Monoammonium Salt Research Articles

Glucaric acid additives for the antiplasticization of fibers wet spun from cellulose acetate/acetic acid/water

Cellulose acetate (CA) receives notable attention as an environmentally friendly, biodegradable polymer from renewable, low-cost resources. CA polymers are believed to have a critical role in shaping a greener and more circular textile economy. However, the mechanical properties of CA fibers are among the lowest in terms of its tensile strength, poor wet strength, and low flexural strength. This study investigates the effect of biobased additives for antiplasticizing the mechanical performance and structure of CA fibers. At up to 5 % of CA, glucaric acid (GA) and its monoammonium salt were added to CA fibers. With 1.5 % GA additive, tensile modulus improved by 155%, tensile strength by 55 %, and CA flexibility according to knot to straight fiber tenacity ratios improved by 107 % when compared to neat CA fibers. Based on the results, green small molecule antiplasticizers do exist, but their performance improvements are observed at low percentages of loading.

Molecular characteristics of volatile components from willow bark

Willow (Salix matsudana) bark is the bark of willow trees, it is rich in resources. Extracting these resources becomes difficult due to the relative lack of systematic and in-depth analysis of the total chemical composition. Analysis was performed using TDS-GC/MS, TG, FTIR and PY-GC/MS techniques. Results and discussion: the extracts form volatile organic compounds are mainly included in the analysis of TDS-GC/MS, such as, organic acids, exters, alcohols, etc. Extracts are rich in VOCs:1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester, its function is mainly as plasticizer. FTIR analysis are further confirmed, the ingredients of total extracts include ethers, The treatment of total heat loss is divided into two distinct phases: the first phase of 50 °C to 100 °C, the second phase of 150 °C to 250 °C, the sequence of quality loss is the second and the first stage, important turning point temperature is 245 °C, with significant changes in quality, for example, high polymer pyrolysis into small volatile molecules. In addition, various pyrolysis VOCs have been analyzed by PY-GC/MS, And have good development space, such as, Carbamic acid, monoammonium salt (4.80%), Glycolaldehyde dimer (4.04%), Catechol (0.44%). etc. Both of them have good development prospects, including many new chemical components produced by the pyrolysis of total extracts and residues, which is a new method to provide high quality applications.

Chiral Ferrocenyl-Bismuthines containing N/O donor pendant arm: Syntheses and molecular structures

Some new chiral substituted ferrocenyl bismuthines CpFe(2-[Me2NCH(R)]C5H3)BiPhCl where R = H (1) or Me (2) and CpFe(2-[Me2NCH(R)]C5H3)BiPh2 where R = H (3) or Me (4) (Cp = cyclopentadienyl) containing a Rac-2-[(Me2NCH(R)] pendant arm on the ferrocenyl ring were synthesized. Nucleophilic substitution reaction of mono ammonium salt Rac-{[CpFe{2-(Me3N+CH2)C5H3}BiPh2][I−] (5) by o-hydroxyacetaphenone, salicyladehyde, N-methylpiperazine and 4′- aminobenzo-15-crown-5 in acetonitrile gave new ferrocenyl bismuthines [CpFe{2-(RCH2)C5H3}BiPh2] where R = OC6H4-2-C(O)Me (6), OC6H4-2-C(O)H (7), N(CH2CH2)2NMe (8) and NHC6H4-3,4-O-cyclo{(CH2)2-O}4 (9) respectively with N or O containing pendant arm. All the new compounds were characterized by 1H NMR, 13C NMR, FAB+, and High-Resolution Mass Spectrometry. All the compounds presented in this work present planar chirality because of 1,2-disubstituted ferrocene. In the solid-state, the presence of the ferrocenyl group influences the stereoelectronic properties in the molecule and Bi···N or Bi···O hypervalent interaction could not be observed in compounds with BiPh2 fragment while this interaction was observed in compounds with BiPhCl fragment. For compounds (1)-(4), (6)-(8) and (10), NMR spectra obtained at different temperatures show the association and/or dissociation of hypervalent N···Bi coordination in these compounds. Molecular structures of compounds (1), (2) and (10) show distorted pseudo-trigonal bipyramidal geometry (see-saw structure) at bismuth center with intramolecular Bi···N hypervalent interaction while (6) and (7) present a distorted pseudo-trigonal pyramidal geometry and do not show hypervalent Bi···O interaction. Crystal structures of these compounds show that CFc-Bi bond length is shorter than CPh-Bi bond length due to lower group electronegativity of ferrocenyl vs phenyl and bidentate nature of FcN ligand in ferrocenyl bismuthines.

Intermediate Product Profile as a Result of Ozone Oxidation of Industrial Wastewater

The following were found when testing the wastewater in the study: 0.38% 7-Hydroxy-7-phenly-3,9-diisopropyl-2,10-dioxadispiri, 1.71% 2-Propanone (CAS) Acetone, 20.87% 2-propanol, 2-methyl- (CAS) tert-Butyl alcohol, 14.92% 2-Butanone (CAS) Methyl ethyl ketone, 62.11% Hydroperoxide, 1,1-dimethyl (CAS) Cadox TBH, COD (10,000-23,725 mg COD / l), total kjeldahl nitrogen ( 9,042 mg / l). The water was then oxidated using ozone (4.1 g / h) and intermediate product formation and COD removal efficiency were studied. The current wastewater characteristics vary in line with product supply and demand.In this study, a cylinder reactor with an internal diameter of 5.8 cm and a height of 1.7 meters was used for ozonation (4.1 g/saat). After seven hours of ozonation, the wastewater pH value fell below four, showing that complex compounds were broken down to organic acids. At the end of the first, third, fourth, fifth and sixth hours of the ozonation process, respectively, nitrogen oxide (H), N, 2-Dimethydodecylamine (K), Propanoic acid, 2-hydroxy-2-methyl (hydroxybutyric) (L), 2-Butanone, 3-hydroxy-3-methyl (M), 2,3 Butanedione (diacetyl) (N), Ammonium bicarbonate (O) ), Carbamicacid, monoammonium salt (Ammonium Carbamat) (P), Acetic acid, ethoxy-, 1-methylethyl ester (R) intermediates were formed. After seven hours of ozonation, the influent COD decreased from 17,000 mg / l to 2,860 mg / l. As a result of the ozone process, the organic substances were mostly transformed into 2-propanone (Acetone) (B) and 2-propanol, 2-methyl (tert-butyl alcohol) (C). Keywords: Ozonation, COD, Industrial wastewater, Intermediate product DOI : 10.7176/CER/11-10-03 Publication date: November 30 th 2019

Formation of Quinone Methides by Ultrafast Photodeamination: A Spectroscopic and Computational Study.

Formation of quinone methides (QMs) by photoelimination of an ammonium salt from cresol derivatives was investigated by femtosecond transient absorption spectroscopy (fs-TA) and computationally by time-dependent density functional theory using the PCM(water)/(TD-)B3LYP/6-311++G(d,p) level of theory. The photoelimination takes place in an adiabatic ultrafast reaction on the S1 potential energy surface delivering the corresponding QMs(S1), which were detected by fs-TA. Computations predicted a high-energy cation intermediate in the pathway between the Franck-Condon state of a monoammonium salt and the corresponding QM(S1) that was not detected by fs-TA. On the other hand, elimination from a disalt in H2O takes place in one step, giving directly the QM(S1). The combined experimental and theoretical investigation fully disclosed the formation of QMs by the deamination reaction mechanism, which is important in the application of cresols or similar molecules in biological systems.

A new polymorph of ammonium succinate - serendipity in action.

Succinic acid has been known since 1546 and was first chemically identified in the mid-19th century. In an attempt to prepare a molecular salt of succinic acid with (S)-(-)-α-methylbenzylamine, we have obtained the second polymorph of the monoammonium salt of succinic acid, NH4+·C4H5O4-. The crystal structure determination proves the structure of the ionic compound and the intimate role of the ammonium ion in the structure, which is compared to the earlier described polymorph.

Urine volatile organic compounds as biomarkers for minimal change type nephrotic syndrome

Urinary volatile organic compounds (VOCs) profiling has recently received considerable attention because it can be obtained noninvasively and conveniently while it can be successfully used in a variety of diseases and can provide unique biomarkers. The aim of current study was to investigate potential biomarkers between minimal change type nephrotic syndrome (MCNS) and normal. Urinary samples were collected from 38 minimal change type nephrotic syndrome patients and 15 healthy controls. Solid phase microextraction (SPME) and chromatography– mass spectrometry (GC-MS) were used to analysis the urinary metabolites. To deal with the final data, the statistical methods principal component analysis (PCA) and orthogonal partial least-squares discriminant analysis (OPLSDA) were performed. Six specific VOC biomarkers were present at abnormal levels in the urine of MCNS patients. These VOCs included trans-2,2-dimethyl-4-decene; pyrrole; carbamic acid, monoammonium salt; 1-butyne, 3,3-dimethyl-; diisopropylamine; and 4-heptanone. These biomarkers may be useful as a new diagnostic method and for monitoring the prognosis for MCNS patients.

Preparation and Physicochemical and Biological Properties of Molecular Associates of Lagochilin and Lagochirsine with Glycyrrhizic Acid and its Monoammonium Salt

Molecular associates of lagochilin and lagochirsine with glycyrrhizic acid and its monoammonium salt in various molar ratios were prepared. Their IR spectra, several physicochemical properties, and hemostatic activities were discussed.

Urinary Volatile Organic Compounds as Potential Biomarkers in Idiopathic Membranous Nephropathy

Objective: To detect urinary volatile organic compounds (VOCs) in patients with idiopathic membranous nephropathy (iMN) and normal controls, and to examine whether or not urinary VOCs can act as biomarkers for the diagnosis of iMN independent of renal biopsy. Materials and Methods: Gas chromatography/mass spectrometry (GC/MS) was used to assess the urine collected from 63 iMN patients and 15 normal controls. The statistical methods of principal component analysis and partial least squares discriminant analysis were performed to process the final data in Common Data Format which were converted from GC/MS data. Results: Six VOCs in the urine samples of iMN patients exhibited significant differences from those of normal controls: carbamic acid monoammonium salt, 2-pentanone, 2,4-dimethyl-pentanal, hydrogen azide, thiourea, and 4-heptanone were significantly higher than in controls (p < 0.05). Conclusions: Six urinary VOCs were isolated from patients with iMN using GC/MS. The analysis of urinary VOCs using GC/MS could be developed into a non-invasive method for the detection of iMN.

Identifikasi Kandungan Ekstrak Kayu Jati Menggunakan Py-GCMS

Teak wood (Tectona grandis Lf.) in the form of sawdust a byproduct/waste from the furniture industry has a considerable amount and has not been utilized optimally. This study aims to determine the content of extractive teak wood (Tectona grandis Lf.). The method used is the hot water solubility. Muna's teak wood powder weighing 4,076 g soaked in distilled water as much as 100 ml glass flask, then heated in a water bath at a temperature of 100 oC for 3 hours. The content of extractive dissolved in a liquid further characterized using Py-GCMS. Results of the analysis of Py-GCMS to extract teak wood showed concentrations of some substances, such as Carbamic acid (70,70%), mono ammonium salt (CAS) Ammonium carbamate (70,70%), Acetic acid (CAS) Ethylic acid (10,52%), Acetic acid (CAS) Ethylic acid (2,35%), Acetic acid (CAS) Ethylic acid (3,26%), and Phenol (CAS) Izal (13,17%)

Identifying the Chemical Composition of Decomposed Residues From Cyanobacterial Bloom Biomass by Pyrolysis‐GC/MS

The frequent occurrence of cyanobacterial blooms in eutrophic lakes can lead to a high amount of biomass in aquatic systems, and following cell death, this autochthonous organic matter will eventually decompose. In this study, the effect of temperature and sediment on the chemical composition of cyanobacterial biomass residue was investigated by microcosm experiment. The results showed that the lowest cyanobacterial bloom biomass (CBB) removal efficiency was recorded at 32°C regardless of the presence or absence of sediment. Based on total organic carbon, the CBB removal efficiencies were higher than 90% at 20–29°C but less than 87.0% at 32°C. Pyrolysis gas chromatography mass spectrometry and Fourier transform infrared analysis indicated that organic nitrogen compounds (e.g., carbamic acid monoammonium salt) and polysaccharides (e.g., 2‐propanone, 1‐hydroxy‐) were the main components in the residues. Based on the determined components in the residues under different conditions, unweighted pair group clustering method with arithmetic averages and principal components analysis further suggested that sediment and temperature had obvious influence on the chemical composition of CBB decomposition residues. Considering that cyanobacteria biomass is produced annually in eutrophic lakes, residues from CBB may contribute to the nitrogen/carbon cycles and macro‐fauna growth in these ecosystems.

Effect of Some Triterpene Glycosides Applied in vitro on Chromatin State in Human Cells

The effect of triterpene glycosides - monoammonium salt of glycyrrhizinic acid (monoammonium glycyrrhizinate) and of alpha-hederin and hederacoside C from ivy (Hedera L.) on chromatin condensation in human buccal epithelium cells was investigated. Heterochromatin granules in cell nuclei were stained with 2% orcein. The state of chromatin was assessed by heterochromatin granules quantity - HGQ at magnification x 600. The number of granules was assessed in 30 nuclei and the mean HGQ value was calculated. Each experiment was done in triplex. In experiments were used cells of 4 donors. Cells were placed in solutions of glycosides in concentrations of 5, 25, and 50 mg/l for 2 hours. Statistical analysis was performed by the Student’s method. The monoammonium glycyrrhizinate was tested in cells of one donor and induced HGQ increase in a concentration of 50 mg/l. The alpha-hederin in a concentration of 25 mg/l caused a significant increase of HGQ in cells of all four donors. Hederacoside C in concentrations 5 and 25 mg/l induced increase of HGQ in cells of three donors of four. Cells of one donor were resistant to hederacoside C. By computation analysis it was shown that triterpene glycosides have low genotoxic activity. The HGQ determination enables to register individual peculiarities in cell response to biologically active compounds which may be used in personalized medicine. Keywords: Alpha-hederin, cell nucleus, glycyrrhizin, heterochromatin, hederacoside C, human buccal epithelium.

Ammonium-exchanged phase of γ-titanium phosphate

The monoammonium salt of γ-titanium phosphate has been prepared by hydrothermal treatment of π-Ti2O(PO4)2·2H2O in the presence of urea and phosphoric acid, and its crystal structure was obtained by Rietveld analysis using powder X-ray diffraction data. γ-Ti(PO4)(NH4HPO4) crystallizes in the monoclinic space group P21/m with a = 5.0725(3) A, b = 6.3101(3) A, c = 11.2435(5) A, β = 97.980(3)° (Z = 2). The structure consists of 2D titanium phosphate layers in the ab-plane. The titanium atoms and one of the phosphate groups are located nearly in the ab-plane of the layer. All the oxygen atoms of this phosphate group are involved in titanium coordination sphere. The other phosphate group located in the layers edges links two neighboring titanium atoms in the a-direction through two of its oxygen atoms. The remaining two oxygens are pointed toward the interlayer space being involved in hydrogen bond interactions with the ammonium ions. Each ammonium ion is shared by four oxygens belonging to four different phosphate hydroxyl groups. γ-Ti(PO4)(NH4HPO4) is stable until 453 K, while above this temperature, it transforms to γ’-Ti(PO4)(NH4HPO4) high temperature polymorph stable until 573 K. Thermal decomposition of this material leads to cubic TiP2O7 structure, with previous formation of two intermediate pseudo-layered compounds: Ti(PO4)(NH4HP2O7)0.5 and Ti(PO4)(H2P2O7)0.5. The activation energy of thermal decomposition has been calculated as a function of the extent of conversion applying the Kissinger–Akahira–Sunose (KAS) isoconversional method to the thermogravimetric data.

Anti‐hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species

ABSTRACTDevelopment of complementary and/or alternative drugs for treatment of hepatitis C virus (HCV) infection is still much needed from clinical and economic points of view. Antiviral substances obtained from medicinal plants are potentially good targets to study. Glycyrrhiza uralensis and G. glabra have been commonly used in both traditional and modern medicine. In this study, extracts of G. uralensis roots and their components were examined for anti‐HCV activity using an HCV cell culture system. It was found that a methanol extract of G. uralensis roots and its chloroform fraction possess anti‐HCV activity with 50%‐inhibitory concentrations (IC50) of 20.0 and 8.0 μg/mL, respectively. Through bioactivity‐guided purification and structural analysis, glycycoumarin, glycyrin, glycyrol and liquiritigenin were isolated and identified as anti‐HCV compounds, their IC50 being 8.8, 7.2, 4.6 and 16.4 μg/mL, respectively. However, glycyrrhizin, the major constituent of G. uralensis, and its monoammonium salt, showed only marginal anti‐HCV activity. It was also found that licochalcone A and glabridin, known to be exclusive constituents of G. inflata and G. glabra, respectively, did have anti‐HCV activity, their IC50 being 2.5 and 6.2 μg/mL, respectively. Another chalcone, isoliquiritigenin, also showed anti‐HCV activity, with an IC50 of 3.7 μg/mL. Time‐of‐addition analysis revealed that all Glycyrrhiza‐derived anti‐HCV compounds tested in this study act at the post‐entry step. In conclusion, the present results suggest that glycycoumarin, glycyrin, glycyrol and liquiritigenin isolated from G. uralensis, as well as isoliquiritigenin, licochalcone A and glabridin, would be good candidates for seed compounds to develop antivirals against HCV.

МОДИФИКАЦИЯ ОСНОВАНИЙ ШИФФА ГОССИПОЛА С ГЕТЕРОЦИКЛИЧЕСКИМИ АМИНАМИ

With MASGK (mono ammonium salt of glycyrrhizin acid) and to obtain a metal (Cu(CH3COO)2·H2O and Ni(CH3COO)2·4H2O) have been modified previously synthesized azomethin derivatives of gossypol with amino compounds heterocyclic nature. Using the methods of UV and IR spectroscopy were studied the structure and identity of the synthesized complexes.

ChemInform Abstract: A Mild and Efficient Synthesis of Bis(indolyl)methane Derivatives Catalyzed by Monoammonium Salt of 12‐Tungstophosphoric Acid.

A simple, highly rapid and efficient electophilic substitution reaction of indole with various aromatic aldehydes has been carried out using 5 wt% of monoammonium salt of 12-tungstophosphoric acid [(NH4)H2PW12O40] as a solid acid catalyst in acetonitrile to afford the corresponding bis(indolyl)methanes in excellent yields (84-95%) at room temperature. The heteropolyacid-based catalyst has the advantages of simple workup procedure, water insolubility with good activity and high yielding reaction for the synthesis of bis(indolyl)methane derivatives.

Comparative toxicity of two glyphosate-based formulations to Eisenia andrei under laboratory conditions

Glyphosate-based products are the leading post-emergent agricultural herbicides in the world, particularly in association with glyphosate tolerant crops. However, studies on the effects of glyphosate-based formulations on terrestrial receptors are scarce. This study was conducted to evaluate the comparative toxicity of two glyphosate-based products: Roundup FG (monoammonium salt, 72% acid equivalent, glyphosate-A) and Mon 8750 (monoammonium salt, 85.4% acid equivalent, glyphosate-B), towards the earthworm Eisenia andrei. Median lethal concentration (LC50) showed that glyphosate-A was 4.5-fold more toxic than glyphosate-B. Sublethal concentrations caused a concentration-dependent weight loss, consistent with the reported effect of glyphosate as uncoupler of oxidative phosphorylation. Glyphosate-A showed deleterious effects on DNA and lysosomal damage at concentrations close to the applied environmental concentrations (14.4μg ae cm−2). With glyphosate-B toxic effects were observed at higher doses, close to its LC50, suggesting that the higher toxicity of formulate A could be attributed to the effects of some of the so-called “inert ingredients”, either due to a direct intrinsic toxicity, or to an enhancement in the bioavailability and/or bioaccumulation of the active ingredient. Our results highlight the importance of ecotoxicological assessment not only of the active ingredients, but also of the different formulations usually employed in agricultural practices.

МАСС-СПЕКТРОМЕТРИЯ И КВАНТОВОХИМИЧЕСКОЕ ИССЛЕДОВАНИЕ ПРОЦЕССОВ САМОАССОЦИАЦИИ МОЛЕКУЛ ГЛИЦИРРИЗИНОВОЙ КИСЛОТЫ

The mass spectrometry with electrospray ionization has used to study the processes of the formation the self-association complexes Glycyrrhizinic acid (GA). The data of mass spectrometry have proved the presence of dimers and trimers of GA for samples of 0,2% Monoammonium salt of GA at pH 5,5 and pH 2. These data are consistent with the quantum-chemical calculations of self-associates of glycyrrhizic acid. The quantum-chemical calculations predict the formation of clusters of the general form Xn with a value of n from 1 to n = 6. The data of mass spectrometry and the results of quantum chemical calculations demonstrated that the most stable clusters have built on the principle of «head – tail». Self-associated complex of GA composed of two molecules of GA create a cavity between them, with the size which is enough to include guest molecules with the similar size.

Simultaneous Quantitative Determination of Nine Active Chemical Compositions in Traditional Chinese Medicine Glycyrrhiza by RP-HPLC with Full-Time Five-Wavelength Fusion Method

A new, simple, accurate and reliable full-time five-wavelength fusion method for the simultaneous separation and determination of nine active chemical compositions (liquiritin apioside, liquiritin, isoliquiritin apioside, ononin, isoliquiritin, liquiritigenin, calycosin, isoliquiritigenin, Glycyrrhizic acid monoammonium salt) in traditional Chinese medicine Glycyrrhiza was developed using reverse phase high-performance liquid chromatography (RP-HPLC) coupled with a diode-array detector (DAD). The chromatographic separation was performed on an Agilent TC-C18 column with gradient elution using 0.04% methanoic acid (A) and acetonitrile (B) at a flow rate of 1.0 mL min(-1) and UV detection at 248 nm, 250 nm, 276 nm, 362 nm, 370 nm. The standard curves were linear over the range of 2.1379-12.8272 μg for liquiritin apioside, 3.9299-23.5794 μg for liquiritin, 1.0432-6.2592 μg for isoliquiritin apioside, 0.8764-5.8584 μg for ononin, 1.0701-6.4205 μg for isoliquiritin, 1.3685-8.2111 μg for liquiritigenin, 0.3927-2.3563 μg for calycosin, 0.2498- 1.4986 μg for isoliquiritigenin, 2.0094-12.0564 μg for Glycyrrhizic acid monoammonium salt, respectively (r(2) > 0.9997). The recoveries and relative standard deviation (RSD) varied from 95.09% to 103.54% and 1.09% to 2.36%, respectively. The precision for all the analytes was less than 2.52%. The method indicated good performance in terms of precision, accuracy and linearity. The method enabled the simultaneous determination of nine active chemical compositions for quality control of Glycyrrhiza.

Application of an Amine Functionalized Biopolymer in the Colonic Delivery of Glycyrrhizin: Design and In Vivo Efficacy Study

In our current study, a newer amine functionalized guar gum derivative was studied for its efficacy in colonic drug delivery. Glycyrrhizic acid mono-ammonium salt was used as the model drug. Drug-loaded microparticles were formulated by ionic crosslinking using sodium tripolyphosphate. The Scanning Electron Microscopic study revealed spherical particles of sizes from 4.9 ± 3.8 μm to 6.9 ± 3.9 μm. The FT-IR studies presented a possible interaction between the drug and the polymer. The drug was encapsulated in amorphous form as observed from the powder X-Ray Diffraction studies. A cumulative drug release study was carried out in simulated gastric, intestinal, and colonic fluids. The cumulative drug release studies presented a burst release followed by a sustained release of the drug in simulated colonic fluid containing rat cecal contents. The drug-polymer ratio was optimised using a 32 factorial design by taking the amounts of glycyrrhizic acid (X1) and guar gum alkyl amine (X2) as the independant variables. The percent cumulative drug release at 240 mins (Q240), 720 mins (Q720), and at 1,440 mins (Q1440) were considered as the dependant variables. The efficacy of the optimized formulation was studied in a 2,4,6-trinitrobenzene sulfonic acid-induced rat colitis model. The tissue’s nitric oxide, malondialdehyde, and myeloperoxidase activities were found to be much lower in the microparticle-treated group compared to free drug-treated group. The histology of the colonic tissue from the treated group of animals revealed almost no infiltration of inflammatory cells in the tissue for the microparticle-treated group of animals. The synthesized amine derivative of guar gum was found to be better in vitro with a better in vivo efficacy in the colonic delivery of glycyrrhizic acid monoammonium salt and can be considered as a newer modified biopolymer for colonic drug delivery.