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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:23 UTC
Update Date2022-03-07 02:53:03 UTC
HMDB IDHMDB0031617
Secondary Accession Numbers
  • HMDB31617
Metabolite Identification
Common NameBenzylideneacetone
DescriptionBenzylideneacetone, also known as trans-benzalacetone, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Benzylideneacetone is a sweet, almond, and anise tasting compound. Benzylideneacetone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Benzylideneacetone.
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

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point41.5 °CNot Available
Boiling Point262.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1345 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.07Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+130.14630932474
DeepCCS[M-H]-127.35930932474
DeepCCS[M-2H]-163.44630932474
DeepCCS[M+Na]+138.69630932474
AllCCS[M+H]+129.232859911
AllCCS[M+H-H2O]+124.532859911
AllCCS[M+NH4]+133.532859911
AllCCS[M+Na]+134.832859911
AllCCS[M-H]-130.832859911
AllCCS[M+Na-2H]-132.132859911
AllCCS[M+HCOO]-133.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzylideneacetoneCC(=O)\C=C\C1=CC=CC=C12001.3Standard polar33892256
BenzylideneacetoneCC(=O)\C=C\C1=CC=CC=C11251.5Standard non polar33892256
BenzylideneacetoneCC(=O)\C=C\C1=CC=CC=C11337.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzylideneacetone,1TMS,isomer #1C=C(/C=C/C1=CC=CC=C1)O[Si](C)(C)C1510.5Semi standard non polar33892256
Benzylideneacetone,1TMS,isomer #1C=C(/C=C/C1=CC=CC=C1)O[Si](C)(C)C1481.3Standard non polar33892256
Benzylideneacetone,1TBDMS,isomer #1C=C(/C=C/C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1755.5Semi standard non polar33892256
Benzylideneacetone,1TBDMS,isomer #1C=C(/C=C/C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1711.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone EI-B (Non-derivatized)splash10-0uea-5900000000-bbca89d5b1a35227985d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone EI-B (Non-derivatized)splash10-0f7k-4900000000-8295a2d505aa2a9f77ce2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone CI-B (Non-derivatized)splash10-0002-0900000000-45fb6240b879abb9c9692017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone EI-B (Non-derivatized)splash10-0f7k-1900000000-17b33cb5075a9d70e5a12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone EI-B (Non-derivatized)splash10-0uea-5900000000-bbca89d5b1a35227985d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone EI-B (Non-derivatized)splash10-0f7k-4900000000-8295a2d505aa2a9f77ce2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone CI-B (Non-derivatized)splash10-0002-0900000000-45fb6240b879abb9c9692018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzylideneacetone EI-B (Non-derivatized)splash10-0f7k-1900000000-17b33cb5075a9d70e5a12018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzylideneacetone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-0a6c0e048f4c5cec78ed2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzylideneacetone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzylideneacetone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f7k-3900000000-8ad3683afcbe5a70c4ef2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylideneacetone 60V, Positive-QTOFsplash10-014l-4900000000-8cfbb3eac18d8d4bf5202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylideneacetone 75V, Positive-QTOFsplash10-00kf-7900000000-8a42abf0dca00c701dfd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylideneacetone 30V, Positive-QTOFsplash10-00kb-0900000000-57afe0bf82d645db42a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylideneacetone 45V, Positive-QTOFsplash10-014j-2900000000-8871dcd67fbc04adb69e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylideneacetone 15V, Positive-QTOFsplash10-00kb-0900000000-330a9e992de2080635fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzylideneacetone 90V, Positive-QTOFsplash10-00kf-9700000000-c7512426dd9d813a53012021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 10V, Positive-QTOFsplash10-002b-0900000000-32d2310b9569d7ac30db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 20V, Positive-QTOFsplash10-004j-1900000000-b58c6c127d639e6aa2042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 40V, Positive-QTOFsplash10-0ufr-8900000000-58ccfbfee6cc23a541d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 10V, Negative-QTOFsplash10-0002-0900000000-18c68bb8112d08b928742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 20V, Negative-QTOFsplash10-0002-0900000000-911f938940970d3262612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 40V, Negative-QTOFsplash10-004i-3900000000-d7fb58553b3833c9ac672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 10V, Negative-QTOFsplash10-0002-0900000000-9d20cdb0d0c7518d00de2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 20V, Negative-QTOFsplash10-0udl-4900000000-f7306fc6af91979742cd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 40V, Negative-QTOFsplash10-004i-9600000000-e2d05750493ccde8fcfd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 10V, Positive-QTOFsplash10-002b-1900000000-20e762b489daca6180c52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 20V, Positive-QTOFsplash10-004i-2900000000-946ac8d3960f9d8f14792021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzylideneacetone 40V, Positive-QTOFsplash10-004l-9200000000-2e1e3fb50e5e85cfbf842021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1291231
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.. .