| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-10-15 22:01:21 UTC |
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| Update Date | 2016-11-09 01:09:15 UTC |
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| Accession Number | CHEM003948 |
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| Identification |
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| Common Name | Dibenzylideneacetone |
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| Class | Small Molecule |
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| Description | Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a bright-yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a sunscreen component and as a ligand in organometallic chemistry, for instance in tris(dibenzylideneacetone)dipalladium(0). In this case, it is a labile ligand that is easily displaced by stronger ligands like triphenylphosphine, hence it serves a useful entry point into palladium(0) chemistry. (1) |
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| Contaminant Sources | |
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| Contaminant Type | - Cosmetic Toxin
- Industrial/Workplace Toxin
- Organic Compound
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| (e)-Dibenzylideneacetone | ChEMBL | | Dibenzylidene acetone | MeSH | | Dibenzalacetone | MeSH |
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| Chemical Formula | C17H14O |
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| Average Molecular Mass | 234.293 g/mol |
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| Monoisotopic Mass | 234.104 g/mol |
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| CAS Registry Number | 538-58-9 |
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| IUPAC Name | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one |
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| Traditional Name | dibenzylideneacetone |
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| SMILES | [H]\C(=C(\[H])C1=CC=CC=C1)C(=O)C(\[H])=C(/[H])C1=CC=CC=C1 |
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| InChI Identifier | InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H/b13-11+,14-12+ |
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| InChI Key | WMKGGPCROCCUDY-PHEQNACWSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. |
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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 | Styrenes |
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| Direct Parent | Styrenes |
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| Alternative Parents | |
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| Substituents | - Styrene
- Alpha,beta-unsaturated ketone
- Enone
- Acryloyl-group
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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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 | | Name | SMPDB Link | KEGG Link |
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| Apoptosis | Not Available | map04210 | | Tetracyclines | Not Available | Not Available | | Proteasome | Not Available | 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 powder |
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| Experimental Properties | | Property | Value |
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| Melting Point | 110-111 °C | | Boiling Point | 130 °C | | Solubility | Insoluble |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0190000000-ee22b8fb743b76064d47 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-2890000000-687c9a41e7355c4564f6 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ufu-5910000000-2d0899b63f5b6b9f269d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0190000000-160a417e4fac191b3436 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0590000000-6ec0691349fce7079206 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ufr-2920000000-9a755463d4b65c454264 | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-001i-5890000000-b80bd1cb912d36e7a4b8 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Dibenzylideneacetone is used as a sunscreen component and as a ligand in organometallic chemistry. (1) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Dibenzylideneacetone is an irritant. |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| 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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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Dibenzylideneacetone |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 640180 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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