Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:57:30 UTC |
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Update Date | 2022-03-07 02:53:38 UTC |
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HMDB ID | HMDB0033244 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dibutyl phthalate |
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Description | Dibutyl phthalate is found in cloves. DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. It was used in some nail polishes; all major producers began eliminating this chemical from nail polishes in the Fall of 2006. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. It is soluble in various organic solvents, e.g. in alcohol, ether and benzene. DBP is also used as an ectoparasiticide. |
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Structure | CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3 |
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Synonyms | Value | Source |
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1,2-Benzenedicarboxylic acid dibutyl ester | ChEBI | Benzene-O-dicarboxylic acid di-N-butyl ester | ChEBI | Benzenedicarboxylic acid dibutyl ester | ChEBI | Butyl phthalate | ChEBI | DBP | ChEBI | Di-N-butyl phthalate | ChEBI | Dibutyl 1,2-benzenedicarboxylate | ChEBI | Dibutyl O-phthalate | ChEBI | Dibutyl-O-phthalate | ChEBI | N-Butyl phthalate | ChEBI | O-Benzenedicarboxylic acid dibutyl ester | ChEBI | Phthalic acid di-N-butyl ester | ChEBI | Phthalic acid dibutyl ester | ChEBI | 1,2-Benzenedicarboxylate dibutyl ester | Generator | Benzene-O-dicarboxylate di-N-butyl ester | Generator | Benzenedicarboxylate dibutyl ester | Generator | Butyl phthalic acid | Generator | Di-N-butyl phthalic acid | Generator | Dibutyl 1,2-benzenedicarboxylic acid | Generator | Dibutyl O-phthalic acid | Generator | Dibutyl-O-phthalic acid | Generator | N-Butyl phthalic acid | Generator | O-Benzenedicarboxylate dibutyl ester | Generator | Phthalate di-N-butyl ester | Generator | Phthalate dibutyl ester | Generator | Dibutyl phthalic acid | Generator | Di N butyl phthalate | MeSH | Phthalate, butyl | MeSH | Phthalate, di-N-butyl | MeSH | Phthalate, dibutyl | MeSH | 1,2-Benzenedicarboxylic acid, 1,2-dibutyl ester | HMDB | 1,2-Benzenedicarboxylic acid, dibutyl ester | HMDB | Araldite 502 | HMDB | Benzene-O-dicarboxylic acid, di-N-butyl ester | HMDB | Benzenedicarboxylic acid, dibutyl ester | HMDB | BUFA | HMDB | Celluflex DPB | HMDB | DBP (Ester) | HMDB | Di-N-butyl phthalate (dbup) | HMDB | Di-N-butylester kyseliny ftalove | HMDB | Di-N-butylorthophthalate | HMDB | Dibutyl 1, 2-benzenedicarboxylate | HMDB | Dibutyl ester OF 1,2-benzenedicarboxylic acid | HMDB | Dibutyl phthalated | HMDB | Dibutyl-1,2-benzenedicarboxylate | HMDB | Dibutyl-phthalate | HMDB | Dibutyll phthalate | HMDB | Dibutylphthatlate | HMDB | Elaol | HMDB | Ergoplast FDB | HMDB | Ersoplast fda | HMDB | Genoplast b | HMDB | Hatcol DBP | HMDB | Hexaplas m/b | HMDB | Kodaflex DBP | HMDB | Morflex 240 | HMDB | N-Butylphthalate | HMDB | O-Benzenedicarboxylic acid, dibutyl ester | HMDB | ortho-Dibutyl phthalate | HMDB | Phthalic acid, dibutyl ester | HMDB | Polycizer DBP | HMDB | Rapidcelltrade markp | HMDB | RC Plasticizer DBP | HMDB | Staflex DBP | HMDB | Uniflex DBP | HMDB | Unimoll DB | HMDB | Uniplex 150 | HMDB | Witcizer 300 | HMDB | Dibutylphthalic acid | Generator |
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Chemical Formula | C16H22O4 |
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Average Molecular Weight | 278.3435 |
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Monoisotopic Molecular Weight | 278.151809192 |
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IUPAC Name | 1,2-dibutyl benzene-1,2-dicarboxylate |
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Traditional Name | dibutyl-phthalate |
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CAS Registry Number | 84-74-2 |
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SMILES | CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC |
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InChI Identifier | InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3 |
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InChI Key | DOIRQSBPFJWKBE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
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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 | Benzoic acids and derivatives |
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Direct Parent | Benzoic acid esters |
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Alternative Parents | |
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Substituents | - Benzoate ester
- Benzoyl
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 35 °C | Not Available | Boiling Point | 337.00 to 340.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 0.011 mg/mL at 25 °C | Not Available | LogP | 4.50 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized) | splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized) | splash10-0002-1910000000-964b3411de1f914de4da | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized) | splash10-0002-0910000000-97464fdc3b8040ec3d36 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized) | splash10-052b-0960000000-7a12a722da333ebed5e0 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized) | splash10-0002-5900000000-bb309d93583ab774d1f9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized) | splash10-0a6s-0490000000-bb10c8ff49d65e9fbcfd | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized) | splash10-0002-1910000000-964b3411de1f914de4da | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized) | splash10-0002-0910000000-97464fdc3b8040ec3d36 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate CI-B (Non-derivatized) | splash10-052b-0960000000-7a12a722da333ebed5e0 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dibutyl phthalate EI-B (Non-derivatized) | splash10-0002-5900000000-bb309d93583ab774d1f9 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dibutyl phthalate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-5190000000-8daed01d42925467217c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dibutyl phthalate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0002-3900000000-ecab0016129a96c4ece7 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-004i-0590000000-d7fd13586fba8d9bcbb8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-003r-0900000000-26a0280d411587ad0406 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-003r-0900000000-01dec35be5d4cb24d183 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-00b9-1900000000-0a9f876d83f5cdff62be | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-004i-6900000000-88c2bba04cf08d8a94e7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-004i-9300000000-6e11d76c309a036870da | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-004i-9000000000-24ad78f1c73dbed6290d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-004i-9000000000-2d5177b1586a4461b278 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , negative-QTOF | splash10-004i-9000000000-4516fb7c10721dc8cedb | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-0002-0910000000-7702573da14ce44e4e73 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-0002-0900000000-78eaf490a7fb4d87b419 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-0002-0900000000-5c75cf8111466a2bd813 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-0002-0900000000-a0747aefa385c43d47b1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-006t-1900000000-29635db4a2da5e62db7f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-00xs-5900000000-02c97dee9727d0badc2e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-014i-9200000000-2b0820b30884f0f997a5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-014i-9000000000-5d4f80a8a661596a7cc8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-QFT , positive-QTOF | splash10-014i-9000000000-f45a033b5a30528756de | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dibutyl phthalate LC-ESI-ITFT , positive-QTOF | splash10-0002-0900000000-19ad0b11756e1ca9188a | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibutyl phthalate 10V, Positive-QTOF | splash10-056r-2090000000-80ca0d0b0000ed2e7f82 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibutyl phthalate 20V, Positive-QTOF | splash10-0a4i-9240000000-62634d519d04aa7360b1 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibutyl phthalate 40V, Positive-QTOF | splash10-0a4i-9500000000-7279733c1ed1974ee785 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibutyl phthalate 10V, Negative-QTOF | splash10-004i-1090000000-5c82ef4822a947c8f20b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibutyl phthalate 20V, Negative-QTOF | splash10-00fr-2590000000-eadc4a21565f062f1e5a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dibutyl phthalate 40V, Negative-QTOF | splash10-0600-5910000000-41f7de518636cfc255d9 | 2016-08-03 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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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 | DB13716 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011261 |
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KNApSAcK ID | C00053140 |
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Chemspider ID | 13837319 |
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KEGG Compound ID | C14214 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Dibutyl_phthalate |
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METLIN ID | Not Available |
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PubChem Compound | 3026 |
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PDB ID | Not Available |
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ChEBI ID | 34687 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1018721 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Kim H, Lee S, Ryu S, Choi HT: Decolorization of Remazol Brilliant Blue R by a purified laccase of Polyporus brumalis. Appl Biochem Biotechnol. 2012 Jan;166(1):159-64. doi: 10.1007/s12010-011-9412-y. Epub 2011 Nov 5. [PubMed:22057907 ]
- Gupta VK, Singh LP, Chandra S, Kumar S, Singh R, Sethi B: Anion recognition through amide-based dendritic molecule: a poly(vinyl chloride) based sensor for nitrate ion. Talanta. 2011 Aug 15;85(2):970-4. doi: 10.1016/j.talanta.2011.05.014. Epub 2011 May 12. [PubMed:21726726 ]
- Cirillo T, Fasano E, Castaldi E, Montuori P, Amodio Cocchieri R: Children's exposure to Di(2-ethylhexyl)phthalate and dibutylphthalate plasticizers from school meals. J Agric Food Chem. 2011 Oct 12;59(19):10532-8. doi: 10.1021/jf2020446. Epub 2011 Sep 19. [PubMed:21894916 ]
- Ito Y, Nakamura T, Yanagiba Y, Ramdhan DH, Yamagishi N, Naito H, Kamijima M, Gonzalez FJ, Nakajima T: Plasticizers May Activate Human Hepatic Peroxisome Proliferator-Activated Receptor alpha Less Than That of a Mouse but May Activate Constitutive Androstane Receptor in Liver. PPAR Res. 2012;2012:201284. doi: 10.1155/2012/201284. Epub 2012 Jun 20. [PubMed:22792086 ]
- Simonsson C, Stenfeldt AL, Karlberg AT, Ericson MB, Jonsson CA: The pilosebaceous unit--a phthalate-induced pathway to skin sensitization. Toxicol Appl Pharmacol. 2012 Oct 1;264(1):114-20. doi: 10.1016/j.taap.2012.07.023. Epub 2012 Jul 27. [PubMed:22842015 ]
- Petersen JH, Jensen LK: Phthalates and food-contact materials: enforcing the 2008 European Union plastics legislation. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Nov;27(11):1608-16. doi: 10.1080/19440049.2010.501825. [PubMed:20737341 ]
- Fishman AI, Noskov AI, Stolov AA: Conformational mobility of small molecules in glass-forming solutions studied by FTIR spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Jun;91:184-91. doi: 10.1016/j.saa.2012.01.060. Epub 2012 Feb 9. [PubMed:22381789 ]
- Tyagi S, Agarwal H, Ikram S: A polyvinylchloride-based cadmium ion-selective electrode using [Mo(2)(OAc)(2)(H(2)-calix[4]arene)] as an electroactive material. Water Sci Technol. 2010;62(11):2510-8. doi: 10.2166/wst.2010.774. [PubMed:21099036 ]
- Brucker-Davis F, Wagner-Mahler K, Bornebusch L, Delattre I, Ferrari P, Gal J, Boda-Buccino M, Pacini P, Tommasi C, Azuar P, Bongain A, Fenichel P: Exposure to selected endocrine disruptors and neonatal outcome of 86 healthy boys from Nice area (France). Chemosphere. 2010 Sep;81(2):169-76. doi: 10.1016/j.chemosphere.2010.06.068. [PubMed:20663538 ]
- Dobrzynska MM, Tyrkiel EJ, Hernik A, Derezinska E, Goralczyk K, Ludwicki JK: [The effects of di-n-butyl phthalate on the somatic cells of laboratory mice]. Rocz Panstw Zakl Hig. 2010;61(1):13-9. [PubMed:20803895 ]
- Carran M, Shaw IC: New Zealand Malayan war veterans' exposure to dibutylphthalate is associated with an increased incidence of cryptorchidism, hypospadias and breast cancer in their children. N Z Med J. 2012 Jul 29;125(1358):52-63. [PubMed:22864157 ]
- Singh AK, Singh P: Determination of cerium ion by polymeric membrane and coated graphite electrode based on novel pendant armed macrocycle. Anal Chim Acta. 2010 Aug 24;675(2):170-80. doi: 10.1016/j.aca.2010.07.023. Epub 2010 Jul 21. [PubMed:20800729 ]
- van Ravenzwaay B, Coelho-Palermo Cunha G, Strauss V, Wiemer J, Leibold E, Kamp H, Walk T, Mellert W, Looser R, Prokoudine A, Fabian E, Krennrich G, Herold M: The individual and combined metabolite profiles (metabolomics) of dibutylphthalate and di(2-ethylhexyl)phthalate following a 28-day dietary exposure in rats. Toxicol Lett. 2010 Oct 5;198(2):159-70. doi: 10.1016/j.toxlet.2010.06.009. Epub 2010 Jun 23. [PubMed:20600714 ]
- Tyagi S, Agarwal H, Ikram S: Potentiometric polymeric membrane electrodes for mercury detection using calixarene ionophores. Water Sci Technol. 2010;61(3):693-704. doi: 10.2166/wst.2010.860. [PubMed:20150706 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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