A new group of synthetic phenolic-containing amphiphilic molecules for multipurpose applications: Physico-chemical characterization and cell-toxicity study

Abstract

Nine synthetic amphiphilic phenolic lipids, varied in phenolic moiety (caffeoyl/dimethylcaffeoyl) and fatty acid chain lengths (8–18) were characterized by differential scanning calorimetry (DSC), temperature-ramp Fourier transform infra-red spectroscopy (FT-IR) and atomic force microscopy (AFM). FT-IR and DSC results revealed that the physical state and lateral packing of synthetic molecules were largely governed by fatty acyls. The critical micelle concentrations (CMC) of synthetic lipids was in the range of 0.1 mM to 2.5 mM, affording generation of stable oil-in-water emulsions; as evidenced by the creaming index (<5%) of emulsions stabilized by compounds C12‒C16, and C12a‒C16a after 7 days’ storage. AFM analysis revealed that compound C14 formed stable double-layers films of 5.2 nm and 6.7 nm. Application studies showed that formulations stabilized by synthesized compounds containing 30% fish oil had superior physical and oxidative stability compared to formulations containing commercial emulsifiers or their mixtures with phenolic acids. Moreover, the synthetic compounds were non-toxic against in vitro transformed keratinocytes from histologically normal skin and Caco-2 cell lines. This study demonstrates the relevance of using a natural hydroxycarboxylic acid as a flexible linker between natural antioxidants, glycerol and fatty acids to generate multifunctional amphiphiles with potential applications in food, pharmaceutical and cosmetic industry.

Effects of Modified DATEMs with Different Alkyl Chain Lengths on Improving Oxidative and Physical Stability of 70% Fish Oil-in-Water Emulsions

“…A recent study reported that DATEM C14 led to lower lipid oxidation (TBARS) when compared with DATEM C12 or C16 in 30% fish oil-in-water emulsions. 24 The first part of this study focused on finding an optimal recipe for emulsifying high fat fish oil-in-water emulsions using CAS and commercial DATEM. For that purpose, we used Box− Behnken design combined with Response Surface Methodologies (RSM).…”

“…Considering the larger head part of the DATEM molecules compared with a phenolipid, we decided to study the longest short- to medium-chain length, which is C12 and one even longer (C14), in order to adjust the hydrophilic–lipophilic balance (HLB) of the molecules. A recent study reported that DATEM C14 led to lower lipid oxidation (TBARS) when compared with DATEM C12 or C16 in 30% fish oil-in-water emulsions …”

Tailored Functionalization of Natural Phenols to Improve Biological Activity

“…Caffeic or 3,4-dimethylcaffeic acids were reacted with malic acid and then coupled with monoglicerids of fatty acids with chain lengths ranging from 8 to 18 C atoms [ 359 ]. The combinations of phenolic and fatty acids gave a series of six amphiphilic compounds that were tested for activity.…”