Antimicrobial, antioxidant, and toxicity assessment of Ammonium-Based deep eutectic solvents with formic acid and butyric acid hydrogen bond donors

Inayat, Shamaila; Ahmad, Sajid Rashid; Awan, Sana Javaid; Muhammad, Nawshad

doi:10.1016/j.molliq.2023.122735

Cited by 9 publications

(3 citation statements)

References 31 publications

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“…Nevertheless, the synthesized DES-Mic and DES-Con showed significantly higher (p < 0.05) antioxidant activity, i. e., 77.9 � 0.1 and 86.1 � 0.9 %, respectively. By comparing with other pure DES, it was found that DES-Mic and DES-Con exhibited higher DPPH free radical scavenging activity than the tetrabutylammonium bromide (TBABr):butyric acid DES (~50 %) but lower than the TBABr:formic acid DES (84 %) reported by Inayat et al [52] Factors such as the choices of HBA and HBD as well as the physicochemical properties of the resultant DES formed could give rise to the differences in DES antioxidant activities. Nonetheless, the superior activity of DES-Mic and DES-Con compared to individual ChCl, and the untreated ChCl: MA aqueous mixture in this study could be due to the quenching of free radicals into the supramolecular lattice of DES.…”

Section: Antioxidant Activity Of Desmentioning

confidence: 85%

“…The antioxidant activity of DES, although uncommonly characterized, has been explored using the DPPH free radical scavenging assay. [52][53] Based on Table 4, ChCl and MA recorded DPPH free radical scavenging activity of 15.6 � 0.8 and 20.0 � 1.4 %, respectively. When these components were mixed at an equivalent molar ratio of DES (but not subjected to synthesis conditions), the antioxidant activity increased to 23.3 � 0.8 %, as indicated by ChCl:MA aq .…”

Section: Antioxidant Activity Of Desmentioning

confidence: 99%

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Microwave‐Assisted Preparation of an Acidic Deep Eutectic Solvent: Green Analysis, Characterization and Application

Yap,

Wang,

Gan

2024

ChemistrySelect

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Microwave irradiation was postulated to reduce time and energy for deep eutectic solvent (DES) production which is in line with the principle of green chemistry. In this study, the choline chloride (ChCl)‐malic acid (MA) DES was prepared using microwave‐assisted (DES‐Mic) and conventional (DES‐Con) approaches. Microwave was a relatively greener approach as it was rapid (5 min) and consumed 92.8 % energy less than DES‐Con. Moreover, DES‐Mic and DES‐Con exhibited similar physicochemical profiles (pH, solubility, density) and rheological properties. Structural profiling through FTIR analysis suggested hydrogen bond formation between the functional groups of ChCl and MA. The FTIR spectra also did not show structural differences in the DES synthesized using different methods. DES‐Mic and DES‐Con exhibited superior 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) (80.8±0.1 and 83.2±0.3 %, respectively) free radical scavenging activities than ChCl (15.6±0.8 %), MA (20.0±1.4 %) and ChCl:MA aqueous mixture without subjected to DES synthesis conditions (ChCl:MAaq; 23.3±0.8 %). Both DES were also proven as more efficient solvents for the extraction of polysaccharides from ramie leaf, as they recorded higher yields (21.4±1.9 and 22.2±1.0 %, respectively) than equimolar of MA (17.7±2.6 %) and ChCl (6.4±0.2 %). Overall, microwave was proven as a more sustainable approach for DES preparation compared to conventional method, which could be further improvised for industrial applications.

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Section: Antioxidant Activity Of Desmentioning

confidence: 85%

Section: Antioxidant Activity Of Desmentioning

confidence: 99%

Microwave‐Assisted Preparation of an Acidic Deep Eutectic Solvent: Green Analysis, Characterization and Application

Yap,

Wang,

Gan

2024

ChemistrySelect

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“…Ionic liquids and deep eutectic solvents (DESs) present significant opportunities for intensifying reactions and separations in process technologies through adjusting their structures and properties, which have recently gained attention as potential alternatives for the deterpenation process of essential oils. − For example, Qin et al evaluated liquid–liquid extraction efficiency of 77 hypothetical DESs in lemon essential oil deterpenation employing COSMO-RS calculation along with experimental validation. Among them, the hypothetical DES tetrabutylammonium bromide (TBAB)/levulinic acid (LEA) (1:2), which consists of tetrabutylammonium bromide and levulinic acid, has emerged as the most promising candidate for an eco-friendly deterpenation process due to its superior performance compared to conventional solvent hydrous ethanol and low toxicity of each component. , …”

Section: Introductionmentioning

confidence: 99%

Experimental and Molecular Insights into Efficient Deterpenation of Essential Oil Intensified by Extraction with Deep Eutectic Solvent

Zhao,

Cheng,

2024

Ind. Eng. Chem. Res.

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Deep eutectic solvents (DESs) have been widely utilized to intensify separations by adjusting their structures and properties, particularly in extractive deterpenation of essential oils as green alternatives to conventional organic solvents. In this work, experimental and molecular insights into efficient deterpenation intensified by a DES containing tetrabutylammonium bromide (TBAB) and levulinic acid (LEA) were investigated with citral extraction from lemon essential oil as a case study. DES formation and preferred liquid operating window were determined through solid−liquid equilibrium; an excellent extraction performance was observed at varying citral concentrations via liquid−liquid equilibria. Extraction process was simulated with a well-correlated nonrandom twoliquid model, and a 7-fold concentration of terpenoids was achieved under optimal conditions. Fourier transform infrared spectra and molecular dynamics simulations elucidated the DES formation and extraction mechanisms. Hydrogen-bonding interactions primarily mediated by −COOH group of LEA and Br − anion of TBAB resulted in lower freezing points of DES, thereby enhancing extraction performance. The results provide valuable insights into the practical applications of DESs in separating structurally similar natural products.

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An Eutectic Mixture in the Tetrabutylammonium Bromide‐Octanol System: Macroscopic and Microscopic Points of View

Di Muzio,

Trequattrini,

Palumbo

et al. 2024

ChemPhysChem

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An eutectic mixture of tetrabutylammonium bromide and octanol in the molar ratio 1‐10 exhibited a melting point of ‐17°C. This system was investigated by means of infrared spectroscopy, in the liquid and in the solid state. Classical molecular dynamics was performed to study the fine details of the hydrogen bond interactions established in the mixture. Both octanol and the mixtures displayed an almost featureless far‐infrared spectrum in the liquid state but it becomes highly structured in the solid phase. DFT calculations suggest that new vibrational modes appearing in the mixture at low temperatures may be related to the population of the higher energy conformers of the alcohol. Mid‐infrared spectroscopy measurements evidenced no shift of the CH stretching bands in the mixture compared to the starting materials, while the OH stretching are blue shifted by a few cm‐1. Consistently, molecular dynamics provides a picture of the mixture in which the hydrogen bonds (HB) of pure octanol are replaced by weaker HB formed with the TBA ion and the Br cation. Due to these interactions the ionic couple becomes more separated. In agreement with this model, the lengths of all HB are much larger than those observed in acids in previous studies.

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Antimicrobial, antioxidant, and toxicity assessment of Ammonium-Based deep eutectic solvents with formic acid and butyric acid hydrogen bond donors

Cited by 9 publications

References 31 publications

Microwave‐Assisted Preparation of an Acidic Deep Eutectic Solvent: Green Analysis, Characterization and Application

Microwave‐Assisted Preparation of an Acidic Deep Eutectic Solvent: Green Analysis, Characterization and Application

Experimental and Molecular Insights into Efficient Deterpenation of Essential Oil Intensified by Extraction with Deep Eutectic Solvent

An Eutectic Mixture in the Tetrabutylammonium Bromide‐Octanol System: Macroscopic and Microscopic Points of View

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