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PubMed1998

Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1,3-dihydroxybenzene) by the denitrifying bacterium Azoarcus anaerobius.

The denitrifying bacterium Azoarcus anaerobius LuFRes1 grows anaerobically with resorcinol (1,3-dihydroxybenzene) as the sole source of carbon and energy. The anaerobic degradation of this compound was investigated in cell extracts. Resorcinol reductase, the key enzyme for resorcinol catabolism in fermenting bacteria, was not present in this organism. Instead, resorcinol was hydroxylated to hydroxyhydroquinone (HHQ; 1,2,4-trihydroxybenzene) with nitrate or K3Fe(CN)6 as the electron acceptor. HHQ was further oxidized with nitrate to 2-hydroxy-1,4-benzoquinone as identified by high-pressure liquid chromatography, UV/visible light spectroscopy, and mass spectroscopy. Average specific activities were 60 mU mg of protein-1 for resorcinol hydroxylation and 150 mU mg of protein-1 for HHQ dehydrogenation. Both activities were found nearly exclusively in the membrane fraction and were only barely detectable in extracts of cells grown with benzoate, indicating that both reactions were specific for resorcinol degradation. These findings suggest a new strategy of anaerobic degradation of aromatic compounds involving oxidative steps for destabilization of the aromatic ring, different from the reductive dearomatization mechanisms described so far.

Anaerobiosis↗
PubMed2006

A case report of fatal oral ingestion of resorcinol.

Resorcinol is a pharmaceutical agent used topically in dermatological treatments for acne, eczema, psoriasis and related skin conditions. Although there are a few studies that indicate chronic toxic effects of resorcinol on humans after topical application, information on the effects of resorcinol in acute poisoning after oral ingestion is limited. Thus, we wish to report the clinical and laboratory findings of a patient who was admitted to our emergency department (ED) after inadvertent oral ingestion of resorcinol and later died, as well as the patient's autopsy findings. The major clinical and laboratory findings were unconsciousness, respiratory failure that required mechanical ventilation, generalized tonic-clonic seizures, leukocytosis and severe metabolic acidosis. In the blood sample taken at the autopsy, a high level of methemoglobin was found. In the serum, resorcinol was revealed by gas chromatography-mass spectrometry. It can be concluded that the basic approach to patients with resorcinol poisoning should include initial stabilization of the patient by supporting the airway, respiration and circulation, and treating complications such as seizures or metabolic acidosis in the ED, as soon as possible after oral ingestion.

Acidosis↗
PubMed1992

A strictly anaerobic nitrate-reducing bacterium growing with resorcinol and other aromatic compounds.

With resorcinol as sole source of energy and organic carbon, two stains of gram-negative, nitrate-reducing bacteria were isolated under strictly anaerobic conditions. Strain LuBRes1 was facultatively anaerobic and catalase- and superoxide dismutase-positive. This strain was affiliated with Alcaligenes denitrificans on the basis of substrate utilization spectrum and peritrichous flagellation. Strain LuFRes1 could grow only under anaerobic conditions with oxidized nitrogen compounds as electron acceptor. Cells were catalase-negative but superoxide dismutase-positive. Since this strain was apparently an obligate nitrate reducer, it could not be grouped with any existing genus. Resorcinol was completely oxidized to CO2 by both strains. Neither an enzyme activity reducing or hydrolyzing the resorcinol molecule, nor an acyl-CoA-synthetase activating resorcylic acids or benzoate was detected in cell-free extracts of cells grown with resorcinol. In dense cell suspensions, both strains produced a compound which was identified as 5-oxo-2-hexenoic acid by mass spectrometric analysis. This would indicate a direct, hydrolytic cleavage of the resorcinol nucleus without initial reduction.

Bacteria, Anaerobic↗
PubMed2006

Kinetic fluorimetric measurement of trace resorcinol in phenol mixtures.

A kinetic spectrofluorimetric method was studied to measure the concentration of trace resorcinol. The proposed method is based on the inhibitory effect of resorcinol on the oxidation of rhodamine B by potassium bromate in the medium of dilute sulfuric acid. The detection limit and linear range of the proposed resorcinol measurement method are 12 microg L(-1) and 24 approximately 280 microg L(-1), respectively. Relative standard derivations of eleven measurements for 80 microg L(-1) and 200 microg L(-1) resorcinol solutions are 2.12% and 1.08%, respectively. The trace of resorcinol can be determined directly by the proposed method without any pre-separation process when phenol and many other phenolic compounds are present.

Bromates↗
PubMed2002

Nematicidal alkylene resorcinols from Lithraea molleoides.

Four new alkylene resorcinols, (Z,Z)-5-(trideca-4,7-dienyl)resorcinol (1), (Z,Z,Z)-5-(trideca-4,7,10-trienyl)resorcinol (2), (Z,Z,E)-5-(trideca-4,7,10-trienyl)resorcinol (3), and (Z)-5-(trideca-4-enyl)resorcinol (4), were isolated from the MeOH-CH(2)Cl(2) extract of Lithraea molleoides. The structures of these compounds were determined by one- and two-dimensional NMR including selective decoupling experiments. In vitro all four compounds showed strong paralyzing effects on the nematode Caenorhabditis elegans at concentrations between 6 and 50 microg/mL, whereas the activity of compounds 1 and 2 against the nematode Trichostrongylus colubriformis was less pronounced and no activity against this nematode was observed for compounds 1-4 in a rodent model.

Alkenes↗
PubMed1976

The benzenediols: catechol, resorcinol and hydroquinone--a review of the industrial toxicology and current industrial exposure limits.

A review of the published industrial toxicology for the benzenediols, catechol, resorcinol and hydroquinone was made to evaluate their proposed or established occupational exposure levels. Acute animal toxicity data for catecholand resorcinol are presented, along with that for phenol because of its analogous signs of illness and intoxication. The comparative acute toxicity data for catechol and phenol are anomalous, but suggest a TLV for catechol similar to that of phenol. The comparative acute toxicity data for resorcinol and phenol clearly show that resorcinol is significantly less toxic than phenol which has a 5 ppm TLV. These data, along with production plant exposures as high as 9.6 ppm without reported effects, suggest an industrial exposure level (TLV) for resorcinol of at least 10 ppm, perhaps 20 ppm or higher. The established 2 mg/M3 TLV for hydroquinone appears to be proper.

Administration, Oral↗
PubMed2004

The oral toxicity of resorcinol during pregnancy: a case report.

Resorcinol (1,3 benzenediol; m-dihydroxybenzene: resorcin) is a pharmaceutical agent used topically in dermatological treatments such as acne and related skin conditions. It could also be used in combination with the other acne treatment agents such as sulphur. It could be very hazardous if taken orally and there are limited reports on its toxic effects in human. The present work aimed to report a resorcinol poisoning case in which resorcinol was taken accidentally by a woman at 30 weeks of pregnancy. The major clinical findings were unconsciousness, drowsiness, and respiratory failure that required mechanical ventilation along with tonic-clonic seizures and hypothermia. In addition, the laboratory findings were leucocytosis, high bilirubin levels, severe metabolic acidosis, and green-colored urine. The fetus was considered dead 24 h after delivery; however, mother's prognosis was well with supportive management. It could be concluded that the basic approach to the patient with resorcinol poisoning should include the initial stabilization of immediate life-threatening problems and elimination of the toxin. This is the first report on resorcinol poisoning in pregnant women, indicating its major clinical and laboratory findings.

Adult↗
PubMed2001

Electrochemical oxidation of resorcinol for wastewater treatment using Ti/TiO2-RuO2-IrO2 electrode.

Electrochemical oxidation of resorcinol for wastewater treatment in the presence of chloride was investigated. Titanium Substrate Insoluble Anode (TSIA) coated with TiO2-RuO2-IrO2 was used as an anode and graphite carbon sheet was used as a cathode. The extent of resorcinol electrochemical oxidation was determined in terms of COD removal. The Box-Behnken second order composite design was used to study the effect of operating parameters such as initial pH, chloride concentration, initial concentration of resorcinol and charge input. The experimental values were in good correlation with predicted values, and the correlation coefficient was found to be good. The effect of current density on resorcinol oxidation, the AOX level during the electrochemical treatment and TOC removal were also studied for selected conditions. It has been observed that the extended electrolysis brings down the AOX concentration to lower levels. The maximum current efficiency was observed at higher resorcinol concentration, higher chloride concentration and increasing current density.

Chlorides↗
PubMed1995

Involvement of phosphorylase kinase inhibition in the effect of resorcinol and proglycosyn on glycogen metabolism in the liver.

The purpose of this study was to identify the mechanism by which proglycosyn and resorcinol decrease the phosphorylase a content and the fructose 2,6-bisphosphate concentration in isolated hepatocytes. The intracellular concentrations of the glucuronide derivatives of proglycosyn and resorcinol have been measured by HPLC in hepatocytes incubated for 5 min or 30 min with different concentrations of these agents. At both times, there was a reciprocal relationship between the phosphorylase a content and the intracellular concentration of the glucuronidated metabolites, half-maximal inactivation being observed at about 2 mumol/g protein and 0.25 mumol/g protein for resorcinylglucuronide and proglycosyn-glucuronide, respectively. Glycogen synthase was not significantly activated by these agents after 5 min but was well activated after 30 min. Preincubation of hepatocytes with 1 mM resorcinol or with 100 microM proglycosyn resulted in a decrease in the rate at which phosphorylase was activated following the addition of glucagon, vasopressin, the protein phosphatase inhibitor calyculin A or the calcium ionophore A 23187, but did not reduce the rate of synthase inactivation. Proglycosynglucuronide and resorcinylglucuronide inhibited phosphorylase kinase in liver Sephadex filtrates, with Ki values of about 0.75 mM and 4 mM, respectively. Preincubation of the filtrates with ATP and cAMP decreased the sensitivity of phosphorylase kinase to resorcinylglucuronide by about fourfold. It is concluded that the effect of resorcinol and proglycosyn on the phosphorylase a content is due, at least partly, to an inhibition of phosphorylase kinase by their glucuronidated metabolites. Resorcinol and proglycosyn caused a parallel decrease in the concentration of fructose 2,6-bisphosphate and of hexose 6-phosphates, without significantly changing the activity of 6-phosphofructo-2-kinase. The decrease in the fructose 2,6-bisphosphate concentration appears therefore to be secondary to the decrease in the hexose 6-phosphate concentration.

Animals↗
PubMed1989

Modification by catechol and resorcinol of upper digestive tract carcinogenesis in rats treated with methyl-N-amylnitrosamine.

Modifying effects of the environmental contaminant catechol, and its isomers resorcinol and hydroquinone, on methyl-N-amylnitrosamine (MNAN)-induced carcinogenesis were studied in male F344 rats. Groups of 15 rats were given three i.p. injections of 25 mg/kg of body weight of MNAN within the initial 2-wk period, and commencing 1 wk thereafter they were administered 0.8% catechol, 0.8% resorcinol, or 0.8% hydroquinone in powdered basal diet or were given basal diet alone for 49 wk. Additional groups of 10 to 15 rats were similarly treated without prior carcinogen exposure. Histological examination after sacrifice at wk 52 revealed that the incidences of tongue papillomas and esophageal squamous cell carcinomas in the groups given MNAN followed by catechol (57.1% and 64.3%) or resorcinol (50% and 58.8%) were significantly higher than those in the carcinogen only controls (9.1, and 0%, respectively). Hydroquinone also enhanced the development of esophageal squamous cell carcinomas but was less active than catechol or resorcinol. The incidence of alveolar hyperplasia in the lungs of the group given MNAN followed by catechol (0%) was, in contrast, significantly reduced as compared to the control value (54.5%). Hydroquinone and resorcinol showed a similar but non-significant tendency. These results indicated that the environmental contaminant, catechol and its isomers, may play a role in the development of human upper gastrointestinal cancer, in addition to exerting modifying effects in other organs.

Animals↗
PubMedDate not supplied

[Multiple effects of resorcinol on thyroid function (author's transl)].

In rats, I.V. injected resorcinol led to a decrease in thyroid radioiodine uptake and labelled iodothyronine/iodotyrosine ratio with no changes in the percent of thyroidal labelled iodide or radioiodine release. When thyroid lobes were incubated in vitro with radioiodine, resorcinol concentrations from 10(-3)M to 10(-6)M gave an increase in the percent of thyroidal labelled iodide and iodotyrosine/iodothyronine ratio. In animals fed 5% resorcinol for 2 weeks we observed an increase in thyroid weight, a decrease in plasma T4, no change in the percent of free T4, a decrease in T4 half life and no significant changes in T3 half life. Thyroidal labelled MIT/DIT and T3/T4 atios increased. Resorcinol, given in diet during 5 days to rats which had a low thyroidal thyroglobulin content after PTU administration for 2 weeks, gave, in comparison with rats fed PTU only, an increase in thyroidal thyroglobulin/DNA ratio and a decrease in thyroidal radioiodine release contrasting with an increase in plasma TSH. These differences did not exist when resorcinol was given for one month.

Administration, Oral↗
PubMed1976

Quantitative determination of resorcinol in presence of phenol.

A simple and accurate method for the quantitative determination of resorcinol in the presence of phenol is reported. The method is based on the formation of indophenol by reacting resorcinol with 2, 6-dibromoquinone-4-chlorimide. The concentration of indophenol can be measured spectrophotometrically. This method is recommended for the determination of resorcinol in resorcinol-phenol-boric acid solution and carbol-fuchsin solution. The decomposition products of resorcinol and phenol, e.g., colored quinones, do not interfere with the assay procedure.

Colorimetry↗
PubMed1986

NTP Toxicology and Carcinogenesis Studies of Diglycidyl Resorcinol Ether (Technical Grade) (CAS No. 101-90-6) In F344/N Rats and B6C3F1 Mice (Gavage Studies).

Diglycidyl resorcinol ether (DGRE), a pale, yellow, translucent, amorphous solid at room temperature, is used as a liquid spray epoxy resin, as a diluent in the production of other epoxy resins used in electrical, tooling, adhesive, and laminating applications, and as a curing agent for polysulfide rubber. Approximately 3,000 workers are exposed to DGRE. The quantity of DGRE produced in the United States is not known. Toxicology and carcinogenesis studies of technical grade diglycidyl resorcinol ether (81% pure) were conducted by administering the chemical in corn oil by gavage to groups of 50 male and 50 female F344/N rats at doses of 25 or 50 mg/kg and to groups of 50 male and female B6C3F1 mice at doses of 50 or 100 mg/kg. A supplemental study of similar design in male and female rats (0 or 12 mg/kg) was started approximately 12 months later because of high mortality in the 50 mg/kg dose groups. Doses were administered five times per week for 103 weeks. Groups of 50 rats and 50 mice of each sex received corn oil by gavage on the same dosing schedule and served as vehicle controls. Throughout most of the primary study, mean body weights of high dose male and female rats and female mice were lower than those of the corresponding vehicle controls. In the supplemental study, body weights of both sexes of the dosed rats were unaffected by administration of DGRE. Survival of dosed rats of each sex in the primary study was dose related and was shorter (P<0.001) than that of the vehicle controls. No high dose male rats and only 1/50 high dose female rats lived to the end of the study. Bronchopneumonia was the most frequent cause of early death among the rats and may have resulted from the animals' aspiration of corn oil containing diglycidyl resorcinol ether. Survival of the dosed male rats in the supplemental study was reduced (P<0.005) when compared to controls. There was no significant difference in survival between dosed and control female rats in the supplemental study. Survival of dosed and control mice was comparable but poorer in females, with 20/50 (40%) of the controls, 13/50 (26%) of the low dose, and 10/50 (20%) of the high dose groups alive at the end of 2 years. These early deaths were due to suppurative and necrotizing inflammation of the reproductive tract, possibly caused by a Klebsiella sp. infection. The incidences of rats and mice with hyperkeratosis and hyperplasia of the forestomach were compound related. For rats and mice of each sex, incidences of animals with squamous cell papillomas, squamous cell carcinomas, or both occurred with statistically significant positive trends and the incidences observed in other organs in dosed groups relative to the controls. An audit of the experimental data was conducted for the 2-year studies of diglycidyl resorcinol ether. No data discrepancies were found that influenced the final interpretations. Under the conditions of these 2-year gavage studies, technical grade diglycidyl resorcinol ether caused hyperkeratosis and hyperplasia of the forestomach in rats and mice. DGRE was carcinogenic for male and female F344/N rats and for male and female B6C3F1 mice, causing both benign and malignant neoplasms of the forestomach. Levels of Evidence of Carcinogenicity: Male Rats: Positive Female Rats: Positive Male Mice: Positive Female Mice: Positive Synonym: DGRE

Journal Article↗
PubMed1977

[Effects of peeling agents (resorcinol, crystalline sulfur, salicylic acid) on the epidermis of guinea pig (author's transl)].

The mode of action of "classical peeling agents" such as resorcinol, crystalline sulfur, and salicylic acid on the epidermis is almost unknown. There are only a few experimental data available. Therefore the effects of resorcinol, crystalline sulfur, and salicylic acid were studied. A 1% and 3% concentration of these chemicals in vaselinum flavum or Unguentum Cordes was applied to the ears and flanks of adult male guinea pigs up to 14 days. Prior to biopsies at various time intervals, 3H-thymidine was injected intradermally. Specimens were paraffin embedded and routinely processed for autoradiographical analysis. The following parameters were assessed: Labelling index (L.I. in %); number of labelled basal cells per unit length of basement membrane; papillomatosis-index; and acanthosis-factor (projection histoplanimetry). The data were statistically analysed. The peeling agents induced a concentration-dependent increase of the L.I., acanthosis, and papillomatosis. Crystalline sulfur caused the most pronounced effect, followed by resorcinol. In contrast salicylic acid caused only a minute acanthosis factor and a slight increase in labelling. The correlation coefficient r of epidermal thickness to the L.I. for all concentrations and peeling agents used reaches the high figure of 0.978 for the ear. The 1% and 3% salicylic acid has a lower acanthosis factor than vaselinum flavum by itself. Preliminary autoradiographical studies in humans with 1% and 10% salicylic acid confirm these data. Salicylic acid counteracts acanthosis. These experiments show that crystalline sulfur and resorcinol have a potent effect on cell proliferation and acanthosis. They peel via proliferation hyperkeratosis. The mode of peeling by salicylic acid must be different, as cell proliferation and acanthosis are barely enhanced. The clinically known "keratolytic" effect of salicylic acid may be due to a direct action on the intercellular cement substance of the horny cells.

Animals↗
PubMed2000

Naphthol- and resorcinol-based azo dyes as metal ion complexants in aqueous biphasic systems.

Aqueous biphasic systems (ABS) are comprised of both a polymer-rich phase (e.g., polyethylene glycol, PEG) and a salt-rich phase [e.g., (NH4)2SO4] such that both phases are 80% water on a molar basis. ABS have demonstrated applications as environmentally-friendly methods to separate relatively hydrophobic anionic species, such as pertechnetate and mercury halide anionic complexes, from high ionic strength solutions although partitioning of hydrated metal ions, such as Fe3+ and actinides, to the PEG-rich phase is negligible without the addition of a metal ion complexant to the system. Four naphthol- or resorcinol-based dyes; 1-(2-pyridylazo)-2-naphthol (PAN), 1-(thiazolylazo)-2-naphthol (TAN), 4-(2-pyridylazo)-resorcinol (PAR) and 4-(2-thiazolylazo)-resorcinol (TAR), each incorporating a naphthol or resorcinol with an ortho azo functional group, have been studied as metal ion extractants in ABS as a function of pH. In the PEG-2000/ (NH4)2SO4 ABS, the distribution ratios of Fe3+, Co2+ and Ni2- were enhanced by several orders of magnitude at high pH in contrast to the behavior of Cs+, Cd2+ and Eu3+ whose partitioning behavior was largely unaffected by the presence of these extractants at any pH. The three extracted metal ions, Fe3+, Co2+ and Ni2+, could be stripped by contact with a fresh salt phase at low pH.

Azo Compounds↗
PubMed2003

PSII inhibitory activity of resorcinolic lipids from Sorghum bicolor.

Resorcinolic lipids were isolated from the root extracts of Sorghum bicolor and identified as 4,6-dimethoxy-2-[(8'Z,11'Z)-8',11',14'-pentadecatriene]resorcinol (4), 4-methoxy-6-ethoxy-2-[(8'Z,11'Z)-8',11',14'-pentadecatriene]resorcinol (5), and 4-hydroxy-6-ethoxy-2-[(10'Z,13'Z)-10',13',16'-heptadecatriene]resorcinol (6). Compounds 4 and 5 inhibited photosynthetic oxygen evolution (IC50 0.09 and 0.20 microM, respectively). Compound 4 could not be enzymatically converted to a quinone, suggesting that the quinone moiety is not required for its photosystem II inhibitory activity. Compounds 5 and 6 are reported for the first time.

Algorithms↗
PubMed2004

Cytotoxicity of resorcinol under short- and long-term exposure in vitro.

Cytotoxicity of resorcinol to 3T3 fibroblast in short- (3 hrs) and long-term (72 hrs or 6 weeks) exposure was investigated. The effects of resorcinol on cell viability (neutral red uptake, NRU assay), mitochondrial function (MTT assay) and total cell protein (Kenacid Blue assay) were estimated. As a model for long-term exposure an INTEGRA CL 6-WELL bioreactor was used. The concentrations of resorcinol producing 20, 50 and 80% inhibition of cell growth in the NRU test were lower than in the MTT test after 3 hrs of exposure. The use of an INTEGRA CL 6-WELL bioreactor allows continuous culturing and exposure to test chemical of cells for several weeks, but the strong adhesiveness of fibroblast and forming aggregates make it difficult to remove them from chambers. Resorcinol in concentration of 1 microg/cm(3) did not decrease the viability of cells to 50% of control in long-term exposure in the bioreactor.

Animals↗
PubMed2003

Resorcinol-formaldehyde resin "Russian Red" endodontic therapy.

Resorcinol-formaldehyde resin is a material used in endodontic therapy in many foreign countries. With immigration to the United States increasing, American dentists need to become familiar with resorcinol-formaldehyde therapy. It contains two potentially toxic components, formaldehyde (liquid) and resorcinol (powder). Zinc oxide or barium sulfate may be used for radiopacity. When 10% sodium hydroxide is added to the mixture, polymerization occurs, which can form a brick-hard red material that has no known solvent. Several variations in technique exist. The catalyst can be mixed in before insertion into the tooth, added after the mixture is inserted, or not used. Providers believe pulp tissue will be fixed and bacteria destroyed apical to the level of resorcinol-formaldehyde resin placement. Canals are frequently not instrumented or obturated to their full length. Few success-failure studies have been published and results are contradictory. Consequently, providers have little guidance regarding when to retreat or for predicting the difficulty of retreatment.

Drug Combinations↗