Abstract
Human milk fat substitutes were synthesized using non-preprocessed natural fats and oils with lipase. Enzymatic interesterification of tripalmitin and oleic acid was carried out in isooctane. The reaction reached equilibrium after 12 h and the reaction conditions were partially optimized as a molar ratio of tripalmitin to oleic acid of 1:5, an initial water content of 0.01 g/L, and a water removal time of 1 h. After interesterification of tripalmitin and oleic acid, the reaction products contained 55.2% 1,3-dioleoyl-2-palmitoyl glycerol (OPO). The OPO yield was 25.2% when commercial palm oil and camellia oil were used as substrates, and the OPO concentration was increased to 53.3% after fractional crystallization of the reaction product.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Breckenridge WC, Marai L, Kuksis A. Triglycerides structure of human milk fat. Can. J. Biochem. 47: 761–769 (1969)
Soumanou MM, Perignon M, Villeneuve P. Lipase-catalyzed interesterification reactions for human milk fat substitutes production: A review. Eur. J. Lipid Sci. Tech. 115: 270–285 (2013)
Karabulut I, Turan S, Vural H, Kayahan M. Human milk fat substitute produced by enzymatic interesterification of vegetable oil blend. Food Technol. Biotech. 45: 434–438 (2007)
Sahin N, Akoh CC, Karaali A. Lipase catalyzed acidolysis of tripalmitin with hazelnut oil fatty acids and stearic acid to produce human milk fat substitutes. J. Agr. Food Chem. 53: 5779–5783 (2005)
Makudo CO, Akoh CC, Park YW. Enzymatic production of infant milk fat analogs containing palmitic acid: Optimization of reactions by response surface methodology. J. Dairy Sci. 90: 2147–2154 (2007)
Zou XQ, Huang JH, Jin QZ, Liu YF, Song ZH, Wang XG. Lipasecatalyzed preparation of human milk fat substitutes from palm stearin in a solvent-free system. J. Agr. Food Chem. 59: 6055–6063 (2011)
Akoh CC, Xu X. Enzymatic production of betapol and other specialty fats. pp. 461–478. In: Lipid Biotechnology. Kuo TM, Gardner H (eds). Marcel Dekker Inc., New York, NY, USA (2002)
Kellens M, Calliauw G. Oil modification processes. pp. 175–194. In: Edible Oil Processing. Hamm W, Hamilton RJ, Calliauw G (eds). Wiley-Blackwell, John Wiley & Sons Ltd., West Sussex, UK (2013)
Kim M, Noh S, Yoon SH. Stereospecific analysis fatty acid composition of chufa (Cyperus esculentus L.) tuber oil. J. Am. Oil Chem. Soc. 84: 1079–1080 (2007)
Noh S, Yoon SH. Stereospecific positional distribution of fatty acids of Camellia (Camellia japonica L.) seed oil. J. Food Sci. 77: C1055–1057 (2012)
AOCS. Official Methods and Recommended Practices of the AOCS. 6th ed. Ce 2-66. American Oil Chemists’ Society, Champaign, IL, USA (2009)
Sehat N, Yurawecz MP, Roach JAG, Mossoba MM, Kramer JKG, Ku Y. Silver-ion high-performance liquid chromatographic separation and identification of conjugated linoleic acid isomers. Lipids 33: 217–221 (1998)
Fischer K. A new method for the analytical determination of the water content of liquids and solids (Neues Verfahren zur maßanalytischen Bestimmung des Wassergehaltes von Flüssigkeiten und festen Körpern). Angew. Chem. 48: 394–396 (1935)
Kwon DY, Song HN, Yoon SH. Synthesis of medium-chain glycerides by lipase in organic solvent. J. Am. Oil Chem. Soc. 73: 1521–1525 (1996)
Kwon DY, Kim HD, Yoon SH. Lipases catalyzed hydrolysis and esterification of glycerides in organic solvent. Food Sci. Biotechnol. 7: 1–5 (1998)
Padley FB, Gunstone FD, Harwood JL. Occurrence and characteristics of oils and fats. pp. 55–129. In: The Lipid Handbook. Gunstone FD, Harwood JL, Padley FB (eds). Chapman and Hall, London, UK (1986)
Dudal Y, Lortie R. Influence of water activity on the synthesis of triolein catalyzed by immobilized Mucor miehei lipase. Biotechnol. Bioeng. 45: 129–134 (1995)
Klibanov AM. Enzyme that work in organic solvents. Chemtech 16: 354–359 (1986)
Soumanou MM, Bornscheuer UT, Schmid U, Schmid RD. Crucial role of support and water activity on the lipase-catalyzed synthesis of structured triglycerides. Biocatal. Biotransfor. 16: 443–459 (1999)
Won K, Jeong JC, Lee SB. Computer-aided real-time estimation of reaction conversion for lipase-catalyzed esterification in solvent-free systems. Biotechnol. Bioeng. 79: 795–803 (2002)
Mattson FH, Volpenhein RA. The specific distribution of unsaturated fatty acids in the triglycerides of plants. J. Lipid Res. 4: 392–396 (1963)
Jurriens G, De Vries B, Schouten L. Quantitative semimicro analysis of triglyceride fatty acid distribution in a Congo palm oil. J. Lipid Res. 5: 366–368 (1964)
Filer Jr. LJ, Mattson FH, Fomon SJ. Triglyceride configuration and fat absorption by the human infant. J. Nutr. 99: 293–298 (1969)
Karupaiah T, Sundram K. Effects of stereospecific positioning of fatty acids in triacylglycerol structure in native and randomized fats: A review of their nutritional implications. Nutr. Metab. 4: 16–32 (2007)
Seriburi V, Akoh CC. Enzymatic interesterification of lard and higholeic sunflower oil with Candida antarctica lipase to produce plastic fats. J. Am. Oil Chem. Soc. 75: 1339–1345 (1998)
Crockett ME, Deuel HJ. A comparison of the coefficient of digestibility and the rate of absorption of several natural and artificial fats as influenced by melting point. J. Nutr. 33: 187–194 (1947)
Timms RE. Fractionation. pp. 199–222. In: Lipid Technologies and Applications. Gunstone FD, Padley FB (eds). Marcel Dekker Inc., New York, NY, USA (1997)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, N.K., Oh, S.W., Kwon, D.Y. et al. Production of 1, 3-dioleoyl-2-palmitoyl glycerol as a human milk fat substitute using enzymatic interesterification of natural fats and oils. Food Sci Biotechnol 24, 433–437 (2015). https://doi.org/10.1007/s10068-015-0057-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10068-015-0057-4