Dijkstra, A.J. (2002). In: Fats in Food Technology (ed. K.K. Rajah), 123–141. Sheffield, UK: Sheffield Academic Press.
- 84Dijkstra, A.J. (1997). Inform 8: 1150–1158.
- 85Koetsier, W.T. (1997). In: Lipid Technologies and Applications (ed. F.D. Gunstone and F.B. Padley), 265–303. New York: Marcel Dekker, Inc.
- 86Singh, D., Rezac, M.E., and Pfromm, P.H. (2009). J. Am. Oil Chem. Soc. 86: 93–101.
- 87Mensink, R.P., Sanders, T.A., Baer, D.J. et al. (2016). Adv. Nutr. 7: 719–729.
- 88Dijkstra, A.J. (2002). Eur. J. Lipid Sci. Technol. 104: 29–35.
- 89Kreutzer, U.R. (1984). J. Am. Oil Chem. Soc. 61: 343–348.
- 90Johnson, R.W. (1988). In: Fatty Acids in Industry (ed. R.W. Johnson and E. Fritz), 217–231. New York: Marcel Dekker, Inc.
- 91Thakur, D.S. and Kundu, A. (2016). J. Am. Oil Chem. Soc. 93: 1575–1593.
- 92Steen, E.J., Kang, Y., Bokinsky, G. et al. (2010). Nature 463: 559–562.
- 93Porter, M.R. (1997). In: Lipid Technologies and Applications (ed. F.D. Gunstone and F.B. Padley), 579–608. New York: Marcel Dekker, Inc.
- 94James, A.D. (1997). In: Lipid Technologies and Applications (ed. F.D. Gunstone and F.B. Padley), 609–631. New York: Marcel Dekker, Inc.
- 95Bogndo, G. (1997). In: Lipid Technologies and Applications (ed. F.D. Gunstone and F.B. Padley), 633–694. New York: Marcel Dekker, Inc.
- 96Franklin, R., Hoey, M.D., and Zachwieja, J. (2001). In: Oleochemical Manufacture and Applications (ed. F.D. Gunstone and R.J. Hamilton), 23–54. Sheffield, UK: Sheffield Academic Press.
- 97Roberts, D.W. (2001). In: Oleochemical Manufacture and Applications (ed. F.D. Gunstone and R.J. Hamilton), 55–73. Sheffield, UK: Sheffield Academic Press.
- 98Colin, V., Bourguignon, N., Gómez, J. et al. (2017). Water Air Soil Pollut. 228: 1–12.
- 99Billenstein, S. and Blaschke, G. (1984). J. Am. Oil Chem. Soc. 61: 353–357.
- 100Dahlgren, L. (2000). Inform 11: 508–512.
- 101Hill, K. (1998). Agro-Food Industry Hi-Tech. September/October: 9–15.
- 102Hill, K. and Rhode, O. (1999). Fette/Lipid 101: 25–33.
- 103 K. Hill, W. Rybinski, and G. Stoll (ed.) (1997). Alkyl Polyglycosides. VCH, Weinheim, FRG.
- 104von Rybinski, W. and Hill, K. (1998). Angew. Chem. Int. Ed. 37: 1328–1345.
10.1002/(SICI)1521-3773(19980605)37:10<1328::AID-ANIE1328>3.0.CO;2-9 PubMed Web of Science® Google Scholar
- 105Adam, M.K., Poisson, J.S., Hu, Y. et al. (2016). Cryobiology 73: 436–436.
10.1016/j.cryobiol.2016.09.143 Google Scholar
- 106Johnson, R.W. (1988). In: Fatty Acids in Industry (ed. R.W. Johnson and E. Fritz), 153–175. New York: Marcel Dekker, Inc.
- 107Knothe, G. (2002). Lipid Technol. 14: 101–104.
- 108Erhan, S.M. and Kleiman, R. (1997). J. Am. Oil Chem. Soc. 74: 605–607.
- 109Isbell, T.A. and Kleiman, R. (1996). J. Am. Oil Chem. Soc. 73: 1097–1107.
- 110Hénon, G., Kemény, Z., Recseg, K. et al. (1999). J. Am. Oil Chem. Soc. 76: 73–81.
- 111SÆbØ, A. (2001). Lipid Technol. Newslett. 7: 9–13.
- 112Destaillats, F. and Angers, P. (2002). Lipids 37: 435–438.
- 113Larock, R.C., Dong, X., Chung, S. et al. (2001). J. Am. Oil Chem. Soc. 78: 447–453.
- 114Barton, D.H.R., Critch, D., and Motherwell, W.B. (1983). Tetrahedron Lett. 24: 4979–4982.
- 115Loreau, O., Maret, A., Poullain, D. et al. (2000). Chem. Phys. Lipids 106: 65–78.
- 116Spener, F. and Mangold, H.K. (1973). Chem. Phys. Lipids 11: 215–218.
- 117Toreki, R. (2002). Organometallic HyperTextBook. http://www.ilpi.com/organomet/olmetathesis.html (accessed 04 September 2019).
- 118Plugge, M.F.C. and Mol, J.C. (1991). Synlett 507–508.
- 119Warwel, S., Jagers, H.G., and Thomas, S. (1992). Fat Sci. Technol. 94: 323–328.
- 120Refvik, M.D., Larock, R.C., and Tian, Q. (1999). J. Am. Oil Chem. Soc. 76: 93–98.
- 121Mol, J.C. (2002). Green Chem. 4: 5–13.
- 122Biermann, U., Fürmeier, S., and Metzger, J.O. (2001). In: Oleochemical Manufacture and Applications (ed. F.D. Gunstone and R.J. Hamilton), 266–299. Sheffield, UK: Sheffield Academic Press.
- 123Gunstone, F.D. (1999). In: Recent Developments in the Synthesis of Fatty Acid Derivatives (ed. G. Knothe and J.T.P. Derksen), 1–19. Champaign, IL: AOCS Press.
10.1201/9781439832073.ch1 Google Scholar
- 124Isbell, T.A. and Plattner, B.A. (1997). J. Am. Oil Chem. Soc. 74: 153–158.
- 125Isbell, T.A. and Steiner, B.A. (1998). J. Am. Oil Chem. Soc. 75: 63–66.
- 126Isbell, T.A. and Mund, M.S. (1998). J. Am. Oil Chem. Soc. 75: 1021–1029.
- 127Metzger, J.O. and Biermann, U. (1993). Liebigs Ann. Chem. 645–650.
- 128Metzger, J.O. and Biermann, U. (1998). Fette/Lipid 100: 2–6.
- 129Biermann, U. and Metzger, J.O. (1999). In: Recent Developments in the Synthesis of Fatty Acid Derivatives (ed. G. Knothe and J.T.P. Derksen), 80–89. Champaign, IL: AOCS Press.
- 130Metzger, J.O., Mahler, R., Francke, G., and Hayen, A. (1999). In: Recent Developments in the Synthesis of Fatty Acid Derivatives (ed. G. Knothe and J.T.P. Derksen), 90–99. Champaign, IL: AOCS Press.
- 131Metzger, J.O., Mahler, R., and Francke, G. (1997). Liebigs Ann./Recueil 2303–2313.
- 132Metzger, J.O., Mahler, R., and Schmidt, A. (1996). Liebigs Ann. Chem. 693–696.
- 133Orsavova, J., Misurcova, L., Ambrozova, J.V. et al. (2015). Int. J. Mol. Sci. 16: 12871–12890.
- 134Kostik, V., Memeti, S., and Bauer, B. (2013). J. Hygienic Eng Des 4: 112–116.
- 135Üstün, G., Akova, A., and Dandik, L. (1996). J. Am. Oil Chem. Soc. 73: 389–391.
- 136Salmon, J., Noor, D.A.M., Nazarizawati, A.T. et al. (2010). Sains Malaysiana 39: 761–764.
- 137Knothe, G. and Dunn, R.O. (2009). J. Am. Oil Chem. Soc. 86: 843–856.
- 138Weast, R.C. (1985). Handbook of Chemistry and Physics, 66e. Boca Raton: CRC Press.
- 139Lide, D.R. (1999). Handbook of Chemistry and Physics, 80e. Boca Raton: CRC Press.
- 140Lide, D.R. (2007). Handbook of Chemistry and Physics, 88e. Boca Raton, FL: CRC Press.
- 141Gunstone, F.D., Harwood, J.L., and Dijkstra, A.J. (2007). The Lipid Handbook, 3e. Boca Raton: CRC Press.
- 142Doss, M.P. Properties of the Principal Fats, Fatty Oils, Waxes, Fatty Acids and Their Salts. Texas, NY.
- 143Gunstone, F.D. and Ismail, I.A. (1967). Chem. Phys. Lipids 1: 264–269.
- 144Schlenk, W. (1969). Liebigs Ann Chem 727: 1–9.
- 145Barve, J.A. and Dunstone, F.D. (1971). Chem. Phys. Lipids 7: 311–323.
- 146Marosi, L. and Schlenk, W. (1973). Liebigs Ann Chem 4: 584–598.
10.1002/jlac.197319730408 Google Scholar
- 147Jalal, I.M., Zografi, G., Rakshit, A.K., and Gunstone, F.D. (1982). Chem. Phys. Lipids 31: 395–404.