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Feruloylated Products from Coconut Oil and Shea Butter

Compton, David L., Goodell, John R., Berhow, Mark A., Kenar, James A., Cermak, Steven C., Evans, Kervin O.
The journal of the American Oil Chemists' Society 2017 v.94 no.3 pp. 397-411
Candida, Food and Drug Administration, absorption, antioxidant activity, bioreactors, carboxylic ester hydrolases, coconut oil, fungibility, liquid chromatography, mass spectrometry, medium chain triacylglycerols, monoacylglycerols, shea butter, soybean oil, transesterification, vegetable oil, United States
The synthesis of feruloylated coconut oil and feruloylated shea butter were demonstrated in 0.5-L scale, shaken, batch reactions. Ethyl ferulate and the vegetable oil/fat were combined in a 1.0:1.3 mol ratio in the presence of Candida antartica lipase B immobilized on an acrylic resin (Novozym 435) at 60 °C. The transesterification of ethyl ferulate with coconut oil and shea butter reached equilibrium conversions, after 22 days, of 63 and 70%, respectively, with the shea butter transesterifications producing a white precipitate not observed in the coconut oil transesterifications. The faster transesterification rates, equilibrium conversions and white precipitate were shown to result from di- and monoacylglycerols (DAG and MAG) present in the shea butter. The transesterification of ethyl ferulate and coconut oil was also tested in a continuous, enzymatic, packed-bed bioreactor using Novozym 435 at 60 °C to produce feruloylated coconut oil at rates of 0.5–0.9 kg/day over 4.5 months. The feruloylated coconut oil acylglycerol species were identified by LC–MS analysis of transesterification reactions of ethyl ferulate with medium chain triacylglycerol (TAG) standards, C8–C14. The feruloylated vegetable oils possessed an ultra violet (UV) absorbing λ ₘₐₓ 328 nm, making them good UVAII absorbers, as defined by the U.S. Food and Drug Administration. The feruloylated coconut oil possessed a 17.5% higher absorption capacity than feruloylated shea butter on a per weight basis. All the feruloylated vegetable oils possessed rapid antioxidant capacity (50% reduction of initial radical concentration <5 min) at the concentrations tested, 0.5–2.5 mM. Feruloylated coconut oil possessed chemical and physical characteristics that suggested it would be fungible for feruloylated soybean oil in current retail formulations.