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
Bioavailability1ChemAxon
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
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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 MEOX)splash10-0kdi-8970000000-e9d06e2f2c7c54d30af4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 MEOX)splash10-056r-8970000000-b92152ec5263740742f5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-056r-7970000000-a1b8a54f7d67050943eeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5890000000-645c9135637f00e29e82View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3590000000-6ea95e5868f03e7f35a2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0kdi-8970000000-e9d06e2f2c7c54d30af4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-056r-8970000000-b92152ec5263740742f5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-056r-7970000000-a1b8a54f7d67050943eeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1920000000-2b429c8f539b9f5b1440View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0190000000-47d4fc561712a9ed0701View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-08d7ed15330077a018abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-355ff6a756011feca044View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a4i-5890000000-0318c8da1ae89104b79dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4i-3590000000-89feb8e1d3fb37ac3c54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0kai-1920000000-d52b48e8f3d60aa65927View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uka-3930000000-ffa76ca3cbb07e0bf832View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kai-1920000000-d52b48e8f3d60aa65927View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-3900000000-5fb804540f4b41916f0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-6a240c4dc86549c5b6b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0940000000-0158cdbb6c513255d642View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-b035f10818fdd63572bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-f2dbf3782664618f2b30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-0f0f84985a536e6e3649View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-2910000000-7c5af61c772ec555bbf9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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