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| 2,4,6-Tribromophenol (TBP) is a brominated derivative of phenol. It is used as a fungicide, as a wood preservative, and an intermediate in the preparation of flame retardants. |
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Read full article at Wikipedia
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| InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H |
| BSWWXRFVMJHFBN-UHFFFAOYSA-N |
| C=1(C(=C(C=C(C1)Br)Br)O)Br |
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Grateloupia elliptica
(NCBI:txid118371)
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See:
PubMed
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Neosiphonia sp.aerocarpa
(WORMS:146348)
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See:
PubMed
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environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
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fungicide
A substance used to destroy fungal pests.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
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fungicide
A substance used to destroy fungal pests.
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View more via ChEBI Ontology
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Outgoing
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2,4,6-tribromophenol
(CHEBI:47696)
has role
environmental contaminant
(CHEBI:78298)
2,4,6-tribromophenol
(CHEBI:47696)
has role
fungicide
(CHEBI:24127)
2,4,6-tribromophenol
(CHEBI:47696)
has role
marine metabolite
(CHEBI:76507)
2,4,6-tribromophenol
(CHEBI:47696)
is a
bromophenol
(CHEBI:33624)
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Incoming
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2-propyn-1-yl 2,4,6-tribromophenyl phthalate
(CHEBI:75345)
has functional parent
2,4,6-tribromophenol
(CHEBI:47696)
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2,4,6-TBP
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ChEBI
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Bromol
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ChemIDplus
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Tribromophenol
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ChemIDplus
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Xeroform
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ChemIDplus
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118-79-6
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CAS Registry Number
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KEGG COMPOUND
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118-79-6
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CAS Registry Number
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ChemIDplus
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118-79-6
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CAS Registry Number
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NIST Chemistry WebBook
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776920
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Reaxys Registry Number
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Reaxys
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Fujii Y, Nishimura E, Kato Y, Harada KH, Koizumi A, Haraguchi K (2014)
Dietary exposure to phenolic and methoxylated organohalogen contaminants in relation to their concentrations in breast milk and serum in Japan.
Environment international 63, 19-25 [PubMed:24263137]
[show Abstract]
This study investigated human exposure to neutral, phenolic, and methoxylated organohalogen contaminants (OHCs) in a duplicate diet study to evaluate their concentrations in breast milk and serum of Okinawan people from Japan during 2004-2009. Dietary intakes of phenolic OHCs were predominantly 2,4,6-tribromophenol (TriBP), followed by tetrabromobisphenol A (TBBPA), and 6-hydroxy-2,2',4,4'-tetrabromodiphenyl ether (6-OH-BDE47). After exposure, TriBP and TBBPA were transferred to breast milk, whereas 6-OH-BDE47 was selectively retained in serum. Despite a lower dietary exposure to pentachlorophenol and 4-hydroxy-CB187, both were retained in serum. For the methoxylated OHCs, 2,4,6-tribromoanisole (TriBA) and 6-methoxy-BDE47 were the predominant dietary contaminants, of which TriBA was present in both breast milk and serum, whereas 6-methoxy-BDE47 was selectively transferred to breast milk. These findings suggest that dietary exposure to phenolic and methoxylated OHCs may result in differential partitioning between breast milk and serum with different pharmacokinetic or exposure routes. | Deng J, Liu C, Yu L, Zhou B (2010)
Chronic exposure to environmental levels of tribromophenol impairs zebrafish reproduction.
Toxicology and applied pharmacology 243, 87-95 [PubMed:19931292]
[show Abstract]
Tribromophenol (2,4,6-TBP) is ubiquitously found in aquatic environments and biota. In this study, we exposed zebrafish embryos (F(0); 2"" days post-fertilization, dpf) to environmental concentration (0.3 microg/L) and a higher concentration (3.0 microg/L) of TBP and assessed the impact of chronic exposure (120 dpf) on reproduction. TBP exposure did not cause a significant increase in the malformation and reduction in the survival in the F(0)-generation fish. After TBP exposure, the plasma testosterone and estradiol levels significantly increased in males and decreased in females. The transcription of steroidogenic genes (3beta-HSD, 17beta-HSD, CYP17, CYP19A, CYP19B) was significantly upregulated in the brain and testes in males and downregulated in the brain and ovary in females. TBP exposure significantly downregulated and upregulated the expression of VTG in the liver of female and male fish, respectively. Meanwhile, TBP exposure altered the sex ratio toward a male-dominant state. The F(1)-generation larvae exhibited increased malformation, reduced survival, and retarded growth, suggesting that TBP in the aquatic environment has significant adverse effects on fish population. | Mardones C, Von Baer D, Silva J, Ruff A, Gutierrez L, Berg A (2009)
Tribromophenol and pentachlorophenol uptake from sawdust to horticultural products.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 26, 1362-1371 [PubMed:19701836]
[show Abstract]
This paper presents a study of the uptake of 2,4,6-tribromophenol (TBP), pentachlorophenol (PCP), and its metabolite pentachloroanisole (PCA) from contaminated sawdust from the forest industry in horticultural products such as apples, raspberries, and fodder maize for cattle feed. The samples were obtained from Bio-Bio Province in South Chile between 2002 and 2006. The analytical parameters of the methodology applied to the different matrices are presented and discussed. The chromatographic method was applied to determine the residues in 413 horticultural product samples. Eleven per cent of fodder maize samples showed detectable or quantifiable levels of PCP, TBP or PCA, 3% of samples presented quantifiable levels, although the concentrations surpassed the maximum allowed concentrations for vegetables (>10 microg kg(-1)) in only two samples. Traces of TBP were detected in eight samples, PCA was detected in 15, and PCP in 14 samples. Based on these results, a risk analysis was performed, indicating a low probability, 0.4% for PCA, 1.6% for TBP and 1.9% for PCP, to find concentrations higher than the allowed maximum. For apples and raspberries, no residues of these compounds were detected. These results indicate that those cultivars directly exposed to sawdust, like fodder maize, could contain detectable residues in several samples. To confirm this observation, a field assay was performed on fodder maize cultivated in the presence of sawdust artificially contaminated with 30 mg of TBP and/or PCP under controlled conditions. The results showed that under the experimental conditions used in the study, TBP can be transferred from sawdust to the plant, with an uptake rate of 0.04% from the TBP applied initially with sawdust but not to the corn ear. Also, the degradation of PCP to PCA was observed in the soil. | Yamada T, Takahama Y, Yamada Y (2008)
Biodegradation of 2,4,6-tribromophenol by Ochrobactrum sp. strain TB01.
Bioscience, biotechnology, and biochemistry 72, 1264-1271 [PubMed:18460800]
[show Abstract]
A bacterium that utilizes 2,4,6-tribromophenol (2,4,6-TBP) as sole carbon and energy source was isolated from soil contaminated with brominated pollutants. This bacterium, designated strain TB01, was identified as an Ochrobactrum species. The organism degraded 100 microM of 2,4,6-TBP within 36 h in a growing culture. In addition, it released 3 mol of bromine ions from 1 mol of 2,4,6-TBP during the complete degradation of 2,4,6-TBP in a resting cell assay. Moreover, cells grown on 2,4,6-TBP degraded 2,6-dibromophenol (2,6-DBP), 4-bromophenol (4-BP), 2,4,6-trichlorophenol (2,4,6-TCP) and phenol. Metabolic intermediates were detected in the reaction mixture of an in vitro assay for 2,4,6-TBP, and they were identified as 2,4-DBP and 2-BP. NADH was required for the debromination of 2,4,6-TBP. These results suggest that 2,4,6-TBP is converted to phenol through sequential reductive debromination reactions via 2,4-DBP and 2-BP by this strain. | Gutiérrez M, Becerra J, Godoy J, Barra R (2005)
Occupational and environmental exposure to tribromophenol used for wood surface protection in sawmills.
International journal of environmental health research 15, 171-179 [PubMed:16134480]
[show Abstract]
This study analyses the occupational and environmental conditions of sawmills where the lumber is protected from microorganism action by dipping it in 2,4,6 tribromophenol (TBP). Three processes were evaluated: hydraulic immersion, chain conveyor system and manual immersion. The biggest occupational exposure to TBP was registered in manual and chain conveyor systems. The average values in the workers' urine for TBP were 6.9 and 5.7 mg/g creatinine, respectively. For environmental exposure, the highest value in well waters was 25.1 microg/L and in soil was 4,602 mg/kg. It could be established that the hydraulic immersion system presents less occupational TBP exposure. Nevertheless, the hydraulic system, as well as the other two anti-stain alternatives, requires the introduction of pollution prevention efforts. To reduce the environmental exposure to TBP, the lumber-dipping tank area, the forklift traffic areas, and the storage areas need to be waterproofed. It is also necessary to implement a TBP solution recovery system to eliminate dripping from the lumber once it is removed from the fungicide dipping tanks. |
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