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Record Information
Version2.0
Creation Date2014-09-11 05:21:51 UTC
Update Date2014-12-24 20:26:59 UTC
Accession NumberT3D4909
Identification
Common NameBenzylideneacetone
ClassSmall Molecule
DescriptionBenzylideneacetone is a flavouring ingredient. Benzylideneacetone is present in hydrolysed soy protein Benzylideneacetone belongs to the family of Phenylpropenes. These are compounds containing a phenylpropene moeity, which consists of a propene substituent bound to a phenyl group.
Compound Type
  • Ester
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(3E)-4-Phenyl-3-buten-2-one
(3E)-4-phenylbut-3-en-2-one
(E)-4-Phenyl-3-buten-2-one
1-Buten-3-one-1-phenyl
2-Phenylvinyl methyl ketone
3-BUTEN,2-ONE,4-PHENYL (TRANS) BENZALACETONE
4-Phenyl-(E)-3-Buten-2-one
4-Phenyl-3-Buten-2-one
4-Phenyl-3-butene-2-one
4-Phenylbut-3-en-2-one
4-Phenylbutenone
Acetocinnamone
Benzalaceton
Benzalacetone
Benzilidene acetone
Benzilideneacetone
Benzylidene acetone
Benzylideneacetone, (e)-isomer
Benzylideneacetone, (z)-isomer
FEMA 2881
Ghl.PD_Mitscher_leg0.147
Ketone, methyl STYRYL
Methyl 2-phenylvinyl ketone
Methyl beta -STYRYL ketone
Methyl beta-STYRYL ketone
Methyl STYRYL acetone
Methyl styryl ketone
Methyl trans-STYRYL ketone
STYRYL methyl ketone
T-Pbo
TPBO
trans-4-Phenyl-3-buten-2-one
trans-4-Phenyl-3-butene-2-one
trans-4-Phenylbut-3-en-2-one
Trans-benzalacetone
Trans-benzylidenacetone
Trans-benzylideneacetone
Chemical FormulaC10H10O
Average Molecular Mass146.186 g/mol
Monoisotopic Mass146.073 g/mol
CAS Registry Number122-57-6
IUPAC Name(3E)-4-phenylbut-3-en-2-one
Traditional NameBENZ
SMILES[H]\C(=C(\[H])C1=CC=CC=C1)C(C)=O
InChI IdentifierInChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+
InChI KeyInChIKey=BWHOZHOGCMHOBV-BQYQJAHWSA-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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point41.5 °C
Boiling Point260-262°C
SolubilityNot Available
LogP2.07
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.23ALOGPS
logP2.47ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)19.68ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.61 m³·mol⁻¹ChemAxon
Polarizability16.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uea-5900000000-bbca89d5b1a35227985dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-4900000000-8295a2d505aa2a9f77ceJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-45fb6240b879abb9c969JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-1900000000-17b33cb5075a9d70e5a1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uea-5900000000-bbca89d5b1a35227985dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-4900000000-8295a2d505aa2a9f77ceJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-45fb6240b879abb9c969JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-1900000000-17b33cb5075a9d70e5a1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-0a6c0e048f4c5cec78edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-32d2310b9569d7ac30dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-1900000000-b58c6c127d639e6aa204JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-8900000000-58ccfbfee6cc23a541d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-18c68bb8112d08b92874JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-911f938940970d326261JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900000000-d7fb58553b3833c9ac67JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0f7k-3900000000-8ad3683afcbe5a70c4efJSpectraViewer | MoNA
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/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31617
PubChem Compound ID637759
ChEMBL IDNot Available
ChemSpider ID21106584
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID217301
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia Link4-Phenyl-3-buten-2-one
References
Synthesis ReferenceNot Available
MSDST3D4909.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXRs is 9-cis retinoic acid. RXRA serves as a common heterodimeric partner for a number of nuclear receptors. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. The RXRA/PPARA heterodimer is required for PPARA transcriptional activity on fatty acid oxidation genes such as ACOX1 and the P450 system genes.
Gene Name:
RXRA
Uniprot ID:
P19793
Molecular Weight:
50810.835 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.22 uMOT_NURR1_NURR1RXRa_0480Odyssey Thera
AC502.92 uMOT_NURR1_NURR1RXRa_1440Odyssey Thera
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]