ContaminantDB: Dibenzylideneacetone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-10-15 22:01:21 UTC

Update Date

2026-04-04 04:10:24 UTC

Accession Number

CHEM003948

Identification

Common Name

Dibenzylideneacetone

Class

Small Molecule

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)

Contaminant Sources

T3DB toxins

Contaminant Type

Cosmetic Toxin
Industrial/Workplace Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-Dibenzylideneacetone	ChEMBL
Dibenzylidene acetone	MeSH
Dibenzalacetone	MeSH

Chemical Formula

C₁₇H₁₄O

Average Molecular Mass

234.293 g/mol

Monoisotopic Mass

234.104 g/mol

CAS Registry Number

538-58-9

IUPAC Name

(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one

Traditional Name

dibenzylideneacetone

SMILES

[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)C(\[H])=C(/[H])C1=CC=CC=C1

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+

InChI Key

WMKGGPCROCCUDY-PHEQNACWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Tetracyclines	Not Available	Not Available
Proteasome	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder

Experimental Properties

Property	Value
Melting Point	110-111 °C
Boiling Point	130 °C
Solubility	Insoluble

Predicted Properties

Property	Value	Source
Water Solubility	0.00098 g/L	ALOGPS
logP	3.88	ALOGPS
logP	4.83	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.03 m³·mol⁻¹	ChemAxon
Polarizability	27.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
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

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Dibenzylideneacetone is used as a sunscreen component and as a ligand in organometallic chemistry. (1)

Minimum Risk Level

Not Available

Health Effects

Dibenzylideneacetone is an irritant.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dibenzylideneacetone

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

640180

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dibenzylideneacetone (CHEM003948)

Structure for CHEM003948: Dibenzylideneacetone