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PubMed1990

Benzoic acid inhibition of the alpha, beta, and gamma isozymes of Agaricus bisporus tyrosinase.

Inhibition of the catecholase and cresolase reactions of the alpha, beta, and gamma isozymes of Agaricus bisporus tyrosinase by benzoic acid was investigated at 25.0 and 8.0 degrees C at pH 5.60 in air-saturated solutions. Benzoic acid is a simple competitive inhibitor of the cresolase reaction of all three isozymes. In the catecholase reaction, however, benzoic acid is a partial uncompetitive inhibitor of the alpha and beta isozymes and a simple competitive inhibitor of gamma-tyrosinase. Equilibrium dialysis experiments, conducted under identical conditions to the kinetic studies, indicate that benzoic acid can bind to the alpha and gamma isozymes in the absence of organic substrate. The dissociation constants obtained by equilibrium dialysis are in good agreement with the kinetic Ki values determined from inhibition studies. Maximum binding of benzoic acid to alpha and gamma tyrosinase, however, is significantly less than one mole per mole of active sites. A scheme in which benzoic acid binds to the oxy-form of tyrosinase is proposed to account for the kinetic and equilibrium results.

Agaricales↗

PubMed2006

Time-dependent conversion of benzyl alcohol to benzaldehyde and benzoic acid in aqueous solutions.

The oxidative reaction: benzyl alcohol-benzaldehyde-benzoic acid was investigated in time in aqueous solutions of benzyl alcohol widely used as a preservative in medicine and cosmetology. The solutions of benzyl alcohol were stored at concentrations from 0.005 to 2.09 mg/ml for a long time under different conditions. The presence of benzaldehyde and benzoic acid in these solutions was controlled by liquid chromatography on silica sorbent in water. The content of benzoic acid and potentially toxic benzaldehyde in solutions depending on the initial concentration of benzyl alcohol, on time, and on storage conditions was evaluated quantitatively.

Anesthetics, Local↗

PubMed1995

Effects of benzoic acid and its analogues on insulin and glucagon secretion in sheep.

The effects of benzoic acid and its analogues on insulin and glucagon secretion were investigated in conscious sheep. Intravenous injections of benzoic acid increased plasma insulin and glucagon concentrations in a dose-dependent manner between 39-1250 mumol/kg, with ED50s for increasing both hormones of about 625 mumol/kg. Various derivatives of benzoic acid (625 mumol/kg) were administered and structure-activity relationships were examined. A single carboxylic group was essential for stimulating insulin and glucagon secretion, since both hormone responses were abolished with compounds in which the carboxylic group was replaced by sulfonic or phosphoric groups, or in which another carboxylic element was introduced (phthalic acids). Most of the compounds which introduced other elements (amino and hydroxy groups, and halogens) onto the benzene ring had an altered stimulating activity. Thus the pancreatic endocrine system can recognize the chemical structure of benzoic acid and its derivatives in detail and induce insulin and glucagon secretion in sheep.

Animals↗

PubMed2004

The antennal benzoic acid receptor cell of the female silk moth Bombyx mori L.: structure-activity relationship studies with halogen substitutes.

Studies on structure-activity relationships were carried out to characterize the response specificity of the benzoic acid cell of the female of the moth Bombyx mori by means of single sensillum electrophysiological recordings. We demonstrated that this cell type responds best to a natural key substance (benzoic acid) and has similar response profiles for less effective compounds, including various halogen substitutes of benzoic acid, benzaldehyde and other derivates of the key compound. Using different halogen substitutes (F, Cl, Br, I), we showed that the cellular response decreases with increasing atomic size of the substitute and that halogen substitutes were most effective in the meta-position. Thus, m-fluor benzoic acid was even more effective than benzoic acid. These results indicate that a critical feature of the stimulus molecule is the inductive effect generated by the halogen substitutes. Increasing the atomic size of the halogen substitute impairs the recognition of the molecule by the receptor cell, possibly due to steric effects. Decreasing the electron density in the aromatic ring improves the receptor response. The benzoic acid receptor cell can be considered as specialist despite not being involved in pheromone detection as it responds maximally to a key substance and has similar response profiles for less effective compounds.

Action Potentials↗

PubMed1991

Mechanism of action of benzoic acid on Zygosaccharomyces bailii: effects on glycolytic metabolite levels, energy production, and intracellular pH.

The effects of benzoic acid in the preservative-resistant yeast Zygosaccharomyces bailii were studied. At concentrations of benzoic acid up to 4 mM, fermentation was stimulated and only low levels of benzoate were accumulated. Near the MIC (10 mM), fermentation was inhibited, ATP levels declined, and benzoate was accumulated to relatively higher levels. Intracellular pH was reduced but not greatly. Changes in the levels of metabolites at different external benzoic acid levels showed that glycolysis was limited at pyruvate kinase and glyceraldehyde dehydrogenase-phosphoglycerate kinase steps. Inhibition of phosphofructokinase and several other glycolytic enzymes was not responsible for the inhibition of fermentation. Instead, the results suggest that the primary action of benzoic acid in Z. bailii is to cause a general energy loss, i.e., ATP depletion.

Adenosine Triphosphate↗

PubMed2005

Adsorption of benzoic acid onto high specific area activated carbon cloth.

The adsorption of benzoic acid from aqueous solution onto high area carbon cloth at different pH values has been studied. Over a period of 125 min the adsorption process was found to follow a first-order kinetics and the rate constants were determined for the adsorption of benzoic acid at pH 2.0, 3.7, 5.3, 9.1, and 11.0. The extents of adsorption and the percentage coverage of carbon cloth surfaces were calculated at 125 min of adsorption. Adsorption isotherms at pH values of 2.0, 3.7, and 11.0 were derived at 25 degrees C. Isotherm data were treated according to Langmuir and Freundlich equations and the parameters of these equations were evaluated by regression analysis. The fit of experimental isotherm data to both equations was good. It was found that both the adsorption rate and the extent of adsorption at 125 min were the highest at pH 3.7 and decreased at higher or lower pH values. The types of interactions governing in the adsorption processes are discussed considering the surface charge and the dissociation of benzoic acid at different pH values.

Adsorption↗

PubMed1979

Protective effect of ketotifen and disodium cromoglycate against bronchoconstriction induced by aspirin, benzoic acid or tartrazine in intolerant asthmatics.

Oral challenge tests with acetylsalicylic acid, tartrazine or benzoic acid were performed in 7 intolerant asthmatic patients after a 3-day treatment with either orally taken ketotifen (1 mg twice daily) or inhaled disodium cromoglycate (20 mg four times daily) at random. Protection was noted with ketotifen in 5, with DSCG in 3 patients. On the evaluation of the mean percentage of the maximum decline in the forced expiratory volume in 1 sec (FEV1) only ketotifen afforded significant protection statistically (p less than 0.05). All the intolerant asthmatics studies showed, as an immunological abnormity, a slight, but significant decrease of the C1-inhibitor levels. Moreover, in three out of these the alpha 1-antitrypsin serum values were under the lower normal range.

Adult↗

PubMed1981

Inhibition of aflatoxin production in groundnut with benzoic acid derivatives and possible toxic effect of their aromatic residues.

Benzoic acid, sodium benzoate, ethyl-rho-aminobenzoate and omicron-hydroxybenzoic acid (salicylic acid) have been found to inhibit mycelial growth and aflatoxin production by A. flavus in groundnut. Benzoic acid (10 mg/g) completely inhibited both mycelial growth and aflatoxin production while sodium benzoate achieved the same result at 24 mg/g of medium. Salicylic acid (20 mg/g) completely inhibited both mycelial growth and aflatoxin in production but ethyl-rho-aminobenzoate inhibited both mycelial growth and aflatoxin production at lower concentrations--3 mg/g of medium for total aflatoxin inhibition and 10 mg/g for complete inhibition of mycelial growth. The results of the possible toxic effects of these aromatic compounds showed that at their effective concentrations they were non-toxic to 1-day-old chicks. Their effects on body and liver weights yielded results similar to the controls. The chicks that were fed aflatoxin-contaminated diets experienced depressed body and liver weights and their livers manifested various pathological changes. Groundnut samples which were supplemented with various concentrations of these aromatic compounds did not give any foul odour. These benzoic acid derivatives could be used, therefore, as fungicides especially against toxigenic A. flavus.

Aflatoxins↗

PubMed2006

Simultaneous determination of sorbic and benzoic acids in food dressing by headspace solid-phase microextraction and gas chromatography.

A facile headspace solid-phase microextraction (HS-SPME) procedure using 85 microm polyacrylate (PA) fiber is presented for the simultaneous determination of preservatives (sorbic and benzoic acids) in food dressing, including Thousand Island Dressing, HellMANN'S Salad Dressing and Tomato Ketchup, by gas chromatography (GC) with flame ionization detector (FID). The method presented preserves the advantages typical of HS-SPME such as simplicity, low intensity of labor, low cost and solvent free. The main factors affecting the HS-SPME process, such as extraction temperature and time, desorption temperature and time, the acidity and salt concentration of the solution, were optimized. Limits of detection (LODs) of the method were 2.00 microg/L for sorbic acid and 1.22 microg/L for benzoic acid. Relative standard deviations (RSDs) for quintuplicate analyses at three concentration levels of 0.10, 2.0 and 20 mg/L ranged between 3.86 and 14.8%. The method also showed good linearity n a range from 0.02 to 40 mg/L with correlation coefficients (R2) of 0.9986 for sorbic acid and 0.9994 for benzoic acid. Recoveries for the two analytes in all the samples tested ranged from 83.44 to 113.2%. Practical applicability was demonstrated through the simultaneous determination of sorbic and benzoic acids in the three complex samples.

Benzoates↗

PubMed2003

Antibacterial activities of phenolic benzaldehydes and benzoic acids against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica.

We evaluated the bactericidal activities of 35 benzaldehydes, 34 benzoic acids, and 1 benzoic acid methyl ester against Campylobacter jejuni, Escherichia coli O157:H7, Listeria monocytogenes, and Salmonella enterica when these compounds were substituted on the benzene ring with 0, 1, 2, or 3 hydroxy (OH) and/or methoxy (OCH3) groups in a pH 7.0 buffer. Dose-response plots were used to determine the percentage of the sample that induced a 50% decrease in CFU after 60 min (BA50). Of the 70 compounds tested, 24 were found to be active against all four pathogens, and additional 4, 10, and 12 were found to be active against three, two, and one of the pathogens, respectively. C. jejuni was approximately 100 times as sensitive as the other three pathogens. The 10 compounds that were most active against the four pathogens (with average BA50 values ranging from 0.026 to 0.166) and are candidates for studies of activity in foods or for disinfections were 2,4,6-trihydroxybenzaldehyde, 2,5-dihydroxybenzaldehyde, 2,3,4-trihydroxybenzaldehyde, 2-hydroxy-5-methoxybenzaldehyde, 2,3-dihydroxybenzaldehyde, 2-hydroxy-3-methoxybenzaldehyde, 4-hydroxy-2,6-dimethoxybenzaldehyde, 2,5-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde. and 2-hydroxybenzaldehyde. Comparison of the chemical structures of the test compounds and their activities revealed that (i) the aldehyde (CHO) group was more active than the carboxyl (COOH) group whether or not OH groups were present; (ii) compounds were most active with trisubstituted OH > disubstituted OH > monosubstituted OH; (iii) for disubstituted derivatives, 2-OH enhanced activities were exhibited by benzaldehyde but not by benzoic acid; (iv) compounds were more active with OH than with OCH3, irrespective of the position of substitution on the benzene ring; (v) compounds with mixed OH and OCH3 groups exhibited variable results, i.e., in some cases OCH3 groups enhanced activity and in other cases they did not; (vi) methoxybenzoic acids were largely inactive; and (vii) gallic acid was 20 times as active against S. enterica at pH 7.0 as it was at pH 3.7, suggesting that the ionization of its OH groups may enhance bactericidal activity.

Anti-Infective Agents↗

PubMed1999

Arieianal, a prenylated benzoic acid from piper arieianum

A new prenylated benzoic acid, arieianal [3,4-dihydroxy-5-(E,E, E-11'-formyl-3',7',15'-trimethylhexadeca-2',6',10', 14'-tetraenyl)benzoic acid, 1], has been isolated from the leaves of Piper arieianum and assigned this structure on the basis of its spectral data.

Journal Article↗

PubMed2000

Purification and characterization of S-adenosyl-L-methionine:benzoic acid carboxyl methyltransferase, the enzyme responsible for biosynthesis of the volatile ester methyl benzoate in flowers of Antirrhinum majus.

S-Adenosyl-L-methionine:benzoic acid carboxyl methyltransferase (BAMT) catalyzes the transfer of the methyl group of S-adenosyl-L-methionine (SAM) to the carboxyl group of benzoic acid to make the volatile ester methyl benzoate, one of the most abundant scent compounds of snapdragon, Antirrhinum majus. The enzyme was purified from upper and lower petal lobes of 5- to 10-day-old snapdragon flowers using DE53 anion exchange, Phenyl-Sepharose 6FF, and Mono-Q chromatography. The purified protein has a pH optimum of 7.5 and is highly specific for benzoic acid, with no activity toward several other naturally occurring substrates such as salicylic acid, cinnamic acid, and their derivatives. The molecular mass values for native and denatured protein were 100 and 49 kDa, respectively, suggesting that the active enzyme is a homodimer. The addition of monovalent cations K+ and NH4+ stimulates BAMT activity by a factor of 2, whereas the addition of Fe2+ and Cu2+ has a strong inhibitory effect. Plant-purified BAMT has Km values of 28 microM and 1.1 mM for SAM and benzoic acid, respectively (87 microM and 1.6 mM, respectively, for plant BAMT expressed in Escherichia coli). Product inhibition studies showed competitive inhibition between SAM and S-adenosyl-L-homocysteine (SAH), with a Ki of 7 microM, and noncompetitive inhibition between benzoic acid and SAH, with a Ki of 14 microM.

Benzoates↗

PubMed1996

Isolation and characterization of a new bacterium carboxylating phenol to benzoic acid under anaerobic conditions.

A consortium of spore-forming bacteria transforming phenol to benzoic acid under anaerobic conditions was treated with antibiotics to eliminate the four Clostridium strains which were shown to be unable to accomplish this reaction in pure culture and coculture. Clostridium ghonii was inhibited by chloramphenicol (10 micrograms/ml), whereas Clostridium hastiforme (strain 3) and Clostridium glycolicum were inhibited by clindamycin (20 micrograms/ml), without the transformation of phenol being affected. Electron microscopic observations of resulting liquid subcultures revealed the presence of two different bacilli: a dominant C hastiforme strain (strain 2) (width, 1 micron) and an unidentified strain 6 (width, 0.6 micron) which was not detected on solid medium. Bacitracin (0.5 U/ml) changed the ratio of the strains in favor of strain 6. C hastiforme 2 was eliminated from this culture by dilution. The isolated strain 6 transformed phenol to benzoic acid and 4-hydroxybenzoic acid to phenol and benzoic acid in the presence of proteose peptone. Both of these activities are inducible. This strain is a gram- variable, flagellated rod with a doubling time of 10 to 11 h in the presence of phenol. It has a cellular fatty acid composition like that of C. hastiforme. However, strain 6 does not hydrolyze gelatin or produce indole. The 16S rRNA sequence of strain 6 was found to be most similar to that of some Clostridium species, with homology ranging from 80 to 86%. Tbe evolutionary relationships of strain 6 to different groups of Clostridium and Clostridium-related species revealed that it does not emerge from any of these groups. Strain 6 most likely belongs to a new species closely related to Clostridium species.

Anaerobiosis↗

PubMed1984

Expanded solubility parameter approach. I: Naphthalene and benzoic acid in individual solvents.

An expanded solubility parameter system was tested in conjunction with the extended Hansen solubility approach and the UNIFAC method to calculate the solubilities of naphthalene and benzoic acid in polar and nonpolar solvents. The expanded parameter system is characterized by delta d for the dispersion force, delta p for dipolar forces, a basic or electron-donor parameter, delta b, and an acidic or electron-acceptor parameter delta a. The correlation between the calculated and observed solubilities of benzoic acid was increased by use of the four-parameter system. An indicator variable was required to bring the solubilities into line in strongly dipolar solvents such as N,N-dimethylformamide. For naphthalene, use of the four-parameter approach proved not to be an improvement over the three-parameter extended Hansen solubility approach. The UNIFAC method was not successful in calculating solubilities of benzoic acid in the 40 polar and nonpolar solvents. A triangular plot of the three Hansen parameters for benzoic acid, p-hydroxybenzoic acid, and methyl p-hydroxybenzoate illustrated the contributions of dispersion, dipolar, and Lewis acid-base (hydrogen bonding) interaction forces among the three benzoic acid compounds and the various classes of solvents. A multiple regression procedure for calculating the four partial solubility parameters of drug solutes was developed.

Benzoates↗

PubMed2004

Benzoic acid, a weak organic acid food preservative, exerts specific effects on intracellular membrane trafficking pathways in Saccharomyces cerevisiae.

Microbial spoilage of food causes losses of up to 40% of all food grown for human consumption worldwide. Yeast growth is a major factor in the spoilage of foods and beverages that are characterized by a high sugar content, low pH, and low water activity, and it is a significant economic problem. While growth of spoilage yeasts such as Zygosaccharomyces bailii and Saccharomyces cerevisiae can usually be retarded by weak organic acid preservatives, the inhibition often requires levels of preservative that are near or greater than the legal limits. We identified a novel synergistic effect of the chemical preservative benzoic acid and nitrogen starvation: while exposure of S. cerevisiae to either benzoic acid or nitrogen starvation is cytostatic under our conditions, the combination of the two treatments is cytocidal and can therefore be used beneficially in food preservation. In yeast, as in all eukaryotic organisms, survival under nitrogen starvation conditions requires a cellular response called macroautophagy. During macroautophagy, cytosolic material is sequestered by intracellular membranes. This material is then targeted for lysosomal degradation and recycled into molecular building blocks, such as amino acids and nucleotides. Macroautophagy is thought to allow cellular physiology to continue in the absence of external resources. Our analyses of the effects of benzoic acid on intracellular membrane trafficking revealed that there was specific inhibition of macroautophagy. The data suggest that the synergism between nitrogen starvation and benzoic acid is the result of inhibition of macroautophagy by benzoic acid and that a mechanistic understanding of this inhibition should be beneficial in the development of novel food preservation technologies.

Autophagy↗

PubMed2006

Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).

The acaricidal activities of paeonol (2'-hydroxy-4'-methoxyacetophenone) and benzoic acid identified in the root bark of tree peony, Paeonia suffruticosa Andrews, against copra mite, Tyrophagus putrescentiae (Schrank), adults were examined using direct contact and vapour phase toxicity bioassays and compared with those of cinnamyl acetate, cinnamyl alcohol and 37 monoterpenoids as well as the acaricides benzyl benzoate, dibutyl phthalate and N,N-diethyl-m-toluamide (DEET). Based on LD(50) values in fabric piece contact toxicity bioassays, the acaricidal activities of benzoic acid (4.80 microg cm(-2)) and paeonol (5.29 microg cm(-2)) were comparable to that of benzyl benzoate (4.46 microg cm(-2)) but more pronounced than those of DEET (30.03 microg cm(-2)) and dibutyl phthalate (25.23 microg cm(-2)). In vapour phase toxicity bioassays, paeonol and benzoic acid were much more effective in closed containers than in open ones, indicating that the effects of these compounds were largely due to action in the vapour phase. As judged by 24 h LD(50) values, (1S)-(-)-verbenone (7.42 mg per disc) was the most toxic fumigant, followed by (1S)-(-)-camphor, (S)-(+)-carvone, (R)-(-)-linalool and (+/-)-camphor (10.45-18.18 mg). Potent fumigant toxicity was also observed with paeonol, (2S,5R)-(-)-menthone, (+/-)-citronellal, benzoic acid, (1S,4R)-(-)-alpha-thujone and (R)-(+)-pulegone (25.10-34.63 mg). Neither benzyl benzoate, DEET nor dibutyl phthalate caused fumigant toxicity. Paeonia root bark-derived materials, particularly paeonol and benzoic acid, as well as the monoterpenoids described, merit further study as potential acaricides or as leads for the control of T. putrescentiae.

Acetophenones↗

PubMed1990

Percutaneous absorption of benzoic acid across human skin. II. Prediction of an in vivo, skin-flap system using in vitro parameters.

The possibility of predicting the behavior of in vivo systems based on physical and chemical parameters determined by in vitro experiments is examined using benzoic acid. The physical and chemical parameters governing percutaneous absorption of benzoic acid--permeability, partition coefficient, and skin thickness--were determined by in vitro experiments as described in Ref. 1. These parameters were used, in combination with benzoic acid elimination kinetics, to predict the results of in vivo experiments using a comprehensive mathematical model. The in vivo system consists of a congenitally athymic (nude) rat with a surgically constructed human skin sandwich (HSSF) flap on which a donor cell is placed. To apply the in vitro parameters to an in vivo system requires a suitable pharmacokinetic model describing distribution and elimination for benzoic acid in the nude rat. Blood concentrations of benzoic acid following a bolus intravenous injection are closely described by a two-compartment open pharmacokinetic model with elimination occurring from only one compartment. The mathematical model of the rat-donor cell system combines this two-compartment model of the rat with a percutaneous absorption model to provide useful estimates of the measured in vivo blood levels. Comparisons of predicted and measured results suggest that the parameters determined by in vitro experimentation can be used to predict the behavior of complex in vivo systems, if a suitable mathematical model is available.

Animals↗

PubMed1989

Relationships between the resistance of yeasts to acetic, propanoic and benzoic acids and to methyl paraben and pH.

Minimum inhibitory concentrations of acetic, propanoic and benzoic acids and methyl paraben were determined at pH 3.50 for 22 isolates of 11 yeast species, differing in their resistance to preservatives. Growth in the presence of benzoic acid enhanced the resistance of yeasts to benzoic and the other weak acid preservatives, but not to methyl paraben. Resistance to acetic, propanoic and benzoic acids was strongly correlated, but was not closely related to resistance to methyl paraben. Minimum pH for growth was not related to resistance to the weak acids. The results suggest that growth in the presence of weak-acid preservatives involves a common resistance mechanism.

Acetates↗