-
Organic Letters Jul 2020Hexafluoroisopropanol (HFIP)-promoted disulfidation and diselenation of C-C unsaturated bonds is reported. Reactions of unactivated alkyne, alkene, and allene,...
Hexafluoroisopropanol (HFIP)-promoted disulfidation and diselenation of C-C unsaturated bonds is reported. Reactions of unactivated alkyne, alkene, and allene, respectively, with disulfides or diselenides in HFIP led to desired products in good to excellent yields (up to 96%). In contrast, other solvents, such as isopropanol and dichloroethane, could not promote the same reaction. This method revealed an example of HFIP-promoted transformations under the mild conditions, which greatly highlighted the unique reactivity of this special solvent.
Topics: Alkenes; Alkynes; Catalysis; Organoselenium Compounds; Propanols; Solvents; Sulfides
PubMed: 32588633
DOI: 10.1021/acs.orglett.0c01834 -
International Journal of Molecular... Jun 2023Vapor pressures and other thermodynamic properties of liquids, such as density and enthalpy of mixtures, are the key parameters in chemical engineering for designing new...
Vapor pressures and other thermodynamic properties of liquids, such as density and enthalpy of mixtures, are the key parameters in chemical engineering for designing new process units, and are also essential for understanding the physical chemistry, macroscopic and molecular behavior of fluid systems. In this work, vapor pressures between 278.15 and 323.15 K, densities and enthalpies of mixtures between 288.15 and 318.15 K for the binary mixture (2-propanol + 1,8-cineole) have been measured. From the vapor pressure data, activity coefficients and excess Gibbs energies were calculated via the Barker's method and the Wilson equation. Excess molar volumes and excess molar enthalpies were also obtained from the density and calorimetric measurements. Thermodynamic consistency test between excess molar Gibbs energies and excess molar enthalpies has been carried out using the Gibbs-Helmholtz equation. Robinson-Mathias, and Peng-Robinson-Stryjek-Vera together with volume translation of Peneloux equations of state (EoS) are considered, as well as the statistical associating fluid theory that offers a molecular vision quite suitable for systems having highly non-spherical or associated molecules. Of these three models, the first two fit the experimental vapor pressure results quite adequately; in contrast, only the last one approaches the volumetric behavior of the system. A brief comparison of the thermodynamic excess molar functions for binary mixtures of short-chain alcohol + 1,8-cineole (cyclic ether), or +di-n-propylether (lineal ether) is also included.
Topics: Eucalyptol; 2-Propanol; 1-Propanol; Thermodynamics; Gases; Propanols
PubMed: 37373528
DOI: 10.3390/ijms241210380 -
Biotechnology Letters Feb 2024Glucuronoyl esterases (GE, family CE15) catalyse the cleavage of ester linkages in lignin-carbohydrate complexes (LCCs), and this study demonstrate how...
PURPOSE
Glucuronoyl esterases (GE, family CE15) catalyse the cleavage of ester linkages in lignin-carbohydrate complexes (LCCs), and this study demonstrate how transesterification reactions with a fungal GE from Cerrena unicolor (CuGE) can reveal the enzyme's preference for the alcohol-part of the ester-bond.
METHODS
This alcohol-preference relates to where the ester-LCCs are located on the lignin molecule, and has consequences for how the enzymes potentially interact with lignin. It is unknown exactly what the enzymes prefer; either the α-benzyl or the γ-benzyl position. By providing the enzyme with a donor substrate (the methyl ester of either glucuronate or 4-O-methyl-glucuronate) and either one of two acceptor molecules (benzyl alcohol or 3-phenyl-1-propanol) we demonstrate that the enzyme can perform transesterification and it serves as a method for assessing the enzyme's alcohol preferences.
CONCLUSION
CuGE preferentially forms the γ-ester from the methyl ester of 4-O-methyl-glucuronate and 3-phenyl-1-propanol and the enzyme's substrate preferences are primarily dictated by the presence of the 4-O-methylation on the glucuronoyl donor, and secondly on the type of alcohol.
Topics: Esterases; Lignin; Carbohydrates; Esters; Glucuronates; Substrate Specificity; Propanols; Polyporales
PubMed: 38150097
DOI: 10.1007/s10529-023-03456-x -
Environmental Science and Pollution... Oct 2022In this work, new CO solubility data on three types of aqueous amine blends were reported to complement existing databases. The experiments were conducted at...
Experimental investigations and the modeling approach for CO solubility in aqueous blended amine systems of monoethanolamine, 2-amino-2-methyl-1-propanol, and 2-(butylamino)ethanol.
In this work, new CO solubility data on three types of aqueous amine blends were reported to complement existing databases. The experiments were conducted at temperatures of 313 K (absorption condition) and 363 K (desorption condition). The effect of the MEA concentration on the CO solubility in several amine blends at low CO partial pressure (8 to 50.65 kPa) were studied in this work, including 0.1, 0.3, 0.5 mol/L MEA + 2 mol/L AMP; 0.1, 0.3, 0.5 mol/L MEA + 2 mol/L BEA; and 0.1, 0.3, 0.5 mol/L MEA + 1, 2 mol/L AMP + 1, 2 mol/L BEA. Besides, an additional group of equilibrium CO solubility data were conducted at 298 K in order to estimate the heat of CO absorption of the blended solvents at a temperature range from 298 to 313 K. A new simplified Kent-Eisenberg model was developed for the predictions of blended solvents, and a multilayer neural network model with Levenberg-Marquardt backpropagation algorithm was developed upon five hundred reliable published experimental data. The predictions from two methods are both in good agreement with the experimental CO solubility data.
Topics: Adenosine Monophosphate; Amines; Carbon Dioxide; Ethanol; Ethanolamine; Propanolamines; Solubility; Solvents; Water
PubMed: 35567679
DOI: 10.1007/s11356-022-20411-x -
Regulatory Toxicology and Pharmacology... Feb 2020The metabolic series approach has successfully linked internal dosimetries of metabolically related compounds reducing cost and time for chemical risk assessments. Here,...
The metabolic series approach has successfully linked internal dosimetries of metabolically related compounds reducing cost and time for chemical risk assessments. Here, we developed a physiologically based pharmacokinetic (PBPK) model in rats and humans for the propyl metabolic series including propyl acetate, 1-propanol, propionaldehyde, and propionic acid. Manufacturers use these compounds as organic solvents and intermediates during chemical synthesis. Public exposures can occur through using consumer products containing propyl compounds like cosmetics, aerosol sprays, or foods, and occupational exposures can occur at manufacturing facilities. To develop the PBPK model, we measured in vitro metabolism of propyl acetate in blood and liver S9 fractions. We measured concentrations of propyl compounds in blood following intravenous (iv) infusion of C-propanol or C-propionic acid and closed chamber inhalation exposures to propyl acetate or propanol in rats. Using these studies and other published data, we modified an existing PBPK model for the butyl metabolic series to simulate time course concentrations of propyl compounds in rats and humans. Consistent with measured in vitro and in vivo data, the optimized propyl series model predicts rapid clearance of propyl acetate, higher concentrations of propanol in blood from propyl acetate inhalation compared to propanol inhalation in rats but not in humans, and low concentrations of propionic acid in blood from exposures to propyl acetate or propanol. Regulators can use this model as a tool for propyl compound risk assessment by linking internal dosimetries under various exposure scenarios.
Topics: 1-Propanol; Acetates; Administration, Inhalation; Aldehydes; Animals; Female; Humans; Infusions, Intravenous; Inhalation Exposure; Liver; Male; Models, Biological; Propionates; Rats, Sprague-Dawley; Risk Assessment
PubMed: 31669189
DOI: 10.1016/j.yrtph.2019.104507 -
Faraday Discussions 2015Over 2100 induction time experiments were carried out for the medium-sized, antipsychotic drug molecule, risperidone in seven different organic solvents. To reach the...
Over 2100 induction time experiments were carried out for the medium-sized, antipsychotic drug molecule, risperidone in seven different organic solvents. To reach the same induction time the required driving force increases in the order: cumene, toluene, acetone, ethyl acetate, methanol, propanol, and butanol, which reasonably well correlates to the interfacial energies as determined within classical nucleation theory. FTIR spectroscopy has been used to investigate any shifts in the spectra and to estimate the interaction of solute and solvent at the corresponding site. The solution condition has also been investigated by Density Functional Theory (DFT) calculations over (1 : 1) solvent-solute binding interactions at 8 different sites on the risperidone molecule. The DFT computational results agree with the spectroscopic data suggesting that these methods do capture the binding strength of solvent molecules to the risperidone molecule. The difficulty of nucleation correlates reasonably to the DFT computations and the spectroscopic measurements. The results of the different measurements suggest that the stronger the solvent binds to the risperidone molecule in solution, the slower the nucleation becomes.
Topics: 1-Propanol; Acetates; Acetone; Benzene Derivatives; Butanols; Crystallization; Methanol; Quantum Theory; Risperidone; Solvents; Toluene
PubMed: 25886651
DOI: 10.1039/c4fd00223g -
Contact Dermatitis Jan 2020Recent studies provide evidence for significant and previously underestimated barrier damaging effects of repeated exposure to 60% n-propanol in healthy skin in vivo.
BACKGROUND
Recent studies provide evidence for significant and previously underestimated barrier damaging effects of repeated exposure to 60% n-propanol in healthy skin in vivo.
OBJECTIVES
To investigate further the cumulative effects of a range of n-propanol concentrations relevant at the workplace in healthy and atopic dermatitis (AD) individuals, and study the modulation of the outcomes by co-exposure and host-related factors.
METHODS
Healthy adult and AD volunteers were exposed to n-propanol concentrations from 30% to 75% in occlusion-modified tandem repeated irritation test with measurements of erythema, transepidermal water loss, capacitance, and the natural moisturizing factor (NMF) levels at baseline and after 96 hours.
RESULTS
n-Propanol exerted significant barrier damaging effects even at the lowest concentration in both groups. Exposure to all n-propanol concentrations significantly reduced the NMF levels. Preceding low-grade trauma by occlusion/water exposure reduced the skin irritation threshold in both groups. The differences in the severity of the barrier function impairment after exposure to the same concentrations under the same conditions between the AD and control groups were significant.
CONCLUSIONS
The negative effects of cumulative exposure to n-propanol in healthy and atopic skin shown in the study suggest the need for critical re-evaluation of its irritant properties in vivo.
Topics: 1-Propanol; Adult; Case-Control Studies; Dermatitis, Atopic; Dermatitis, Irritant; Dermatitis, Occupational; Female; Hand Sanitizers; Humans; Male; Occupational Exposure; Risk Factors; Skin Tests; Water Loss, Insensible
PubMed: 31373027
DOI: 10.1111/cod.13368 -
Journal of Dairy Science Dec 2014The objective of this work was to evaluate the effects of biological and chemical silage additives on the production of volatile organic compounds (VOC; methanol,...
The objective of this work was to evaluate the effects of biological and chemical silage additives on the production of volatile organic compounds (VOC; methanol, ethanol, 1-propanol, methyl acetate, and ethyl acetate) within corn silage. Recent work has shown that silage VOC can contribute to poor air quality and reduce feed intake. Silage additives may reduce VOC production in silage by inhibiting the activity of bacteria or yeasts that produce them. We produced corn silage in 18.9-L bucket silos using the following treatments: (1) control (distilled water); (2) Lactobacillus buchneri 40788, with 400,000 cfu/g of wet forage; (3) Lactobacillus plantarum MTD1, with 100,000 cfu/g; (4) a commercial buffered propionic acid-based preservative (68% propionic acid, containing ammonium and sodium propionate and acetic, benzoic, and sorbic acids) at a concentration of 1 g/kg of wet forage (0.1%); (5) a low dose of potassium sorbate at a concentration of 91 mg/kg of wet forage (0.0091%); (6) a high dose of potassium sorbate at a concentration of 1g/kg of wet forage (0.1%); and (7) a mixture of L. plantarum MTD1 (100,000 cfu/g) and a low dose of potassium sorbate (91 mg/kg). Volatile organic compound concentrations within silage were measured after ensiling and sample storage using a headspace gas chromatography method. The high dose of potassium sorbate was the only treatment that inhibited the production of multiple VOC. Compared with the control response, it reduced ethanol by 58%, ethyl acetate by 46%, and methyl acetate by 24%, but did not clearly affect production of methanol or 1-propanol. The effect of this additive on ethanol production was consistent with results from a small number of earlier studies. A low dose of this additive does not appear to be effective. Although it did reduce methanol production by 24%, it increased ethanol production by more than 2-fold and did not reduce the ethyl acetate concentration. All other treatments increased ethanol production at least 2-fold relative to the control, and L. buchneri addition also increased the 1-propanol concentration to approximately 1% of dry matter. No effects of any treatments on fiber fractions or protein were observed. However, L. buchneri addition resulted in slightly more ammonia compared with the control. If these results hold under different conditions, a high dose of potassium sorbate will be an effective treatment for reducing VOC production in and emission from silage. Regulations aimed at reducing VOC emission could be ineffective or even increase emission if they promote silage additives without recognition of different types of additives.
Topics: 1-Propanol; Animal Feed; Animals; Bacteria; Dietary Fiber; Esters; Ethanol; Lactobacillus; Silage; Sorbic Acid; Volatile Organic Compounds; Yeasts; Zea mays
PubMed: 25282409
DOI: 10.3168/jds.2014-8537 -
Journal of Proteome Research Jan 2019We have developed a streamlined proteomic sample preparation protocol termed Accelerated Barocycler Lysis and Extraction (ABLE) that substantially reduces the time and...
We have developed a streamlined proteomic sample preparation protocol termed Accelerated Barocycler Lysis and Extraction (ABLE) that substantially reduces the time and cost of tissue sample processing. ABLE is based on pressure cycling technology (PCT) for rapid tissue solubilization and reliable, controlled proteolytic digestion. Here, a previously reported PCT based protocol was optimized using 1-4 mg biopsy punches from rat kidney. The tissue denaturant urea was substituted with a combination of sodium deoxycholate (SDC) and N-propanol. ABLE produced comparable numbers of protein identifications in half the sample preparation time, being ready for MS injection in 3 h compared with 6 h for the conventional urea based method. To validate ABLE, it was applied to a diverse range of rat tissues (kidney, lung, muscle, brain, testis), human HEK 293 cell lines, and human ovarian cancer samples, followed by SWATH-mass spectrometry (SWATH-MS). There were similar numbers of quantified proteins between ABLE-SWATH and the conventional method, with greater than 70% overlap for all sample types, except muscle (58%). The ABLE protocol offers a standardized, high-throughput, efficient, and reproducible proteomic preparation method that when coupled with SWATH-MS has the potential to accelerate proteomics analysis to achieve a clinically relevant turn-around time.
Topics: 1-Propanol; Animals; Biopsy; Cell Line, Transformed; Deoxycholic Acid; HEK293 Cells; Humans; Mass Spectrometry; Proteolysis; Proteomics; Rats; Specimen Handling
PubMed: 30444966
DOI: 10.1021/acs.jproteome.8b00684 -
Chemical Biology & Drug Design Nov 2017We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective...
We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective antileishmanial activity against stationary promastigote forms of Leishmania amazonensis (IC < 15.0 μm), and an influence of compound lipophilicity on activity was suggested. Most of the compounds were poorly selective, as they showed toxicity toward murine macrophages, except 17 and 18, which presented good selective indexes (SI ≥ 10.0). The five more active compounds (2, 3, 13, 17, and 18) were selected for the treatment of infected macrophages, and all of them were able to reduce the number of internalized parasites by more than 80%, as well as the number of infected macrophages by more than 70% in at least one of the tested concentrations. Altogether, these results demonstrate the potential of these compounds as new hits of antileishmanial agents and open future possibilities for them to be tested in in vivo studies.
Topics: Animals; Female; Humans; Inhibitory Concentration 50; Leishmania mexicana; Leishmaniasis, Cutaneous; Macrophages; Mice, Inbred BALB C; Propanols; Trypanocidal Agents
PubMed: 28590516
DOI: 10.1111/cbdd.13024