Acetic Acid Esters Research Articles

Modulating the behavior of ethyl cellulose-based oleogels: The impact food-grade amphiphilic small molecules on structural, mechanical, and rheological properties

This work evaluates the ability of various lipid-based amphiphilic small molecules (ASMs) to modulate the mechanical and rheological properties of oleogels principally structured by ethyl cellulose (EC). Six ASMs varying in the chemical structure of their polar headgroups were used to produce EC-ASM oleogels. Stearic acid (StAc), monoacylglycerol (MAG), sodium stearoyl lactylate (SSL), and citric acid esters of monoglycerides (CITREM) all provided a dramatic enhancement in gel strength, while lactic acid (LACTEM) and acetic acid (ACETEM) esters produced only a marginal increase. Those additives which crystallized above 20 °C displayed pronounced changes in their network organization and crystal morphology in the presence of EC. Differences in the solid/liquid phase change behavior were also observed in select samples using differential scanning calorimetry. Both the small and large amplitude oscillatory shear responses were dependent on the ASM which was dependent on the chemistry of the headgroup, crystal network organization, and ability to plasticize the polymer network. The extent of thixotropic recovery was largely dependent on the polarity of functional groups in the ASMs, but was also influenced by the formation of a secondary crystal network. In general, ASMs which formed larger, system-spanning crystal networks (MAG, StAc) produced more brittle gels, while the highly hydrophilic, charged headgroup of SSL promoted a homogeneous distribution of small crystals, resulting in a tougher material. In the absence of a crystal network, stronger polar species in the ASM headgroup produced higher gel strength and increased elasticity. Thus, both ASM chemical structure and crystallization properties strongly contribute to the functionality of the resulting combined oleogelator systems.

Mechanistic studies on an isothiourea-catalyzed reaction of an aromatic ester with an imine

Increasing attention is being paid to divergent chemical reactions as a strategy for synthesizing complex organic molecules simply by regulating and adjusting reaction conditions. However, the factors controlling this switchable transformation remain unclear. A systematic study was conducted using density functional theory (DFT) at the M06–2X level to determine the mechanism of an isothiourea-catalyzed divergent chemical reaction of an aryl acetic acid ester with an imine in different solvents (acetonitrile and ethanol). The origins of the stereoselectivity and chemoselectivity of the reaction were determined using noncovalent interaction (NCI) and electrostatic potential surface (EPS) analyses. Lactamization reaction occurs preferentially in acetonitrile, and esterification proceeds preferentially in ethanol. The reaction of an ammonium enolate intermediate with an alkynyl imine preferentially generates the SS-configured isomer. The results of this theoretical study provide insight into the general mechanism of isothiourea-catalyzed reactions in which the key intermediate is ammonium enolate.

A Prodrug Strategy to Reposition Atovaquone as a Long-Acting Injectable for Malaria Chemoprotection.

Recent malaria drug discovery approaches have been extensively focused on the development of oral, smallmolecule inhibitors for disease treatment whereas parenteral routes of administration have been avoided due to limitations in deploying a shelf-stable injectable even though it could be dosed less frequently. However, an updated target candidate profile from Medicines for Malaria Venture (MMV) and stakeholders have advocated for long-acting injectable chemopreventive agents as an important interventive tool to improve malaria prevention. Here, we present strategies for the development of a long-acting, intramuscular, injectable atovaquone prophylactic therapy. We have generated three prodrug approaches that are contrasted by their differential physiochemical properties and pharmacokinetic profiles: mCBK068, a docosahexaenoic acid ester of atovaquone formulated in sesame oil, mCKX352, a heptanoic acid ester of atovaquone formulated as a solution in sesame oil, and mCBE161, an acetic acid ester of atovaquone formulated as an aqueous suspension. As a result, from a single 20 mg/kg intramuscular injection, mCKX352 and mCBE161 maintain blood plasma exposure of atovaquone above the minimal efficacious concentration for >70 days and >30 days, respectively, in cynomolgus monkeys. The differences in plasma exposure are reflective of the prodrug strategy, which imparts altered chemical properties that ultimately influence aqueous solubility and depot release kinetics. On the strength of the pharmacokinetic and safety profiles, mCBE161 is being advanced as a first-in-class clinical candidate for first-in-human trials.

Expanding Complex Morpholines Using Systematic Chemical Diversity.

The morpholine heterocycle is a structural unit found in many bioactive compounds and FDA-approved drugs, but the generation of more complex C-functionalized morpholine derivatives remains considerably underexplored. Using systematic chemical diversity (SCD), a concept that guides the expansion of saturated drug-like scaffolds through regiochemical and stereochemical variation, we describe the synthesis of a collection of methyl-substituted morpholine acetic acid esters starting from enantiomerically pure amino acids and amino alcohols. In total, 24 diverse substituted morpholines were produced that vary systematically in regiochemistry and stereochemistry (relative and absolute). These diverse C-substituted morpholines can be directly applied in fragment screening or incorporated as building blocks in medicinal chemistry and library synthesis.

Microbial community dynamics and spatial distribution of flavor compound metabolism during solid-state fermentation of Baijiu enhanced by Wickerhamomyces anomalus

Biofortification of Baijiu fermentation process using exogenous functional strains can change the microbial community structure in the fermentation system, which in turn affects the flavor of Baijiu. In this study, we used a simulated solid-state fermentation of Baijiu to investigate the effects of the addition of Wickerhamomyces anomalus strain YM001 on the improvement of Baijiu flavor compounds and its mechanism. The results of microbial diversity analysis showed that Wickerhamomyces and Lactiplantibacillus were the dominant genera in the biofortified fermentation system. In addition, W. anomalus YM001 drove the change of bacteria with moisture and alcohol content, which will synthesise esters using ethanol and moisturet as substrates. The addition of W. anomalus YM001 increased the content of total esters in fermentation samples, especially ethyl acetate, and other compounds such as acetic acid and phenylethyl ester to some extent. W. anomalus YM001 altered the correlation between microorganisms and flavor compounds, with Latilactobacillus and Pediococcus showing a significant positive correlation with ethyl acetate and Weissella showing a significant negative correlation with ethyl caproate and ethanol. In addition, the metabolic properties of ethyl acetate, ethyl decanoate and phenethyl acetate were also altered. In summary, biofortification with W. anomalus YM001 altered the microbial community composition and the physicochemical properties of the fermented grains in the Baijiu brewing system, while elevating the contents of ethyl acetate, ethyl decanoate and phenyl acetate. These findings suggest that biofortification during Baijiu brewing improves Baijiu flavor and contributes to the overall quality of Baijiu.

SYNTHESIS AND RESEARCH OF NEW DERIVATIVES OF ALKYLXANTHATATE ACETIC ACID AS ADDITIVES WITH TRIBOLOGICAL PROPERTIES

The work is devoted to the synthesis and study of new derivatives of alkylxanthateacetic acid, obtained by the interaction of potassium alkylxanthates with allyl ester of monochloroacetic acid. The structure of the synthesized compounds was confirmed by IR and 1H NMR spectroscopy data, as well as by the study of their physicochemical properties, including the determination of the refractive indices and specific gravity and the calculation of molecular refraction based on them, followed by their comparison. It has been established that the synthesized compounds have high extreme pressure properties in transmission oils, while esters of alkylxanthate acetic acid have anticorrosion properties, so they can be used to make prototypes of transmission oils used in various friction units. Using the example of allyl ester of ethylxsanthateacetic acid, the dependence of the yields of the synthesized compounds on the nature of the solvent was revealed. The dependence of the effectiveness of the lubricating properties of the synthesized compounds on the length of alkyl radicals has been revealed

Facile synthesis and cytotoxicity of substituted uracil-1'(N)-acetic acid and 4-pyridone-1'(N)-acetic acid esters of 20(S)-camptothecins

A series of novel substituted uracil-1'(N)-acetic acid esters (5–9) and 4-pyridone-1'(N)-acetic acid esters (10–11) of 20(S)-camptothecins (CPTs) have been synthesized by the acylation method. All of these new esters were assayed for in vitro cytotoxicity against five human cancer cell lines A549, Bel7402, BGC-823, HCT-8 and A2780. The in vitro bioassay results showed that all the synthesized compounds 5–11 had cytotoxities that were higher than TPT and comparable to CPT on these five tumor cell lines, some of them even showed comparable or superior cytotoxic activity to CPT. The in vitro data exhibited the cytotoxicity of the ester depended on that of its parent compound. The ester 5, 6, 8, 10, 11 even possessed the cytotoxity activity comparable to or even a little better than CPT on A549, HCT-8 and A2780. The compound 11 had the same level of cytoxity on Bel7402 as that of CPT. Here the synthesis and the in vitro antitumor evaluation of a series of novel 20-O-linked substituted uracil-1'(N)-acetic acid and 4-pyridone-1'(N)-acetic acid esters derivatives of CPTs are reported.

Synthesis and characterization of 3,4-dihydroxyphenyl acetic acid esters and study of their efficacy in bulk fish oil

Lipophilization of natural antioxidants is a proven strategy to enhance the solubility in bulk oil systems, thereby increasing their efficacy against oxidative degradation. This study aims to synthesize esters of 3,4-dihydroxyphenylacetic acid (3,4-DHPA) using Amberlyst-15 and to study the application of these esters in refined fish oil. Lipophilic esters were synthesized by esterification and transesterification of 3,4-DHPA in various solvent systems. Esters of methanol, butanol and hexanol were obtained with percent conversion of 81.1, 69.3 and 78.8 respectively, and were subjected to molecular characterization and in vitro oxidant assays. The 3,4-DHPA and its methyl ester showed 36% reduction in the TOTOX value over 30 days of storage. The length of the acyl chain in the ester was found to exert a high influence on its efficacy and lipophilicity. This is the first report of 3,4-DHPA and its lipophilic esters studied for enhancing the oxidative stability of fish oil.

ANALYSIS OF DISSOLVING ABILITY OF LOWER ALCOHOLS AND ESTERS AQUEOUS AND HYDROCARBON SOLUTIONS TO ORGANIC MATTER OF BAZHENOV FORMATION ROCKS

This work is devoted to studying the characteristics of treatments with organic solvents on bazhenov formation rock samples, which contains a large amount of unconverted organic matter (kerogen, bitumen). This article contains the results of studying the dissolving abilities of individual low-molecular alcohols and esters, and solutions of these compounds in water and in a non-polar aromatic solvent (petroleum solvent). Among the individual solvents studied, esters of acetic acid showed the greatest dissolving ability; alcohols are less active. Petroleum solvent slightly dissolves the rock’s organic matter and needs the addition of more polar organic compounds. The dependences of dissolving ability of alcohols’ hydrocarbon solutions on alcohol concentration is extreme, with a maximum of 10 wt.%. Based on the obtained results, the mutual influence of solvents in the hydrocarbon fluid was additionally evaluated. It has been established that solutions of isopropanol and aromatic solvent show a synergistic effect to the dissolution of rock organic matter more than hydrocarbon solutions of esters. For the compositions that showed the greatest dissolving ability, a qualitative and semi-quantitative analysis was made for establishing changes in the composition of rock samples after extraction using X-Ray diffraction and Fourier-transform infrared spectroscopy. It is shown that mixtures of polar and non-polar solvents provide a more regular extraction of aliphatic and aromatic components of rock organic matter. Systems containing petroleum solvent, isopropanol and isopropyl acetate have been identified as the basis for the development of process fluids for increasing oil recovery in organic-rich reservoirs.

Synthesis and quantification of short-chain fatty acid esters of hydroxy fatty acids in rat intestinal contents and fecal samples by LC-MS/MS

Short-chain fatty acid esters of hydroxy fatty acids (SFAHFAs) are a new class of endogenous lipids belonging to the fatty acid esters of the hydroxy fatty acid family. We previously uncovered their chemical structure and discussed their potential biological significance. We anticipate an increased need for SFAHFA measurements as markers of metabolic and inflammatory health. In this study, we synthesized sixty isomeric SFAHFAs by combining 12 hydroxy fatty acids (C16–C24) and five short-chain fatty acids (C2–C6) including a labelled internal standard. SFAHFA enrichment was achieved by solid-phase extraction and established a sensitive method for their quantitation by targeted LC-MS/MS. The method was applied to profile SFAHFAs in intestinal contents and fecal samples collected from rats fed a high-fat diet (HFD). The results demonstrated a significant decrease in SFAHFAs in the intestinal contents of the HFD group compared with the control group. The fecal time course (0–8 weeks) profile of SFAHFAs showed significant downregulation of acetic and propanoic acid esters in just 2 weeks after HFD administration. This study offers the first synthesis and quantitation method for SFAHFAs, demonstrating their potential use in elucidating SFAHFA sources, their role in various diseases, and potential biochemical signalling pathways.

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines.

A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine.

REACTION KINETICS OF ACETIC ACID WITH ETHANOL TO ETHYL ACETATE WITH SULFURIC ACID CATALYST

Ethyl acetate is an ester of ethanol and acetic acid. This compound is a colorless liquid with a characteristic odor. Ethyl acetate is widely used as a solvent because of its high solubility. The manufacture of ethyl acetate (ethyl ester) is referred to as the esterification process. This esterification reaction is an exothermic reaction, is reversible and generally runs very slowly so it requires a catalyst to obtain maximum ester. Domestic demand for ethyl acetate is increasing, while production in Indonesia is still lacking. Reactor design requires a reaction mechanism and kinetic data in the form of reaction rate equations and reaction rate constants. This study aims to determine the kinetics of the etherification of acetic acid presented in the form of the reaction rate equation, the value of the reaction rate constant, and the reaction equilibrium constant. In addition, this research also studied how the influence of sulfuric acid catalyst on the reaction rate constant and the reaction balance. The esterification reaction was carried out in a batch reactor. 99% acetic acid and H2SO4 catalyst whose concentrations are varied, are mixed in a reactor equipped with a magnetic stirrer which is operated at 400 rpm, then 96% ethanol is poured with a volume ratio of 1:1 to acetic acid, 5 mL of sample is taken to analyze the remaining acid after The reaction takes place, every certain time interval a sample is taken to be analyzed until an equilibrium point is obtained. From the results of this study it can be concluded that the esterification reaction of acetic acid with ethanol to produce ethyl acetate is a second order reaction with the reaction rate equation (-rA) = k1CACB – k2CCCD. By using a reaction temperature of 34oC and a stirring speed of 400 rpm, the best conditions were obtained using a catalyst of 5.3% by volume, with the reaction rate constant to the right (k1) being 0.014 L/(gmol min), the value of the equilibrium constant (K=k1/k2) is 5.51 and the balance conversion is 77%.

When Does Milk Spoil? The Use of Rejection Threshold Methodology to Investigate the Influence of Total Microbial Numbers on the Acceptability of Fresh Chilled Pasteurised Milk

The consumer rejection threshold (RjT) method was applied to determine the total microbial numbers (TMNs) where consumers find that the quality of whole fresh chilled pasteurised milk (WFCPM) and skim milk (Trim) stored at 4.5 ± 0.5 °C is no longer acceptable. Food spoilage progression was supported by measurements of VOCs and the terms consumers used to describe the ageing fresh chilled pasteurised milk (FCPM). RjTs for TMN of 7.43 and 7.34 log10 CFU.mL−1 for WFCPM and Trim, respectively were derived using Hill’s equation from a series of paired preference tests comparing fresh and aged milks (3–26 days) assessed by consumers (WFCPM, n = 55; Trim, n = 52). A poor relationship between storage time and TMN was found, owing mainly to batch-to-batch and within-batch variation in the milk’s post-pasteurization contamination (PPC) levels. At the RjT, there was a significant change in the signal intensities for a number of spoilage-related VOCs that occurred in the FCPM headspace (p ≤ 0.05), which were measured using proton transfer reaction–mass spectrometry (PTR-MS), including m/z 33, 45, 47, 61, 63, 69, 71, 87, and 89, tentatively identified as methanol; acetaldehyde; ethanol; acetate (acetic acid and acetate esters); dimethyl sulphide (DMS); isoprene, furan, and aldehydes; 2-butanone; and pentanal and butyrates (butyric acid and butyrate esters), respectively. Consumers described the milks at TMN greater than the RjTs using terms like off, expired, sour, spoilt or rancid. This multidisciplinary study has provided data on the importance of PPC and subsequent increases in TMN on VOCs associated with FCPM and consumer’s preferences and highlighted the value of measuring a range of variables when investigating consumer’s perception of food quality and shelf-life.

Heterocyclisation of <i>N</i>-(2-cycloalk-1-en-1-yl-6-methylphenyl)-<i>N</i>-(2-hydroxyethyl)-4-methylbenzenesulfonamides to benzoxazocines

The article cover the results of a study on the synthesis of benzoxazocines condensed with cycloalkenes. By reacting the corresponding N -tosyl-2-(1-cycloalken-1-yl)anilines with 2-bromoethyl ester of acetic acid, the products of substitution of bromine for the arylamide group were synthesized. The resulting esters were converted by alkaline hydrolysis into N -(2-cycloalk-1-en-1-yl-6-methylphenyl)- N -(2-hydroxyethyl)-4-(methylbenzene)sulfonamides. The interaction of these amides with molecular bromine gives benzo[ e ]cycloalka[ g ][1,4]oxazocine N -tosylates with predominant a R *, R *-stereochemistry, which in solution slowly turn into a S *, R *-atropisomers reaching a ratio of 2.7:1 in the case of cyclohexenyl and 1.4:1 in the case of cyclopentenyl homologues.

Research on the kinetics and degradation pathways of gaseous acetic acid ester organics

ABSTRACT Designed to meet the specific needs of the printing industry exhaust gas emissions, this paper proposes a method for the degradation of gaseous acetic acid ester organics that is environmentally friendly, safe, and simple to use: micro-nano cavitation technology. In the process of using micro-nano cavitation technology to degrade acetic acid ester organics, the products in the degradation process were analyzed by gas chromatography-mass (GC-MS) spectrometry, and the degradation pathways of acetic acid ester organics were identified. Under high temperatures and high pressure caused by cavitation collapse, the C–C bond and C–O bond on the main chain of organic matter are cleaved to form low molecular products. Low-molecular intermediate products are continuously produced as the reaction advances, and these intermediate products are further oxidized and decomposed into carbon dioxide and water. Besides, the factors that influence the degradation rate of acetic acid ester organics were investigated. Based on the experimental data, acetic acid esters can degrade with the greatest efficiency when their initial concentration is 200 ± 50 mg/m3 and their treatment time is 20∼30 min. Moreover, the experiment was optimized using the response surface method. The results suggested that for an initial concentration of 155.544 mg/m3 and a reaction time of 21.961 min, the best degradation rate was 0.251 min−1. Micro-nano cavitation technology is a novel and promising technology for the degradation of volatile organic compounds, with a wide range of practical applications.

Sorption Properties of PET Copolyesters and New Approach for Foaming with Filament Extrusion Additive Manufacturing

The mass transfer process of binary esters of acetic acid in polyethylene terephthalate (PET), polyethylene terephthalate with a high degree of glycol modification (PETG), and glycol-modified polycyclohexanedimethylene terephthalate (PCTG) was studied. It was found that the desorption rate of the complex ether at the equilibrium point is significantly lower than the sorption rate. The difference between these rates depends on the type of polyester and temperature and allows the accumulation of ester in the volume of the polyester. For example, the stable content of acetic ester in PETG at 20 °C is 5 wt.%. The remaining ester, which has the properties of a physical blowing agent, was used in the filament extrusion additive manufacturing (AM) process. By varying the technological parameters of the AM process, foams of PETG with densities ranging from 150 to 1000 g/cm3 were produced. Unlike conventional polyester foams, the resulting foams are not brittle.

Integrated metabolomics and lipidomics evaluate the alterations of flavor precursors in chicken breast muscle with white striping symptom.

White striping (WS) is the most common myopathy in the broiler chicken industry. To reveal flavor changes of WS meat objectively, flavor precursors of WS breast muscle were evaluated systematically with integrated metabolomics and lipidomics. The results showed that WS could be distinguished from normal controls by E-nose, and four volatile compounds (o-xylene, benzene, 1,3-dimethyl, 2-heptanone and 6-methyl and Acetic acid and ethyl ester) were detected as decreased compounds by gas chromatography-mass spectrometry. Lipidomic analysis showed that WS breast fillets featured increased neutral lipid (83.8%) and decreased phospholipid molecules (33.2%). Targeted metabolomic analysis indicated that 16 hydrophilic metabolites were altered. Thereinto, some water-soluble flavor precursors, such as adenosine monophosphate, GDP-fucose and L-arginine increased significantly, but fructose 1,6-bisphosphate and L-histidine significantly decreased in the WS group. These results provided a systematic evaluation of the flavor precursors profile in the WS meat of broiler chickens.

Comparison of volatile compounds of anal sac secretions between the sexes of domestic dog (Canis lupus familiaris).

Volatile compounds of anal sac secretions are odorant chemicals used across the carnivores for social communication such as identifying individuals and group membership. Odor profiles taken from expressed anal sac secretions of some species of carnivores have been detected in previous studies. In this study, the volatile compounds of anal sac secretions between five male and five female domestic dogs (Canis lupus familiaris) were compared. Volatile chemicals were extracted, separated, and analyzed by gas chromatography-mass spectrometry with solid-phase micro-extraction and identified from their electron ionization mass spectra and Kovats retention indices. The results showed the presence of various types of compounds including organic fatty acids, ketones, aldehydes, esters, and alcohols in the anal sac secretions of dogs. Greater amounts of diversity and esters, and lower amounts of alcohols were detected in the anal sac secretions of females compared to males. This was accompanied by finding citrate and acetic acid ester only in the females. Furthermore, presence of some sex-specific organic compounds like dimethylcyclopentyl ethanone indicates that the volatile profiles of anal sac secretions in 10 domestic dogs are differentiated by host sex.

Исследование относительной реакционной способности паров алкилацетатов по отношению к компонентам плазмы импульсного разряда в воздухе

A study was made of the relative reactivity of vapors of a number of acetic acid esters (alkyl acetates) with respect to plasma components of a pulsed corona discharge with a voltage of 100 kV and a duration of 40 ns. On model mixtures based on methyl-, ethyl-, propyl-, isopropyl, isobutyl-, butyl-, and vinyl acetate with a content of 250–500 ppm in air and nitrogen, the relative reactivity parameters were obtained. The reactivity of acetic acid esters increases with an increase in the hydrocarbon substituent. The high reactivity of vinyl acetate is due to the double bond reaction with ozone.

Study of Membrane-Immobilized Oxidoreductases in Wastewater Treatment for Micropollutants Removal.

The development of efficient strategies for wastewater treatment to remove micropollutants is of the highest importance. Hence, in this study, we presented a rapid approach to the production of biocatalytic membranes based on commercially available cellulose membrane and oxidoreductase enzymes including laccase, tyrosinase, and horseradish peroxidase. Effective enzyme deposition was confirmed based on Fourier transform infrared spectra, whereas results of spectrophotometric measurements showed that immobilization yield for all proposed systems exceeded 80% followed by over 80% activity recovery, with the highest values (over 90%) noticed for the membrane-laccase system. Further, storage stability and reusability of the immobilized enzyme were improved, reaching over 75% after, respectively, 20 days of storage, and 10 repeated biocatalytic cycles. The key stage of the study concerned the use of produced membranes for the removal of hematoporphyrin, (2,4-dichlorophenoxy)acetic acid (2,4-D), 17α-ethynylestradiol, tetracycline, tert-amyl alcohol (anesthetic drug), and ketoprofen methyl ester from real wastewater sampling at various places in the wastewater treatment plant. Although produced membranes showed mixed removal rates, all of the analyzed compounds were at least partially removed from the wastewater. Obtained data clearly showed, however, that composition of the wastewater matrix, type of pollutants as well as type of enzyme strongly affect the efficiency of enzymatic treatment of wastewater.