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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2013-12-17 17:00:44 UTC |
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Update Date | 2020-11-09 23:21:49 UTC |
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HMDB ID | HMDB0061385 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Triclosan |
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Description | Triclosan is an antibacterial and antifungal agent. It is a polychloro phenoxy phenol. It is widely used as a preservative and antimicrobial agent in personal care products such as soaps, skin creams, toothpaste and deodorants as well as in household items such as plastic chopping boards, sports equipment and shoes. According to the Food and Drug Administration (FDA) at the present time there is no evidence that triclosan in personal care products provides an extra benefit to health beyond its anti-gingivitis effect in toothpaste. The FDA does not recommend changing consumer use of triclosan containing products one way or the other due to currently insufficient safety evidence. Studies by the Environmental Protection Agency (EPA) found triclosan to be an effective antibacterial. Triclosan safety is currently under review by the FDA and Health Canada. Triclosan is only found in individuals that have used or taken this drug. |
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Structure | |
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Synonyms | Value | Source |
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2,4,4'-Trichloro-2'-hydroxydiphenyl ether | ChEBI | 5-Chloro-2-(2,4-dichloro-phenoxy)-phenol | ChEBI | Triclosanum | ChEBI | Stri-dex cleansing bar | Kegg | Aquasept | HMDB | Irgasan DP 300 | HMDB | 2-Hydroxy-2',4,4'-trichlorodiphenyl ether | HMDB | Pharmachem brand OF triclosan | HMDB | Procter and gamble brand OF triclosan | HMDB | Tersaseptic | HMDB | GlaxoSmithKline brand OF triclosan | HMDB | Irgasan DP300 | HMDB | Irgasan-DP300 | HMDB | Sapoderm | HMDB | SterZac bath concentrate | HMDB | Trisan | HMDB | Triclosan pharmachem brand | HMDB | Clearasil daily face wash | HMDB | Cliniclean | HMDB | DP300, Irgasan | HMDB | Dermtek brand OF triclosan | HMDB | Johnson and johnson brand OF triclosan | HMDB | Manusept | HMDB | Microshield T | HMDB | Oxy skin wash | HMDB | Reckitt brand OF triclosan | HMDB | SSL Brand OF triclosan | HMDB | Ster zac bath concentrate | HMDB | Ster-zac bath concentrate | HMDB | trans Canaderm brand OF triclosan | HMDB | Triclosan reckitt brand | HMDB | PHisoHex | HMDB |
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Chemical Formula | C12H7Cl3O2 |
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Average Molecular Weight | 289.542 |
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Monoisotopic Molecular Weight | 287.951162589 |
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IUPAC Name | 5-chloro-2-(2,4-dichlorophenoxy)phenol |
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Traditional Name | triclosan |
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CAS Registry Number | 3380-34-5 |
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SMILES | OC1=CC(Cl)=CC=C1OC1=C(Cl)C=C(Cl)C=C1 |
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InChI Identifier | InChI=1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H |
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InChI Key | XEFQLINVKFYRCS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Diphenylethers |
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Direct Parent | Diphenylethers |
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Alternative Parents | |
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Substituents | - Diphenylether
- Diaryl ether
- Phenoxy compound
- Phenol ether
- 1,3-dichlorobenzene
- 3-chlorophenol
- 3-halophenol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Chlorobenzene
- Halobenzene
- Aryl chloride
- Aryl halide
- Ether
- Organic oxygen compound
- Organohalogen compound
- Organochloride
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Route of exposure: Biological location: |
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Role | Environmental role: Industrial application: |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-0490000000-dfb0757bfac1ad90e7a4 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9468000000-8ac957d92fb0baadf85d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0006-0900000000-58c362c848ddc0ea6b7d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0006-0900000000-d33e377d9d635f1ce853 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0006-0900000000-86a497478420de6dd62b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-01ox-1900000000-3924bb3259de13cc0c32 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-01p9-9500000000-1eea0ef329f1eda65753 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-9000000000-c0811786de4d26d32f19 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0udi-0090000000-1e8f398c881d4511de15 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0udi-0090000000-1e8f398c881d4511de15 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-0090000000-901f5a26f0a84efe9ab9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-0190000000-665be7c9535346c9a726 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-7662f8b4bedcaffe0a5f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0090000000-62befab95441bb9ec2f0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udj-3980000000-375beaf060515d4bc75b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-0a0e87adf47e90d9ec1b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-40be759356bf6e86ef46 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ikc-2980000000-85ef168fbb3f3d0db80a | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-029g-9780000000-d39624d358bdeff3e131 | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Blood
- Breast Milk
- Saliva
- Urine
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.000249 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.0553 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.00173 +/- 0.00294 uM | Adult (>18 years old) | Both | N/A | | details | Blood | Detected and Quantified | 0.0038 +/- 0.00415 uM | Adult (>18 years old) | Both | N/A | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Breast Milk | Detected and Quantified | 0.0000656 uM | Adult (>18 years old) | Female | Normal | | details | Breast Milk | Detected and Quantified | 0.00187 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.00387 (0.00289-0.0052) umol/mmol creatinine | Children (1-13 years old) | Not Specified | N/A | | details | Urine | Detected and Quantified | 0.00426 (0.00324-0.00555) umol/mmol creatinine | Adolescent (13-18 years old) | Not Specified | N/A | | details | Urine | Detected and Quantified | 0.00539 (0.00485-0.00598) umol/mmol creatinine | Adult (>18 years old) | Not Specified | N/A | | details | Urine | Detected and Quantified | 0.00485 (0.00379-0.00621) umol/mmol creatinine | Elderly (>65 years old) | Not Specified | N/A | | details | Urine | Detected and Quantified | 0.00481 (0.00414-0.00555) umol/mmol creatinine | Not Specified | Female | N/A | | details | Urine | Detected and Quantified | 0.0052 (0.00442-0.0061) umol/mmol creatinine | Not Specified | Male | N/A | | details | Urine | Detected and Quantified | 0.00640 (0.00535-0.00773) umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.00554 (0.00484-0.00640) umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB08604 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | C12059 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Triclosan |
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METLIN ID | Not Available |
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PubChem Compound | 5564 |
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PDB ID | Not Available |
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ChEBI ID | 164200 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00029827 |
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References |
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Synthesis Reference | Michael A. Mitchell, “Process For Producing Triclosan-Coated Superabsorbents.” U.S. Patent US20120157302, issued June 21, 2012. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Russell AD: Whither triclosan? J Antimicrob Chemother. 2004 May;53(5):693-5. Epub 2004 Apr 8. [PubMed:15073159 ]
- Heath RJ, Rubin JR, Holland DR, Zhang E, Snow ME, Rock CO: Mechanism of triclosan inhibition of bacterial fatty acid synthesis. J Biol Chem. 1999 Apr 16;274(16):11110-4. [PubMed:10196195 ]
- Fan F, Yan K, Wallis NG, Reed S, Moore TD, Rittenhouse SF, DeWolf WE Jr, Huang J, McDevitt D, Miller WH, Seefeld MA, Newlander KA, Jakas DR, Head MS, Payne DJ: Defining and combating the mechanisms of triclosan resistance in clinical isolates of Staphylococcus aureus. Antimicrob Agents Chemother. 2002 Nov;46(11):3343-7. [PubMed:12384334 ]
- Moss T, Howes D, Williams FM: Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether). Food Chem Toxicol. 2000 Apr;38(4):361-70. [PubMed:10722890 ]
- Fang JL, Stingley RL, Beland FA, Harrouk W, Lumpkins DL, Howard P: Occurrence, efficacy, metabolism, and toxicity of triclosan. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev. 2010 Jul;28(3):147-71. doi: 10.1080/10590501.2010.504978. [PubMed:20859822 ]
- ON THE FATE OF TRICLOSAN IN HUMANS [Link]
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