T3DB: Dibenzylideneacetone

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

Record Information

Version

2.0

Creation Date

2014-10-15 22:01:21 UTC

Update Date

2014-12-24 20:27:01 UTC

Accession Number

T3D4994

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)

Compound Type

Cosmetic Toxin
Industrial/Workplace Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
(e)-Dibenzylideneacetone

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

InChIKey=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
LogP	Not Available

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	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-ee22b8fb743b76064d47	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2890000000-687c9a41e7355c4564f6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufu-5910000000-2d0899b63f5b6b9f269d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0190000000-160a417e4fac191b3436	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0590000000-6ec0691349fce7079206	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-2920000000-9a755463d4b65c454264	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-5890000000-b80bd1cb912d36e7a4b8	2014-10-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-10-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Not Available	2014-10-20	View 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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

640180

ChEMBL ID

CHEMBL17201

ChemSpider ID

555548

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Dibenzylideneacetone

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Wikipedia. Dibenzylideneacetone. Last Updated 22 April 2014. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Dibenzylideneacetone (T3D4994)

Structure for T3D4994: Dibenzylideneacetone