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| Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns.
Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. |
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Read full article at Wikipedia
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| InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H |
| ISWSIDIOOBJBQZ-UHFFFAOYSA-N |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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disinfectant
An antimicrobial agent that is applied to non-living objects to destroy harmful microorganisms or to inhibit their activity.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
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antiseptic drug
A substance used locally on humans and other animals to destroy harmful microorganisms or to inhibit their activity (cf. disinfectants, which destroy microorganisms found on non-living objects, and antibiotics, which can be transported through the lymphatic system to destroy bacteria within the body).
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View more via ChEBI Ontology
acide carbolique
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NIST Chemistry WebBook
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acide phénique
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ChEBI
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Benzenol
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KEGG COMPOUND
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carbolic acid
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NIST Chemistry WebBook
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Carbolsäure
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ChEBI
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Hydroxybenzene
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KEGG COMPOUND
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Karbolsäure
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ChEBI
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Oxybenzene
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HMDB
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Phenic acid
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KEGG COMPOUND
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Phenic acid
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HMDB
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Phenol
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KEGG COMPOUND
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PHENOL
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PDBeChem
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phenol
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UniProt
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phénol
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ChEBI
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Phenylic acid
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KEGG COMPOUND
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Phenylic alcohol
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HMDB
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PhOH
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ChemIDplus
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4266
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DrugCentral
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C00002664
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KNApSAcK
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C00146
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KEGG COMPOUND
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c0128
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UM-BBD
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C15584
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KEGG COMPOUND
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D00033
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KEGG DRUG
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D06536
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KEGG DRUG
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DB03255
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DrugBank
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HMDB0000228
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HMDB
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IPH
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PDBeChem
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Phenol
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Wikipedia
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| View more database links |
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108-95-2
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CAS Registry Number
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NIST Chemistry WebBook
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108-95-2
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CAS Registry Number
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ChemIDplus
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2794
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Gmelin Registry Number
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Gmelin
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969616
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Reaxys Registry Number
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Reaxys
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Lu D, Zhang Y, Niu S, Wang L, Lin S, Wang C, Ye W, Yan C (2012)
Study of phenol biodegradation using Bacillus amyloliquefaciens strain WJDB-1 immobilized in alginate-chitosan-alginate (ACA) microcapsules by electrochemical method.
Biodegradation 23, 209-219 [PubMed:21809019]
[show Abstract]
An aerobic microorganism with an ability to utilize phenol as sole carbon and energy source was isolated from phenol-contaminated wastewater samples. The isolate was identified as Bacillus amyloliquefaciens strain WJDB-1 based on morphological, physiological, and biochemical characteristics, and 16S rDNA sequence analysis. Strain WJDB-1 immobilized in alginate-chitosan-alginate (ACA) microcapsules could degrade 200 mg/l phenol completely within 36 h. The concentration of phenol was determined using differential pulse voltammetry (DPV) at glassy carbon electrode (GCE) with a linear relationship between peak current and phenol concentration ranging from 2.0 to 20.0 mg/l. Cells immobilized in ACA microcapsules were found to be superior to the free suspended ones in terms of improving the tolerance to the environmental loadings. The optimal conditions to prepare microcapsules for achieving higher phenol degradation rate were investigated by changing the concentrations of sodium alginate, calcium chloride, and chitosan. Furthermore, the efficiency of phenol degradation was optimized by adjusting various processing parameters, such as the number of microcapsules, pH value, temperature, and the initial concentration of phenol. This microorganism has the potential for the efficient treatment of organic pollutants in wastewater. | González PS, Maglione GA, Giordana M, Paisio CE, Talano MA, Agostini E (2012)
Evaluation of phenol detoxification by Brassica napus hairy roots, using Allium cepa test.
Environmental science and pollution research international 19, 482-491 [PubMed:21822930]
[show Abstract]
IntroductionMeristematic mitotic cells of Allium cepa constitute an adequate material for cytotoxicity and genotoxicity evaluation of environmental pollutants, such as phenol, which is a contaminant frequently found in several industrial effluents.Results and discussionIn the present work, Brassica napus hairy roots (HR) were used for phenol removal assays. The toxicity of post-removal solutions (PRS) and phenol solutions was analyzed. These HR removed the contaminant with high efficiency (100-80% for phenol solutions containing 10-250 mg/L, respectively). Phenol solutions treated with B. napus HR showed a significant reduction of general toxicity compared to untreated phenol solutions, since the IC50 values were 318.39 and 229.02 mg/L, respectively. Moreover, PRS presented lower cytotoxicity and genotoxicity than that found in phenol solutions untreated. The mitotic index (MI) observed in meristematic cells treated with PRS (100 and 250 mg/L of phenol) showed an increase of 35% and 42%, whereas the chromosome aberrations showed a significant decrease. According to these results, B. napus HR cultures could be used for the treatment of solutions contaminated with phenol, since we observed not only high removal efficiency, but also an important reduction of the general toxicity, cytotoxicity, and genotoxicity. | Becerro de Bengoa Vallejo R, Losa Iglesias ME, Jules KT, Trepal MJ (2012)
Renal excretion of phenol from physicians after nail matrix phenolization: an observational prospective study.
Journal of the European Academy of Dermatology and Venereology : JEADV 26, 344-347 [PubMed:21492257]
[show Abstract]
BackgroundAnimal studies have shown that many signs of acute poisoning result from phenol entry into the systemic circulation by absorption or ingestion. While no evidence of systemic complications in patients who have undergone phenol nail matrixectomies have been reported, the safety of phenol vapour inhalation by physicians performing this treatment has yet to be investigated.ObjectiveThe goal of this study was to determine whether the levels of phenol to which physicians are exposed to during a phenol-based matrixectomy procedure are within the limits of safe exposure.MethodsA continuous prospective study was carried out to measure the urinary phenol concentrations from physicians after performing chemical matrixectomy for ingrown toenails.ResultsThe highest concentration of urinary phenol was measured at almost 10 mg/L within the first 2 h after exposure, and subsequently decreased approximately 1 mg/L every 2 h for the first 10 h post exposure. The levels dropped to 3 mg/L at 72 h post exposure.ConclusionsThe risk associated with phenol exposure while performing chemical phenol matrixectomy was well below the current safety limits when the physician is exposed to 90% phenol vapour for approximately 20 min. Thus, no further specific safety recommendations are required for physicians performing this procedure. | Christen P, Davidson S, Combet-Blanc Y, Auria R (2011)
Phenol biodegradation by the thermoacidophilic archaeon Sulfolobus solfataricus 98/2 in a fed-batch bioreactor.
Biodegradation 22, 475-484 [PubMed:20886261]
[show Abstract]
Toxic at low concentrations, phenol is one of the most common organic pollutants in air and water. In this work, phenol biodegradation was studied in extreme conditions (80°C, pH = 3.2) in a 2.7 l bioreactor with the thermoacidophilic archaeon Sulfolobus solfataricus 98/2. The strain was first acclimatized to phenol on a mixture of glucose (2000 mg l(-1)) and phenol (94 mg l(-1)) at a constant dissolved oxygen concentration of 1.5 mg l(-1). After a short lag-phase, only glucose was consumed. Phenol degradation then began while glucose was still present in the reactor. When glucose was exhausted, phenol was used for respiration and then for biomass build-up. After several batch runs (phenol < 365 mg l(-1)), specific growth rate (μ(X)) was 0.034 ± 0.001 h(-1), specific phenol degradation rate (q(P)) was 57.5 ± 2 mg g(-1) h(-1), biomass yield (Y(X/P)) was 52.2 ± 1.1 g mol(-1), and oxygen yield factor (Y(X/O2)) was 9.2 ± 0.2 g mol(-1). A carbon recovery close to 100% suggested that phenol was exclusively transformed into biomass (35%) and CO(2) (65%). Molar phenol oxidation constant (Y(O2/P)) was calculated from stoichiometry of phenol oxidation and introducing experimental biomass and CO(2) conversion yields on phenol, leading to values varying between 4.78 and 5.22 mol mol(-1). Respiratory quotient was about 0.84 mol mol(-1), very close to theoretical value (0.87 mol mol(-1)). Carbon dioxide production, oxygen demand and redox potential, monitored on-line, were good indicators of growth, substrate consumption and exhaustion, and can therefore be usefully employed for industrial phenol bioremediation in extreme environments. | Wang Y, Song J, Zhao W, He X, Chen J, Xiao M (2011)
In situ degradation of phenol and promotion of plant growth in contaminated environments by a single Pseudomonas aeruginosa strain.
Journal of hazardous materials 192, 354-360 [PubMed:21689881]
[show Abstract]
For bioremediation of contaminated environments, a bacterial strain, SZH16, was isolated and found to reduce phenol concentration in a selective medium. Using the reaction vessel containing the soil mixed with phenol and bacteria, we found that the single strain degraded efficiently the phenol level in soil samples. The strain was identified as Pseudomonas aeruginosa on the basis of biochemical tests and by comparison of 16S rDNA sequences, and phosphate solubilization and IAA production were not observed in the strain. Simultaneous examination of the role of strain SZH16 in the plant growth and phenol biodegradation was performed. Results showed that inoculation of the single strain in the phenol-spiked soil resulted in corn growth promotion and in situ phenol degradation and the increase in plant biomass correlated with the decrease in phenol content. Colonization experiments showed that the population of the SZH16 strain remained relatively constant. All these findings indicated that the corn growth promotion might be due to reduction in phytotoxicity, a result of phenol biodegradation by the single strain SZH16. Furthermore, the strain was found to stimulate corn growth and reduce phenol concentration simultaneously in phenol-containing water, and even historically contaminated field soils. It is attractive for environment remediation and agronomic applications. | Zhao Z, He X, Bi Y, Xia Y, Tao N, Li L, Ma Q (2009)
Induction of CYP4F3 by benzene metabolites in human white blood cells in vivo in human promyelocytic leukemic cell lines and ex vivo in human blood neutrophils.
Drug metabolism and disposition: the biological fate of chemicals 37, 282-291 [PubMed:19029204]
[show Abstract]
Exposure to benzene elicits a spectrum of hematotoxicity ranging from reduction of peripheral blood cell counts to aplastic anemia and leukemia. The molecular mechanism by which benzene damages hematopoietic cells is unclear; in particular, benzene-induced aberrant gene expression has not been addressed. We analyzed differential gene expression in the peripheral white blood cells from seven female patients with occupational benzene poisoning and seven matched control subjects. In this study, we report altered expression of cytochrome P450 in the patients. All patients exhibited elevated expression of CYP4F3A encoding the leukotriene B4 (LTB(4)) omega-hydroxylase critical in the inactivation of LTB(4) in polymorphonuclear leukocytes with a -fold induction between 3 and 71. Four patients had high expression of CYP1A1, and two patients had elevated expression of CYP1B1. Expressions of CYP2B6, CYP51, and CYP27A1 were also altered in certain patients. Mechanistic analysis revealed that phenol, a major metabolite of benzene, significantly induced the expression of CYP4F3A at both mRNA and protein levels in cultured promyelocytic leukemia cells (HL-60), similarly to all-trans retinoic acid. Induction of CYP4F3 by phenol was also observed in differentiated HL-60 cells, in the proerythroid cell line K562, and ex vivo in human neutrophils. On the other hand, hydroquinone induced extensive apoptosis of the cells. The findings demonstrated, for the first time, that benzene and metabolites induce CYP4F3 in human blood cells both in vivo and in vitro. Induction of CYP4F3 may play a role in the development of benzene hematotoxicity and serve as a biomarker of benzene exposure. | Gupta S, Ashrith G, Chandra D, Gupta AK, Finkel KW, Guntupalli JS (2008)
Acute phenol poisoning: a life-threatening hazard of chronic pain relief.
Clinical toxicology (Philadelphia, Pa.) 46, 250-253 [PubMed:17852157]
[show Abstract]
BackgroundPhenol (carbolic acid, a higher alcohol) has been used for local analgesic therapy for a long time. Several complications of phenol therapy can occur by exposure through inhalational, oral, and dermal routes. Renal and pulmonary toxicity arising from the exposure to injectable phenol, however, has only been reported in a few case reports.Case presentationA 50-year-old man inadvertently received 10 cc of 89% phenol injection. It resulted in the development of acute respiratory and renal failure requiring intubation and hemodialysis, respectively. He improved clinically with the recovery of renal function. However, the chest x-ray and CT scan showed persistent nodular pulmonary infiltrates which resolved by six months.ConclusionWe report here an unusual case of acute respiratory and acute renal failure following accidental overdose of phenol. The case highlights potential development of multiple organ failure with persistence of organ dysfunction, an unusual danger associated with the overdose of injectable phenol for neurolysis. | Sperlingová I, Dabrowská L, Stránský V, Kucera J, Tichý M (2007)
Human urine certified reference material CZ 6010: creatinine and toluene metabolites (hippuric acid and o-cresol) and a benzene metabolite (phenol).
Analytical and bioanalytical chemistry 387, 2419-2424 [PubMed:16953321]
[show Abstract]
A reference material for the biological monitoring of occupational exposure to toluene, benzene and phenol was prepared. O-cresol and hippuric acid (metabolites of toluene) are used for the biological monitoring of occupational exposure to toluene. Phenol, a metabolite of benzene, is used for the biological monitoring of exposure to benzene, but phenol can of course also be used as an indicator of exposure to phenol as well. The reference material (RM) used for the determination of these metabolites was prepared by freeze-drying pooled urine samples obtained from healthy persons occupationally exposed to toluene and those taking part in an inhalation experiment. Tests for homogeneity and stability were performed by determining urine concentrations of o-cresol, hippuric acid, creatinine and phenol. To investigate the stability of the RM, the urinary concentrations of o-cresol and phenol were monitored for eighteen months using GC and HPLC, while those of hippuric acid and creatinine were followed for five and six years, respectively, using HPLC. Analysis of variance showed that the concentrations did not change. The certified concentration values (and their uncertainties) of the substances in this reference material (phenol concentration c=6.46+/-0.58 mg l(-1); o-cresol concentration c=1.17+/-0.15 mg l(-1); hippuric acid concentration c=1328+/-30 mg l(-1); creatinine concentration c=0.82+/-0.10 g l(-1)) were evaluated via the interactive statistical programme IPECA. | Gupta AK, Ahmad I, Summerbell RC (2002)
Fungicidal activities of commonly used disinfectants and antifungal pharmaceutical spray preparations against clinical strains of Aspergillus and Candida species.
Medical mycology 40, 201-208 [PubMed:12058733]
[show Abstract]
The antifungal efficacy of commercial chemical disinfectants and pharmaceutical antifungal agents against medically important moulds and yeast species was investigated. Chlorine, phenol, sodium dodecyl sulfate and quaternary ammonium salts were the chemical disinfectants, and bifonazole and terbinafine were the antifungal pharmaceutical products tested against clinical isolates of Aspergillus and Candida species. Fungal inocula were obtained from conidial preparations of two A. ochraceus strains and yeast cells of C. albicans, C. krusei and C. parapsilosis. The antifungal activities were evaluated either by determining the kill rate in a cell suspension media at different contact periods, or by examining the viability and growth on plates sprayed with the active ingredient. Chlorine (1%) was the only disinfectant with the ability to cause a rapid inactivation of all five strains. Phenol (5%) was equally effective against Candida species; however, a number of A. ochraceus conidia were able to survive this treatment for up to 1 h. Benzalkonium chloride (0.5%) and cetrimide (0.5%) were also able to disinfect the three Candida species rapidly; however, these two quaternary ammonium compounds were relatively ineffective against A. ochraceus. In spray experiments, quaternary ammonium compounds had a fungicidal activity against Candida species and were fungistatic against A. ochraceus conidia. All five fungal strains were able to resist 0.5% sodium dodecyl sulfate, present either in the suspension solution or on the sprayed plate. Of the two pharmaceutical antifungal products tested, bifonazole (1%) were essentially ineffective against all five strains. Terbinafine (1%) had a fungicidal activity against A. ochraceus and C. parapsilosis. In suspension experiments, an exposure to 0.01% terbinafine required a contact period of 1 h for a complete inactivation of A. ochraceus conidia and an onset of fungicidal effect on C. parapsilosis yeast cells. Terbinafine was only moderately effective against C. albicans and was completely ineffective against C. krusei. |
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