214779-01-8

Upstream product

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 111-87-5 octanol 
• 22329-76-6 methyl ferulate 

Relevant academic research and scientific papers

Evaluation of deep eutectic solvent-water binary mixtures for lipase-catalyzed lipophilization of phenolic acids

This work reports the first lipase-catalyzed reactions between substrates of different polarities using deep eutectic solvents as a medium. The model reaction consisted of a lipophilization process based on the alcoholysis of phenolic esters using immobilized Candida antarctica lipase B as a biocatalyst. Results showed that water could dramatically improve the lipase activity and change the reactivity of phenolic substrates. Indeed, very low conversions (2%) were observed in pure DES, whereas in DES-water binary mixtures, quantitative conversions were achieved. After investigating the role of various parameters, such as the substrate concentration and ratio, pH or thermodynamic activity of water, the effect of the presence of water in pure DES based on urea or glycerol was discussed. In this paper, we propose new perspectives for the enzymatic modification of polar substrates using this novel generation of green, inexpensive and easy-to-handle solvents.

Alkyl Ferulate Esters as Multifunctional Food Additives: Antibacterial Activity and Mode of Action against Escherichia coli in Vitro

This work aims to prepare ferulic acid alkyl esters (FAEs) through the lipase-catalyzed reaction between methyl ferulate and various fatty alcohols in deep eutectic solvents and ascertain their antibacterial activities and mechanisms. Screens of antibacterial effects of FAEs against Escherichia coli ATCC 25922 (E. coli) and Listeria monocytogenes ATCC 19115 (L. monocytogenes) revealed that hexyl ferulate (FAC6) exerted excellent bacteriostatic and bactericidal effects on E. coli and L. monocytogenes (minimum inhibitory concentration (MIC): 1.6 and 0.1 mM, minimum bactericidal concentration (MBC): 25.6 and 0.2 mM, respectively). The antibacterial mechanism of FAC6 against E. coli was systematically studied to facilitate its practical use as a food additive with multifunctionalities. The growth and time-kill curves implied the partial cell lysis and inhibition of the growth of E. coli caused by FAC6. The result related to propidium iodide uptake and cell constituents' leakage (K+, proteins, nucleotides, and β-galactosidase) implied that bacterial cytomembranes were substantially compromised by FAC6. Variations on morphology and cardiolipin microdomains and membrane hyperpolarization of cells visually verified that FAC6 induced cell elongation and destructed the cell membrane with cell wall perforation. SDS-PAGE analysis and alterations of fluorescence spectra of bacterial membrane proteins manifested that FAC6 caused significant changes in constitutions and conformation of membrane proteins. Furthermore, it also could bind to minor grooves of E. coli DNA to form complexes. Meanwhile, FAC6 exhibited antibiofilm formation activity. These findings indicated that that FAC6 has promising potential to be developed as a multifunctional food additive.

Antioxidant properties and efficacies of synthesized alkyl caffeates, ferulates, and coumarates

Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.

Ionic liquid-assisted solubilization for improved enzymatic esterification of phenolic acids

Lipophilic derivatives of phenolic acids could greatly extend their applications in the lipophilic bio-environment and food processing, therefore, developing an efficient lipophilization reaction system constitutes an interesting topic of biocatalysis. Low solubility of phenolic acids in most enzyme-benign solvents represents the main reason for the inefficiency of enzymatic production of lipophilic phenolic derivatives. This work reports a novel approach to improve Candida antartica lipase B (Novozym 435) catalyzed lipophilization of phenolic acids by means of ionic liquids (IL), trioctylmethylammonium trifluoro-acetate (tOMA.TFA) assisted solubilization of the substrate. In this approach, the IL plays two major roles, namely, to dissolve phenolic acids at high concentration so as to create a homogeneous system with another substrate-1-octanol, and to be benign to the enzyme to keep the biocatalyst active; which is proved itself to be a correct strategy as improved conversion and volumetric productivity are obtained. The results showed that dosage of IL (denoted as the volume ratio of 1-octanol/tOMA.TFA), concentration of dihydrocaffeic acid (DHCA) and temperature are the key parameters governing the reaction efficiency. A maximum conversion of DHCA was achieved at the ratio of 1-octanol/tOMA.TFA 12:1 (v/v) (1-octanol/ DHCA, 38:1 (mol/mol)). A temperature of 70 °C was correct to obtain optimal conversion of DHCA. Even though the conversion of DHCA was higher at lower concentrations of DHCA, the overall volumetric productivity (reaction rate) was much higher when a high concentration of DHCA (1.6 M) was applied, due to IL-assisted solubilization of DHCA. Remarkable enhancement of the conversions of ferulic and caffeic acids were achieved, when the same reaction approach (tOMA.TFA assisted solubilization) was applied to these two phenolic acids, indicating the general applicability of this novel approach.