Record Information
Version1.0
Creation date2011-09-21 00:24:42 UTC
Update date2015-10-09 22:33:12 UTC
Primary IDFDB023102
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.[2] The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.[3] 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).[4] [HMDB]
CAS Number94-41-7
Structure
Thumb
Synonyms
SynonymSource
(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
BenzylidenecetophenoneHMDB
beta-BenzoylstyreneHMDB
beta-PhenylacrylophenoneHMDB
Chalcone (acd/name 4.0)HMDB
ChalkoneHMDB
CinnamophenoneHMDB
Phenyl 2-phenylvinyl ketoneHMDB
Phenyl styryl ketoneHMDB
Styryl phenyl ketoneHMDB
1,3 Diphenyl 2 propen 1 oneHMDB
ChalconeMeSH
3-phenyl-Acrylophenonehmdb
chalcone (ACD/Name 4.0)hmdb
Predicted 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 RuleYesChemAxon
Chemical FormulaC15H12O
IUPAC name(2E)-1,3-diphenylprop-2-en-1-one
InChI IdentifierInChI=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
Isomeric SMILESO=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C1
Average Molecular Weight208.2552
Monoisotopic Molecular Weight208.088815006
Classification
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:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 MEOX)splash10-0kdi-8970000000-e9d06e2f2c7c54d30af4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 MEOX)splash10-056r-8970000000-b92152ec5263740742f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-056r-7970000000-a1b8a54f7d67050943eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5890000000-645c9135637f00e29e82JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3590000000-6ea95e5868f03e7f35a2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0kdi-8970000000-e9d06e2f2c7c54d30af4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-056r-8970000000-b92152ec5263740742f5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-056r-7970000000-a1b8a54f7d67050943eeJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1920000000-2b429c8f539b9f5b1440JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0190000000-47d4fc561712a9ed0701JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-08d7ed15330077a018abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-355ff6a756011feca044JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a4i-5890000000-0318c8da1ae89104b79dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4i-3590000000-89feb8e1d3fb37ac3c54JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0kai-1920000000-d52b48e8f3d60aa65927JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uka-3930000000-ffa76ca3cbb07e0bf832JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kai-1920000000-d52b48e8f3d60aa65927JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-3900000000-5fb804540f4b41916f0fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-6a240c4dc86549c5b6b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0940000000-0158cdbb6c513255d642JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-b035f10818fdd63572bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-f2dbf3782664618f2b30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-0f0f84985a536e6e3649JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-2910000000-7c5af61c772ec555bbf9JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID553346
ChEMBL IDCHEMBL7976
KEGG Compound IDC15589
Pubchem Compound ID637760
Pubchem Substance IDNot Available
ChEBI ID27618
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03066
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChalcone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference