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Deep Eutectic Solvents Based on Natural Ascorbic Acid Analogues and Choline Chloride.

ABSTRACT: Deep eutectic solvents (DES) are one of the most promising green technologies to emerge in recent years given their combination of environmentally friendly credentials and useful functionalities. Considering the continued search for new DES - especially those that exemplify the aforementioned characteristics, we report the preparation of DES based on natural analogues of l-ascorbic acid for the first time. The onset of eutectic melting occurred at temperatures far below the melting point of the individual components and resulted in the generation of glass forming fluids with glass transition temperatures, viscosities and flow behavior that are comparable to similar systems. This work expands the current array of DES that can be produced using naturally occurring components, which given their potential to be bio-derived, interesting physicochemical properties (e.?g. propensity to supercool and vitrify) and apparent antibacterial nature, may provide utility within a range of applications.

SUBMITTER: Maneffa AJ

PROVIDER: S-EPMC7197082 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Deep Eutectic Solvents Based on Natural Ascorbic Acid Analogues and Choline Chloride.

Maneffa Andrew J AJ Harrison Adrian B AB Radford Stewart J SJ Whitehouse A Steve AS Clark James H JH Matharu Avtar S AS

ChemistryOpen 20200504 5

Deep eutectic solvents (DES) are one of the most promising green technologies to emerge in recent years given their combination of environmentally friendly credentials and useful functionalities. Considering the continued search for new DES - especially those that exemplify the aforementioned characteristics, we report the preparation of DES based on natural analogues of l-ascorbic acid for the first time. The onset of eutectic melting occurred at temperatures far below the melting point of the ...[more]

PMID: 32373425

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Project description:Huge quantities of oil palm (Elaeis guineensis Jacq.) leaves (OPL) are generated as agricultural biomass from oil palm plantations. OPL are known to contain significant amounts of flavonoids. For maximal exploitation of these valuable antioxidant compounds, an innovative and sustainable extraction method employing natural deep eutectic solvents (NaDES) combined with ultrasonic assisted extraction was developed. Various NaDES composed of choline chloride as the hydrogen bond donor (HBD) and 1,2 propanediol (PD), 1,4 butanediol (BD), glycerol (GLY), glucose (GLU), maltose (MAL), and lactic acid (LA) as the hydrogen bond acceptor (HBA) were synthesized. The influence of these compositions, the methods of their synthesis, molar ratios, and water contents on their capacity to extract flavonoids from OPL was evaluated. Based on the results, it was found that methods which incorporate a heating step produced NaDES with the best capacity to extract OPL flavonoids. These thermal methods combined with molar ratios of 1:3 or 1:4 and water contents of 17 to 50% were found to be the optimal conditions for preparing NaDES, specifically when applied to the PD, BD, and GLY NaDES. Subsequently, UHPLC-UV/PDA-MS/MS analysis revealed NaDES extracts recovered by macroporous adsorption resin XAD7HP were able to optimally extract at least twelve luteolin and apigenin derivatives in OPL NaDES extracts prepared from glycerol and 1,4-butanediol demonstrated better and comparable efficiency as aqueous methanol in extracting flavonoids from OPL. The in vitro studies of antioxidant and wound healing properties supported these findings by exhibiting good free radical scavenging, cell proliferation, and migration activities. Additionally, the NaDES extracts also showed non-cytotoxicity effects at 1000 µg/mL and below on 3T3 fibroblast cells. Results of the study showed that NaDES could be a promising eco-friendly green solvent to extract bioactive OPL flavonoids that have great potential for applications as wound healing agents.

Project description:The rheological studies of Lactic Acid (LA)-based Natural Deep Eutectic Solvents (NADES) are provided in the present investigation. Those mechanisms were also studied in which three distinct Hydrogen Bond Acceptors (HBAs) of Choline Chloride (ChCl), Betaine (Be), and β-Alanine (β-Al), after being added to a specific Hydrogen Bond Donor (HBD) at a predefined mole-to-mole ratio of 1:1, affected the rheological properties of the prepared NADES. The alterations in the rheology-related characteristics in association with the mechanical and physical properties indicate the tolerance of the material under various operational conditions in the field and show their potential utilization as environmentally suitable and feasible solvents for industrial applications. In the present research, the viscoelastic properties of the three samples of NADES were assessed along with their shear flow properties. The backward and forward temperature change in the Apparent Viscosity (AV) pattern related to the NADES system was described by a rheogram. Furthermore, the density was determined and compared with the AV while considering the temperature-related factor. On a further note, the viscoelastic characteristics were utilized in describing and investigating the network disturbance on the level of the microstructure of NADES upon frequency sweep. A series of experiments were carried out using Thermogravimetry Analysis (TGA) to investigate the thermo-physical properties to optimize them. The rheological properties of shear flow measurements were analyzed using the Bingham model that is best suited for the AV developed with the shear rate with the dynamic yield stress of three systems. The Bingham model was used to determine the lowest stress necessary to disturb the network structure and commence the flow of LA-based NADES. Overall, the viscoelastic behavior of the LA-based NADES revealed the dissimilarity between their strength and viscosity. In addition, shear flow investigations demonstrated that LA-based NADES systems exhibit non-Newtonian properties and substantial shear-thinning effects equivalent to those of alternative IL sorbents. Assessing the rheological properties of LA-based NADES is crucial for a better understanding the key challenges associated with high viscosity. Defining the transport yield stress requirements for NADES systems under different conditions benefits their future development and potentially opens the door to more challenging applications.

Dataset Information

Deep Eutectic Solvents Based on Natural Ascorbic Acid Analogues and Choline Chloride.

Publications

Deep Eutectic Solvents Based on Natural Ascorbic Acid Analogues and Choline Chloride.

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