Browse
Submit Data
Databases
API
Help

Dataset Information

31 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Quantification of Caffeine Interactions in Choline Chloride Natural Deep Eutectic Solvents: Solubility Measurements and COSMO-RS-DARE Interpretation

ABSTRACT: Solubility of active pharmaceutical ingredients is an important aspect of drug processing and formulation. Although caffeine was a subject of many studies aiming to quantify saturated solutions, many applied solvents suffer from not being environmentally friendly. This work fills this gap by presenting the results of solubility measurements in choline chloride natural deep eutectic solvents, ccNADES, comprising one of seven of the following polyalcohols: glycerol, sorbitol, xylitol, glucose, sucrose, maltose and fructose. The ratio of ccNADES components was optimized for maximizing caffeine solubility at room temperature. Additionally, temperature dependent solubility was measured for the first four systems exhibiting the highest solubility potential, both in their neat forms and in mixtures with water. Results were used for intermolecular interactions assessments using the COSMO-RS-DARE approach, which led to a perfect match between experimental and computed solubility values. An important methodological discussion was provided for an appropriate definition of the systems. Surprising linear trends were observed between the values of fitting parameters and water-ccNADES composition. In addition, comments on selection of the values of the fusion thermodynamic parameters were provided, which led to the conclusion that COSMO-RS-DARE solubility computations can effectively compensate for the inaccuracies of these important physicochemical properties.

SUBMITTER: Jelinski T

PROVIDER: S-EPMC9323268 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Screening Deep Eutectic Solvents for CO2 Capture With COSMO-RS.

Project description:In this work, 502 experimental data for CO2 solubilities and 132 for Henry's constants of CO2 in DESs were comprehensively summarized from literatures and used for further verification and development of COSMO-RS. Large systematic deviations of 62. 2, 59.6, 63.0, and 59.1% for the logarithmic CO2 solubilities in the DESs (1:2, 1:3, 1:4, 1:5), respectively, were observed for the prediction with the original COSMO-RS, while the predicted Henry's constants of CO2 in the DESs (1:1.5, 1:2, 1:3, 1:4, 1:5) at temperatures ranging of 293.15-333.15 K are more accurate than the predicted CO2 solubility with the original COSMO-RS. To improve the performance of COSMO-RS, 502 data points of CO2 solubility in the DESs (1:2, 1:3, 1:4, 1:5) were used for correcting COSMO-RS with a temperature-pressure dependent parameter, and the CO2 solubility in the DES (1:6) was predicted to further verify the performance of the corrected model. The results indicate that the corrected COSMO-RS can significantly improve the model performance with the ARDs decreasing down to 6.5, 4.8, 6.5, and 4.5% for the DESs (1:2, 1:3, 1:4, and 1:5), respectively, and the corrected COSMO-RS with the universal parameters can be used to predict the CO2 solubility in DESs with different mole ratios, for example, for the DES (1:6), the corrected COSMO-RS significantly improves the prediction with an ARD of 10.3% that is much lower than 78.2% provided by the original COSMO-RS. Additionally, the result from COSMO-RS shows that the σ-profiles can reflect the strength of molecular interactions between an HBA (or HBD) and CO2, determining the CO2 solubility, and the dominant interactions for CO2 capture in DESs are the H-bond and Van der Waals force, followed by the misfit based on the analysis of the predicted excess enthalpies.

| S-EPMC7031488 | biostudies-literature

Application of a computational model of natural deep eutectic solvents utilizing the COSMO-RS approach for screening of solvents with high solubility of rutin.

Project description:The screening of natural deep eutectic solvents (NADES) to identify those with the ability to strongly solvate rutin was conducted using the COSMO-RS methodology. A NADES model was constructed that took into account the possible ionic and neutral forms of its constituents. The distributions of all forms were computed based on the equilibrium constants of neutralization reactions between amino and carboxylic acids. The proposed model was validated against the experimental solubilities of 15 NADES. A linear relationship between these data and the estimated activity coefficient values was found. The screening encompassed 126 different NADES. It was found that ten of them outperformed the best reference system. The most effective two-component solvent comprised proline combined with 2,3-diaminosuccinic acid, and the solubility of rutin in this solvent was found to be 130% greater than its solubility in the best reference system. The amino acids associated with the highest rutin solubilities were all cyclic, and the use of carboxylic acids with two carboxyl groups and a main chain consisting of two methylene groups with two amino substituents was observed to yield the best rutin solubilities. Because of the acidic properties of rutin, the presence of basic sites on the components of the NADES generally leads to enhanced solubility.

| S-EPMC6021465 | biostudies-other

Application of COSMO-RS-DARE as a Tool for Testing Consistency of Solubility Data: Case of Coumarin in Neat Alcohols.

Project description:Coumarin is a naturally occurring lactone-type benzopyrone with various applications in the pharmaceutical, food, perfume, and cosmetics industries. This hydrophobic compound is poorly soluble in water but dissolves well in protic organic solvents such as alcohols. Despite the extensive use of coumarin, there are only a few reports documenting its solubility in organic solvents, and some reported data are incongruent, which was the direct impulse for this study. To resolve this problem, a theoretical congruency test was formulated using COSMO-RS-DARE for the determination of intermolecular interaction parameters, which allowed for the identification of outliers as suspicious datasets. The perfect match between back-computed values of coumarin solubility and the experimental ones confirms the reliability of the formulated theoretical approach and its adequacy for testing solubility data consistency. As the final approval, the temperature-related coumarin solubility in seven neat alcohols was determined experimentally. Four solvents (methanol, ethanol, 1-propanol, and 2-propanol) were used for reproducibility purposes, and an additional three (1-butanol, 1-pentanol, and 1-octanol) were used to extend the information on the homologous series. The consistency of this extended solubility dataset is discussed in terms of the comparison of remeasured solubility values with the ones already published and within the series of structurally similar solvents. The proposed procedure extends the range of applicability of COSMO-RS-DARE and provides a real and useful tool for consistency tests of already published solubility data, allowing for the approval/disapproval of existing data and filling gaps in datasets. Linear regressions utilizing a 2D molecular descriptor, SpMin2_Bhm, or the distance between solute and solvent in the Hansen solubility space, Ra, were formulated for the estimation of COMSO-RS-DARE integration parameters.

| S-EPMC9413568 | biostudies-literature

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

Project description: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.

| S-EPMC7197082 | biostudies-literature

Evolution of microscopic heterogeneity and dynamics in choline chloride-based deep eutectic solvents.

Project description:Deep eutectic solvents (DESs) are an emerging class of non-aqueous solvents that are potentially scalable, easy to prepare and functionalize for many applications ranging from biomass processing to energy storage technologies. Predictive understanding of the fundamental correlations between local structure and macroscopic properties is needed to exploit the large design space and tunability of DESs for specific applications. Here, we employ a range of computational and experimental techniques that span length-scales from molecular to macroscopic and timescales from picoseconds to seconds to study the evolution of structure and dynamics in model DESs, namely Glyceline and Ethaline, starting from the parent compounds. We show that systematic addition of choline chloride leads to microscopic heterogeneities that alter the primary structural relaxation in glycerol and ethylene glycol and result in new dynamic modes that are strongly correlated to the macroscopic properties of the DES formed.

| S-EPMC8752670 | biostudies-literature

Choline chloride-based deep eutectic solvents as effective electrolytes for dye-sensitized solar cells.

Project description:Electrolytes for dye-sensitized solar cells remain a challenge for large-scale production and commercialization, hindering the wide application of solar cells. We have developed two new electrolyte-based deep eutectic solvents using a mixture of choline chloride with urea and with ethylene glycol for dye-sensitized solar cells. The prominent features of the two deep eutectic solvent electrolytes are simple preparation for large-scale production with inexpensive, available, and nontoxic starting materials and biodegradability. The solar cell devices proceeded in a safe manner as the two deep eutectic solvents afforded low-cost technology and comparative conversion efficiency to a popular ionic liquid, namely 1-ethyl-3-methylimidazolium tetracyanoborate. Results showed that devices with choline chloride and urea electrolyte exhibited improved open circuit voltage values (V OC), while the ones with choline chloride and ethylene glycol showed an increase in the short circuit current (I sc). Characterization of the devices by electrochemical impedance spectroscopy helped explain the effects of their molecular structures on the enhancement of either V OC or I sc values. These new solvents expand the electrolyte choices for designing dye-sensitized solar cells, especially for the purpose of using low-cost and eco-friendly materials for massive production.

| S-EPMC9034084 | biostudies-literature

Natural Deep Eutectic Solvents Based on Choline Chloride and Phenolic Compounds as Efficient Bioadhesives and Corrosion Protectors.

Project description:Natural deep eutectics solvents (NADES), owing to their high solvation capacity and nontoxicity, are actively being sought for many technological applications. Herein, we report a series of novel NADES based on choline chloride and plant-derived polyphenols. Most of the obtained phenolic NADES have a wide liquid range and high thermal stability above 150 °C. Among them, small-sized polyphenols, like pyrogallol, vanillyl alcohol, or gentisic acid, lead to low-viscosity liquids with ionic conductivities in the order of 10-3 S cm-1 at room temperature. Interestingly, polyphenols possess valuable properties as therapeutic agents, antioxidants, adhesives, or redox-active compounds, among others. Thus, we evaluated the potential of these novel NADES for two applications: bioadhesives and corrosion protection. The mixture of choline chloride-vanillyl alcohol (2:3 mol ratio) and gelatin resulted in a highly adhesive viscoelastic liquid (adhesive stress ≈ 135 kPa), affording shear thinning behavior. Furthermore, choline chloride-tannic acid (20:1) showed an extraordinary ability to coordinate iron ions, reaching excellent corrosion inhibitive efficiencies in mild steel protection.

| S-EPMC9241144 | biostudies-literature

A Comprehensive Study of CO2 Absorption and Desorption by Choline-Chloride/Levulinic-Acid-Based Deep Eutectic Solvents.

Project description:Amine absorption (or amine scrubbing) is currently the most established method for CO2 capture; however, it has environmental shortcomings and is energy-intensive. Deep eutectic solvents (DESs) are an interesting alternative to conventional amines. Due to their biodegradability, lower toxicity and lower prices, DESs are considered to be "more benign" absorbents for CO2 capture than ionic liquids. In this work, the CO2 absorption capacity of choline-chloride/levulinic-acid-based (ChCl:LvAc) DESs was measured at different temperatures, pressures and stirring speeds using a vapour-liquid equilibrium rig. DES regeneration was performed using a heat treatment method. The DES compositions studied had ChCl:LvAc molar ratios of 1:2 and 1:3 and water contents of 0, 2.5 and 5 mol%. The experimental results showed that the CO2 absorption capacity of the ChCl:LvAc DESs is strongly affected by the operating pressure and stirring speed, moderately affected by the temperature and minimally affected by the hydrogen bond acceptor (HBA):hydrogen bond donator (HBD) molar ratio as well as water content. Thermodynamic properties for CO2 absorption were calculated from the experimental data. The regeneration of the DESs was performed at different temperatures, with the optimal regeneration temperature estimated to be 80 °C. The DESs exhibited good recyclability and moderate CO2/N2 selectivity.

| S-EPMC8465201 | biostudies-literature

Switchable product selectivity in dehydration of <i>N</i>-acetyl-d-glucosamine promoted by choline chloride-based deep eutectic solvents.

Project description:Herein, we report choline chloride-based deep eutectic solvents (DESs) promoted conversion of N-acetyl-d-glucosamine (GlcNAc) into nitrogen-containing compounds, i.e., 3-acetamido-5-(1',2'-dihydroxyethyl) furan (Chromogen III) and 3-acetamido-5-acetylfuran (3A5AF). The binary deep eutectic solvent choline chloride-glycerin (ChCl-Gly), was found to promote the dehydration of GlcNAc to form Chromogen III, which reaches a maximum yield of 31.1%. On the other hand, the ternary deep eutectic solvent, choline chloride-glycerol-B(OH)3 (ChCl-Gly-B(OH)3), promoted the further dehydration of GlcNAc into 3A5AF with a maximum yield of 39.2%. In addition, the reaction intermediate, 2-acetamido-2,3-dideoxy-d-erythro-hex-2-enofuranose (Chromogen I), was detected by in situ nuclear magnetic resonance (NMR) techniques when promoted by ChCl-Gly-B(OH)3. The experimental results of the 1H NMR chemical shift titration showed ChCl-Gly interactions with α-OH-3 and α-OH-4 of GlcNAc, which is responsible for promoting the dehydration reaction. Meanwhile, the strong interaction between Cl- and GlcNAc was demonstrated by 35Cl NMR.

| S-EPMC10276235 | biostudies-literature

Carbon Dioxide Solubility in Nonionic Deep Eutectic Solvents Containing Phenolic Alcohols.

Project description:Deep eutectic solvents (DES) are a new class of green solvents that have shown unique properties in several process applications. This study evaluates nonionic DES containing phenolic alcohols as solvents for carbon dioxide (CO2) capture applications. Potential phenolic alcohols and the molar ratio between DES constituents were preselected for experimental investigations based on the conductor-like screening model for realistic solvation (COSMO-RS). CO2 solubility was experimentally determined in two different DES, namely, L-menthol/thymol in 1:2 molar ratio and thymol/2,6-xylenol in 1:1 molar ratio, at various temperatures and pressures. CO2 solubility in the studied systems was higher than that reported in the literature for ionic DES and ionic liquids. This study demonstrates that nonionic DES containing phenolic alcohols can be excellent, inexpensive, and simple solvents for CO2 capture.

| S-EPMC8980276 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data