Structured lipids: Lipase-catalyzed interesterification of tricaproin and trilinolein
Purchase on Springer.com
$39.95 / €34.95 / £29.95*
Rent the article at a discountRent now
* Final gross prices may vary according to local VAT.
Structured lipids were synthesized by interesterification of trilinolein and tricaproin with sn-1,3-specific (IM 60) and nonspecific (SP 435) lipases. The interesterification reaction was performed by incubating a 1:2 mole ratio of trilinolein and tricaproin in 3 mL hexane at 45°C for the IM 60 lipase from Rhizomucor miehei, and at 55°C for the SP 435 lipase from Candida antarctica. Reaction products were analyzed by reverse-phase high-performance liquid chromatography with an evaporative light-scattering detector. The fatty acids at the sn-2 position were identified after pancreatic lipase hydrolysis and analysis with a gas chromatograph. IM 60 lipase produced 53,5 mol% dicaproyllinolein (total carbon number = C33) and 22.2% monocaproyldilinolein (C45). SP 435 lipase produced 41% C33 and 18% C45. When caproic acid was used in place of tricaproin as the acyl donor, the IM 60 lipase produced 62.9% C33. The effects of variation in mole ratio, temperature, added water, solvent polarity, and time course on the interesterification reaction were also investigated. In the absence of organic solvent, IM 60 lipase produced 52.3% C33.
- Svendsen, A., in Lipases: Their Structure, Biochemistry and Application, edited by P. Woolley and S.B. Petersen, Cambridge University Press, Cambridge, 1994, pp. 1–21.
- Arbige, M.V., and W.H. Pitcher, Industrial Enzymology: A Look Towards the Future, Trends Biotechnol. 7:330–335 (1989). CrossRef
- Zaks, A., and A.J. Russell, Enzymes in Organic Solvents: Properties and Applications, J. Biotechnol. 8:259–270 (1988). CrossRef
- Villeneuve, P., and T.A. Foglia, Lipase Specificities: Potential Application in Lipid Bioconversion, INFORM 8:640–650 (1997).
- Jensen, R.G., Characteristics of the Lipase from the Mold Geotrichum candidum: A Review, Lipids 9:149–157 (1974). CrossRef
- Vulfson, E.N., Industrial Applications of Lipases, in Lipases: Their Structure, Biochemistry and Application, edited by P. Woolley and S.B. Petersen, Cambridge University Press, Cambridge, 1994, pp. 271–288.
- Roy, S.S., and D.K. Bhattacharyya, Distinction Between Enzymically and Chemically Catalyzed Interesterification, J. Am. Oil Chem. Soc. 70:1293–1294 (1993). CrossRef
- Ray, S., and D.K. Bhattacharyya, Comparative Nutritional Study of Enzymatically and Chemically Interesterified Palm Oil Products, Ibid.:327–330 (1995). CrossRef
- Jandacek, R., J.A. Whiteside, B.N. Holcombe, R.A. Volpenheim, and J.D. Taulbee, The Rapid Hydrolysis and Efficient Absorption of Triacylglycerols with Octanoic Acid in the 1,3-Position and Long-Chain Fatty Acid in the 2-Position, Am. J. Clin. Nutr. 45:940–945 (1987).
- Luddy, F.E., R.A. Barford, S.F. Herb, P. Magidman, and R.W. Riemenschneider, Pancreatic Lipase Hydrolysis of Triglycerides by a Semi-Micro Technique, J. Am. Oil Chem. Soc. 41:693–696 (1964).
- Soumanou, M.M., U.T. Bornscheuer, U. Menge, and R.D. Schmid, Synthesis of Structured Triglycerides from Peanut Oil with Immobilized Lipase, Ibid.:427–433 (1997). CrossRef
- Atomi, H., M.M. Soumanou, H.D. Beer, G. Wohlfahrt, and R.D. Schmid, Microbial Lipases—from Screening to Design, in Oils-Fats-Lipids, edited by W.A.M. Castenmiller, P.J. Barnes & Associates, Bridgwater, England, Vol. 1, 1995.
- Kuo, S.J., and K.L. Parkin, Substrate Preference for Lipase-Mediated Acyl-Exchange Reactions with Butteroil Are Concentration-Dependent, J. Am. Oil Chem. Soc. 70:393–399 (1993). CrossRef
- Huang, K.H., and C.C. Akoh, Enzymatic Synthesis of Structured Lipids: Transesterification of Triolein and Caprylic Acid Ethyl Esters, Ibid.:245–250 (1996). CrossRef
- Dordick, J.S., Enzymatic Catalysis in Monophasic Organic Solvents, Enzyme Microb. Technol. 11:194–211 (1989). CrossRef
- Hirata, H., K. Higuchi, and T. Yamashina, Lipase-Catalyzed Transesterification in Organic Solvent: Effect of Water and Solvent, Thermal Stability and Some Applications, J. Biotechnol. 14:157–167 (1990). CrossRef
- Laane, C., S. Boeren, K. Vos, and C. Veeger, Rules for Optimization of Biocatalysis in Organic Solvents, Biotechnol. Bioeng. 30:81–87 (1987). CrossRef
- Gorman, L.S., and J.S. Dordick, Organic Solvents Strip Water Off Enzymes, Ibid.:392–397 (1992). CrossRef
- Zaks, A., and A.M. Klibanov, The Effect of Water on Enzyme Action in Organic Media, J. Biol. Chem. 263:8017–8021 (1988).
- Claon, P.A., and C.C. Akoh, Effect of Reaction Parameters on SP435 Lipase-Catalyzed Synthesis of Citronellyl Acetate in Organic Solvent, Enzyme Microb. Technol. 16:835–838 (1994). CrossRef
- Manjon, A., J.L. Iborra, and A. Arocas, Short-Chain Flavour Ester Synthesis by Immobilized Lipase in Organic Media, Biotechnol. Lett. 13:339–344 (1991). CrossRef
- Structured lipids: Lipase-catalyzed interesterification of tricaproin and trilinolein
Journal of the American Oil Chemists' Society
Volume 75, Issue 3 , pp 405-410
- Cover Date
- Print ISSN
- Online ISSN
- Additional Links
- Candida antarctica
- organic solvent
- Rhizomucor miehei
- structured lipid
- Industry Sectors