American Journal of Food Science and Technology
ISSN (Print): 2333-4827 ISSN (Online): 2333-4835 Website: Editor-in-chief: Hyo Choi
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American Journal of Food Science and Technology. 2017, 5(6), 228-232
DOI: 10.12691/ajfst-5-6-1
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Catalyzed Interesterification of Mixed Short & Medium Chain Fatty Acid Triacylglycerols as a Potential Dietary Food Lipid Source: Synthesis and Characterization

Ronald P. D’Amelia1, , Gabrielle Cabrera1, Ling Huang1 and William F. Nirode1

1Department of Chemistry, Hofstra University, Hempstead New York, USA

Pub. Date: October 28, 2017

Cite this paper:
Ronald P. D’Amelia, Gabrielle Cabrera, Ling Huang and William F. Nirode. Catalyzed Interesterification of Mixed Short & Medium Chain Fatty Acid Triacylglycerols as a Potential Dietary Food Lipid Source: Synthesis and Characterization. American Journal of Food Science and Technology. 2017; 5(6):228-232. doi: 10.12691/ajfst-5-6-1


Interesterifcation reactions, more commonly called ester-exchange, are a process by which the arrangement of fatty acids in the triacylglycerol molecule is changed. Ester-exchange reactions lead to a random distribution of fatty acids resulting in a triacylglycerol composition that is predictable from the overall fatty acid composition of the starting reaction mixture. In this report, we synthesized various triacylglycerols containing different ratios of saturated short chain fatty acids (SCFA) such as: acetic, propionic and butyric, with a saturated medium chain fatty acid (MCFA) of octanoic acid. The interesterification of these triacylglycerols was prepared by the NaOCH3 catalyzed interesterification of model reactions performed with different molar ratios of Triacetin, Tripropionin, Tributyrin and Trioctanoin. The reaction products were characterized by Gas Chromatography (GC) and Proton NMR. We found that the difference in fatty acid size and the reduced steric demands of the S/MCFA did not give rise to positional specificity and we found no observable deviations from the random interesterification chemistry model. The potential of having different short and medium fatty acids triacylglycerol on one molecule for direct ingestion and metabolism can be of significant importance to maintaining gut health.

interesterification triacylglycerols triglycerides short chain fatty acids medium chain fatty acids ester-exchange randomization theory

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[1]  Cummings, J.H., “Short Chain Fatty Acids in the Human Colon”, Gut., 22, 763-779, 1981.
[2]  Scheppach, W., “Effects of Short Chain Fatty Acids on Gut morphology and Function”, Gut., 35(1 suppll), S35-S38, 1994.
[3]  MacFarlane, S., MacFarlane, G.T. Regulation of Short-Chain Fatty Acid Production, The Proceedings of the Nutritional Society, 62, 67-72, 2003.
[4]  Wonj, J.M.; DeSouza, R.; Kendal, C.W.; Eman, A.; Jenkins, D.J. Colonic Health: Fermentation and Short Chain Fatty Acids, Journal of Clinical Gastroentrology, 40, 235-240, 2006.
[5]  Hamer, H.M.; Jonkers, D.; Venema, K.; VanHoutoin, S.; Troost, F.J.; Brummer, R. J. Review article: The Role of Butyrate on Colonic Function, Alimentary Pharmacology and Therapeutics, 27, 104-110, 2008.
[6]  Cook, S.I.; Sellin, J.H. Review article: Short Chain Fatty Acids in Health and Disease, Aliment. Pharmcol. Ther., 12, 499-507, 1998.
[7]  Sun, Y.; O’Riordan, M.X.D. Regulation of Bacterial Pathogenesis by Intestinal Short Chain Fatty Acids, Advances in Applied Microbiology, 85, 93-118, 2013.
[8]  Tan, J.; McKenize, C,; Potamitis, M.; Thorburn, A.; Mackay, C.R.; Macia, L. The role of Short Chain Fatty Acids in Health and Disease, Advances in Immunology, 121, 1-119, 2014.
[9]  Cotter, R.; Tucker, H. Use of Short Chain Fatty Acid containing Lipids to Maintain Gastrointestional Integrity and Function in Patients, U.S. Patent 5,919, 822, 1999.
[10]  Aoyama,T; Nosaka, N; Kasai, M, Research on the Nutritional Characteristics of Medium Chain Fatty Acids, The journal of Medical Investigation, 54, vol 3-4, 385-8, 2007.
[11]  Labarthe, F.O.; Gelinas, R.; DesRosiers, C. “Medium-chain Fatty Acids as Metabolic Therapy in Cardiac Disease” Cardiovascular Drugs and Therapy”, 22 9(2) 97-106, 2008.
[12]  Kaunitz, H. “Medium Chain Triglycerides in Aging & Atherosclerosis” Advances in Human Nutrition Vol 3 by J.Kabara (Ed) Chem-Ordital, Pob 134, Park Forest, IL 60466.
[13]  Rial, S. A,; Karelis, A.D.; BerGeron, K.F.; Mounier, C. “Gut Micro Biota & Metabolic Health: The Potential Beneficial Effects of a Medium Chain Triglyceride Diet in Obese Individuals” Nutrients, 8 (5), 281-303, May 2016.
[14]  Shah, N.D.; Limketkai, B.N. “The use of Medium Chain Triglycerides in Gastrointestional Disorders” Practical Gastroenterolgy, p20-28, Feb 2017
[15]  Sreenivasan, B. Interesterification of Fats. J Am. Oil Chem. Soc., 55, 796-805, 1978.
[16]  Rozendaal,A. Interesterification of Oils and Fats. World Conference on Edible Oils and Fats; American Oil Chemists’ Society: Champaign, IL, pp152-157, 1989.
[17]  Bauer, F. J.; Lange, W. Plastic Shortenings and Process of Producing Same. U.S. Patent 2, 614, 937, 1949.
[18]  Klemann, L.P.;Aji, K.; Chrysam, M.M.; D’Amelia, R.P. “Random Nature of Triacylglycerols Produced by the Catalyzed Interesterification of Short- and Long-Chain Fatty Acid Triglycerides J. Agric. Food Chem. 42, 442-446, 1994.
[19]  D’Amelia, Ronald P., Alexander E. Bleich, Lee Honig, and William F. Nirode. "Synthesis and Characterization of Mixed Short Chain Fatty Acid Triacylglycerols as a Potential Dietary Food Lipid Source." American Journal of Food Science and Technology AJFST 2.6 175-78, 2014.