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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:30 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003066
Secondary Accession Numbers
  • HMDB03066
Metabolite Identification
Common NameChalcone
DescriptionChalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones. They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.Chalcones can be prepared by an aldol condensation between a benzaldehyde and an acetophenone in the presence of sodium hydroxide as a catalyst. This reaction has been found to work in without any solvent at all - a solid-state reaction. The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education. In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 degree centigrade).
Structure
Data?1582752262
Synonyms
ValueSource
(2E)-1,3-Diphenyl-2-propen-1-oneChEBI
(e)-1,3-Diphenyl-2-propen-1-oneChEBI
(e)-BenzylideneacetophenoneChEBI
(e)-ChalconeChEBI
1,3-Diphenyl-2-propen-1-oneChEBI
BenzylideneacetophenoneChEBI
Phenyl (e)--2-phenylethenyl ketoneChEBI
Phenyl trans-styryl ketoneChEBI
trans-BenzalacetophenoneChEBI
trans-BenzylideneacetophenoneChEBI
1, 3-Diphenyl-1-propen-3-oneHMDB
1,3-Diphenyl-2-propenoneHMDB
1,3-DiphenylpropenoneHMDB
1-Benzoyl-1-phenyletheneHMDB
1-Benzoyl-2-phenyletheneHMDB
1-Benzoyl-2-phenylethyleneHMDB
1-Phenyl-2-benzoylethyleneHMDB
2-BenzalacetophenoneHMDB
2-BenzylideneacetophenoneHMDB
3-Phenyl-acrylophenoneHMDB
3-PhenylacrylophenoneHMDB
a-BenzylideneacetophenoneHMDB
alpha-BenzylideneacetophenoneHMDB
b-BenzoylstyreneHMDB
b-PhenylacrylophenoneHMDB
BenzalacetophenoneHMDB, MeSH
BenzylidenecetophenoneHMDB
beta-BenzoylstyreneHMDB
beta-PhenylacrylophenoneHMDB
Chalcone (acd/name 4.0)HMDB
ChalkoneHMDB, MeSH
CinnamophenoneHMDB
Phenyl 2-phenylvinyl ketoneHMDB
Phenyl styryl ketoneHMDB
Styryl phenyl ketoneHMDB
1,3 Diphenyl 2 propen 1 oneMeSH, HMDB
ChalconeMeSH
Chemical FormulaC15H12O
Average Molecular Weight208.2552
Monoisotopic Molecular Weight208.088815006
IUPAC Name(2E)-1,3-diphenylprop-2-en-1-one
Traditional Nametrans-chalcone
CAS Registry Number94-41-7
SMILES
O=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+
InChI KeyDQFBYFPFKXHELB-VAWYXSNFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct ParentRetrochalcones
Alternative Parents
Substituents
  • Retrochalcone
  • Aryl ketone
  • Styrene
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point57.5 °CNot Available
Boiling Point346.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility92.93 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.018Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0062 g/LALOGPS
logP3.63ALOGPS
logP3.89ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)16.91ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.88 m³·mol⁻¹ChemAxon
Polarizability23.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+150.15630932474
DeepCCS[M-H]-147.7630932474
DeepCCS[M-2H]-180.9730932474
DeepCCS[M+Na]+156.06930932474
AllCCS[M+H]+146.532859911
AllCCS[M+H-H2O]+142.132859911
AllCCS[M+NH4]+150.732859911
AllCCS[M+Na]+151.932859911
AllCCS[M-H]-148.232859911
AllCCS[M+Na-2H]-147.832859911
AllCCS[M+HCOO]-147.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChalconeO=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C12797.6Standard polar33892256
ChalconeO=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C11915.1Standard non polar33892256
ChalconeO=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C11979.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Chalcone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 MEOX)splash10-0kdi-8970000000-e9d06e2f2c7c54d30af42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chalcone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 MEOX)splash10-056r-8970000000-b92152ec5263740742f52014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chalcone GC-MS (Non-derivatized)splash10-056r-7970000000-a1b8a54f7d67050943ee2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chalcone EI-B (Non-derivatized)splash10-0a4i-5890000000-645c9135637f00e29e822017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chalcone EI-B (Non-derivatized)splash10-0a4i-3590000000-6ea95e5868f03e7f35a22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chalcone GC-EI-TOF (Non-derivatized)splash10-0kdi-8970000000-e9d06e2f2c7c54d30af42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chalcone GC-EI-TOF (Non-derivatized)splash10-056r-8970000000-b92152ec5263740742f52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chalcone GC-MS (Non-derivatized)splash10-056r-7970000000-a1b8a54f7d67050943ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chalcone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1920000000-2b429c8f539b9f5b14402017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chalcone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-0190000000-47d4fc561712a9ed07012012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0udi-0900000000-08d7ed15330077a018ab2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9200000000-355ff6a756011feca0442012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone EI-B (JEOL JMS-D-3000) , Positive-QTOFsplash10-0a4i-5890000000-0318c8da1ae89104b79d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone EI-B (HITACHI M-80) , Positive-QTOFsplash10-0a4i-3590000000-89feb8e1d3fb37ac3c542012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0kai-1920000000-d52b48e8f3d60aa659272012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone LC-ESI-qTof , Positive-QTOFsplash10-0uka-3930000000-ffa76ca3cbb07e0bf8322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone LC-ESI-QTOF , positive-QTOFsplash10-0kai-1920000000-d52b48e8f3d60aa659272017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone , positive-QTOFsplash10-0udi-3900000000-5fb804540f4b41916f0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 6V, Positive-QTOFsplash10-0udi-1900000000-671c9baa28b3d75213f22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 10V, Positive-QTOFsplash10-0a59-0970000000-c3af16631498daa4e7442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 10V, Positive-QTOFsplash10-0a4i-0190000000-a403ba02ae79994b5e462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 6V, Positive-QTOFsplash10-0a59-0970000000-8f46ddaaa1f5e7c63dbf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 6V, Positive-QTOFsplash10-0a4i-0190000000-3a33b42ab0e322dadfcd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 50V, Positive-QTOFsplash10-0udi-1900000000-085214f488f9862c99fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 10V, Positive-QTOFsplash10-0a59-0970000000-02a4860e78115302e9272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 50V, Positive-QTOFsplash10-0ufr-4910000000-93ddc77e35b5c8408eb22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 50V, Positive-QTOFsplash10-0udi-2910000000-d6f4902ce9b3d6fd2fe82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalcone 30V, Positive-QTOFsplash10-0udi-1900000000-6e52bb319087e6f38b5b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalcone 10V, Positive-QTOFsplash10-0a4i-0290000000-6a240c4dc86549c5b6b22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalcone 20V, Positive-QTOFsplash10-0a4i-0940000000-0158cdbb6c513255d6422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalcone 40V, Positive-QTOFsplash10-0udi-4900000000-b035f10818fdd63572bd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalcone 10V, Negative-QTOFsplash10-0a4i-0190000000-f2dbf3782664618f2b302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalcone 20V, Negative-QTOFsplash10-0a4i-0390000000-0f0f84985a536e6e36492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalcone 40V, Negative-QTOFsplash10-0zi0-2910000000-7c5af61c772ec555bbf92017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB023102
KNApSAcK IDC00053160
Chemspider ID553346
KEGG Compound IDC15589
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChalcone
METLIN ID3342
PubChem Compound637760
PDB IDNot Available
ChEBI ID48965
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1414721
References
Synthesis ReferenceBi, Xian-shu; Zhou, Ning-huai. Research for the synthesis of chalcone by microwave irradiation using KF/Al2O3 catalyst. Guangxi Shifan Daxue Xuebao, Ziran Kexueban (2000), 18(1), 60-62.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hawkins DR, Chasseaud LF, Weston KT: Aspects of the metabolism of the peripheral vasodilator mecinarone (14C-6809 MD) in rat, dog and man. Eur J Drug Metab Pharmacokinet. 1980;5(3):145-52. [PubMed:7202432 ]