Tmic
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Database of hazardous chemicals.
Record Information
Version1.0
Creation Date2014-10-15 22:01:21 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003948
Identification
Common NameDibenzylideneacetone
ClassSmall Molecule
DescriptionDibenzylideneacetone 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)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Cosmetic Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(e)-DibenzylideneacetoneChEMBL
Dibenzylidene acetoneMeSH
DibenzalacetoneMeSH
Chemical FormulaC17H14O
Average Molecular Mass234.293 g/mol
Monoisotopic Mass234.104 g/mol
CAS Registry Number538-58-9
IUPAC Name(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one
Traditional Namedibenzylideneacetone
SMILES[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)C(\[H])=C(/[H])C1=CC=CC=C1
InChI IdentifierInChI=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+
InChI KeyWMKGGPCROCCUDY-PHEQNACWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
TetracyclinesNot AvailableNot Available
ProteasomeNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder
Experimental Properties
PropertyValue
Melting Point110-111 °C
Boiling Point130 °C
SolubilityInsoluble
Predicted Properties
PropertyValueSource
Water Solubility0.00098 g/LALOGPS
logP3.88ALOGPS
logP4.83ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.03 m³·mol⁻¹ChemAxon
Polarizability27.36 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-ee22b8fb743b76064d47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2890000000-687c9a41e7355c4564f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-5910000000-2d0899b63f5b6b9f269dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-160a417e4fac191b3436View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0590000000-6ec0691349fce7079206View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-2920000000-9a755463d4b65c454264View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-5890000000-b80bd1cb912d36e7a4b8View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDibenzylideneacetone is used as a sunscreen component and as a ligand in organometallic chemistry. (1)
Minimum Risk LevelNot Available
Health EffectsDibenzylideneacetone is an irritant.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDibenzylideneacetone
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available