Record Information |
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Version | 2.0 |
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Creation Date | 2009-06-22 16:08:30 UTC |
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Update Date | 2014-12-24 20:24:32 UTC |
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Accession Number | T3D1724 |
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Identification |
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Common Name | Bronopol |
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Class | Small Molecule |
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Description | Bronopol is a chemical compound of bromine and an antimicrobial substance. It is used as a preservative in pharmaceuticals, as well as numerous consumer products such as shampoos and cosmetics. It is also used as an antimicrobial in many industrial environments such as paper mills, oil exploration and production facilities, as well as cooling water disinfection plants. Its use is declining due to its recognized potential to decompose into carcinogenic nitrosamines. It is also a formaldehyde releaser. (10, 13) |
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Compound Type | - Bromide Compound
- Cosmetic Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Inorganic Compound
- Organic Compound
- Organobromide
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 2-Bromo-1-nitro-1,3-propanediol | 2-Bromo-2-nitro-1, 3-propanediol | 2-Bromo-2-nitro-1,3-propanediol | 2-Bromo-2-nitropropan-1,3-diol | 2-Bromo-2-nitropropane-1,3-diol | 2-Nitro-2-bromo-1, 3-propanediol | 2-Nitro-2-bromo-1,3-propanediol | b-bromo-b-nitrotrimethyleneglycol | Beta-bromo-beta-nitrotrimethyleneglycol | Bioban BNPD-40 | Bronidiol | Bronocot | Bronopol-boots | Bronopolu | Bronosol | Bronotak | Broponol | C3H6BrNO4 | Canguard 409 | Epon(r) substitute embedding medium kit | Epoxy embedding medium kit | Lexgard bronopol | Myacide as plus | Myacide S-1, S-2 | Onyxide 500 |
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Chemical Formula | C3H6BrNO4 |
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Average Molecular Mass | 199.988 g/mol |
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Monoisotopic Mass | 198.948 g/mol |
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CAS Registry Number | 52-51-7 |
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IUPAC Name | 2-bromo-2-nitropropane-1,3-diol |
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Traditional Name | bronopol |
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SMILES | OCC(Br)(CO)[N+]([O-])=O |
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InChI Identifier | InChI=1S/C3H6BrNO4/c4-3(1-6,2-7)5(8)9/h6-7H,1-2H2 |
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InChI Key | InChIKey=LVDKZNITIUWNER-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon. |
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Kingdom | Organic compounds |
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Super Class | Organic 1,3-dipolar compounds |
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Class | Allyl-type 1,3-dipolar organic compounds |
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Sub Class | Organic nitro compounds |
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Direct Parent | C-nitro compounds |
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Alternative Parents | |
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Substituents | - Bromohydrin
- Halohydrin
- C-nitro compound
- Organic oxoazanium
- Propargyl-type 1,3-dipolar organic compound
- Alcohol
- Hydrocarbon derivative
- Organic zwitterion
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organobromide
- Organic oxide
- Organohalogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Alkyl halide
- Alkyl bromide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White to pale yellow crystals. |
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Experimental Properties | Property | Value |
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Melting Point | 131.5°C | Boiling Point | 140°C (decomposes) | Solubility | 250 mg/mL at 22°C [YALKOWSKY,SH & HE,Y (2003)] | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-ae7a9387ae98df20c0b7 | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-1726ceff75d5b918516e | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fsi-1900000000-f0e3840a9d77d1045332 | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-05837c913cd09c367877 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1900000000-e42c22307dc905229af1 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udj-4900000000-e9ccc4cb82ffd0a98572 | 2016-08-03 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-057r-9800000000-96a2fa8203c140ebd484 | 2014-09-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | Not Available | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental) | Not Available | 2014-09-23 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral (4) ; inhalation (4) ; dermal (4) |
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Mechanism of Toxicity | While Bronopol is not in itself a nitrosating agent, under conditions where it decomposes (alkaline solution and/or elevated temperatures) it can liberate nitrite and low levels of formaldehyde. These decomposition products can react with any secondary amines or amides (which may contaminate cosmetic products) to produce significant levels of nitrosamines, which are believed to be carcinogenic. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. Formaldehyde itself is also carcinogenic. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (11, 10, 12, 1, 2, 3, 4, 13) |
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Metabolism | Nitrosamines can enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase. Formaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. (1, 2, 14, 11) |
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Toxicity Values | LD50: 250 mg/kg (Oral, Dog) (5)
LD50: 64-160 mg/kg (Dermal, Rat) (6)
LC50: >5 mg/L over 6 hours (Inhalation, Rat) (5) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity (not listed by IARC). (9) |
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Uses/Sources | Bronopol is used as a preservative in pharmaceuticals, as well as numerous consumer products such as shampoos and cosmetics. It is also used as an antimicrobial in many industrial environments such as paper mills, oil exploration and production facilities, as well as cooling water disinfection plants. (10) |
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Minimum Risk Level | Not Available |
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Health Effects | Bronopol may react to produce nitrosamines, which are believed to be carcinogenic. It also releases formaldehyde, a known human carcinogen. (11, 4) |
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Symptoms | Not Available |
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Treatment | EYES: irrigate opened eyes for several minutes under running water.
INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.
SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention.
INHALATION: supply fresh air. If required provide artificial respiration. |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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PubChem Compound ID | 2450 |
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ChEMBL ID | CHEMBL1408862 |
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ChemSpider ID | 2356 |
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KEGG ID | C13034 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | Not Available |
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BioCyc ID | Not Available |
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CTD ID | C006827 |
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Stitch ID | Bronopol |
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PDB ID | Not Available |
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ACToR ID | 6861 |
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Wikipedia Link | Bronopol |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D1724.pdf |
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General References | - Oyama T, Sugio K, Uramoto H, Iwata T, Onitsuka T, Isse T, Nozoe T, Kagawa N, Yasumoto K, Kawamoto T: Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis. Front Biosci. 2007 May 1;12:4497-503. [17485391 ]
- Sasaki S, Sata F, Katoh S, Saijo Y, Nakajima S, Washino N, Konishi K, Ban S, Ishizuka M, Kishi R: Adverse birth outcomes associated with maternal smoking and polymorphisms in the N-Nitrosamine-metabolizing enzyme genes NQO1 and CYP2E1. Am J Epidemiol. 2008 Mar 15;167(6):719-26. doi: 10.1093/aje/kwm360. Epub 2008 Jan 23. [18218609 ]
- Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. [15380096 ]
- Lanigan RS: Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. Int J Toxicol. 2001;20 Suppl 1:1-14. [11358107 ]
- Yapi HF, Ahiboh H, Ago K, Ake M, Monnet D: [Protein profile and vitamin A in children of school age in Ivory Coast]. Ann Biol Clin (Paris). 2005 May-Jun;63(3):291-5. [15951260 ]
- Hinterhuber G, Cauza K, Dingelmaier-Hovorka R, Diem E, Horvat R, Wolff K, Foedinger D: Expression of RPE65, a putative receptor for plasma retinol-binding protein, in nonmelanocytic skin tumours. Br J Dermatol. 2005 Oct;153(4):785-9. [16181461 ]
- USEPA/Office of Pesticide Programs (2005). Reregistration Eligibility Decision Document - Bronopol.
- Tomlin CDS (ed) (2007). Bronopol (52-51-7). In: The e-Pesticide Manual, Version 2.2. Surrey UK: British Crop Protection Council.
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
- Wikipedia. Bronopol. Last Updated 16 May 2009. [Link]
- ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- Wikipedia. Nitrosamine. Last Updated 16 November 2009. [Link]
- Wikipedia. Formaldehyde releaser. Last Updated 25 May 2008. [Link]
- Wikipedia. Sarcosine. Last Updated 16 October 2009. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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