You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:23 UTC
Update Date2019-07-23 06:09:08 UTC
HMDB IDHMDB0031617
Secondary Accession Numbers
  • HMDB31617
Metabolite Identification
Common NameBenzylideneacetone
DescriptionBenzylideneacetone, also known as trans-benzalacetone or 4-phenylbutenone, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Benzylideneacetone is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzylideneacetone is a sweet, almond, and anise tasting compound. Benzylideneacetone is a potentially toxic compound. Benzylideneacetone is the organic compound described by the formula C6H5CHCHC(O)CH3. Benzylideneacetone can be efficiently prepared by the NaOH-induced condensation of the readily available reagents acetone and benzaldehyde:CH3C(O)CH3 + C6H5CHO → C6H5CHCHC(O)CH3 + H2OHowever, the benzylideneacetone formed via this reaction can undergo another Claisen-Schmidt condensation with another molecule of benzaldehyde to form dibenzylideneacetone. Its original preparation demonstrated the scope of condensation reactions to construct new, complex organic compounds. Therefore, the most efficient way to make benzylideneacetone is to use equimolar amounts of LDA (in THF), acetone, and benzaldehyde. The reaction must be done with anhydrous chemicals as LDA breaks down in water. Benzylideneacetone is used as a flavouring ingredient in food and perfumes. Hydrogenation of benzylideneacetone results in a preparation of benzylacetone. Although both cis- and trans-isomers are possible for the α,β-unsaturated ketone, only the trans isomer is observed. The reaction of 4-Hydroxycoumarin with this compound yields Warfarin. It reacts with Fe2(CO)9 to give (benzylideneacetone)Fe(CO)3, a reagent for transferring the Fe(CO)3 unit to other organic substrates. As with most methyl ketones, benzylidineacetone is moderately acidic at the alpha position, and it can be readily deprotonated to form the corresponding enolateThe compound undergoes the reactions expected for its collection of functional groups: e.g., the double bond adds bromine, the heterodiene adds electron-rich alkenes in Diels-Alder reactions to give dihydropyrans, the methyl group undergoes further condensation with benzaldehyde to give dibenzylideneacetone, and the carbonyl forms hydrazones. If, on the other hand, lithium diisopropylamide (LDA) is used as the base, all of the acetone will deprotonated, making enolate ion quantitatively.
Structure
Data?1563862148
Synonyms
ValueSource
Methyl trans-styryl ketoneChEBI
trans-4-Phenyl-3-butene-2-oneChEBI
trans-BenzalacetoneChEBI
(3E)-4-Phenyl-3-buten-2-oneHMDB
(3E)-4-Phenylbut-3-en-2-oneHMDB
(e)-4-Phenyl-3-buten-2-oneHMDB
1-Buten-3-one-1-phenylHMDB
2-Phenylvinyl methyl ketoneHMDB
3-BUTEN,2-one,4-phenyl (trans) benzalacetoneHMDB
4-Phenyl-(e)-3-buten-2-oneHMDB
4-Phenyl-3-buten-2-oneHMDB
4-Phenyl-3-butene-2-oneHMDB
4-Phenylbut-3-en-2-oneHMDB
4-PhenylbutenoneHMDB
AcetocinnamoneHMDB
BenzalacetonHMDB
BenzalacetoneHMDB
Benzilidene acetoneHMDB
BenzilideneacetoneHMDB
Benzylidene acetoneHMDB
Benzylideneacetone, (e)-isomerHMDB
Benzylideneacetone, (Z)-isomerHMDB
FEMA 2881HMDB
Ghl.PD_Mitscher_leg0.147HMDB
Ketone, methyl styrylHMDB
Methyl 2-phenylvinyl ketoneHMDB
Methyl beta -styryl ketoneHMDB
Methyl beta-styryl ketoneHMDB
Methyl styryl acetoneHMDB
Methyl styryl ketoneHMDB
STYRYL methyl ketoneHMDB
T-PboHMDB
TPBOHMDB
trans-4-Phenyl-3-buten-2-oneHMDB
trans-4-Phenylbut-3-en-2-oneHMDB
trans-BenzylidenacetoneHMDB
trans-BenzylideneacetoneHMDB
BenzylideneacetoneMeSH
Chemical FormulaC10H10O
Average Molecular Weight146.1858
Monoisotopic Molecular Weight146.073164942
IUPAC Name(3E)-4-phenylbut-3-en-2-one
Traditional NameBENZ
CAS Registry Number122-57-6
SMILES
CC(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+
InChI KeyBWHOZHOGCMHOBV-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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point41.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.07Not Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uea-5900000000-bbca89d5b1a35227985dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-4900000000-8295a2d505aa2a9f77ceSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-45fb6240b879abb9c969Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-1900000000-17b33cb5075a9d70e5a1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uea-5900000000-bbca89d5b1a35227985dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-4900000000-8295a2d505aa2a9f77ceSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0900000000-45fb6240b879abb9c969Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f7k-1900000000-17b33cb5075a9d70e5a1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-0a6c0e048f4c5cec78edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-32d2310b9569d7ac30dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-1900000000-b58c6c127d639e6aa204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-8900000000-58ccfbfee6cc23a541d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-18c68bb8112d08b92874Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-911f938940970d326261Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900000000-d7fb58553b3833c9ac67Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f7k-3900000000-8ad3683afcbe5a70c4efSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008255
KNApSAcK IDNot Available
Chemspider ID21106584
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzylideneacetone
METLIN IDNot Available
PubChem Compound637759
PDB IDNot Available
ChEBI ID78399
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .