Synthesis of cocoa butter triacylglycerols using a model acidolysis system


  • Ozan Nazim Çiftçi University of Gaziantep, Faculty of Engineering, Gaziantep
  • Sibel Fadiloǧlu University of Gaziantep, Faculty of Engineering, Gaziantep
  • Boleslaw Kowalski Warsaw University of Life Sciences, Warsaw
  • Fahrettin Göǧüş University of Gaziantep, Faculty of Engineering, Gaziantep



Acidolysis, Cocoa butter equivalents, HPLC, Model systems, 1, 3 specific lipase


The effects of reaction parameters such as substrate mole ratio, reaction temperature, enzyme load, water content and reaction time were studied in a model enzymatic acidolysis system. Palmitic and stearic acids were incorporated into triolein (OOO) under the catalysis of sn-1,3 specific lipase to produce the three major triacylglycerols (TAGs) in cocoa butter (CB), namely, 1,3-dipalmitoyl-2-oleoyl--glycerol (POP), 1(3)-palmitoyl-3(1)-stearoyl-2-oleoyl-glycerol (POS) and 1,3distearoyl-2-oleoyl-glycerol (SOS). TAG contents of the reaction products were analyzed by High Performance Liquid Chromatograph (HPLC).The best results (15.2% POP, 30.4% POS, 15.2 % SOS) were obtained at 1:3:3 (OOO:palmitic acid:stearic acid) substrate mole ratio and reaction parameters: time 10 h, temperature 45 oC, enzyme load 20 %, water content 5 %. The results obtained in this model system might be used for the optimization and application of lipase catalyzed acidolysis reactions in natural systems to produce cocoa butter equivalents (CBEs).


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Fomuso LB, Akoh CC. 1998. Structured lipids: Lipase catalyzed interesterification of tricaproin and trilinolein. JAOCS 75, 405-410. doi:10.1007/s11746-998-0059-y

Hoy CE, Xu X. 2001. Structured triacylglycerols, Gunstone F.D. (Ed.) Structured and Modified Lipids, 209-239.

Marcel Dekker Inc., New York. Kuo SJ, Parkin KL. 1993. Substrate preferences for lipase mediated acyl-exchange reactions with butter oil are concentration-dependent. JAOCS 70, 393-399. doi:10.1007/BF02552713

Lipp M, Anklam E. 1998. Review of cocoa butter and alternative fats for use in chocolate-Part A. Compositional data. Food Chem., 62, 73-97. doi:10.1016/S0308-8146(97)00160-X

Lipp M, Simoneau C, Ulberth F, Anklam E, Crews C, Prereton P, Greyt W, Schwack W, Wiedmaier C. 2001. Composition of genuine cocoa butter and cocoa butter equivalents. J. Food Compos. Anal. 14, 399-408. doi:10.1006/jfca.2000.0984

Liu KJ, Shaw JF. 1997. Synthesis of cocoa butter equivalent by lipase-catalyzed interesterification in supercritical carbon dioxide. JAOCS 74, 1477- 1482. doi:10.1007/s11746-997-0257-z

Macrae AR, Hammond RC. 1985. Present and future application of lipases. Biotechnol. Genetic Eng. Rev. 3, 193-217.

Mojovic L, Siler-Marinkovic S, Kukic G, Vunjak- Novakovic G. 1993. Rhizopus arrhizus lipasecatalyzed interesterification of the midfraction of palm oil to a cocoa butter equivalent fat. Enzyme Microb. Tech. 15, 438-443. doi:10.1016/0141-0229(93)90132-L

Paez BC, Medina AR, Rubio FC, Cerdan LE, Grima EM. 2003. Kinetics of lipase-catalyzed interesterification of triolein and caprylic acid to produce structured lipids. J. Chem. Technol. and Biot. 78, 461-470. doi:10.1002/jctb.810

Saldana MDA, Mohamed RS, Mazzafera P. 2002. Extraction of cocoa butter from Brazilian cocoa beans using supercritical CO2 and ethane. Fluid Phase Equilibr. 194-197, 885-894. doi:10.1016/S0378-3812(01)00719-1

Sellappan S, Akoh CC. 2000. Enzymatic acidolysis of tristearin with lauric and oleic acids to produce coating lipids. JAOCS 77, 1127-11132. doi:10.1007/s11746-000-0177-3

Smith KW. 2001. Cocoa butter and cocoa butter equivalents, in Gunstone FD (Ed.) Structured and Modified Lipids, Marcel Dekker, Inc., New York, pp. 401-422.

SPSS. 1999. SPSS 10.0 for Windows, Statistical Software, SPSS Inc., Chicago, IL.

Sridhar R, Lakshminarayana G, Kaimal T. 1991. Modification of selected Indian vegetable fats into cocoa butter substitutes by lipase-catalyzed ester interchange. JAOCS 68, 726-730. doi:10.1007/BF02662160

Undurraga D, Markovits A, Erazo S. 2001. Cocoa butter equivalent through enzymic interesterification of palm oil midfraction. Process Biochem. 36, 933-939. doi:10.1016/S0032-9592(00)00260-0

Wang H.X, Wu H, Ho C.T, Weng X.C. (2006). Cocoa butter equivalent from enzymatic interesterification of tea seed oil and fatty acid metyl esters. Food Chem. 97, 661-665. doi:10.1016/j.foodchem.2005.04.029

Xu X. 2000. Enzymatic production of structured lipids: Process reactions and acyl migration. INFORM 11, 1121-1131.

Yang T, Fruekilde MB, Xu X. 2005. Supression of acyl migration in enzymatic production of structured lipids through temperature programming. Food Chem. 92, 101-107. doi:10.1016/j.foodchem.2004.07.007

Yankah VV, Akoh CC. 2000. Lipase-catalyzed acidolysis of tristearin with oleic or caprylic acids to produce structured lipids. JAOCS 74, 495-500. doi:10.1007/s11746-000-0079-4

Zhao H, Lu Z, Bie X, Lu F, Liu Z. 2005. Lipase catalyzed acidolysis of lard with capric acid in organic solvent. J. Food Eng.78, 41-46. doi:10.1016/j.jfoodeng.2005.08.049




How to Cite

Çiftçi ON, Fadiloǧlu S, Kowalski B, Göǧüş F. Synthesis of cocoa butter triacylglycerols using a model acidolysis system. grasasaceites [Internet]. 2008Dec.30 [cited 2022Dec.6];59(4):316-20. Available from: