Compounds Benzoic Acid Research Articles

8-Acyloxy-1,3-benzoxazine-2,4-diones as siderophore components for antibiotics.

8-Acyloxy-1,3-benzoxazine-2,4-diones as masked catechol derivatives represent a novel type of siderophore components, whose growth promoting activity is low or not existing if tested alone. But after conjugation with beta-lactam antibiotics the resulting conjugates show a significantly increased antibacterial activity against Gram-negative bacteria compared with their parent antibiotics. Investigations using a set of penetration and iron transport mutants demonstrated that the conjugates use iron transport systems to penetrate the bacterial outer membrane. Title compounds were synthesized from (2,3-dimethoxycarbonyloxy)-benzoic acid and different amino compounds. Conjugates with penicillins and cephalosporins were prepared.

Ionic-Liquid-Modified, Hybrid Silica Monolithic Column for Capillary Electrochromatography

Abstract An ionic liquid, 1-allyl-3-methyl imidazole chloride (AMIMCl), was synthesized to modify a terminal-vinyl organic-inorganic hybrid silica monolithic column by free-radical polymerization procedure using 2,2′-azodiisobutyronitrile (AIBN) as an initiator. Nucleotide monophosphates, phenols and benzoic acid compounds were successfully separated on this column under acidic conditions. The electroosmotic flow (EOF) was in the direction opposite to electrophoretic migration, and separation selectivity was apparently improved compared with an unmodified monolithic column, which can be attributed to the hydrophobic interactions on amyl chain, hydrogen bonding interactions on imidazole ring and electrostatic interactions. Repeatabilities of migration times for benzoic acid compounds were reasonable with RSD less than 4.0% for five consecutive within-column runs and 9.0%–9.8% for column-to-column measurements of three columns.

Simultaneous Separation and Determination of Benzoic Acid Compounds in the Plant Medicine by High Performance Capillary Electrophoresis

AbstractA simple and inexpensive high performance capillary electrophoresis (HPCE) was applied to separate five benzoic acid compounds simultaneously. The investigation was carried out by micellar electrokinetic capillary chromatography (MECC). To avoid a time‐consuming and tedious procedure, orthogonal experimental design OA9 (34) for separation experiments was applied to find the optimal conditions in terms of the resolution and analytical time. The best conditions for separation were obtained using a 20 mM borax and 30 mM sodium dodecyl sulfate (SDS) buffer (pH 9.8) containing 2 mM β‐CD and 4% methanol (v/v). Online UV detection was performed at 250 nm. A voltage of 16 kV was applied and the temperature was controlled at 25 °C. Injection was performed for 5 s. The method was validated for the quantification of benzoic acid, salicylic acid and ortho‐aminobenzoic acid in Radix Isatidis, a traditional plant medicine with removal of endotoxin. The separation and determination were satisfactory and quick.

ChemInform Abstract: Synthesis and Antitumor Activity of Hydrosoluble Analogs of p-(3,3-Dimethyl-1-triazeno)benzoic Acid Potassium Salt.

The hydrosoluble triazene derivatives of phenylacetic, phenylbutyric and cinnamic acid have been synthesized and their logP and pKa values were simultaneously determined according to a multiparametric fitting of potentiometric data. The antitumor activity caused by the synthesized compounds in mice bearing either Lewis lung carcinoma or TLX5 lymphoma was evaluated and discussed in comparison with the parent compound (p-(3,3-dimethyl-1-triazeno)benzoic acid potassium salt (DM-COOK, CAS 70055-49-1). The tested compounds were at least as active as DM-COOK, the cinnamic and the phenylacetic derivatives being the more active compounds in mice bearing TLX5 lymphoma and Lewis lung carcinoma, respectively.

Study on QSTR of Benzoic Acid Compounds with MCI

Quantitative structure-toxicity relationship (QSTR) plays an important role in toxicity prediction. With the modified method, the quantum chemistry parameters of 57 benzoic acid compounds were calculated with modified molecular connectivity index (MCI) using Visual Basic Program Software, and the QSTR of benzoic acid compounds in mice via oral LD50 (acute toxicity) was studied. A model was built to more accurately predict the toxicity of benzoic acid compounds in mice via oral LD50: 39 benzoic acid compounds were used as a training dataset for building the regression model and 18 others as a forecasting dataset to test the prediction ability of the model using SAS 9.0 Program Software. The model is LogLD50 = 1.2399 × 0JA +2.6911 × 1JA – 0.4445 × JB (R2 = 0.9860), where 0JA is zero order connectivity index, 1JA is the first order connectivity index and JB = 0JA × 1JA is the cross factor. The model was shown to have a good forecasting ability.

Anti-inflammatory drugs selectively target sporangium development in Mucor

It is known that acetylsalicylic acid, an anti-inflammatory and anti-mitochondrial drug, targets structure development and functions of yeasts depending on elevated levels of mitochondrial activity. Using antibody probes, we previously reported that sporangia of Mucor circinelloides also contain increased mitochondrial activity, yielding high levels of 3-hydroxyoxylipins. This was, however, not found in Mortierella alpina (subgenus Mortierella). In this study we report that acetylsalicylic acid (aspirin) also targets sporangium development of Mucor circinelloides selectively, while hyphae with lower levels of mitochondrial activity are more resistant. Similar results were obtained when the anti-inflammatory compounds benzoic acid, ibuprofen, indomethacin, and salicylic acid were tested. The anti-inflammatory drugs exerted similar effects on this dimorphic fungus as found under oxygen-limited conditions. Interestingly, sporangium development of Mortierella alpina was found not to be selectively targeted by these drugs. Mortierella alpina, which could not exhibit dimorphic growth under oxygen-limited conditions, was also more sensitive to the anti-inflammatory drugs when compared with Mucor circinelloides. These results prompt further research to assess the applicability of these antimitochondrial antifungals to protect plants and animals against Mucor infections.

An Isocratic Reversed-Phase High-Performance Liquid Chromatographic Method for the Simultaneous Determination of Benzoyl Peroxide and the Related Compounds Benzoic Acid, Benzaldehyde, Ethyl Benzoate, Methylparaben, and Propylparaben in Dermal Preparations

A reversed-phase high-performance liquid chromatographic method was developed for the simultaneous determination of benzoyl peroxide and the related compounds benzoic acid (BA), methylparaben, benzaldehyde, propylparaben, and ethyl benzoate. The compounds are separated on a column containing octadecyl silane chemically bonded to porous silica particles. The mobile phase is acetonitrile-buffer (45 + 55, v/v). Solutions are injected into the chromatographic system under isocratic conditions at a constant flow rate of 1.5 mL/min with UV detection at 235 nm. Analysis of stability samples showed rapid accumulation of BA by thermal degradation. A rationale has been established for the acceptable limit of BA in the formulation, which already contains BA (0.2%) as a preservative. The proposed method is efficient and determines the active compound and 5 related compounds in a run time of 20 min. The method was validated according to the guidelines of the International Conference on Harmonization and demonstrated good agreement with the validation requirements.

Quantitative structure–activity relationship studies of mushroom tyrosinase inhibitors

Here, we report our results from quantitative structure-activity relationship studies on tyrosinase inhibitors. Interactions between benzoic acid derivatives and tyrosinase active sites were also studied using a molecular docking method. These studies indicated that one possible mechanism for the interaction between benzoic acid derivatives and the tyrosinase active site is the formation of a hydrogen-bond between the hydroxyl (aOH) and carbonyl oxygen atoms of Tyr98, which stabilized the position of Tyr98 and prevented Tyr98 from participating in the interaction between tyrosinase and ORF378. Tyrosinase, also known as phenoloxidase, is a key enzyme in animals, plants and insects that is responsible for catalyzing the hydroxylation of tyrosine into o-diphenols and the oxidation of o-diphenols into o-quinones. In the present study, the bioactivities of 48 derivatives of benzaldehyde, benzoic acid, and cinnamic acid compounds were used to construct three-dimensional quantitative structure-activity relationship (3D-QSAR) models using comparative molecular field (CoMFA) and comparative molecular similarity indices (CoMSIA) analyses. After superimposition using common substructure-based alignments, robust and predictive 3D-QSAR models were obtained from CoMFA (q2 = 0.855, r2 = 0.978) and CoMSIA (q2 = 0.841, r2 = 0.946), with 6 optimum components. Chemical descriptors, including electronic (Hammett sigma), hydrophobic (pi), and steric (MR) parameters, hydrogen bond acceptor (H-acc), and indicator variable (I), were used to construct a 2D-QSAR model. The results of this QSAR indicated that pi, MR, and H-acc account for 34.9, 31.6, and 26.7% of the calculated biological variance, respectively. The molecular interactions between ligand and target were studied using a flexible docking method (FlexX). The best scored candidates were docked flexibly, and the interaction between the benzoic acid derivatives and the tyrosinase active site was elucidated in detail. We believe that the QSAR models built here provide important information necessary for the design of novel tyrosinase inhibitors.

Synthesis and phase behaviour of hydrogen‐bonded liquid crystalline complexes of allyloxybenzoic acid compounds with 4,4′‐bipyridine

Three kinds of benzoic acid compounds were synthesized and characterized; the corresponding symmetric hydrogen‐bonded liquid crystalline complexes based on these benzoic acid compounds and 4,4′‐bipyridine (BPy) were then prepared. The existence of the hydrogen bonds was verified by Fourier transform infrared spectroscopy. The liquid crystalline properties of the complexes were demonstrated by polarizing microscopy and differential scanning calorimetry. 4‐Allyloxy‐2‐fluorobenzoic acid and two fluorinated hydrogen‐bonded complexes exhibited only nematic phases, whereas the non‐fluorinated complex showed both smectic and nematic phases. The clearing points and mesophase thermal range of the complexes decreased with increasing number of lateral fluorine atoms on the rigid core.

Stability of the OECD model compound benzoic acid in receptor fluids of Franz diffusion cells.

The stability of benzoic acid, one of the model compounds recommended for skin absorption studies in the OECD guidelines, in Franz diffusion cell receptor fluids was studied. According to the results, addition of a preservative (sodium azide) to the solution is recommended for long-term skin permeation experiments.

水銀電極に吸着する物質ＩＩＩ―カルボン酸（１）

Adsorption of organic compounds on electrodes involves the competition between organic molecules and the water molecules near the electrodes. From the thermodynamic analysis of electrocapillary curves, it is impossible to obtain surface excess of water. Therefore, another methods are required to know about the water molecules near the electrodes. In this monograph at first the adsorption of water molecules on the electrodes by various methods are reviewed. Adsorption of carboxylic acids on mercury electrodes are reviewed as in the last review (Sawamoto, 2006). Carboxylic acids described here are linear mono-carboxylic acids such as acetic acid, propionic acid and di-carboxylic acids such as oxalic acid, benzoic acid and related compounds.

Small energy differences in molecular crystals: A first principles study of tautomerism and dynamics in benzoic acid derivatives

The carboxylic acid dimer unit (COOH)2 is a common hydrogen bonding motif that frequently exhibits tautomerism-driven proton disorder in the solid state. This study considers such disorder in the representative compounds benzoic acid, 4-chlorobenzoic acid and terephthalic acid, in which the energy scales for tautomerism have been determined experimentally to lie in the range 0.5–2 kJ mol−1. Periodic plane-wave PBE functional calculations are shown to yield accurate relative energies for such tautomers, whereas LDA calculations underestimate the energy differences. The implications of these findings are discussed within the wider context of polymorphism. The optimised structures obtained from gas phase and solid-state calculations are compared, and the contributions of various contacts (including weak C–H⋯O bonding) to cohesive energies are determined within a supercell approach. The anharmonic vibrational spectra of benzoic and terephthalic acid are obtained from finite temperature molecular dynamics, and compared with previous experimental and theoretical results.

Effects of benzoyl and salicyl compounds on ripening of physiologically mature green tomato fruits in storage

The effects of benzoyl and satcliyl compounds on the post-harvest ripening and storage life of tomato fruit cv. Roma F.V. were evaluated. The treatments were benzoly compounds: benzoic acid, salicylic acid (2-hydroxybenzoic acid), 2-chlorobenzoic acid, vanillic acid (3-methoxy-4-hydroxybenzoic acid), gallic acid (3,4,5-trihydroxybenzoic acid) and salicyl compounds: benzoate, salicin (2-[hydroxymethyl]-phenyl-β-D-glucopyranoside), saligenin (Salicyl alcohol), salicylamide and salicyaldehyde. The treatment concentration ranged from 10µm to 500µm. Physiologically mature green tomato fruits were immersed in each treatment solution for 30 minutes after which they were stored in baskets at ambient temperature. The experiment was laid out as completely randomised design with three replication at the Nicansol Research Laboratory, University of Agriculture, Makurdi in 2001. Benzoly compounds inhibited ripening and prolonged the storage period of the tomato fruits. Salicylic acid and gallic both at 500µm were the most effective by the 8th day of storage. Similarly, salicyl compounds delayed ripening to tomato fruits. Saligenin and salicin at 500µm proved most effective and delayed ripening by 18 and 16days respectively. The study showed that harvest treatment with salicylic acid, gallic acid, saligenin and salicin at 500µm could be utilised to delay ripening and prolong storage life to tomato fruits.Keywords: tomato fruits, benzoyl, salicyl compounds, ripening, storage lifePlant Products Research Journal Vol. 9 2005: 19-22

Synthesis and HPLC evaluation of carboxylic acid phases on a hydride surface

Three organic moieties containing carboxylic acid functional groups are attached to a particulate silica surface through silanization/hydrosilation. Two compounds (undecylenic acid and 10-undecynoic acid) have 11 carbon chains and the other is a five-carbon acid (pentenoic acid). Bonding is confirmed through carbon elemental analysis, diffuse reflectance infrared fourier transform spectroscopy, and carbon-13 and silicon-29 CP-MAS NMR spectroscopy. The bonded phases are tested by HPLC using PTH amino acids, nucleic acids, theophylline-related compounds, anilines, benzoic acid compounds, choline, and tobramycin. The latter two compounds are used to investigate the aqueous normal phase properties of the three bonded materials.

Effects of temperature on biological degradation of phenols, benzoates and phthalates under methanogenic conditions

Abstract The effect of temperature on the efficiency of degradation of the aromatic compounds benzoic acid, 2,3,5-trichlorobenzoic acid, phthalic acid, methyl- and ethylphthalate, resorcinol, phenol, pentachlorophenol, 4-nitrophenol, 4-ethylphenol and o-, m- and p-cresol by a mesophilic or a thermophilic anaerobic community was examined. Anaerobic batch systems were incubated at different temperatures and inoculated with microbial communities from either of two biogas reactors fed with the same substrate, but run at 37 °C or 55 ∘ C. Benzoic acid, phthalic acid, methylphthalate, phenol, m- and p-cresol were mineralised by the mesophilic cultures incubated at 37 ∘ C. Apart from benzoic acid, no aromatic compounds were mineralised by the thermophilic community incubated at 55 ∘ C, suggesting that channelling reactions to the central intermediate benzoyl-CoA were inoperative in this microbial community. The restricted degradation of phenols observed at 55 ∘ C was confirmed by chemical analyses of the anaerobic digestion residue, which contained a higher level of phenols ( 322 μ g g - 1 total solids) in the system that was run at 55 ∘ C than that run at 37 ∘ C ( 65 μ g g - 1 ) . However, a decrease from 55 ∘ C to 48 ∘ C triggered the degradation of phenol by the thermophilic batch system, most likely due to an activation of enzymes involved in the phenol degradation.

Monitoring of the generation of non-mutagenic benzoic acid compounds during the manufacture of erythrosine

The generation of 2-(2′,4′-dihydroxybenzoyl) benzoic acid (DHBBA) and 2-(2′,4′-dihydroxy-3′,5′-diiodobenzoyl) benzoic acid (DHDIBBA) during the manufacture of erythrosine (Food Red No. 3) was examined. DHBBA is formed as an intermediate during the synthesis of fluorescein, and as fluorescein is produced, it is gradually consumed. However, under inappropriate reaction conditions, it remains in the resulting fluorescein at the termination of synthesis. DHDIBBA is easily obtained by the iodination of DHBBA. These compounds are also found when erythrosine is heated in excessive alkali. The results of the Ames test using DHBBA and DHDIBBA showed they did not possess mutagenic activity. The results clearly demonstrated that establishment of an upper limit for DHBBA and DHDIBBA is important in the quality control of fluorescein and erythrosine.

Preparation and catalytic application of MCM-41 modified with a ferrocene carboxyphosphine and a ruthenium complex

Abstract Reaction of 1′-(diphenylphosphino)ferrocenecarboxylic acid (Hdpf) with mesoporous molecular sieve MCM-41 gives immobilized carboxyphosphine (3), which was further reacted with [{Ru(η6-p-cymene)Cl(μ-Cl)}2] (1) to afford Ru/carboxyphosphine-modified molecular sieve 4. A simple reaction between MCM-41 and 1 afforded Ru-only modified molecular sieve 5. Materials 4 and 5 were tested as catalysts for the reaction of propargyl alcohol with benzoic acid to give 2-oxopropyl benzoate (6). The reactions catalyzed with immobilized catalysts are slower and give lower yields of the ester as compared to the homogeneous precatalyst [Ru(η6-p-cymene)(Hdpf-κP)Cl2] (2), which was prepared from Hdpf and the dimer 1. Formation of ester 6 catalyzed with 4 and 5 competes with a parallel, propargyl alcohol consuming process, which occurs also with MCM-41 itself in the absence of benzoic acid and ruthenium compounds. The solid-state structure of 2·CH2Cl2 has been determined by single-crystal X-ray diffraction.

Adsorption of Some Aromatic Compounds by a Synthetic Mesoporous Silicate

Water pollution by toxic organic compounds is of concern and demands for effective adsorbents for removal of the toxic compounds are increasing. Here we synthesized a mesoporous material, FSM-16, and investigated its ability to take up model compounds (benzene, toluene, phenol, and benzoic acid) from aqueous solutions by batch experiments. The adsorption isotherms were linear and adsorption capacities were small. Benzene and toluene have very similar adsorption isotherms, suggesting the side chain of toluene, i.e., alkyl chain, did not have significant effect on its adsorption. The amount of adsorption and isotherm slope were in the order of toluene ≈ benzene > benzoic acid > phenol. The occupation ratios of those organic compounds on the surfaces of FSM-16 were estimated less than 1%. Solubility of the compounds seems the major factor determining their adsorption by FSM-16. Phenol has the highest solubility and thus was least adsorbed by FSM-16. In contrast, toluene and benzene have very low solubilities and are the most adsorbed ones.

Factors influencing drug release from stearic acid based compacts

Fatty acids are potentially suitable carriers for use in the design of drug delivery systems, being biocompatible, biodegradable inexpensive and of low toxicity. The release of the model compound benzoic acid from fatty acid compacts of stearic acid was evaluated using the USP Apparatus 2 dissolution assembly in phosphate buffer pH 7.4. Matrix controlled drug release was expected. Release profiles were approximated by square root of time kinetics. Release rate was independent of stirring speed in the rpm range 50–150, however, at 200 rpm a significant increase in release rate was observed particularly at later times, the amount released versus square root of time plots becoming non-linear. Release was independent of compression pressure in the range 1–7 tons. The particle size of the benzoic acid and stearic acid used had a significant influence on release. The use of particles in the range 250–500 μm gave release rate constants ( k, g/cm 2 per min 0.5) ∼1.5 greater than those of smaller particle size (63–125 μm). The formation factor ( F) tended to increase exponentially with drug loading, the increase being steeper for compacts prepared from the larger particle sizes. At 80% drug loading for large sized systems the matrix appeared to offer little resistance to drug release and F approached one.

Photocatalytic oxidation of gaseous toluene on anatase TiO 2 catalyst: mechanistic aspects and FT-IR investigation

Photo-oxidation of toluene has been carried out in gas–solid regime by using polycrystalline anatase TiO 2 as the catalyst. The reacting gaseous mixture was toluene, air and water in various molar ratios. A pyrex fixed-bed continuous photoreactor irradiated by a medium pressure Hg lamp was used for performing the photoreactivity experiments. The main oxidation product was benzaldehyde but benzene, benzyl alcohol and traces of benzoic acid, phenol and unidentified compounds were also detected. The molar conversion to benzaldehyde with respect to the initial amount of toluene was ca. 20% in the best experimental conditions. Benzene was produced only as a transient product during the first 3–4 h of irradiation. The dependence of feed composition and flow rate on the toluene fractional conversion was investigated. Selected experiments were performed by using N 2 or CO 2 instead of air. The presence of oxygen was essential for the occurrence of the photoreaction while water played an important role in order to maintain the catalyst activity. Moreover, a Fourier-transform infrared spectroscopy (FT-IR) investigation was carried out simulating the experimental conditions used during the photoreactivity experiments. The results indicated that toluene is weakly stabilised on the hydrated TiO 2 particles by hydrogen-bonding with surface hydroxyl groups, and that it is photo-oxidised to benzaldehyde only in the presence of surface OH groups.