A Simple and High-yield Synthesis of Hexadecyl Ferulate and Its In Vitro Antioxidant Potential

Abstract

Ferulic acid (FA) is a phenolic compound with well-known antioxidant potential that can be used as a promising anti-inflammatory and anti-cancer molecule. Furthermore, it has been reported to have neuroprotective activity. One of the main problems, which limit its clinical use, is its low bioavailability when administered orally. This limitation can be circumvented by changes in their structure and/or for preparing lipid-based formulations. The aim of this study was to synthesize a derivative of FA, the hexadecyl ferulate (HF). This compound would be more susceptible to pass through blood-brain barrier (BBB) due to its lipophilic character. The HF was obtained by Steglich esterification and yielded 76.77 ± 1.35%. Its structural characterization was performed by spectroscopic methods of Fourier-transformed infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR). FTIR spectrum of HF presented two typical bands of ester group, a C=O ester stretching band at 1725 cm-1 and a CO stretching band at 1159 cm-1. The 1 H and 13 C spectral data confirmed the chemical structure of HF. Regarding the 13 C NMR spectrum, HF showed a chemical shift at δ 167.39 ppm which corresponded to the carbonyl carbon of the ester group. Concerning the in vitro antioxidant potential, HF had equivalent or improved scavenger activity than FA leading to IC50 values of 0.083 ± 0.009 nmol.mL-1 and 0.027 ± 0.002 nmol.mL-1 in DPPH radical scavenging and ABTS radical cation decolorization assays, respectively. Further studies are required in order to investigate the antioxidant effect of HF in biological media.

Antibacterial Activity of Ferulic Acid Ester against Ralstonia solanacearum and Its Synergy with Essential Oils

“…Based on this esterification method [29] with minor modifications and following the general procedure as shown in Scheme 1, in brief, 1 (5 mmol), 4-dimethylaminopyridine (0.25 mmol), and N, N -dicyclohexylcarbodiimide (6 mmol) was dissolved in 20 mL of tetrahydrofuran, alcohol (30 mmol) was slowly added dropwise to the mixed solution. Then it was stirred for 12 h under nitrogen flow at room temperature.…”

“…Based on this esterification method [29] with minor modifications and following t general procedure as shown in Scheme 1, in brief, 1 (5 mmol), 4-dimethylaminopyridi (0.25 mmol), and N, N′-dicyclohexylcarbodiimide (6 mmol) was dissolved in 20 mL tetrahydrofuran, alcohol (30 mmol) was slowly added dropwise to the mixed solutio Then it was stirred for 12 h under nitrogen flow at room temperature. After filtration an concentration, the required product was purified by column chromatography (petroleu ether: ethyl acetate = 6:1), and their structures were characterized by FT-IR NMR and M Scheme 1.…”

Novel Biobased Multifunctional Emollients for Cosmetic Applications: Toward the Ingredient-List Reduction

“…urea derivatives), respectively, and were discarded. 24 Starting from the corresponding aldehyde, vanillin, the Wittig reaction 25 or Knoevenagel condensation 21,26 could be envisaged. The first one using triphenyl phosphonium salt presented a poor atom economy profile, whereas the second one could be sustainable but a purification step was needed to eliminate the remaining aldehyde.…”

“…For the modification of ferulic acid into the corresponding emollients, different synthetic pathways have been considered. Fisher or Steglich esterifications would have required intensive distillation to remove excess fatty alcohol or unsustainable conditions and a delicate purification step (i.e., removing urea derivatives), respectively, and were discarded . Starting from the corresponding aldehyde, vanillin, the Wittig reaction or Knoevenagel condensation , could be envisaged.…”