Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate

Abstract

Ferulic acid in ester form has shown a stronger ability in ameliorating certain pathological conditions and inhibiting lipid oxidation. In present study, a solvent-free and reduced pressure evaporation system was developed for lipase-catalyzed synthesis of 2-ethylhexyl ferulate (2-EF) from ferulic acid and 2-ethylhexanol. A Box-Behnken design with response surface methodology (RSM) and artificial neural network (ANN) was selected to model and optimize the process. Based on the yields of 2-EF, reaction temperature was shown to be the most important process factor on the molar conversion among all variables. The residual values and the coefficient of determination (R 2 ) calculated from the design data indicated that ANN was better than RSM in data fitting. Overall, the present lipase-catalyzed approach for 2-EF synthesis at low reaction temperature in a reduced pressure evaporation system shows high 2-EF production efficiency. Notably, this approach can reduce the enzyme denaturation and ferulic acid oxidation that usually occur during long-term biosynthetic operations at high temperature.

Novozym 40086 as a novel biocatalyst to improve benzyl cinnamate synthesis

“…Compared with chemical catalysts, due to the thermal instability of cinnamic acid, biocatalysts have attracted more attention for the esterication. [13][14][15][16] For example, in the reports of Wang et al and Zhang et al, 10,12 lipozyme TLIM was used as a biocatalyst to prepare benzyl cinnamate, and a high yield (97%) can be obtained. For the immobilized biocatalysts, the carrier features can affect the activity and stability of immobilized enzymes.…”

An Efficient Approach for Lipase-Catalyzed Synthesis of Retinyl Laurate Nutraceutical by Combining Ultrasound Assistance and Artificial Neural Network Optimization

“…In this study, the data generated from the CCD ( Table 1 ) were employed in an ANN model for the optimization of enzymatic synthesis of retinyl laurate. The various architectures for ANN models were developed using Neural Power software (CPC-X Software, version 2.5, Carnegie, PA, USA), and the best set of parameters was determined based on the maximization of R 2 value and minimization of the RMSE value [ 33 ]. The proposed ANN consisted of three layers in the present work, including an input layer with four neurons (reaction time, reaction temperature, enzyme amount, and substrate molar ratio), a hidden layer with several neurons, and an output layer containing one output neuron (relative conversion).…”

Developing a High-Temperature Solvent-Free System for Efficient Biocatalysis of Octyl Ferulate

“…Samples were centrifuged and diluted with hexanol/2-methyl-2-butanol (1:100). Analyses were done according to the procedure modified by Huang et al [36]. The flow rate was set at 1.0 mL/min, followed by detection at a wavelength of 325 nm.…”

“…This process could reduce the reaction time but increase the synthesized yield of esters [9,23]. Additionally, the solvent-free reaction system commonly contains simple substrates and offers reaction benefits, including the maximization of substrate concentration, a higher volumetric productiveness, less environmental hazard, and a cost savings in both the reactor design of large-scale production and the chemical separation/purification of products [36]. However, to increase the yield of FA esters, it is required to develop a solvent-free system that operates at a high temperature.…”