A 3D-QSAR Study on C-3 Substituted 4,6-Dichloroindole-2- Carboxylic Acids with Comparative Molecular Field Analysis

Aim and Method Comparative molecular field analysis (CoMFA), a threedimensional quantitative structure-activity relationship (3D-QSAR) method was applied to a novelseries of C-3 substituted 4, 6-dichloioindole-2-carboxylic acids to study the relationship betweentheir structure and the affinity for the glycine site of the NMDA receptor. Result Hie coefficientsof cross-validation q^2 and non cross-validation r^2 for the model established by the study are0.744 and 0.993, respectively, the value of variance ratio F is 261.343, and standard error estimate(SE) is 0.039. Conclusion These values indicate that the CoMFA model may have a good prediction forthe activity of C-3 substituted 4, 6-dichloroin-dole-2-carboxylic acids. As a consequence, thepredicted activity values of new designed compounds supports our conclusion from the model.

A METHOD OF SYNTHESIS OF PHENYL-LACTIC ACID AND SUBSTITUTED PHENYL LACTIC ACIDS

A method for the conversion of α-acetamido-β-substituted phenyl acrylic acid (αtβSPAA)into substituted phenyl lactic acid(SPLA)is described and an improved Clemmensen reduction reagent is used.

Organophosphonotungstic HPA of Keggin Type with Sulfo,Taurine and Glycine Substituted Ethylphosphonic Acids as the Coordinate Center

The title compounds 2ac were synthesized and characterized for the first time. Their proton numbers are around 3.2±0.15 and are not in proportion with the valid acidity-basicity of the central phosphonic acids. The entirety of phosphonic acids 1a-c is as the coordinate center of heteropoly anions of 2ac.

Direct reduction of some benzoic acids to alcohols via NaBH_4-Br_2

Direct reduction of seven benzoic acids to alcohols via sodium borohydride-bromine （NaBH4-Br2） reagent was developed. The isolated yields for the seven acids to reduce reached 60.6-90.1%. This new synthesis route has the advantages of simple of application, low cost, mild nature, and satisfactory yields.

Dietary supplementation of benzoic acid and essential oils combination enhances intestinal resilience against LPS stimulation in weaned piglets

Background The benefits of combining benzoic acid and essential oils(BAO)to mitigate intestinal impairment during the weaning process have been well established,while the detailed underlying mechanism has not been fully elucidated.Previous research has primarily focused on the reparative effects of BAO on intestinal injury,while neglecting its potential in enhancing intestinal stress resistance.Methods In this study,we investigated the pre-protective effect of BAO against LPS-induced stress using a modified experimental procedure.Piglets were pre-supplemented with BAO for 14 d,followed by a challenge with LPS or saline to collect blood and intestinal samples.Results Our findings demonstrated that BAO supplementation led to significant improvements in piglets’final weight,average daily gain,and feed intake/body gain ratio.Additionally,BAO supplementation positively influenced the composition of intestinal microbiota,increasing beneficial Actinobacteriota and Alloprevotella while reducing harmful Desulfobacterota,Prevotella and Oscillospira.Furthermore,BAO supplementation effectively mitigated oxidative disturbances and inflammatory responses induced by acute LPS challenge.This was evidenced by elevated levels of T-AOC,SOD,and GSH,as well as decreased levels of MDA,TNF-α,and IL-6 in the plasma.Moreover,piglets subjected to LPS challenge and pre-supplemented with BAO exhibited significant improvements in intestinal morphological structure and enhanced integrity,as indicated by restored expression levels of Occludin and Claudin-1 compared to the non-supplemented counterparts.Further analysis revealed that BAO supplementation enhanced the jejunal antioxidative capacity by increasing GSH-Px levels and decreasing MDA levels under the LPS challenge and stimulated the activation of the Nrf2 signaling pathway.Additionally,the reduction of TLR4/NF-κB/MAPK signaling pathways activation and proinflammatory factor were also observed in the jejunal of those piglets fed with BAO.Conclusions In summary,our study demonstrates that pre-supplementation of BAO enhances the anti-stress capacity of weaned piglets by improving intestinal microbiota composition,reinforcing the intestinal barrier,and enhancing antioxidative and anti-inflammatory capabilities.These effects are closely associated with the activation of Nrf2 and TLR4/NF-κB/MAPK signaling pathways.

One-pot synthesis of 2-(1-acyloxypentyl)benzoic acids

A one-pot synthesis of 2-（1-acyloxypcntyl） benzoic acids by trapping the carboxylatc/alkoxide dianion with acylating reagents following Grignard addition with n-BuMgBr to 2-formylbcnzoic acid was described. Compared with routine synthetic method, this novel procedure has the advantage of convenient operation and higher yields.

Density Functional Study of the Cluster Model of SnO₂(110) Surface Modified by Benzoic Acids

The properties of the modified surface of SnO2(110) with benzoic acid (Y-C6H4-COOH: Y is para position relative to -COOH group) derivatives were investigated using density functional theory. Zehner et al. mentioned that the modification of surface dipole moment made it possible to tune the work function of the system. The experiment of Ganzorig et al. showed that there was a linear relationship between the dipole moment of the binding molecule and the work function change of the system using the modified surface of indium-tin oxide (ITO) with some benzoic acid derivatives. To elucidate the relation between the dipole moment of the molecule and the work function change, we investigated the modified surface of SnO2(110) using Sn7O14 cluster model which was embedded in the fixed point charges. On the modification of the surface, benzoic acid derivatives were bound to SnO2 surface. By changing the terminal group of benzoic acid with H, Cl, F, CF3 and CCl3, the work function changed and the dipole moment of the binding molecules of the modified SnO2(110) were evaluated. The results showed that there was a linear relationship between the dipole moment of the binding molecules and the work function changed. From this relation, the average value of the dipole moments of Sn-OOC linkage at the surface was also evaluated.

Chelation in Metal Intoxication XLIV: Efficacy of α-Mercapto β-(5-Substituted, 2-Furyl) Acrylic Acids in Mobilizing Intracellularly Bound Cadmium in Rat

The efficacy of α mercapto β (2_furyl) acrylic acid (MFA), α mercapto β (5_sodiumsulfonate, 2_furyl) acrylic acid (MSFA) and α mercapto β (5_acetoxymethyl, 2_furyl) acrylic acid (MAFA) to mobilize intracellularly bound cadmium in liver and kidney was investigated in rats pre_exposed to cadmium. MFA was effective in reducing cadmium levels of hepatic and renal supernatant cytosolic fraction (SCF) while MSFA and MAFA were effective in lowering cadmium levels of renal SCF and hepatic SCF respectively. All the chelating agents also enhanced the excretion of cadmium more in feces than in urine. However, substitution on the furan ring lowered cadmium mobilizing efficacy of the parent compound, MFA. The treatment with MFA did not affect the status of endogenous zinc and copper while the treatment with MSFA and MAFA enhanced their excretion. MSFA increased hepatic and renal zinc and renal copper while MAFA increased their copper levels.

Antifungal Activity and Toxicity of the 3,4,5-Trihydroxybenzoic and 3,4,5-Tris(Acetyloxy)Benzoic Acids

Invasive fungal infections have been gaining notoriety due to several factors, mainly their increasing incidence in immunocompromised patients. The aim of the present study was to evaluate the antifungal activity and toxicity of the 3,4,5-trihydroxybenzoic acid (3,4,5-THB) and of its derivative, the 3,4,5-tris(acetyloxy)benzoic acid (3,4,5-TAB). The 3,4,5-THB was purchased and its derivative was obtained by purifying and characterizing performed using semisynthesis reactions (esterification), recrystallization, column chromatography and infrared analytical techniques and nuclear magnetic resonance. Minimum inhibitory concentration (MIC) and minimum lethal concentration (MLC) were determined in order to evaluate the antifungal activity of the compounds against four clinical isolates and four standard strains of Candida sp. and five clinical isolates of dermatophytes, following the Clinical and Laboratory Standards Institute protocols. The toxicity of the compounds was evaluated by determining the lethal dosis (LD50) using lethality assay of Artemia salina. The most sensitive yeasts to the 3,4,5-THB were C. albicans ATCC 10231 and C. krusei ATCC 6258, both presenting a MIC of 128 μg·mL-1. For Trichophyton sp. and Epidermophyton floccosum, the MIC was 32 μg·mL-1. The 3,4,5-TAB showed a lower inhibitory activity against Candida and dermatophyte species tested. The LD50 of 3,4,5-THB was 222.60 μg·mL-1 and the 3,4,5-TAB showed 481.69 μg·mL-1 of LD50. In conclusion, the 3,4,5-trihydroxybenzoic acid showed antifungal activity against species of medical importance, mainly dermatophytosis-causing fungi, and the 3,4,5-tris(acetyloxy)benzoic acid showed no increasing antifungal activity and toxicity in relation to the original compound.

Interference of endogenous benzoic acid with the signatures of sulfonic acid derivatives and carbohydrates in fermented dairy products

Endogenous benzoic acid causes detrimental effects on public health,but the underlying mechanisms often remain elusive.Benzoic acid(0.00-40.00 mg L^(−1))was detected from sixty fermented goat milk samples in six replicates,indicating the existence of endogenous benzoic acid.Herein,we investigated the effects of benzoic acid on the variations of metabolome and proteome signatures in fermented goat milk via integrative metabolomics(LOQ 2.39-98.98𝜇g L^(−1))and proteomics approach based on UHPLC-Q-Orbitrap HRMS.Explicitly,benzoic acid reduced the content of taurine(7.06-4.80 mg L^(−1))and hypotaurine(3.86-1.74 mg L^(−1))due to a significant decrease in the levels of glutamate decarboxylase 1 by benzoic acid.The reduction in lactose(7.13-5.31 mg L^(−1))and d-galactose(4.39-3.37 mg L^(−1))content was related to the decrease inβ-lactalbumin and𝛽-galactosidase levels,respectively,in fermented goat milk containing 40.00 mg L^(−1)benzoic acid.Meanwhile,the levels of maltose(22.84-16.53 mg L^(−1))and raffinose(4.19-3.10 mg L^(−1))progressively decreased with increasing benzoic acid concentrations(0.00-40.00 mg L^(−1)),which had detrimental effects on the nutritional quality of fermented goat milk.Additionally,the concentration of benzoic acid and fermentation temperature are the most important factors to control the loss of nutrients in fermented dairy products.

Synthesis of (2S,4S)-2-Substituted-3- (3-Sulfanylpropanoyl)-6- Oxohexahydropyrimidine-4-Carboxylic Acids as Potential Antihypertensive Drugs

Proceeding from natural amino acid L-asparagine and commercially available aldehydes a stereoselective synthesis was developed of (2S,4S)-2-alkyl(aryl)-3-(3-sulfanylpropanoyl)-6-oxohexahy- dropyrimidine-4-carboxylic acids, potential antihypertensive drugs, inhibitors of the angiotensin converting enzyme.

Enhanced Sensitivity and Stability in Gelatin-Based Fricke gel Dosimeters:Impact of Benzoic Acid on Low-Dose Radiation Measurements

Fricke gel dosimetry is a critical technique for accurate radiation dose measurement, leveraging the radiation-induced oxidation of ferrous to ferric ions within a hydrogel matrix. This study aimed to advance the field by preparing and evaluating seventy-one Fricke gel dosimeter(FGD) samples with varying chemical compositions, focusing on the incorporation of benzoic acid. Two gelatin-based samples demonstrated superior sensitivity, particularly for low-dose measurements. Our findings indicated that the sample without benzoic acid exhibited a 1.75 times higher sensitivity compared to the sample containing benzoic acid, with lower limits of detection at 0.04 Gy and 0.1 Gy, respectively. Stability tests revealed temperature-dependent responses, with better performance observed under refrigerated conditions. Reproducibility was confirmed through consistent calibration curves across multiple trials. Additionally, the dosimeters' responses varied with different radiation types, underscoring the need for specific calibrations. The study concludes that while benzoic acid slightly reduces sensitivity, it provides consistent responses across various radiation energies, suggesting its potential as a beneficial additive in diverse clinical scenarios. This research contributes to the ongoing optimization of FGDs for precise radiation dose assessment.

Chemiluminescence Determination of Benzoic Acid Using A Solid-Phase Verdigris Reactor

A new chemiluminescence flow system has been developed for sequential determina-tion of benzoic acid based on the reaction of the compound with copper carbonate entrapped in a solid-phase reactor. It was found that the unsaturated complex of Cu(II) and benzoic acid (1:1) has strong catalytic effect on the luminol-H2O2 chemiluminescence reaction. The calibration graph is linear over the range of 0.025 ~ 60 g/mL of benzoic acid, with a relative standard deviation of less than 3.0 %, and the detection limit is 0.01礸穖L-1. The proposed method was applied to the determination of benzoic acid content in different pharmaceutical formulations.

ATR-FTIR and XPS study on the structure of complexes formed upon the adsorption of simple organic acids on aluminum hydroxide

Information on the binding of organic ligands to metal （hydr）oxide surfaces is useful for understanding the adsorption behaviour of natural organic matter on metal （hydr）oxide. In this study, benzoate and salicylate were employed as the model organic ligands and aluminum hydroxide as the metal hydroxide. The attenuated total reflectance Fourier transform infrared （ATR-FTIR） spectra revealed that the ligands benzoate and salicylate do coordinate directly with the surface of hydrous aluminum hydroxide, thereby forming innersphere surface complexes. It is concluded that when the initial pH is acidic or neutral, monodentate and bridging complexes are to be formed between benzoate and aluminum hydroxide while bridging complexes predominate when the initial pH is alkalic. Monodentate and bridging complexes can be formed at pH 5 while precipitate and bridging complexes are formed at pH 7 when salicylate anions are adsorbed on aluminum hydroxide. The X-ray photoelectron （XP） spectra demonstrated the variation of C 1 s binding energy in the salicyate and phenolic groups before and after adsorption. It implied that the benzoate ligands are adsorbed through the complexation between carboxylate moieties and the aluminum hydroxide surface, while both carboxylate group and phenolic group are involved in the complexation reaction when salicylate is adsorbed onto aluminum hydroxide. The information offered by the XPS confirmed the findings obtained with ATR-FTIR.

PROPERTIES AND THERMODYNAMICS OF ADSORPTION OF BENZOIC ACID ONTO XAD-4 AND A WATER-COMPATIBLE HYPERCROSSLINKED ADSORBENT

The adsorption behavior of benzoic acid onto a water-compatible hypercrosslinked polymeric adsorbent NJ-8 wascompared with that onto macroporous Amberlite XAN-4. This paper focuses on the static equilibrium adsorption behaviors,the adsorption thermodynamics and the column dynamic adsorption profiles. Five isotherm models are used to fit the results.This shows that the Freundlich equation can give a perfect fit. The specific surface area of NJ-8 is about as high as that ofAmberlite XAD-4, but the adsorbing capacity for benzoic acid on NJ-8 is about 14.9%-64.8% higher than that on AmberliteXAD-4, which is attributed to its microporous mechanism and partial polarity. The negative values of the adsorptionenthalpy are indicative of an exothermic process. Both enthalpy and free energy changes of adsorption manifest a physicalsorption process. The negative values of the adsorption entropy indicate that adsorption is well consistent with the restrictedmobilities and the configurations of the adsorbed molecules on the surface of the studied adsorbents with superficialheterogeneity. Both adsorbents were used in mini-column experiments to demonstrate the higher breakthrough adsorbing capacity of the hypercrosslinked polymeric adsorbent NJ-8 to benzoic acid, as compared with that of Amberlite XAD-4.

Effect of manganese and potassium addition on CeO_2-Al_2O_3 catalyst for hydrogenation of benzoic acid to benzaldehyde

A series of Mn/CeO2-Al2O3 and K/CeO2-Al2O3 catalysts for hydrogenation of benzoic acid to benzaldehyde were prepared to in- vestigate the effect of Mn, K addition on CeO2-Al2O3 catalyst. X-ray diffraction (XRD) and H2-temperature-programmed reduction (H2-TPR) results suggested that the interaction between CeO2 and MnOx enhanced the reducibility of catalysts and therefore benzoic acid conversion. The addition of K increased the number of basic number on the catalyst which leads to a high selectivity to benzaldehyde, but excessive addition imposed negative effects on the catalyst performance. A Mn-K/CeO2-Al2O3 catalyst was developed and investigated in the reaction. The simultaneous addition of Mn and K enhanced not only the catalytic activity but also the capacity to resist the coke formation over catalyst.

Synthesis of Pharmaceutical Intermediates by Toluene Benzylation over Heteropoly Acids on Different Support

Selective formation of pharmaceutical intermediates like diphenylmethane, dimethyldiphenylmethane, benzyl toluene and benzoic acid by liquid phase, toluene benzylation with benzyl chloride as a benzylating agent, was systematically studied over plane clay （K-10, montmorillonite）, plane H-Beta, plane MFI structured titanosilicate （TS-1） and heteropoly acids [HPA, namely dodecatungstophosphoric acid [H3PO4.12WOa-xH2O] （TPA）, dodeca-molybdo phosphoric acid ammonium salt hydrate [H12Mo12N3040P＋aq] （DMAA）, sodium tungstate hydrated purified [Na12WO4.2H2O] （STH）] supported on clay, H-beta and TS-1. The 20%TPA/Clay, 30%TPA/H-Beta and 30%TPA/TS-1, were observed to be the best catalyst samples over plane clay, plane H-Beta and plane TS-1. The catalyst samples are compared with respect to benzyl chloride conversion and selectivities for diphenylmethane, dimethyl-diphenylmethane, benzyl toluene and benzoic acid. The reaction follows the pseudo-first order rate power law model. The apparent rate constants are calculated and compared with the reported ones.

1D Lanthanide Coordination Polymers Based on 3-(Pyridin-4-yl)benzoic Acid: Syntheses, Structures and Luminescent Properties

ABSTRACT Four novel 1D lanthanide coordination polymers with formula [Ln（3,4-pybz）3（HzO）2. H2O]n （Ln = 1 Sm; 2 Eu; 3 Tb; 4 Dy, 3,4-Hpybz = 3-（pyridin-4-yl）benzoic acid） have been synthesized by hydrothermal reactions of lanthanide oxide and 3-（pyridine-4-yl） benzoic acid. Single-crystal X-ray diffraction shows that the four compounds are isostructural. They all crystallize in a monoelinic system, space group P1^-. They have a doubly carboxylate-bridged infinite-chain structure with alternating Ln-（carboxylate）2-Ln linkages and one chelating carboxylate group on each metal center. The Ln ion also combines to two water molecules to form an eight-coordinate square antiprismatic geometry. The pyridine nitrogen atoms of the ligand do not coordinate to the metal centers but direct the formation of a 3D network through hydrogen bonding with coordinated water molecules. The photoluminescent properties of 2 and 3 have been also studied.

A New Luminescent Cd(Ⅱ) Coordination Polymer Constructed with 2-(Carboxymethoxy) benzoic Acid

In this work, we synthesized a new Cd（Ⅱ） coordination polymer, [Cd（L）(cmb)H;O]· H;O（1）, by using mixed 2-（carboxymethoxy）benzoic acid（H2 cmb） and typical chelating N-donor ligands 2-（2-fluoro-6-fluorophenyl）-1 H-imidazo[4,5-f][1,10]phenanthroline ligand（L）. 1 crystallizes in monoclinic, space group P21/c with a = 17.6150（8）, b = 9.7811（4）, c = 18.1603（8） ?, β = 118.9150（10）o, V = 2738.9（2） ?;, Z = 4, C28 H20 CdF2 N4 O7, Mr = 674.88, Dc = 1.637 g/cm3, F（000） = 1352, μ（Mo Ka） = 0.865 mm–1, R = 0.0643 and w R = 0.1976. In 1, the cmb2– anions link neighboring Cd（Ⅱ） atoms in a bis-chelating mode, yielding a one-dimensional chain structure along the b axis. The L ligands are attached on one side of the chain through chelating the Cd（Ⅱ） atoms, and are stacked with those of an adjacent chain through π-π interactions to generate a one-dimensional double-chain structure. Furthermore, the one-dimensional double-chains are stacked by C–H???π interactions between the carbon atom of L ligand and the benzene ring of cmb2–ligand to give a layer structure. Moreover, the solid state luminescent property of 1 was also investigated at room temperature.

Crystal Structure, Thermal Behavior and Luminescence of a New Copper Coordination Polymer Constructed with 4-(Carboxymethoxy)-benzoic Acid

A new Cu(Ⅱ) coordination polymer, [Cu(L1)(L2)](1), was synthesized under hydrothermal conditions(H_2L1 = 4-(carboxymethoxy)benzoic acid, L2 = 2-(4-fluorophenyl)-1 H-imidazo[4,5-f][1,10]phenanthroline). Crystallographic data for 1: triclinic, space group P1 with a = 9.750(5), b = 10.148(5), c = 12.869(5) ?, α = 104.904(5), β = 102.133(5), γ = 95.219(5)°, V = 1188.7(10) ?~3, Z = 2, C_(28)H_(17)FN_4O_5Cu, Mr = 572.01, D_c = 1.598 g/cm^3, F(000) = 582, μ(MoKa) = 0.977 mm^(-1), R = 0.0474 and w R = 0.1144. The TGA behaviors and luminescence of 1 have been studied in detail. The L1 dianions link neighboring Cu(Ⅱ) atoms in a bis-chelating mode, yielding a one-dimensional chain structure along the b axis. The L2 ligands are attached on one side of the chain through chelating the Cu(Ⅱ) atoms, and are stacked with those of an adjacent chain through π-π interactions, yielding a layer structure. Additionally, the N–H???O hydrogen bonds further stabilize the structure of 1.