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PubMed1985

Identification by nuclear magnetic resonance and mass spectrometry of a glucuronic acid conjugate of o-hydroxybenzoic acid in normal urine and uremic plasma.

An endogenous compound (included in the fraction of uremic toxins often called the "uremic middle molecules") was separated from plasma of uremic patients and urine from normal persons. As elucidated by mass spectrometry, enzymatic hydrolysis, and 1H, 13C nuclear magnetic resonance, it appears to be a conjugate of o-hydroxybenzoic acid with glucuronic acid. Its presence in urine of healthy subjects indicates its physiological character.

Adult↗
PubMed1977

Psychopharmacological properties of the viminol-p-hydroxybenzoate.

The authors studied the viminol-p-hydroxybenzoate (RN: Dividol) through some psychopharmacological tests, making its comparison with neuroleptic and narcotic drugs, with the principal aim of determining if its analgesic action is correlated with a narcotic or psychotropic activity or both of them. The results are discussed.

Animals↗
PubMed1980

Purification and properties of protocatechuate 3,4-dioxygenase from Chaetomium piluliferum induced with p-hydroxybenzoic acid.

1. Protocatechuate 3,4-dioxygenase (protocatechuate : oxygen 3,4-oxidoreductase, EC 1.13.11.3) was isolated from mycelium of Chaetomium piluliferum induced with p-hydroxybenzoic acid. The enzyme was purified about 80-fold by ammonium sulphate fractionation and DEAE-cellulose and Sephadex G-200 chromatography, and was homogeneous on polyacrylamide-gel electrophoresis. 2. The enzyme showed high substrate specificity; its pH optimum was 7.5-8.0, and molecula weight about 76 000 as determined by filtration on Sephadex G-200. The Michaelis constant for protocatechuic acid was 11.1 microM.

Ascomycota↗
PubMed1998

Utilization of quinate and p-hydroxybenzoate by actinomycetes: key enzymes and taxonomic relevance.

474 strains of the actinomycete genera Streptomyces (including species of the former genera Chainia and Streptoverticillium), Pseudonocardia and Micromonospora were examined for their ability to degrade quinate (Q) and p-hydroxybenzoate (pHB); selected strains were also tested for their capacity to catabolize benzoate (B). Whereas in the case of Q (5-10 g/l of a mineral salts agar medium) the growth response signalizes assimilation, pHB has to be supplied in lower concentration (routinely 0.3 g/l together with small amounts of peptone and yeast extract in liquid broth), and its degradation has to be determined spectrophotometrically. 27% of the streptomycete strains were able to grow with Q, and 57% with pHB. The three strains of "Chainia" that were tested metabolized Q and pHB, but none of the fourty species of "Streptoverticillium" showed this ability. 80% of the 30 strains of Psn. autotrophica grew with Q, and 100% degraded pHB and B. Two of the five Micromonospora strains gave a positive response with pHB, but not with Q.-Toluene treated cells (preincubated with Q, pHB or B, respectively) gave a positive Rothera reaction with protocatechuate or catechol respectively, thus demonstrating that these organisms employed the beta-ketoadipate pathway (orthofission) for the degradation of Q, pHB and B. The assay of five relevant enzymes in cell-free extracts of nine selected organisms showed that in nocardioform actinomycetes (Pseudonocardia, Rhodococcus) all enzymes of the protocatechuate branch of the ketoadipate pathway seem to be induced by beta-ketoadipate as demonstrated here for protocatechuate-3,4-dioxygenase. In contrast, in Streptomyces this enzyme appears to be induced by its substrate, protocatechuate, whereas the regulation of the other enzymes of this pathway remains to be elucidated.

2,4-Dichlorophenoxyacetic Acid↗
PubMed2002

Fast capillary electrochromatographic analysis of parabens and 4-hydroxybenzoic acid in drugs and cosmetics.

A fast capillary electrochromatographic method was developed for the analysis of paraben preservatives in drugs and cosmetics in the presence of their main metabolite and/or impurity, 4-hydroxybenzoic acid. The separation was optimized in a 75 num ID capillary, fully packed with 5 num C18 stationary phase, studying the effects of mobile phase pH and composition (buffer type and organic solvent content). The mobile phase 5 mM ammonium formate, pH 3.0, containing 65% acetonitrile allowed us to obtain the baseline separation of methyl-, ethyl-, propyl-, butyl-, and benzylparabens from a mixture in less than 2.5 min with repeatability and linearity using the short-end injection method (8 cm separation capillary effective length). Under the optimum experimental conditions, the method provided high separation efficiency for parabens, in the range of 129 312-140 325 number of theoretical plates per meter, and analyte quantitation limits (LOQs) in the range of 1.25-2.50 nug/mL. The method was successfully applied to the quantitative analysis of paraben preservatives in pharmaceutical and cosmetic industrial samples with direct injection or after reduced sample pretreatment.

Chromatography, High Pressure Liquid↗
PubMed2002

Toluene bioconversion to p-hydroxybenzoate by fed-batch cultures of recombinant Pseudomonas putida.

A microbial oxidation process for the production of p-hydroxybenzoate (HBA) from toluene is reported. The oxidation reaction was studied in fed-batch fermentations using a recombinant Pseudomonas putida grown on glutamate as the sole carbon and energy source with salicylate and IPTG induction of tmoABCDE, and pchCF and phbz pathway genes, respectively. An average volumetric HBA productivity of 13.4 mg HBA x L(-1) x h(-1) was obtained under rapid growth conditions (glutamate excess), giving an HBA titer of 132 mg x L(-1) after 9.8 h of fermentation. This corresponded to an average specific HBA productivity of 7.2 microg HBA (mg total protein)(-1) x h(-1). In contrast, maximum HBA titers of 35 mg HBA x L(-1) were achieved in 27 h in comparative studies employing glutumate limited fed-batch cultures. A specific productivity of 4.1 microg HBA (mg total protein)(-1) x h(-1) and volumetric productivity of 1.3 mg HBA x L(-1) x h(-1) were calculated for the growth-rate restricted cultures. The differences in HBA production between the two cultures could be correlated to the levels of specific toluene-4-monooxygenase (T4MO) polypeptides. T4MO catalyzes the rate-limiting step in the pathway. Using experimental data, the half-life value of TmoA was calculated to be approximately 28 h. Assuming linear, monomolecular decay of TmoA, a specific degradation constant of 0.025 x h(-1) was calculated, which placed the stability of recombinant TmoA in the range of relatively stable proteins, even in the absence of co-expression of tmoF, the terminal oxidoreductase subunit of T4MO.

Cell Division↗
PubMed1976

The role of 9-hydroxybenzo(a)pyrene in the microsome mediated binding of benzo(a)pyrene to DNA.

A study of the liver microsome-mediated binding to added DNA of the phenol metabolites of benzo(a)pyrene (BP-OH) and of 7,8-dihydro-7,8-dihydroxybenzo(a)pyrene (BP-7,8-diol) suggested that as in the case of BP itself the reaction was catalysed by the enzyme aryl hydrocarbon hydroxylase. The addition of glutathione to the microsomal incubation inhibited the binding of BP and BP-OH more than that of BP-7,8-diol. Analysis by LH20 chromatography of the deoxyribonucleoside products from BP-DNA showed greater inhibition by glutathione of formation of the major product believed to result from further metabolism of BP-OH, than of the product arising by metabolism of BP-7,8-diol. The chromatographic behaviour and fluorescence spectrum of this major product were consistent with its derivation from 9-hydroxybenzo(a)pyrene (BP-9-OH) and furthermore suggested that BP-9-OH-4,5-oxide was the derivative whose reaction with DNA yielded this microsome-mediated BP-DNA product.

Alkylation↗
PubMedDate not supplied

Significance of the detection of esters of p-hydroxybenzoic acid (parabens) in human breast tumours.

This issue of Journal of Applied Toxicology publishes the paper Concentrations of Parabens in Human Breast Tumours by Darbre et al. (2004), which reports that esters of p-hydroxybenzoic acid (parabens) can be detected in samples of tissue from human breast tumours. Breast tumour samples were supplied from 20 patients, in collaboration with the Edinburgh Breast Unit Research Group, and analysed by high-pressure liquid chromatography and tandem mass spectrometry. The parabens are used as antimicrobial preservatives in underarm deodorants and antiperspirants and in a wide range of other consumer products. The parabens also have inherent oestrogenic and other hormone related activity (increased progesterone receptor gene expression). As oestrogen is a major aetiological factor in the growth and development of the majority of human breast cancers, it has been previously suggested by Darbre that parabens and other chemicals in underarm cosmetics may contribute to the rising incidence of breast cancer. The significance of the finding of parabens in tumour samples is discussed here in terms of 1). Darbre et al's study design, 2). what can be inferred from this type of data (and what can not, such as the cause of these tumours), 3). the toxicology of these compounds and 4). the limitations of the existing toxicology database and the need to consider data that is appropriate to human exposures.

Breast Neoplasms↗
PubMedDate not supplied

Molecularly imprinted polymer using-p-hydroxybenzoic acid, p-hydroxyphenylacetic acid and p-hydroxyphenylpropionic acid as templates.

Molecularly imprinted polymers (MIPs) using p-hydroxybenzoic acid (p-HB), p-hydroxyphenylacetic acid (p-HPA) and p-hydroxyphenylpropionic acid (p-HPPA) as templates were synthesized. The performance of the templates and their analogues on polymer-based high performance liquid chromatography (HPLC) columns was studied. The imprinting effect of the MIP using p-HB as template is more obvious than that of MIP using either p-HPA or p-HPPA as template, and the mixture of p-HB and p-HPA can be well separated on the MIP using p-HB as template, but not on the blank. Interestingly, the recognition of MIP (p-HB as the template) to p-HB showed a synergistic effect. The retention factor of p-HB is not the sum of those of phenol and benzoic acid. We also found that the imprinting effect decreased when increasing the concentration of acetic acid in mobile phase. The possible reason is that acetic acid molecules occupied the binding sites of the polymer, thereby decreasing the concentration of binding sites. Furthermore, polymers, which showed specificity to 3,4-dihydroxybenzoic acid, can be prepared with p-HB as template. It is thus possible to synthesize a specific polymer for a compound that is either expensive or unstable by using a structurally similar compound as template.

Acetates↗
PubMed2006

Phase equilibria and thermodynamics of p-hydroxybenzoic acid.

The prevalence of phases and associated solubilities of p-hydroxybenzoic acid have been investigated in methanol, acetonitrile, acetic acid, acetone, water, and ethyl acetate at temperatures from 10 to 50 degrees C. Thermodynamic data was acquired through determination of van't Hoff enthalpy of solution, enthalpy of fusion, and melting temperature. Indications of polymorphic enantiotropy were found primarily through solubility analysis and FTIR-ATR. A comprehensive thermodynamic investigation disclosed correlation between the van't Hoff enthalpy of solution and the solubility in different solvents. A higher solubility is linked to a lower van't Hoff enthalpy of solution. A thermodynamic analysis to discriminate between different solid phases is presented.

Acetates↗
PubMed1987

Determination of partial and total cohesion parameters of caffeine, theophylline, and methyl p-hydroxybenzoate by gas-solid chromatography.

For the first time, the total and partial solubility parameters, delta t, delta d, and delta s, of caffeine, theophylline, and methyl p-hydroxybenzoate were obtained by gas-solid chromatography (from the adsorption internal energy), by using the Keller, Karger, and Snyder equation. In comparison with the solubilization techniques, this method has the advantage of giving single solubility parameter values. The experimental work has been reduced to a minimum by the optimization of the matrix of experiments, according to the D-criterion, without any diminution in the quality of the results.

Caffeine↗
PubMed1993

4-Hydroxybenzoate uptake in Klebsiella pneumoniae is driven by electrical potential.

The uptake of 4-hydroxybenzoic acid (4-HBA) in intact cells of a mutant of Klebsiella pneumoniae was investigated. Uptake of 4-HBA was shown to be an inducible system. This uptake system, at pH 7.0, has a high affinity for its substrate (apparent Kt = 13 microM) and a maximal velocity of 27.6 nmol min-1 mg protein-1. Competition studies with various structural analogs indicated a very narrow specificity of the 4-HBA uptake system. The transport system has been inhibited by inhibitors of energy metabolism and its activity has not been detected in the crude shock extracts. The effect of two ionophores, nigericin and valinomycin, on 4-HBA uptake with respect to the external pH has been studied. All observations indicate that 4-HBA uptake is active and energized by the membrane potential.

Benzoates↗
PubMed1997

Estrogenic effects of p-hydroxybenzoic acid in CD1 mice.

Xenobiotic estrogens in the environment or diet have received much attention as a possible source of certain hormonal disease states in human and wildlife. Therefore, the detection of estrogenic activity of any substance, especially those related to the food industry, is important. The estrogenic activity of p-hydroxybenzoic acid (PHBA), a compound related to a commonly used group of preservatives in food, cosmetic, and pharmaceutical preparations, was evaluated with immature and adult ovariectomized female mice (CD1) using two well-known bioassays. Subcutaneous administrations (s.c.) of different doses of PHBA were compared with estradiol (E2), and their effects on vaginal cornification and uterotrophic activities were evaluated. Different groups of animals were treated s.c. daily for 3 days with vehicle (corn oil, 0.3 ml/100 g), E2 (1 microgram/100 g), and PHBA (0.5, 5, 50, and 500 micrograms/100 g). Four days after treatment, PHBA produced a dose-dependent response on vaginal cornification and uterotrophic activity in both immature and adult ovariectomized mice. The relative uterotrophic potency of PHBA (500 micrograms/100 g) to E2 (1 microgram/100 g) was 0.0011 in immature mice and 0.0018 in ovariectomized animals.

Animals↗
PubMed2002

Thermodynamic properties of the aqueous solution of potassium salts of some 4-((alkylcarbonyl)amino)-2-hydroxybenzoic acids at 298 and 313 K.

To understand the aggregation behavior of surface-active ligands with a salycilic polar head, we undertook a systematic study of some classes of anionic surfactants where the presence and the position of the -OH and the carboxylic group differ. This paper reports the dilution heats at 298 and 313 K of aqueous solutions of potassium 4-((alkylcarbonyl)amino)-2-hydroxybenzoate (KPAS-C(n) where n stands for the number of carbon atoms in the chain) in KOH at 0.1 m, measured as a function of concentration. From the experimental data, apparent and partial molar enthalpies vs concentration were obtained. By using a pseudo-phase-transition approach, the enthalpy changes upon micelle formation (DeltaH(m)) and assuming that in the restricted range of temperature examined heat capacities are constant, the heat capacity changes have been obtained. Micelle formation enthalpies are seen to be additive with a group contribution for the methylene group of -1.5+/-0.1 kJ mol(-1) per group at 298 K and -2.3+/-0.1 kJ mol(-1) per group at 313 K, comparable with that obtained for similar anionic compounds in the same experimental conditions and for N-alkylnicotinamide chlorides (cationic surfactants). The -CH(2)- group contribution to the micelle formation heat capacities is -53+/-1 J K(-1) mol(-1).

Journal Article↗
PubMed1993

Complete oxidation of benzoate and 4-hydroxybenzoate by a new sulfate-reducing bacterium resembling Desulfoarculus.

A new sulfate-reducer "strain SAX" was isolated from an anaerobic marine sediment [Saxild, Denmark]. The isolate was a gram-negative, motile and non-spore-forming rod which sometimes appeared as a curved rod. Strain SAX differed from all described Desulfovibrio-, Desulfobotulus- and Desulfoarculus-species by the ability to degrade aromatic compounds such as benzoate, 4-hydroxybenzoate and phenol completely to CO2. Electron donors used included lactate, pyruvate, malate, fumarate, crotonate and butyrate, while pyruvate was fermented in the absence of an external electron acceptor. Sulfate, thiosulfate or sulfite served as electron acceptors with benzoate as the donor, while nitrate and nitrite did not. The sulfate-reducing bacterium required vitamins and NaCl-concentrations of about 20 g/l. The optimum temperature for growth of strain SAX was 30 degrees C and the optimum pH value was 7.3. The DNA base composition was 62.4 mol% G+C. The strain possessed cytochrome c3, but no desulfoviridin. On the basis of these characteristics and because strain SAX could not be ascribed to any of the existing species therefore assignment as a new species to the genus Desulfoarculus was suggested.

Benzoates↗
PubMed1994

On the origins and functions of the enzymes of the 4-chlorobenzoate to 4-hydroxybenzoate converting pathway.

This review examines the enzymes of 4-chlorobenzoate to 4-hydroxybenzoate converting pathway found in certain soil bacteria. This pathway consists of three enzymes: 4-chlorobenzoate: Coenzyme A ligase, 4-chlorobenzoyl-Coenzyme A dehalogenase and 4-hydroxybenzoyl-Coenzyme A thioesterase. Recent progress made in the cloning and expression of the pathway genes from assorted bacterial strains is described. Gene order and sequence found among these strains are compared to reveal independent enzyme recruitment strategies. Sequence alignments made between the Pseudomonas sp. strain CBS3 4-chlorobenzoate pathway enzymes and structurally related proteins contained within the protein sequence data banks suggest possible origins in preexisting beta-oxidation pathways. The purification and characterization of the physical and kinetic properties of the pathway enzymes are described. Where possible a comparison of these properties between like enzymes from different bacterial sources are made.

Amino Acid Sequence↗
PubMed1996

Pentachlorophenol enhances 9-hydroxybenzo [a] pyrene-induced hepatic DNA adduct formation in vivo and inhibits microsomal epoxide hydrolase and glutathione S-transferase activities in vitro: likely inhibition of epoxide detoxication by pentachlorophenol.

We recently reported that co-administration to female mice of tamoxifen or 4-hydroxytamoxifen (4-OH-tamoxifen) with pentachlorophenol (PCP), but not with 2,6-dichloro-4-nitrophenol (DNCP) results in strong intensification of a specific subgroup, termed group I, of tamoxifen-DNA adducts in female mouse liver. As both PCP and DCNP are sulfotransferase inhibitors, we concluded that the intensification of tamoxifen group I adducts is probably not due to inhibition of sulfation by these phenols of a tamoxifen metabolite. Since epoxide derivatives of 4-OH-tamoxifen are potential candidates involved in tamoxifen-induced DNA damage, the hypothesis was developed and tested that PCP inhibits epoxide detoxication. As 4-OH-tamoxifen metabolites were unavailable to us, we employed indirect approaches to test this hypothesis. In the first set of experiments we determined whether PCP would augment DNA adduct formation from the benzo[a]pyrene metabolite, 9-hydroxybenzo[a]pyrene (9-OH-BP), as 9-OH-BP-4,5-epoxide is known to be involved in the metabolic activation of this compound. Female mice were given a single i.p. dose of 9-OH-BP (50 mumol/kg) either alone or in combination with PCP (75 mumol/kg), and hepatic DNA adducts were measured 24 h later by nuclease P1-enhanced bisphosphate 32P-postlabeling. Co-administration of PCP with 9-OH-BP resulted in a statistically significant 1.5- to 1.7-fold increase in 9-OH-BP adduct levels versus 9-OH-BP controls. In order to determine whether PCP inhibits the enzymatic detoxication of epoxides in vitro, in a second set of experiments, the effects of PCP on liver microsomal epoxide hydrolase (mEH) and purified equine liver glutathione S-transferase (GST) activities were studied using, respectively, styrene-7,8-oxide and 1-chloro-2,4-dinitrobenzene (CDNB) as substrates. Incubation of mouse liver microsomes with PCP (10-100 microM) strongly inhibited (by 21-97%) mEH activity in a dose-dependent manner, the IC50 being 35 microM. DCNP was ineffective as a mEH inactivator. PCP also inhibited purified equine liver GST activity, with an IC50 of 23.5 microM. Taken together, the results of this study strongly support the hypothesis that PCP inhibited enzymatic detoxication of epoxides in vivo and in vitro. By this mechanism PCP would lead to enhancement of DNA damage caused by 9-OH-BP, and possibly other drugs and their metabolites, which undergo epoxidation prior to DNA binding.

Animals↗
PubMed2002

4-Hydroxybenzoate uptake in Klebsiella planticola strain DSZ1 is driven by DeltapH.

Klebsiella planticola strain DSZ1 has the ability to degrade different aromatic compounds such as benzoate and organochlorinated as propachlor and alachlor. DSZ1 strain cells mineralised 4-hydroxybenzoate (4HBA) through a meta-cleavage pathway, yielding protocatechuate as dihydroxylated intermediate, with a specific rate of CO2 formation 0.12 x 10-6 (cpm/OD) h-1, and a rate of 4-HBA utilisation of 0.75 mmol h-1. Aerobically the 4HBA transport system is driven by gradient of protons (DeltapH), but is not ATP-driven. Under anaerobic conditions, the system can use the nitrate reduction as a final electron acceptor in respiration. A kinetic analysis of the 4HBA transport system revealed a Kt value of 16 microM with a Vmax value of 25 nmol/min.mg at pH 7.

Adenosine Triphosphate↗