Record Information
Version2.0
Creation Date2014-10-15 22:01:21 UTC
Update Date2014-12-24 20:27:01 UTC
Accession NumberT3D4994
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)
Compound Type
  • Cosmetic Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(e)-Dibenzylideneacetone
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 KeyInChIKey=WMKGGPCROCCUDY-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
LogPNot Available
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 KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-ee22b8fb743b76064d472016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2890000000-687c9a41e7355c4564f62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-5910000000-2d0899b63f5b6b9f269d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-160a417e4fac191b34362016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0590000000-6ec0691349fce70792062016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-2920000000-9a755463d4b65c4542642016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-5890000000-b80bd1cb912d36e7a4b82014-10-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-10-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-10-20View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID640180
ChEMBL IDCHEMBL17201
ChemSpider ID555548
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkDibenzylideneacetone
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Wikipedia. Dibenzylideneacetone. Last Updated 22 April 2014. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available