Synthesis of Structured Triglycerides Based on Canarium Oil for Food Application

Johnner Sitompul, Tutus Gusdinar, Kusnandar Anggadiredja, Hamidah Rahman, Tursino Tursino


This paper concerns the synthesis of structured triglycerides containing different proportions and positions from medium- (M) and long-chain (L) fatty acids on a glycerol backbone. Structured triglycerides of MLM type were synthesized by utilizing canarium oil and incorporating caprylic acid (C8:0) as a source for the medium chain (M) fatty acids. Synthesis was performed through a two-step enzymatic reaction, with ethanolysis as the first step and esterification as the second step. Both reactions use the sn-1,3 specific lipase as a catalyst, which has specific activity at positions sn-1 and sn-3 of the triglyceride structure. The results from high-performance liquid chromatography showed that the stereospecific distribution of fatty acids in the structured triglyceride was 29.52±0.59 and 44.28±0.88 mol% of caprylic acid in the positions of sn-1,2,3 and sn-1,3, respectively. Furthermore, analysis of the physicochemical properties of both the native canarium oil and the structured triglycerides using an independent-sample t-test at p < 0.05 indicated that the two samples were significantly different for saponification number, iodium number, and average molecular weight. The results of this study showed that canarium oil can be exploited as a starting material for functional food application.


canarium oil; enzymatic reaction; fatty acids; functional food; physicochemical properties; structured triglyceride.

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Kim, B.H. & Akoh, C.C., Recent Research Trends on the Enzymatic Synthesis of Structured Lipids, Journal of Food Science, 80, pp. C1713-24, 2015.

Hita, E., Robles, A., Camacho, B., Gonzales, P.A., Esteban, L., Jimenez, M.J., Munio, M.M. & Molina, E., Production of Structured Triacylglycerol’s by Acidolysis Catalyzed by Lipases Immobilized in a Packed Bed-Reactor, Biochemical Engineering Journal, 46, pp. 257-264, 2009.

Oh, J., Lee, K.W., Park, H.K., Kim, J.Y., Kwon, K.I, Kim, J.W., Kim H.R. & Kim, I.H., Lipase-Catalyzed Acidolysis of Olive Oil with Capric Acid: Effect of Water Activity on Incorporation and Acyl Migration, Journal of Agricultural and Food Chemistry, 57, pp. 9280-9283, 2009.

Savaghebi, D., Safari, M., Rezaei, K., Ashtari, P. & Farmani, J., Structured Lipid Produced Through Lipase-Catalyzed Acidolysis of Canola Oil, Journal of Agricultural and Science Technology, 14, pp. 1297-1310, 2012.

Xu, X., Fomuso, L.B. & Akoh, C.C., Synthesis of Structured Triacylglycerol’s by Lipase-Catalyzed Acidolysis in a Packed Bed Reactor, Journal of Agricultural and Food Chemistry, 48, pp. 3-10, 2000.

Araujo, M.E.M.B., Campos, P.R.B., Noso, T.M., Alberici, R.M., Cunha, I.B.S., Simas, R.C., Eberlin, M.N. & Carvalho, P.O., Response Surface Modelling of the Production of Structured Lipids from Soybean Oil Using Rhizomucor miehei Lipase, Food Chemistry, 127, pp. 28-33, 2011.

Nunes, P.A., Pires-Cabral, P., Guillen, M., Valero, F. & Ferreira-Dias, S., Batch Operational Stability of Immobilized Heterologous Rhizopus oryzae Lipase during Acidolysis of Virgin Olive Oil with Medium-Chain Fatty Acids, Biochemical Engineering Journal, 67, pp. 265-268, 2012.

Godoy, L.C., Marty, A., Sandoval, G. & Dias, S.F., Optimization of Medium Chain Length Fatty Acid Incorporation into Olive Oil Catalyzed by Immobilized Lip2 from Yarrowia lipolytic, Biochemical Engineering Journal, 77, pp. 20-27, 2013.

Farfan, M., Villalon, M.J., Ortiz, M.E., Nieto, S. & Bouchon, P., The Effect of Interesterification on the Bioavailability of Fatty Acids in Structured Lipid, Food Chemistry, 139, pp. 571-577, 2013.

Munio, M.d.M.M., Robles, A., Esteban, L., Gonzalez P.A. & Molina, E., Synthesis of Structured Lipids by Two Enzymatic Steps: Ethanolysis of Fish Oils and Esterification of 2-monoacylglycerols, Process Biochemistry, 44, pp. 723-730, 2009.

Esteban, L., Munio, M.d.M.M., Robles, A., Hita, E., Jimenez, M.J., Gonzalez, P.A., Camacho, B. & Molina, E., Synthesis of 2-monoacylglycerols (2-MAG) by Enzymatic Alcoholysis of Fish Oils using Different Reactor Types, Biochemical Engineering Journal, 44, pp. 271-279, 2009.

Soumanou, M.M., Bornscheuer, U.T. & Schmid, R.D., Two-step Enzymatic Reaction for the Synthesis of Pure Structured Triacylglycerides, Journal of American Oil Chemists’ Society, 75, pp. 703-710, 1998.

Arcos, J.A., Garcia, H.S. & Hill, G.G., Regioselective Analysis of the Fatty Acid Compositions of Triacylglyceroles with Conventional High-Performance Liquid Chromatography, Journal of American Oil Chemists’ Society, 77, pp. 507-512, 2000.

Turan, D., Yesilcubuk, N.S. & Akoh, C.C., Enrichment of sn-2 Position of Hazelnut Oil with Palmitic Acid: Optimization by Response Surface Methodology, LWT-Food Science and Technology, 50, pp. 766-772, 2013.

Rahman, H., Tursino, Sitompul, J.P., Anggadiredja, K. & Gusdinar, T., The Nutritional Fatty Acids Profiles and Physicochemical Properties of Canarium indicum Nut Oil, International Journal of Pharmacognocy and Phytochemical Research, 7, pp. 1222-1226, 2015.

Rahman, H., Sitompul, J.P., Anggadiredja, K., Lee, H.W. & Gusdinar, T., The Stereospecific Analysis of Canarium indicum Oil-Fatty Acid Based in Triglycerides using High-Performance Liquid Chromatography, International Journal of Pharmaceutical and Clinical Research, 8, pp. 403-406, 2016.

Munio, M.d.M.M., Esteban, L., Robles, A., Hita, E., Jimenez, M.J., Gonzales, P.A., Camacho, B., & Molina, E., Synthesis of 2-Monoacylglycerols Rich in Polyunsaturated Fatty Acid by Ethanolysis of Fish oil Catalyzed by 1,3 Specific Lipases, Process Biochemistry, 43, pp. 1033-1039, 2008.

Fomuso, L.B. & Akoh, C.C., Structured Lipids: Lipase-Catalyzed Interesterification of Tricaproin and Trilinolein, Journal of American Oil Chemists’Society, 73, pp. 405-410, 1998.

Perignon, M., Lecomte, J., Pina, M., Renault, A., Simonneau-Deve, C. & Villeneuve, Activity of Immobilized Thermomyces lanuginosus and Candida antarctica B Lipases in Interesterification Reactions: Effect of the Aqueous Microenvironment, Journal of the American Oil Chemists Society, 90, pp. 1151-1156, 2013.

International Olive Council, Method of Analysis: Determination of the Difference between Actual and Theoretical Content of Triaylglycerols with ECN 42, (December 12, 2014).

Hunter, J.E., Studies on Effects of Dietary Fatty Acids as Related to Their Position on Triglycerides, Lipids, 36, pp. 655-668, 2001.

Mu, H. & Porsgaard, T., Review the Metabolism of Structured Triacylglycerols, Progress in Lipid Research, 44, pp. 430-448, 2005.



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