Acyl Migration Kinetics of Vegetable Oil 1,2-Diacylglycerols |
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Authors: | Joseph A Laszlo David L Compton Karl E Vermillion |
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Affiliation: | (1) New Crops and Processing Technology Research Unit, National Center for Agricultural Utilization Research, USDA, Agricultural Research Service, 1815 N. University St., Peoria, IL 61604, USA |
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Abstract: | The acyl migration kinetics of long-chain 1,2-diacylglycerol (1,2-DAG) to form 1,3-diacylglycerol (1,3-DAG) over the temperature
range of 25–80 °C were examined using 1H-NMR spectroscopy. Lipase-catalyzed ethanolysis of high-oleic sunflower oil, followed by a series of solvent extraction steps,
generated high purity 1,2-DAG (0.93 mol fraction of the DAG content). The 1,2-DAG mole fraction of 0.32 at equilibrium was
found to be insensitive to temperature, indicating that long-chain acyl group migration is neither endothermic nor exothermic.
Determination of the temperature-dependent, first-order reaction kinetic parameters revealed a 1,2-DAG half life (t
1/2) of 3,425 h and 15.8 h at 25 and 80 °C, respectively. A comparison of 1,2-DAG with 2-monoacylglycerol indicated that there
is no difference between the two in the potential energy state (ΔG
‡) of their respective transitions states or cyclic intermediates.
Product names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard
of the product, and the use of the name by the USDA implies no approval of the product to the exclusion of others that may
be suitable. |
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Keywords: | Acyl migration Structured lipids 1 2-Diacylglycerol Alcoholysis NMR Lipase |
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