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Lipase-catalyzed alcoholysis of cod liver oil in supercritical carbon dioxide

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Journal of the American Oil Chemists’ Society

Abstract

Enzymatic alcoholysis of cod liver oil, with an immobilized lipase, was carried out in supercritical carbon dioxide. The enzyme was catalytically active under the experimental conditions used. The reaction medium was investigated to preferentially extract ethyl esters, synthesized during the course of the experiment, from the unconverted cod liver oil substrate and side-products. The effect of pressure changes on the amount of tri-, di-, and monoglycerides and ethyl esters, present in both the extract and the remaining lipid residue, was determined. Furthermore, the fatty acid compositions of the lipid classes were analyzed, and the relative amounts of both eicosapentaenoic acid and docosahexaenoic acid to palmitic acid were determined. The results show that it is possible to preferentially extract the synthesized ethyl esters at low pressures. The extract collected at 9 MPa contained 64 g ethyl esters/100 g extract, while the total amount of all other lipid classes detected was 19 g/100 g extract. As the pressure was increased, the relative amount of the other lipid classes detected in the extract, especially triglycerides, was enhanced. The relative amounts of both eicosapentaenoic acid and docosahexaenoic acid to palmitic acid increased for some lipid classes in the extract. This increase was most pronounced for the monoglyceride lipid class. The integration of biocatalysis and product fractionation, applied in this study, suggests that the potential for biocatalysis in industrial processes is considerably wider than had been thought.

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References

  1. Kamat, S., E.J. Beckman and A.J. Russell,Enzyme Microb. Technol. 14:265 (1992).

    Article  CAS  Google Scholar 

  2. Randolph, T.W., H.W. Blanch, J.M. Prausnitz and C.R. Wilke,Biotechnol. Lett. 7:325 (1985).

    Article  CAS  Google Scholar 

  3. Nakamura, K., Y.M. Chi, Y. Yamada and T. Yano,Chem. Eng. Commun. 45:207 (1986).

    CAS  Google Scholar 

  4. Hammond, D.A., M. Karel, A.M. Klibanov and V.J. Krukonis,Appl. Biochem. Biotechnol. 11:393 (1985).

    CAS  Google Scholar 

  5. Taniguchi, M., M. Kamihira and T. Kobayashi,Agric. Biol. Chem. 51:593 (1987).

    CAS  Google Scholar 

  6. Kasche, V., R. Schlothauer and G. Brunner,Biotechnol. Lett. 10:569 (1988).

    Article  CAS  Google Scholar 

  7. Erickson, J.C., P. Schyns and C.L. Cooney,AIChE J. 36:299 (1990).

    Article  CAS  Google Scholar 

  8. Randolph, T.W., H.W. Blanch and J.M. Prausnitz, Ibid.:1354 (1988).

    Article  CAS  Google Scholar 

  9. Marty, A., W. Chulalaksananukul, J.-S. Condoret, R.M. Willemot and G. Durand,Biotechnol. Lett. 12:11 (1990).

    Article  CAS  Google Scholar 

  10. Marty, A., W. Chulalaksananukul, R.M. Willemot and J.-S. Condoret,Biotechnol. Bioeng. 39:273 (1992).

    Article  CAS  Google Scholar 

  11. Aaltonen, O., and M. Rantakyla, inProceedings of the 2nd International Symposium on SCF, Boston, 1991, pp. 146–149.

  12. Chi, Y.M., K. Nakamura and T. Yano,Agric. Biol. Chem. 52:1541 (1988).

    CAS  Google Scholar 

  13. van Eijs, A.M.M., J.P.J. de Jong, H.J. Doddema and D.R. Lindeboom, inProceedings of the International Symposium on SCF, Nice, 1988, pp. 933–942.

  14. Dumont, T., D. Barth and M. Perrut, inProceedings of the 2nd International Symposium on SCF, Boston, 1991, pp. 150–153.

  15. Dumont, T., D. Barth, C. Corbier, G. Branlant and M. Perrut,Biotechnol. Bioeng. 39:329 (1992).

    Article  Google Scholar 

  16. Chulalaksananukul, W., J.S. Condoret and D. Combes,Enzyme Microb. Technol. 15:691 (1993).

    Article  CAS  Google Scholar 

  17. Steytler, D.C., P.S. Moulson and J. Reynolds, Ibid.:221 (1991).

    Article  CAS  Google Scholar 

  18. Kremer, J.M., A.V. Michalek, L. Lininger, C. Huyck, J. Bigauoette, M.A. Timchalk, R.I. Rynes, J. Zieminski and L.E. Bartholomew,Lancet I(8422):184 (1985).

    Article  Google Scholar 

  19. Kremer, J.M., D.A. Lawrence, W. Jubiz, R. DiGiacomo, R. Rynes, L.E. Bartholomew and M. Sherman,Arthritis Reum. 33:810 (1990).

    Article  CAS  Google Scholar 

  20. Leaf, W., and P.C. Weber,N. Engl. J. Med. 318:549 (1988).

    Article  CAS  Google Scholar 

  21. Ackman, R.G., inKlinische Pharmakologie, Clinical Pharmacology Vol. 5, Fish, Fish Oil and Human Health, edited by J.C. Frölich and C. von Schacky, W. Zuckschwerdt Verlag, Munchen, 1992, pp. 14–24.

  22. Krukonis, V.J., inSupercritical Fluid Extraction and Chromatography, ACS Symposium Series 366, edited by B.A. Charpentier, and M.R. Sevenants, American Chemical Society, Washington, D.C., 1988, pp. 26–43.

    Google Scholar 

  23. Casey, J., and A. Macrae,INFORM 3:203 (1992).

    Google Scholar 

  24. Haraldsson, G.G., and B. Hjaltason, Ibid.:626 (1992).

    Google Scholar 

  25. Staby, A., and J. Mollerup,J. Am. Oil Chem. Soc. 70:583 (1993).

    Article  CAS  Google Scholar 

  26. Bharath, R., H. Inomata, K. Arai, K. Shoji and Y. Noguchi,Fluid Phase Equilibria 50:315 (1989).

    Article  CAS  Google Scholar 

  27. Liang, J.H. and A.-I. Yeh,J. Am. Oil Chem. Soc. 68:687 (1991).

    CAS  Google Scholar 

  28. Liong, K.K., N.R. Foster and S.S.T. Ting,Ind. Eng. Chem. Res. 31:400 (1992).

    Article  CAS  Google Scholar 

  29. Staby, A., Application of Supercritical Fluid Techniques on Fish Oil and Alcohols, Ph.D. Thesis, Technical University of Danmark, DTH, Denmark, 1993.

    Google Scholar 

  30. Nilsson, W.B., G.T. Seaborn and J.K. Hudson,J. Am. Oil Chem. Soc. 69:305 (1992).

    CAS  Google Scholar 

  31. Eisenbach, W.,Ber. Bunsenges. Phys. Chem. 88:882 (1984).

    CAS  Google Scholar 

  32. Nilsson, W.B., E.J. Gauglitz, Jr., J.K. Hudson, V.F. Stout and J. Spinelli,J. Am. Oil Chem. Soc. 65:109 (1988).

    Article  CAS  Google Scholar 

  33. Nilsson, W.B., E.J. Gauglitz, Jr. and J.K. Hudson, Ibid.:1596 (1989).

    Article  CAS  Google Scholar 

  34. Marty, A., D. Combes and J.-S. Condoret,Biotechnol. Bioeng. 43:497 (1994).

    Article  CAS  Google Scholar 

  35. Novo Nordisk, Novozym 435 (product information sheet), Bagsvaerd, 1992.

  36. Ackman, R.G., and J.C. Sipos,J. Am. Oil Chem. Soc. 41:377 (1964).

    CAS  Google Scholar 

  37. Bannon, C.D., J.D. Craske and A.E. Hilliker, Ibid.:105 (1986).

    CAS  Google Scholar 

  38. Craske, J.D., and C.D. Bannon, Ibid.:1190 (1988).

    Article  Google Scholar 

  39. Christie, W.W., R.C. Noble and J.H. Moore,Analyst 95:940 (1970).

    Article  CAS  Google Scholar 

  40. Hammam, H., Lipids in Supercritical Carbon Dioxide—Physical Functional Aspects, Ph.D. Thesis, University of Lund, Sweden, 1994.

    Google Scholar 

  41. Arai, K., and S. Saito,Fractionation of Fatty Acids and Their Derivatives by Extractive Crystallization Using Supercritical Gas as a Solvent, paper presented at World Congress III of Chemical Engineering, Tokyo, 1986.

  42. Lie, Ø., and G. Lambertsen,Fette Seifen Anstrichm. 88:365 (1986).

    Article  CAS  Google Scholar 

  43. Langholz, P., P. Andersen, T. Forskov and W. Schmidtsdorff,J. Am. Oil Chem. Soc. 66:1120 (1989).

    CAS  Google Scholar 

  44. Hills, M.J., I. Kiewitt and K.D. Mukherjee, Ibid.:561 (1990).

    Article  CAS  Google Scholar 

  45. Bamberger, T., J.C. Erickson and C.L. Cooney,J. Chem. Eng. Data 33:327 (1988).

    Article  CAS  Google Scholar 

  46. Nilsson, W.B., E.J. Gauglitz, Jr. and J.K. Hudson,J. Am. Oil Chem. Soc. 68:87 (1991).

    CAS  Google Scholar 

  47. Nilsson, W.B., and J.K. Hudson, Ibid.:749 (1993).

    Article  CAS  Google Scholar 

  48. Mittelbach, M., Ibid.:168 (1990).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Food Technology, Chemical Center, P.O. Box 124, 22100, Lund, Sweden

    Helga Gunnlaugsdottir & Björn Sivik

Authors
  1. Helga Gunnlaugsdottir
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  2. Björn Sivik
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Gunnlaugsdottir, H., Sivik, B. Lipase-catalyzed alcoholysis of cod liver oil in supercritical carbon dioxide. J Am Oil Chem Soc 72, 399–405 (1995). https://doi.org/10.1007/BF02636078

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  • DOI: https://doi.org/10.1007/BF02636078

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