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PubMed2005

Oxidation of benzoic acid by electrochemically generated Ce(IV).

This paper presents a study of the oxidation of benzoic acid in aqueous solutions by Ce(IV), which functions as an electrogenerated mediator. In this reaction, benzoic acid is oxidized to CO2, and the reaction displayed pseudo-first-order kinetics for the conditions 0.15-0.45 mM Ce(SO4)2, 0.5-3.0 mM benzoic acid, and 0.2 M H2SO4 at 25 degrees C. The k1 values were in the range 0.40 x 10(-4)-0.59 x 10(-4) s(-1) and increased with temperature within the range studied, 25-45 degrees C. The activation parameters for the reaction, deltaH++, deltaG++, and deltaS++, were determined to be 10.5 kcal/mol, 23.3 kcal/mol, and -43 cal/(mol K), respectively. The electrolysis of Ce(III) in a stirred solution at 25 degrees C and with 1.5 V constant potential generated a 96% Ce(IV)-4% Ce(III) distribution in 140 min. The k for the generation of Ce(IV) was 0.0003 s(-1). Electrolysis under similar conditions but with a large excess of benzoic acid in solution produced a steady-state conversion of 87% Ce (IV) and the corresponding k was 0.00027 s(-1). This reduction in k is consistent with the relative magnitudes of the oxidation reactions for Ce(III) and benzoic acid. Correspondingly, the electrolysis of benzoic acid (0.594 mM) in a 0.2 M H2SO4 solution containing 0.25 mM Ce2(SO4)3 was accomplished by applying 1.5 V to the stirred solution at 25 degrees C. The benzoic acid concentration was reduced to 0.026 mM, or by 96%, in 456 h. In this experiment the potential was applied for 3 h and then turned off for 48 h, and the sequence was repeated 8 times.

Benzoic Acid↗

PubMed1998

Interphase Transport of Benzoic Acid in Emulsions.

The kinetics of transport of benzoic acid in triglyceride-in-water emulsions stabilized by Tween 80 was measured by a continuous flow kinetic apparatus. The determination of the liquid-liquid partitioning of the solute in two-phase systems enabled estimation of the retention of benzoic acid by the triglycerides and the micellar solution and calculation of the solute theoretical distribution in emulsions. The initial rates of release of benzoic acid from 2 to 5 mmol m-2 s-1 were found proportional to the initial concentration of benzoic acid in the emulsions. Copyright 1998 Academic Press.

Journal Article↗

PubMed2000

3-hydroxy-3-phenylpropanoic acid is an intermediate in the biosynthesis of benzoic acid and salicylic acid but benzaldehyde is not.

Stable-isotope-labelled (2H6, 18O) 3-hydroxy-3-phenylpropanoic acid, a putative intermediate in the biosynthesis of benzoic acid (BA) and salicylic acid (SA) from cinnamic acid, has been synthesized and administered to cucumber (Cucumis sativus L.) and Nicotiana attenuata (Torrey). Analysis of the products by gas chromatography-mass spectrometry revealed incorporation of labelling into BA and SA, but not into benzaldehyde. In a separate experiment, 3-hydroxy-3-phenylpropanoic acid was found to be a metabolite of phenylalanine, itself the primary metabolic precursor of BA and SA. These data suggest that cinnamic acid chain shortening is probably achieved by beta-oxidation, and that the proposed "non-oxidative" pathway of side-chain degradation does not function in the biosynthesis of BA and SA, in cucumber and N. attenuata.

Benzaldehydes↗

PubMed1984

Determination of benzoic acid in air.

A gas chromatographic method is described for direct determination of free benzoic acid in air samples. Benzoic acid is absorbed from air on Porapak Q packing in the presence of other compounds, thermally desorbed at 240 degrees C with helium flow into a capillary column, and detected with a flame ionization detector. The method is calibrated by injecting benzoic acid standard solutions into the Porapak Q. The method was validated with dynamic standards and recovery yields were good. Benzoic acid levels of 0.1-1.0 ppm (v/v) in air can be determined with sampling volumes of 8-24 L.

Air Pollutants, Occupational↗

PubMedDate not supplied

Liquid chromatographic determination of benzoic acid in orange juice: interlaboratory study.

An interlaboratory study was carried out for the determination of benzoic acid in orange juice by liquid chromatography. The orange juice was fortified with 0.5-10 ppm benzoic acid. Statistical analysis of the results showed that relative reproducibility (RSDR) between laboratories ranged from 6.92 to 15.97% for juice fortified with 1-10 ppm benzoic acid; RSDR was 27.90% for juice fortified with 0.5 ppm benzoic acid. Mean recoveries ranged from 94.5% for 4 ppm benzoic acid to 114% for 0.5 ppm benzoic acid. Total variability increased with increasing fortification level as measured by standard deviation for reproducibility (SR).

Benzoates↗

PubMed2001

Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate.

Benzyl Alcohol is an aromatic alcohol used in a wide variety of cosmetic formulations as a fragrance component, preservative, solvent, and viscosity-decreasing agent. Benzoic Acid is an aromatic acid used in a wide variety of cosmetics as a pH adjuster and preservative. Sodium Benzoate is the sodium salt of Benzoic Acid used as a preservative, also in a wide range of cosmetic product types. Benzyl Alcohol is metabolized to Benzoic Acid, which reacts with glycine and excreted as hippuric acid in the human body. Acceptable daily intakes were established by the World Health Organization at 5 mg/kg for Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate. Benzoic Acid and Sodium Benzoate are generally recognized as safe in foods according to the U.S. Food and Drug Administration. No adverse effects of Benzyl Alcohol were seen in chronic exposure animal studies using rats and mice. Effects of Benzoic Acid and Sodium Benzoate in chronic exposure animal studies were limited to reduced feed intake and reduced growth. Some differences between control and Benzyl Alcohol-treated populations were noted in one reproductive toxicity study using mice, but these were limited to lower maternal body weights and decreased mean litter weights. Another study also noted that fetal weight was decreased compared to controls, but a third study showed no differences between control and Benzyl Alcohol-treated groups. Benzoic Acid was associated with an increased number of resorptions and malformations in hamsters, but there were no reproductive or developmental toxicty findings in studies using mice and rats exposed to Sodium Benzoate, and, likewise, Benzoic Acid was negative in two rat studies. Genotoxicity tests for these ingredients were mostly negative, but there were some assays that were positive. Carcinogenicity studies, however, were negative. Clinical data indicated that these ingredients can produce nonimmunologic contact urticaria and nonimmunologic immediate contact reactions, characterized by the appearance of wheals, erythema, and pruritus. In one study, 5% Benzyl Alcohol elicited a reaction, and in another study, 2% Benzoic Acid did likewise. Benzyl Alcohol, however, was not a sensitizer at 10%, nor was Benzoic Acid a sensitizer at 2%. Recognizing that the nonimmunologic reactions are strictly cutaneous, likely involving a cholinergic mechanism, it was concluded that these ingredients could be used safely at concentrations up to 5%, but that manufacturers should consider the nonimmunologic phenomena when using these ingredients in cosmetic formulations designed for infants and children. Additionally, Benzyl Alcohol was considered safe up to 10% for use in hair dyes. The limited body exposure, the duration of use, and the frequency of use were considered in concluding that the nonimmunologic reactions would not be a concern. Because of the wide variety of product types in which these ingredients may be used, it is likely that inhalation may be a route of exposure. The available safety tests are not considered sufficient to support the safety of these ingredients in formulations where inhalation is a route of exposure. Inhalation toxicity data are needed to complete the safety assessment of these ingredients where inhalation can occur.

Animals↗

PubMed1996

Kinetic evidence for facilitated peritoneal transport of benzoic acid in rats.

To evaluate the dose dependency in apparent peritoneal permeability (Pd) of benzoic acid as a model compound for a monocarboxylic acid transport system, a kinetic model, which involves changes in the volume and osmolality of the dialysate as well as the diffusion and convection of drugs across the peritoneum, was applied. We compared the Pd value of benzoic acid to that of phenobarbital which is a more lipophilic drug than benzoic acid. The concentration-time courses of phenobarbital in both peritoneal cavity and serum after the intraperitoneal administration with various doses were parallel according to dose, whereas those of benzoic acid varied in a dose-dependent manner. Using the values of unbound fraction (Fu), the value of Pd for unbound drugs was estimated. The Pd values of benzoic acid at 20 micrograms mL-1 was three times the value determined at 1000 micrograms mL-1. We suggest that certain facilitated transport systems constitute the mechanism of enhanced peritoneal membrane permeability of benzoic acid.

Animals↗

PubMed2006

Sensitized emission of luminescent lanthanide complexes based on 4-naphthalen-1-yl-benzoic acid derivatives by a charge-transfer process.

The photophysical properties of 4-naphthalen-1-yl-benzoic acid ligands and their Eu(III)-cored complexes were systematically investigated to elucidate the effective energy-transfer pathway in luminescent lanthanide complexes. A series of 4-naphthalen-1-yl-benzoic acid ligands, such as 4-naphthalen-1-yl-benzoic acid (NA-1), 4-[4-(4-methoxyphenyl)-naphthalen-1-yl]-benzoic acid (NA-2), and 4-{4-[4-(4-methoxyphenyl)-naphthalen-1-yl]-benzyloxy}-benzoic acid (NA-3), were synthesized and utilized for the synthesis of their Eu(III)-cored complexes, corresponding to NAC-1, NAC-2, and NAC-3. The fluorescence spectra of NA-1 and NA-2 show large Stokes shifts with increasing solvent polarity. These large Stokes shifts might be dominantly due to the formation of an intramolecular charge transfer (ICT) complex in the excited state. Also, the intensive luminescence of the Eu(III) ions by the photoexcitation of the ligand in NAC-1 and NAC-2 in polar solvents supports that the energy transfer from the ligand to the Eu(III) ion takes place efficiently. In the case of NA-3, which has a -CH2OPh- group that acts as a blocking group, there is no dependence of the fluorescence spectrum on the solvent nature and no luminescence of the Eu(III) ions by the photoexcitation of the ligand, indicating no formation of the ICT state. This can be due to the fact that the formation of the ICT state in NA-3 was prevented because the -OCH2- group acts as a blocking group by interrupting the pi-conjugation between the benzoic acid and the naphthalene unit. From these photophysical studies, we suggest that the ICT state plays a very important role in the energy-transfer pathway from the ligand to the Eu(III) ion. To our best knowledge, this is the first demonstration of sensitized emission of luminescent lanthanide complexes based on 4-naphthalen-1-yl-benzoic acid derivatives by the charge-transfer process.

Journal Article↗

PubMed2001

Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum.

Biosynthesis of benzoic acid from cinnamic acid has been studied in cell cultures of Hypericum androsaemum L. The mechanism underlying side-chain shortening is CoA-dependent and non-beta-oxidative. The enzymes involved are cinnamate:CoA ligase, cinnamoyl-CoA hydratase/lyase and benzaldehyde dehydrogenase. Cinnamate:CoA ligase was separated from benzoate:CoA ligase and 4-coumarate:CoA ligase, which belong to xanthone biosynthesis and general phenylpropanoid metabolism, respectively. Cinnamoyl-CoA hydratase/lyase catalyzes hydration and cleavage of cinnamoyl-CoA to benzaldehyde and acetyl-CoA. Benzaldehyde dehydrogenase finally supplies benzoic acid. In cell cultures of H. androsaemum, benzoic acid is a precursor of xanthones, which accumulate during cell culture growth and after methyl jasmonate treatment. Both the constitutive and the induced accumulations of xanthones were preceded by increases in the activities of all benzoic acid biosynthetic enzymes. Similar changes in activity were observed for phenylalanine ammonia-lyase and the xanthone biosynthetic enzymes benzoate:CoA ligase and benzophenone synthase.

Acetates↗

PubMed2001

ATR-FTIR spectroscopic investigations on the effect of solvents on the permeation of benzoic acid and salicylic acid through silicone membranes.

The effect of a series of alcohols on the permeation of salicylic acid (SA) and benzoic acid (BA) through silicone membrane was evaluated, using Franz-type diffusion cells. Although permeants were applied at the same thermodynamic activity in all vehicles, the resulting fluxes were found to differ significantly. This was a consequence of the interactions between the vehicles and the membrane. The interactions between the vehicles and the membrane were further investigated using ATR-FTIR spectroscopy. With this technique, it was possible to identify two different diffusion processes when the membrane was pre-treated with buffer, whereas one single diffusion process was observed when the membrane was pre-soaked with the vehicle. The technique was successfully used to deconvolute the relative magnitude of partition and diffusion in the permeation process. It was shown that the permeation of both acids was affected by the effect of the vehicles on the diffusion coefficient and the partition coefficient in the silicone membrane. The solubility of the drug in the impregnated membrane was found to be proportional to the saturated solubility in the vehicle used to treat the membrane. The solubility of BA in the impregnated silicone membrane was twice that of SA.

Antifungal Agents↗

PubMed2005

Two new polymorphs of 4-(N,N-dimethylamino)benzoic acid.

Two new polymorphs of 4-(N,N-dimethylamino)benzoic acid, C9H11NO2, resulting from the attempted cocrystallization in ethanol of 4-(N,N-dimethylamino)benzoic acid and a mixture of 3-(N,N-dimethylamino)benzoic acid and 3-(3-pyridyl)-2-pyridone producing one polymorph, and a mixture of 3-(N,N-dimethylamino)benzoic acid and 5-methoxy-3,3'-bipyridine producing the second polymorph, have been crystallographically characterized. The primary intermolecular O-H...O hydrogen bonds generate a dimeric acid-acid motif that is present in all three polymorphs.

Journal Article↗

PubMed1981

[Excessive allergy due to benzoic acid followed by anaphylactic shock. (author's transl)].

The case of a trained chemical worker highly sensitive to benzoic acid is described. He suffered from allergic reactions of increasing intensity while being constantly exposed to benzoic acid during work. After oral exposure to benzoic acid he suffered a severe anaphylactic shock and later on showed similar but milder reactions when eating food containing benzoic acid. No allergic reactions reoccurred avoiding every contact with benzoic acid especially observing a strict benzoic acid-free diet.

Adult↗

PubMed1997

Enzymic method for the spectrophotometric determination of benzoic acid in soy sauce and pickles.

A simple spectrophotometric method for the determination of benzoic acid is described. Benzoic acid is measured enzymically through its reaction with benzoate 4-hydroxylase coupled with NADPH and O2. The entire enzymic procedure required 20 min to complete. The method greatly simplifies the procedure for benzoic acid determination and permits the routine inspection of a number of samples with very little laboratory equipment. The method was compared with HPLC and satisfactory agreement was achieved.

Benzoates↗

PubMed1997

Evaluation of liver function by co-administration methodology using 13C-labelled benzoic acid and hippuric acid coupled with nuclear magnetic resonance spectroscopy.

The amount of hippuric acid synthesized and excreted in the urine after benzoic acid loading (hippuric acid test) is a useful index of liver function. However, the hippuric acid test gives erroneous results in the event of failure of renal excretory function. A new stable isotope co-administration methodology using nuclear magnetic resonance (NMR) spectroscopy has been developed to overcome this defect. [7-(13)C]Benzoic acid and [glycine carbonyl-13C]hippuric acid ([gly-13C]hippuric acid), each 0.4-0.6 mmol kg(-1) were simultaneously administered intravenously as probes to normal or liver-injured rats and the urine was analysed by 100 MHz 13C NMR spectroscopy. Consequently, urinary excretion of [7-(13)C]hippuric acid formed from [7-(13)C]benzoic acid and [gly-13C]hippuric acid was successfully traced with very simple and convenient procedures. The urinary excretion of [7-(13)C]hippuric acid indicated the combined functions of hippuric acid synthesis and renal excretion, whereas that of [gly-13C]hippuric acid was indicative of renal excretion of hippuric acid only. The heights of resonances for C7 of [7-(13)C]hippuric acid and the glycine carbonyl carbon of [gly-13C]hippuric acid were used to calculate the concentrations of labelled hippuric acids. [7-(13)C]Hippuric acid was excreted more slowly than [gly-13C]hippuric acid by both normal and liver-injured rats. The liver-injured rats excreted the labelled hippuric acids more slowly than the normal rats. The kinetic parameters were computed for the individual rats on the basis of Michaelis-Menten elimination for benzoic acid and first-order elimination for hippuric acid. The maximum rates of metabolism (Vmax) (4.8-5.8 micromol min(-1) kg(-1)) and the renal elimination rate constants of hippuric acid (Kre) (0.010-0.021 min(-1)) in the liver-injured rats were lower than those (Vmax 6.7-11.8 micromol min(-1) kg(-1); Kre 0.026-0.045 min(-1)) in the normal rats. These results have demonstrated that liver function can be evaluated from the Vmax value even though the renal function of hippuric acid excretion (Kre) is impaired. Thus the co-administration methodology is feasible and can remove the defect of the previous hippuric acid test. These results could form the basis for a more convenient and reliable hippuric acid test in man.

Animals↗

PubMed2005

Benzoic acid transformation via conjugation with peptides and final fate of conjugates in higher plants.

Transformation of [1(14)C]- and [7(14)C] benzoic acids in sterile seedlings of maize (Zea mays) and pea (Pisum sativum) was studied. The tested labeled compounds were supplied in plants through roots as water solutions. The larger part of the assimilated benzoic acid forms conjugates with low-molecular-weight plant peptides. As a result of hydrolytic cleavage of the conjugation products, initial labeled benzoic acid molecules and unlabeled amino acids are released. It is supposed that conjugation takes place between the benzoic acid carboxyl group and the peptide functional groups. The amino acid composition of the conjugate peptides was determined. After removal of the plants from the labeled benzoic-acids-containing medium, the amount of conjugation products gradually decreases and the process is accompanied by the emission of labeled carbon dioxide, indicating that the conjugation products are degraded and that their radioactive component carbon atoms are then oxidized to carbon dioxide. Parallel to the conjugation reaction, a smaller part of the benzoic acid that entered the plant is transformed via oxidation, as a result of which an aromatic ring is cleaved and the resulting aliphatic fragment is incorporated into regular cell metabolism. The smallest part of the assimilated benzoic acid radiolabel is incorporated into a cell biopolymer fraction. Benzoic acid, of which the radioactive label is detected in the plant subcellular organelles and finally deposited in the vacuoles, affects the cell ultrastructural organization and the activities of the main metabolic enzymes. Intensification of catabolic processes takes place, indicating an energy demand needed for xenobiotic detoxification.

Amino Acids↗

PubMed1992

Quantitative structure-metabolism relationships for substituted benzoic acids in the rat. Computational chemistry, NMR spectroscopy and pattern recognition studies.

An extensive set of computed molecular properties, both steric and electronic, have been calculated using molecular orbital and empirical methods for benzoic acid (1) and a congeneric series of substituted benzoic acids, i.e. 2-, 3- and 4-fluorobenzoic acids (2-4), 2-, 3- and 4-trifluoromethyl benzoic acids (5-7), 2-, 3- and 4-methylbenzoic acids (8-10), 4-amino benzoic acid (11), 2-fluoro-4-trifluoromethyl benzoic acid (12), 4-fluoro-2-trifluoromethyl benzoic acid (13), 3-trifluoromethyl-4-fluorobenzoic acid (14). We have monitored the urinary excretion profiles and determined the metabolic fate of compounds 2-7, 12-14 in the rat using high resolution 1H and 19F NMR spectroscopy. Corresponding data for compounds 1,8-11 are taken from the literature. In all cases phase II glucuronidation or glycine conjugation reactions dominated the metabolism of these compounds. Compounds 5, 7, 12, 13 have ester glucuronides as their major metabolites; the rest primarily form glycine conjugates. Compounds (1-12) have been classified according to their calculated physicochemical properties using pattern recognition methods and principal components maps have been used as a novel type of structure-metabolism diagram. The maps of compounds in the physicochemical property space served to separate the compounds into the two major classes which related to their principal metabolic fate in vivo, namely glucuronidation versus glycine conjugation. Compounds 13 and 14 were used as further probes of the property space, and dominant metabolic fates of glucuronidation and glycine conjugation, respectively, were predicted from the previous "training set map". The metabolic fate of compounds 1-14 can thus be classified according to a simple set of physicochemical rules. Investigation of the physicochemical properties which are important in distinguishing the metabolic fate of the compounds may give insight into key features of the drug-metabolizing enzyme active sites and hence provide information on basic mechanisms of benzoate metabolism.

Animals↗

PubMed2000

Degradation of phenol and benzoic acid in a three-phase fluidized-bed reactor.

Degradation of phenol and benzoic acid was studied in a fluidized-bed reactor (liquid volume 2.17 L) under nonsterile conditions with special emphasis on maximizing the flow through the reactor and investigating reactor performance at fluctuating feeds. Reactor response to substrate pulses was investigated by applying substrate square-wave inputs at a liquid flow of 1.00 L h(-1). A twofold increase of the phenol and benzoic acid feed concentrations for 2.5 h did not lead to accumulation and breakthrough. The cells were able to survive four to fivefold increases of the feed concentration for 1 h without loss of viability, although the phenol pulse lead to phenol accumulation in the reactor. Reactor performance at constantly fluctuating loads was investigated by varying the feed concentrations using sine wave functions. No accumulation of phenol or benzoic acid was observed. Influence of induction was studied using shift experiments. After 35 days of operation (369 hydrodynamic residence times) with phenol as sole substrate (carbon source) the reactor was able to mineralize benzoic acid without any adaptation or lag phase. The capability of phenol degradation, on the other hand, was lost by most cells after only 3 days operation with benzoic acid as the sole substrate. The experiments underline the importance of induction. In order to maximize the flow through the reactor, the liquid flow was increased stepwise while the feed concentrations were reduced correspondingly, keeping the volumetric conversion rates of phenol (0.24 g L(-1) h(-1)) and benzoic acid (0.17 g L(-1) h(-1)) constant. By this means, liquid flow could be increased up to 13.32 L h(-1), which was more than 20-fold higher than the maximum liquid flow achievable in a chemostat using the same conditions.

Benzoic Acid↗

PubMed1977

Effect of p-nitro-substitution on the metabolism of benzoic acid in the Indian fruit bat.

The introduction of a nitro-group at the 4-position of benzoic acid does not alter remarkably the metabolic pattern of benzoic acids in the fruit bat. It is shown here that the Indian fruit bat does not form hippuric acid with nitro benzoic acid, the main conjugate being the glucuronide in addition to other conjugates suspected to be p-amino benzoylglutamic acid and p-nitro benzoylglutamic acid respectively. More unmetabolized nitrobenzoic acid is present in the 24hr. urine than reported for unsubstituted benzoic acid. The Indian fruit bat exhibits an appreciable ability to reduce the nitrogroup in nitrobenzoic acid to the amino compound and to acetylate the amino group to the acetamido compound.

Animals↗