Synthesis of 2-monoacylglycerols (2-MAG) by enzymatic alcoholysis of fish oils using different reactor types

Biochemical Engineering Journal

Volumn 44, Issue 2-3, 2009, Pages 271-279

  Esteban, Luis ^a   Muñío, María del Mar ^a   Robles, Alfonso ^a   Hita, Estrella ^a   Jiménez, María J ^a   González, Pedro A ^a   Camacho, Belén ^a   Molina, Emilio ^a  

^a UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

2 Monoacylglycerol (2 MAG); Alcoholysis; Bioreactors; Enzyme; Extraction; Packed bed reactor (PBR); Stirred tank reactor (STR)

Indexed keywords

2-MONOACYLGLYCEROL (2-MAG); 2MONOACYLGLYCEROLS (2-MAG); ALCOHOLYSIS; CANDIDA ANTARCTICA; COD LIVER OIL; CONTINUOUS MODES; DISCONTINUOUS MODES; EICOSAPENTAENOIC ACIDS; ENZYMATIC ALCOHOLYSIS; ETHANOLYSIS; ETHYL ESTERS; FATTY ACID PROFILES; FISH OIL; LOW TOXICITIES; MONOACYLGLYCEROLS; NOVOZYM 435; OPERATIONAL VARIABLES; PACKED BED; PACKED BED REACTOR (PBR); POLYUNSATURATED FATTY ACIDS; REACTION MIXTURES; RECOVERY YIELDS; RHIZOPUS ORYZAE; STIRRED TANK REACTOR (STR); STIRRED TANKS; TUNA OIL;

ACIDS; BIOREACTORS; ENVIRONMENTAL PROTECTION AGENCY; ENZYMES; ESTERS; ETHANOL; FATTY ACIDS; FLUORESCENCE; GLYCEROL; HEXANE; INDUSTRIAL CHEMICALS; LIPASES; LIVER; ORGANIC SOLVENTS; PACKED BEDS; SOLVENT EXTRACTION; SOLVENTS; TANKS (CONTAINERS); TIMING CIRCUITS;

GAS WELDING;

2 MONOACYLGLYCEROL DERIVATIVE; FISH OIL; GLYCEROL DERIVATIVE; OMEGA 3 FATTY ACID; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ALCOHOLYSIS; ARTICLE; BIOSYNTHESIS; CANDIDA ANTARCTICA; CONTROLLED STUDY; INTERMETHOD COMPARISON; MUCOR; MUCOR MIEHEI; NONHUMAN; PACKED BED REACTOR; PRIORITY JOURNAL; RHIZOPUS ORYZAE; STIRRED REACTOR;

CANDIDA ANTARCTICA; RHIZOMUCOR MIEHEI; RHIZOPUS ORYZAE; SCOMBRIDAE;

EID: 61449130386     PISSN: 1369703X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bej.2009.01.004     Document Type: Article

References (28)

1. Simopoulos A.P. Omega-3 fatty acids in health and disease and in growth and development. Am. J. Clin. Nutr. 54 (1991) 438-463
2. Nettleton J.A. Are n-3 fatty acids essential nutrients for fetal and infant development?. J. Am. Dietetic Assoc. 93 (1993) 58-64
3. Mu H., and Porsgaard T. The metabolism of structured triacylglycerols. Prog. Lipid Res. 44 (2005) 430-448
4. Xu X., Hoy C.-E., Balchen S., and Adler-Nissen J. Specific-structured lipid: nutritional perspectives and production potentials. Proceedings of International Symposium on the Approach to Functional Cereals and Oils. CCOA, Beijing (1997) 806-813
5. Akoh C.C., and Huang K.H. Enzymatic synthesis of structured lipids: transesterification of triolein and caprylic acid. J. Food Lipids 2 (1995) 219-230
6. Shimada Y., Sugihara A., Maruyama K., Nagao T., Nakayama S., Nakano H., and Tominaga Y. Production of structured lipids containing docosahexaenoic and caprylic acids using immobilized Rhizopus delemar lipase. J. Ferment. Bioeng. 81 (1996) 299-303
7. Shimada Y., Suenaga M., Sugihara A., Nakai S., and Tominaga Y. Continuous production of structured lipid containing γ-linolenic and caprylic acids by immobilised Rhizopus delemar lipase. J. Am. Oil Chem. Soc. 76 (1999) 189-193
8. Xu X., Balchen S., Hoy C.-E., and Adler-Nissen J. Pilot batch production of specific-structured triacylglycerols by lipase-catalyzed interesterification in a laboratory-scale continuous reactor. J. Am. Oil Chem. Soc. 75 (1998) 301-308
9. Camacho Páez B., Robles Medina A., Camacho Rubio F., González Moreno P., and Molina Grima E. Production of structured triglycerides rich in n-3 polyunsaturated fatty acids by the acidolysis of cod liver oil and caprylic acid in a packed-bed reactor: equilibrium and kinetics. Chem. Eng. Sci. 57 (2002) 1237-1249
10. Hita E., Robles A., Camacho B., Ramírez A., Esteban L., Jiménez M., Muñío M.M., González P.A., and Molina E. Production of structured triacylglycerols (STAG) rich in docosahexaenoic acid (DHA) in position 2 by acidolysis of tuna oil catalyzed by lipases. Process Biochem. 42 (2007) 415-422
11. Schmid U., Bornscheuer U.T., Soumanou M.M., McNeill F.P., and Schmid R.D. Optimization of the reaction conditions in the lipase-catalyzed synthesis of structured triglycerides. J. Am. Oil Chem. Soc. 75 (1998) 1527-1531
12. Soumanou M.M., Bornscheuer U.T., and Schmid R.D. Two-step enzymatic reaction for the synthesis of pure structured triacylglycerides. J. Am. Oil Chem. Soc. 75 (1998) 703-710
13. Irimescu R., Furihata K., Hata Y., Iwasaki Y., and Yamane T. Utilization of reaction medium-dependent regiospecificity of C. antarctica lipase (Novozym 435) for the synthesis of 1 3-dicapryloyl-2-docosahexanoyl (or eicosapentanoyl) glycerol. J. Am. Oil Chem. Soc. 78 3 (2001) 285-289
14. Irimescu R., Furihata K., Hata Y., Iwasaki Y., and Yamane T. Two-step enzymatic synthesis of docosahexaenoic acid-rich symmetrically structured triacylglycerols via 2-monoacylglycerols. J. Am. Oil Chem. Soc. 78 7 (2001) 743-748
15. Millqvist Fureby A., Virton C., Adlercreutz P., and Mattiasson B. Acyl group migration in 2-monoolein. Biocatal. Biotransform. 14 (1996) 89-111
16. Watanabe Y., Shimada Y., Sugihara A., and Tominaga Y. Stepwise ethanolysis of tuna oil using immobilized Candida antarctica lipase. J. Biosci. Bioeng. 88 6 (1999) 622-626
17. Deng L., Xu X., Haraldsson G., Tan T., and Wang F. Enzymatic production of alkyl esters through alcoholysis: a critical evaluation of lipases and alcohols. J. Am. Oil Chem. Soc. 82 5 (2005) 341-347
18. Muñío M.M., Esteban L., Robles A., Hita E., Jiménez M.J., González P.A., Camacho B., and Molina E. Synthesis of 2-monoacylglycerols rich in polyunsaturated fatty acids by ethanolysis of fish oil catalyzed by 1,3 specific lipases. Process Biochem. 43 (2008) 1033-1039
19. Esteban Cerdán L., Robles Medina A., Giménez Giménez A., Ibáñez González M.J., and Molina Grima E. Synthesis of polyunsaturated fatty acid-enriched triglycerides by lipase-catalyzed esterification. J. Am. Oil Chem. Soc. 75 (1998) 1329-1337
20. Lepage G., and Roy C. Improved recovery of fatty acid through direct transesterification without prior extraction or purification. J. Lipid Res. 25 (1984) 1391-1396
21. Rodríguez-Ruiz J., El Hassan Belarbi J.L., García Sánchez D., and López Alonso. Rapid simultaneous lipid extraction and transesterification for fatty acid analysis. Biotechnol. Tech. 12 9 (1999) 689-691
22. Robles Medina A., Esteban Cerdán L., Giménez Giménez A., Camacho Páez B., Ibáñez González M.J., and Molina Grima E. Lipase-catalyzed esterification of glycerol and polyunsaturated fatty acids from fish and microalgae oils. J. Biotechnol. 70 (1999) 379-391
23. Henderson R.J., and Tocher D.R. In: Hamilton R.J., and Hamilton S. (Eds). Thin-layer Chromatography. Lipids Analysis: A Practical Approach (1993), IRL Press at Oxford University Press
24. Shimada Y., Ogawa J., Watanabe Y., Nagao T., Kawashima A., Kobayashi T., and Shimizu S. Regiospecific analysis by ethanolysis of oil with immobilized Candida antarctica lipase. Lipids 38 12 (2003) 1281-1286
25. Shen Z., and Wijasundera Ch. Evaluation of ethanolysis with immobilized Candida antarctica lipase for regiospecific analysis of triacylglycerols containing highly unsaturated fatty acids. J. Am. Oil Chem. Soc. 83 (2006) 923-927
26. J.M. Coulson, J.F. Richardson, Ingeniería Química, Tomo III, Ed. Reverté, Barcelona, 1984, pp. 87-88.
27. González Moreno P.A., Robles Medina A., Camacho Rubio F., Camacho Páez B., and Molina Grima E. Production of structured lipids by acidolysis of an EPA-enriched fish oil and caprylic acid in a packed bed reactor: analysis of three different operation modes. Biotechnol. Prog. 20 (2004) 1044-1052
28. González Moreno P.A., Robles Medina A., Camacho Rubio F., Camacho Páez B., Esteban Cerdán L., and Molina Grima E. Production of structured triacylglycerols in an immobilized packed-bed reactor: batch mode operation. J. Chem. Biotechnol. 80 (2005) 35-43