Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Chlorophenols”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 703 records · Page 39Linked to original sources
PubMed1985

Pyrolysis products of PCBs.

Model compound studies which were previously done for impurities and environmental residues of chlorophenols and for wastes of chlorination processes were extended to the impurities and pyrolysis products of polychlorinated biphenyls (PCBs). Model compounds were commercial products or synthesized and their structures proven by spectroscopic methods. These models were used as analytical reference substances in GC/ECD and GC/MS studies of the pyrolyzed PCB samples. In addition to previously known neutral components like polychlorinated dibenzofurans (PCDFs), chlorophenolic substances, especially polychlorophenols (PCPs) and polychlorinated biphenylols (PCB-OHs) were observed as major pyrolysis products of PCBs. Capacitor fires are suggested to produce in many cases chlorophenols which are major toxic hazards to people.

Chromatography, Gas↗
PubMed1992

[Excretion of p-chloroaniline metabolites into urine. Excretion of 2,4-dichloroaniline and p-chloroformanilide].

Previously, we identified by gas chromatography/mass spectrometry (GC/MS) urinary metabolites of p-chloroaniline (p-CA) in a patient with acute p-CA poisoning. Among these metabolites there is a possibility that 2,4-dichloroaniline (2,4-DCA) and p-chloroformanilide (p-CFA) are produced through some unknown metabolic pathways in human. In order to clarify whether 2,4-DCA and p-CFA were produced within the human body or not, an attempt was made to detect these metabolites in the patient's urine samples prepared by various pretreatments, using both GC/MS and high performance liquid chromatograph. In addition, the detection of these metabolites in non-exposed person's urine samples spiked with p-CA and 2-amino-5-chlorophenol was attempted by GC/MS using same the procedures in order to examine whether p-CA and 2-amino-5-chlorophenol excreted as metabolites were further changed to 2,4-DCA or p-CFA in the urine or not. 2,4-DCA was found abundantly in the ethereal extracts from the patient's urine samples hydrolyzed with hydrochloric, sulfuric and nitric acids, but only small amounts from intact urine samples by GC/MS. No 2,4-DCA was detected in the urine samples to which were added p-CA and 2-amino-5-chlorophenol. p-CFA was found in the ethereal samples which were extracted at acidic conditions from the patient's urine samples by GC/MS at the injection port temperature of 250 degrees C of the gas chromatograph, but the p-CFA peak disappeared at the injection port temperature of 150 degrees C.(ABSTRACT TRUNCATED AT 250 WORDS)

Aniline Compounds↗
PubMed2004

Characterization of effects of selected organic substances on decomposition of hydrogen peroxide during Fenton reaction.

This study aims to investigate the effects of selected organic substances on the degradation of hydrogen peroxide during the Fenton reaction. Since the presence of organic substances can strongly affect the mechanism of the Fenton reaction, the information on effects of organic substances on the reaction would be a vital guide to the success of its application to the destruction of organics in wastewater. Several organic compounds having different structures were selected as model pollutants: 4-chlorophenol, 1,4-dioxane, chloroform, a dye (reactive black-5), and EDTA. Oxidation of 4-chlorophenol and reactive black-5 resulted in enormously fast degradation of hydrogen peroxide, while others such as 1,4-dioxane and chloroform showed much slower degradation. These experimental data were compared to simulation results from a computational model based on a simple *OH-driven oxidation model. Modelling results for chloroform and 1,4-dioxane were in relatively good agreement with the experimental data, while those for 4-chlorophenol and reactive black-5 were very different from the experimental data. The results for EDTA showed a different trend to those for other compounds. From these results, classification of organic substances into several sub-groups was tried.

Chelating Agents↗
PubMed1990

[An application of electrochemical detector to dental pharmacology].

The electrochemical detection (ECD) is highly sensitive and can distinguish selectively electrochemically active materials. A sensitive and selective ECD is widely used for high-performance liquid chromatography (HPLC) of phenolic compounds, such as catecholamines, indoleamines and phenolic steroids in biological materials. In the present study, the HPLC/ECD system was applied for the simultaneous determination of various dental drugs, such as phenol, guaiacol, m-cresol, o-chlorophenol, p-chlorophenol, m-chlorophenol, eugenol, pyrogallol and resorcin. As a compromise between sensitivity and stability, the applied voltage was set at 1.2 V vs the reference electrode. These drugs were rapidly and selectively separated on a reversed-phase column using 10 mM acetate buffer (pH 4.0)-methanol (7:3, v/v) as a mobile phase. The detection limits of these drugs were determined to be 0.25 pmol per injection. These results imply that the HPLC/ECD method should be capable of determining these dental drugs with high sensitivity. The ECD was also applied to determine the enzyme activity. A highly sensitive and specific assay for alkaline and acid phosphatases and N-acetyl-beta-glucosaminidase in biological materials, such as plasma, saliva and bone, has been established. Phenol, formed enzymatically from the substrate, was determined by HPLC/ECD. The retention time of phenol was 7 min and no other peaks were observed. The method is rapid and sensitive with a detection limit for phenol of as little as 0.5 pmol. Thus, as little as 0.5 microliters of rat plasma or 10 microliters of human saliva is all that is required for both alkaline and acid phosphatase assays. The assay is accurate and reproducible. Using this assay, alkaline and acid phosphatase activities in human saliva and in rat saliva elicited by pilocarpine and isoproterenol were determined. It will be possible to apply this new assay method to extremely small biological samples. Thus, the application of the HPLC/ECD system to determine dental drugs and enzyme activity with high sensitivity should prove to be of great value in the field of dental pharmacology.

Acid Phosphatase↗
PubMed1999

Maternal occupational exposure to chemical substances and the risk of infants small-for-gestational-age.

BACKGROUND: The association between maternal occupational exposure to specific chemical substances (organic solvents, carbon tetrachloride, herbicides, chlorophenols, polychlorinated biphenyls, aromatic amines, lead and lead compounds, mercury and mercury compounds) and birth of small-for-gestational-age (SGA) infants was evaluated using data from a prospective cohort study of 3,946 pregnant women in West Germany from 1987 to 1988. METHODS: Occupational, medical, and psychosocial information was gathered through a questionnaire from pregnant women who were recruited between 15 and 28 gestational weeks. Exposure to chemical substances at the current workplace was assessed by a job-exposure matrix constructed by Pannett in 1985 and weighted for the number of working hours per week. Women not working at the time of the interview, women with multiple births, and women with stillbirths were excluded from analysis. Data were analyzed using dichotomous and polytomous logistic regression to control for age, smoking status, alcohol consumption, body mass index, and number of former births. RESULTS: The results of the dichotomous logistic regression analysis suggest that leather work might be associated with the birth of infants small-for-gestational-age through exposure to chlorophenols (P = 0.02) and aromatic amines (P = 0.05). In the polytomous logistic regression analysis, only the association between exposure to mercury and growth retardation reached statistical significance (P = 0.02); however, the power of the study is limited. Further adjustment for income, shift work, and heavy physical work had no substantial effect on the results. CONCLUSIONS: These findings suggest that maternal exposure to specific chemicals at work may be a risk factor for the birth of SGA infants.

Adolescent↗
PubMed1985

Degradation of phenolic compounds by the yeast Candida tropicalis HP 15. I. Physiology of growth and substrate utilization.

The yeast Candida tropicalis HP 15 was able to utilize phenol up to concentrations of 2.5 g/l as a sole carbon and energy source. Phenol was metabolized via the beta-ketoadipate pathway by an inducible enzyme system. Besides phenol, resorcinol, quinol, hydroxyquinol, catechol, and to a lesser extend 4-chlorocatechol, protocatechuate, p-cresol, m-chlorophenol, and p-chlorophenol were metabolized by the yeast. A total of 30 aromatic compounds were tested as substrates.

Adipates↗
PubMed2001

Suitability of the trans/cis ratio of unsaturated fatty acids in Pseudomonas putida NCTC 10936 as an indicator of the acute toxicity of chemicals.

This study explored the suitability of using the trans/cis ratio of unsaturated fatty acids as an indicator of the acute toxicity of membrane active hazardous chemicals. The conversion of cis into trans fatty acids in Pseudomonas putida NCTC 10936 in response to 4-chlorophenol and temperature changes was compared with the results from another kind of toxicity test using the same organism, based on the sensitivity of its xylose oxidation-driven ATP synthesis to uncoupling. The response of both indicators is believed to be largely due to changes in the fluidity of the cytoplasmic membrane. However, the electron transport phosphorylation reacted faster and more sensitively to the fluidizing effect of 4-chlorophenol than the isomerization of unsaturated fatty acids. Therefore, measuring the trans/cis ratio does not provide as good early warning signals of acute toxicity as monitoring the response of the electron transport phosphorylation. If used as an indicator of chemostress, with Pseudomonas species as test organisms, the ratio should only be used in conjunction with other parameters reflecting the energetic state of the cells.

Adenosine Triphosphate↗
PubMedDate not supplied

Degradation of polychlorinated phenols by Streptomyces rochei 303.

The strain Streptomyces rochei 303 (VKM Ac-1284D) is capable of utilizing 2-chloro-, 2,4-, 2,6-dichloro- and 2,4,6-trichlorophenols as the sole source of carbon. Its resting cells completely dechlorinated and degraded 2-, 3-chloro-; 2,4-, 2,6-, 2,3-, 2,5-, 3,4-, 3,5-dichloro-; 2,4-, 2,6-dibromo-; 2,4,6-, 2,4,5-, 2,3,4-, 2,3,5-, 2,3,6-trichlorophenols; 2,3,5,6-tetrachloro- and pentachlorophenol. During chlorophenol degradation, a stoichiometric amount of chloride ions was released and chlorohydroquinols were formed as intermediates. In cell-free extracts of S. rochei, the activity of hydroxyquinol 1,2-dioxygenase was found. The enzyme was induced with chlorophenols. Of all so far described strains degrading polychlorophenols, S. rochei 303 utilized a wider range of chlorinated phenols as the sole sourse of carbon and energy.

Biodegradation, Environmental↗
PubMed1996

Anaerobic dechlorination and mineralization of pentachlorophenol and 2,4,6-trichlorophenol by methanogenic pentachlorophenol-degrading granules.

Anaerobic granules developed for the treatment of pentachlorophenol (PCP) completely mineralized 14C-labeled PCP to 14CH4 and 14CO2. Release of chloride ions from PCP was performed by live cells in the granules under anaerobic conditions. No chloride ions were released under aerobic conditions or by autoclaved cells. Addition of sulfate enhanced the initial chloride release rate and accelerated the process of mineralization of 14C-labeled PCP. Addition of molybdate (10 mM) inhibited the chloride release rate and severely inhibited PCP mineralization. This suggests involvement of sulfate-reducing bacteria in PCP dechlorination and mineralization. Addition of 2-bromoethane sulfonate slightly decreased the chloride release rate and completely stopped production of 14CH4 and 14CO2 from [14C]PCP. 2,4,6-trichlorophenol was observed as an intermediate during PCP dechlorination. On the basis of experimental results, dechlorination of 2,4,6-trichlorophanol by the granules was conducted through 2,4-dichlorophenol, 4-chlorophenol or 2-chlorophenol to phenol at pH 7.0-7.2.

Alkanesulfonates↗
PubMed2004

Formation and emission of chloroanisoles as indoor pollutants.

GOAL, SCOPE AND BACKGROUND: Complaints by residents of frame-houses about musty odour in the houses has become an increasing problem within the last years. An additional problem is that the odour is transferred to clothes and skin. The persons themselves do not recognize the smell after a while because of adaptation. Serious social problems are the result. For a long time, the smell was explained to be from mould due to construction-based humidity problems. However, in an increasing number of houses, no indications were found for elevated levels of mould growth. METHODS: Air and material samples were taken from 5 houses, which show typical musty odours, and analysed with respect to chlorophenols and chloroanisoles. Additionally, some samples were analysed for lindane and its metabolites, because lindane was commonly used together with pentachlorophenol (PCP) for wood protection. RESULTS AND DISCUSSION: Meticulous analysis resulted in the identification of chloroanisoles, mainly 2,3,4,6-tetrachloroanisole. These substances are known from corky wines and from contamination of food from pentachlorophenol (PCP) treated pallets and result from microbiological metabolic processes. Pentachlorophenol was commonly used to protect wood from fungi in Germany mainly in the later 60s and 70s. Details of these processes, as well as effective methods to identify chloroanisoles in the problem houses, are described. CONCLUSIONS: Chloroanisoles formed by metabolism of PCP have been well known to contaminate food or wine. Here, they were identified and are probably responsible for the musty odours in the frame houses. Since it is quite clear that these substances were not components of building materials used in the houses, an explanation for chloroanisole formation is proposed. Localized dampness probably favours microbial growth associated with metabolic conversion of chlorophenols to the corresponding chloroanisoles, primarily 2,3,4,6-tetrachloroanisol, which spread throughout the buildings, resulting in the observed odours. RECOMMENDATIONS AND OUTLOOK: The group of chloroanisoles has been recognized as important indoor pollutants as they possess musty odours at extremely low concentrations, e.g. for 2,4,6-trichloroanisole in a range of 5-10 ppt in air (Staples 2000). On the basis of currently available toxicological data, exposure of the occupants to the concentrations of chloroanisoles measured is not associated with a health risk. No correlation could be observed between concentrations of chloroanisoles and PCP in house dust and indoor air. However, chloroanisoles are good indicators for possible PCP-treatment of wood in frame houses and their detection should initiate investigations on PCP contamination. Research is continuing to identify the microorganisms involved and to devise a remediation procedure for affected houses.

Air Pollution, Indoor↗
PubMed2001

Trends of organochlorine compounds in Finnish inland waters. Results of mussel incubation monitoring 1984-1998.

Caged common lake mussels (Anodonta piscinalis) have been used in the monitoring of organochlorine compounds in pulp and paper mill recipient watercourses of Finland annually from 1984 to 1998. Statistically significant decreasing trends of chlorophenols and chloroguaiacols originating from chlorobleaching were observed in all recipients in parallel with the decreasing discharges from the mills. Metabolites of chlorophenols, chloroanisoles and chloroveratroles had no or slightly increasing trends. Elevated PCB concentrations were measured in four watercourses. In two areas, PCBs were found to be significantly increasing, in two other cases they showed no trend. A mill producing recycled paper was apparently responsible for an increase of PCBs and DDE in recipient watercourses. Overall decreases were observed for other chlorohydrocarbons except for DDT. Material flows of chlorohydrocarbons were positively correlated with waterflows (Q) in some cases.

Animals↗
PubMed2004

A novel 2-aminophenol 1,6-dioxygenase involved in the degradation of p-chloronitrobenzene by Comamonas strain CNB-1: purification, properties, genetic cloning and expression in Escherichia coli.

Comamonas strain CNB-1 was isolated from a biological reactor treating wastewater from a p-chloronitrobenzene production factory. Strain CNB-1 used p-chloronitrobenzene as sole source of carbon, nitrogen, and energy. A 2-aminophenol 1,6-dioxygenase was purified from cells of strain CNB-1. The purified 2-aminophenol 1,6-dioxygenase had a native molecular mass of 130 kDa and was composed of alpha- and beta-subunits of 33 and 38 kDa, respectively. This enzyme is different from currently known 2-aminophenol 1,6-dioxygenases in that it: (a) has a higher affinity for 2-amino-5-chlorophenol (K(m)=0.77 microM) than for 2-aminophenol (K(m)=0.89 microM) and (b) utilized protocatechuate as a substrate. These results suggested that 2-amino-5-chlorophenol, an intermediate during p-chloronitrobenzene degradation, is the natural substrate for this enzyme. N-terminal amino acids of the alpha- and beta-subunits were determined to be T-V-V-S-A-F-L-V and M-Q-G-E-I-I-A-E, respectively. A cosmid library was constructed from the total DNA of strain CNB-1 and three clones (BG-1, BG-2, and CG-13) with 2-aminophenol 1,6-dioxygenase activities were obtained. DNA sequencing of clone BG-2 revealed a 15-kb fragment that contained two ORFs, ORF9 and ORF10, with N-terminal amino acid sequences identical to those of the beta- and alpha-subunits, respectively, from the purified 2-aminophenol 1,6-dioxygenase. The enzyme was actively synthesized when the genes coding for the ORF9 and ORF10 were cloned into Escherichia coli.

Amino Acid Sequence↗
PubMed1996

Desulfitobacterium sp. strain PCE1, an anaerobic bacterium that can grow by reductive dechlorination of tetrachloroethene or ortho-chlorinated phenols.

A strictly anaerobic bacterium, strain PCE1, was isolated from a tetrachloroethene-dechlorinating enrichment culture. Cells of the bacterium were motile curved rods, with approximately four lateral flagella. They possessed a gram-positive type of cell wall and contained cytochrome c. Optimum growth occurred at pH 7.2-7.8 and 34-38 degrees C. The organism grew with L-lactate, pyruvate, butyrate, formate, succinate, or ethanol as electron donors, using either tetrachloroethene, 2-chlorophenol, 2,4,6-trichlorophenol, 3-chloro-4-hydroxy-phenylacetate, sulfite, thiosulfate, or fumarate as electron acceptors. Strain PCE1 also grew fermentatively with pyruvate as the sole substrate. L-Lactate and pyruvate were oxidized to acetate. Tetrachloroethene was reductively dechlorinated to trichloroethene and small amounts ( 5%) of cis-1,2-dichloroethene and trans-1,2-dichloroethene. Chlorinated phenolic compounds were dechlorinated specifically at the ortho-position. On the basis of 16S rRNA sequence analysis, the organism was identified as a species within the genus Desulfitobacterium, which until now only contained the chlorophenol-dechlorinating bacterium, Desulfitobacterium dehalogenans.

Bacteria, Anaerobic↗
PubMed1998

Biomarker responses in whitefish (Coregonus lavaretus L. s.l.) experimentally exposed in a large lake receiving effluents from pulp and paper industry.

Physiological and biochemical biomarker responses were studied in juvenile whitefish (Coregonus lavaretus L. s.l.) exposed experimentally to effluent from the forest industry. The large study area (609 km2), Southern Lake Saimaa, in Southeast Finland, receives 330,000 m3 d-1 of biologically and 55,000 m3 d-1 of chemically treated effluents, discharged from two integrated elementary chlorine free (ECF) bleached kraft pulp and paper mills, from one ECF pulp mill, and from one mill producing unbleached pulp and cardboard. The assessment of exposure to effluent discharged from the mills was based on lake water chlorophenolics (CPs) and resin acids (RAs) measured in samples collected from the 22 experimental sites along the area. Despite the low levels of effluent constituents in the lake, they were still accumulated in detectable levels in fish bile, indicating an exposure to the bioactive compounds of effluents. In comparison to the reference area, a two- to four-fold increase in ethoxyresorufin O-deethylase (EROD) activity was observed in whitefish exposed in the vicinity (1-6 km) of all the mills. However, cytochrome P450 1A1 (CYP1A1) gene expression was increased in only one of the receiving areas, indicating higher sensitivity of the EROD activity in the present study. There were no statistically significant correlations between EROD activity and the ambient water concentrations of the CPs, the RAs, or effluent dilution expressed by water sodium concentration. Neither bile chlorophenolics nor bile resin acids showed a significant correlation with EROD. No significant changes in circulating reproductive steroids, 17beta-estradiol and testosterone, in juvenile whitefish were observed. The vitellogenin gene was expressed in the vicinity of the pulp mill discharging the most wood-derived compounds, i.e. resin acids and wood-sterols, including beta-sitosterol. No differences were observed in plasma immunoglobulin M, glucose, or lactate concentrations between the effluent sources.

Animals↗
PubMed1998

Simulation of in situ subsurface biodegradation of polychlorophenols in air-lift percolators.

Air-lift percolator experiments simulated in situ subsurface degradation of 2,4,6-trichlorophenol, 2,3,4,6-tetrachlorophenol and pentachlorophenol, in mixtures and individually, by indigenous microorganisms from a chlorophenol-contaminated aquifer. Inoculation with a chlorophenol(CP)-degrading gram-positive isolate from the CP-contaminated groundwater did not significantly increase CP degradation rates. Feed concentrations of up to 55 mg CP l-1 were degraded. Stable CP degradation was maintained for over 6 months. CP degradation rates up to 54.3 mg l-1 day-1 and effluent concentrations below 40 micrograms CP l-1 were achieved. CP were mineralized as shown by CP reduction, dissolved organic carbon removal and release of inorganic chloride.

Bacteria↗
PubMed1998

Organic halogen removal from chlorinated humic ground water and lake water by nitrifying fluidized-bed biomass characterised by electron microscopy and molecular methods.

The dechlorinating and genotoxicity-removing activities of nitrifying fluidized-bed reactor biomass towards chlorinated organic compounds in water were shown at level below 1 ppm. The removal rates of adsorbable organic halogens were 200 micrograms Cl (g VS day)-1 for chlorinated humic ground water and 50 micrograms Cl (g VS day)-1 for chlorinated lake water when studied in batch mode. In a sequenced batch mode the removal rates [micrograms Cl (g VS day)-1] were 2000 from chlorohumus, 1400-1800 from chlorophenols in chlorinated ground water, and 430-720 from chlorohumus in chlorinated lake water. Genotoxicity was removed to a large extent (60%-80%) from the chlorinated waters upon incubation with nitrifying reactor biomass. 2,6-Di-, 2,4,6-tri and 2,3,4,6-tetrachlorophenols competed with chlorinated water organohalogens for dechlorination. The dechlorination of chlorophenols and chlorohumus required no ammonia and was not prevented by inhibitors of ammonia oxidation, nitrapyrin, parathion, sodium diethyldithiocarbamate, or allylthiourea. Electron microscopical inspection of the biomass showed the dominance of clusters of bacteria resembling known nitrifying species, Nitrosomonas, Nitrobacter, and Nitrosospira. This was supported by polymerase chain reaction amplification of the biomass DNA with four different primers, revealing the presence of 16S rDNA sequences assignable to the same species. The most intensive band obtained with the Nitroso4E primer was shown to be closely related to Nitrosomonas europaea by restriction analysis.

Ammonia↗
PubMed2001

Tetrachloroethylene, trichloroethylene, and chlorinated phenols induce toluene-o-xylene monooxygenase activity in Pseudomonas stutzeri OX1.

Pseudomonas stutzeri OX1 naphthalene-oxidation activity is induced 3.0-fold by tetrachloroethylene (PCE) and 3.1-fold by trichloroethylene (TCE) at 100 microM. With the mutant P. stutzeri M1, which does not express toluene-o-xylene monooxygenase (ToMO, product of the tou operon), no naphthalene-oxidation activity induction by PCE and TCE was found; hence, PCE and TCE induce ToMO of P. stutzeri OX1. The chlorinated phenols 2-, 3-, and 4-chlorophenol induced ToMO expression 0.58-, 0.23- and 0.37-fold, respectively, compared to the direct inducer of the pathway, o-cresol. Using P. putida PaW340 (pPP4062, pFP3028), which has the tou promoter fused to the reporter catechol-2,3-dioxygenase, and the regulator gene touR, it was determined that the tou promoter was induced directly 5.7-, 7.1-, and 5.1-fold for 2-, 3-, and 4-chlorophenol, respectively (compared to an 8.8-fold induction with o-cresol). In addition, it was found that TCE and PCE do not directly induce the tou pathway and that components other than the tou structural and regulatory genes are necessary for induction. Gas chromatography results also showed that 100 microM TCE induced its own degradation (8-9%) in 16 h in P. stutzeri OX1, and all of the stoichiometric chloride from the degraded TCE was detected in solution.

Biodegradation, Environmental↗
PubMed2005

Induction of glutathione S-transferase and glutathione by toxic compounds and elicitors in reed canary grass.

Treatment of read canary grass leaves with phenol, 4-chlorophenol, naphthalic anhydride and phenylethylisothiocyanate increased glutathione S-transferase activity by 1.4-2.4-fold (control 17 U g(-1) DW). Benzothiadiazole, beta-aminobutyric acid and salicylic acid increased activity by 1.3-1.8-fold. Total glutathione pool was increased by the toxic compounds by 1.2-2-fold and by the elicitors 1.4-1.6-fold (control 593 nmol g(-1) DW). Unlike the other compounds, benzothiadiazole and salicylic acid did not decrease the redox state. Benzothiadiazole acted synergistically with chlorophenol on glutathione S-transferase and glutathione levels and counteracted the decrease in redox state caused by the xenobiotic. Reed canary grass thus has a strong potential to neutralize toxic compounds, which may be further enhanced by elicitors.

Aminobutyrates↗