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
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 RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSChalcone, 1 MEOX, GC-MS Spectrumsplash10-0kdi-8970000000-e9d06e2f2c7c54d30af4Spectrum
GC-MSChalcone, 1 MEOX, GC-MS Spectrumsplash10-056r-8970000000-b92152ec5263740742f5Spectrum
GC-MSChalcone, non-derivatized, GC-MS Spectrumsplash10-056r-7970000000-a1b8a54f7d67050943eeSpectrum
GC-MSChalcone, non-derivatized, GC-MS Spectrumsplash10-0a4i-5890000000-645c9135637f00e29e82Spectrum
GC-MSChalcone, non-derivatized, GC-MS Spectrumsplash10-0a4i-3590000000-6ea95e5868f03e7f35a2Spectrum
GC-MSChalcone, non-derivatized, GC-MS Spectrumsplash10-0kdi-8970000000-e9d06e2f2c7c54d30af4Spectrum
GC-MSChalcone, non-derivatized, GC-MS Spectrumsplash10-056r-8970000000-b92152ec5263740742f5Spectrum
GC-MSChalcone, non-derivatized, GC-MS Spectrumsplash10-056r-7970000000-a1b8a54f7d67050943eeSpectrum
Predicted GC-MSChalcone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1920000000-2b429c8f539b9f5b1440Spectrum
Predicted GC-MSChalcone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0190000000-47d4fc561712a9ed07012012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-08d7ed15330077a018ab2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-355ff6a756011feca0442012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a4i-5890000000-0318c8da1ae89104b79d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4i-3590000000-89feb8e1d3fb37ac3c542012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0kai-1920000000-d52b48e8f3d60aa659272012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uka-3930000000-ffa76ca3cbb07e0bf8322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kai-1920000000-d52b48e8f3d60aa659272017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-3900000000-5fb804540f4b41916f0f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-1900000000-671c9baa28b3d75213f22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0970000000-c3af16631498daa4e7442021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-a403ba02ae79994b5e462021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a59-0970000000-8f46ddaaa1f5e7c63dbf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0190000000-3a33b42ab0e322dadfcd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0udi-1900000000-085214f488f9862c99fd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0970000000-02a4860e78115302e9272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0ufr-4910000000-93ddc77e35b5c8408eb22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0udi-2910000000-d6f4902ce9b3d6fd2fe82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-1900000000-6e52bb319087e6f38b5b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-6a240c4dc86549c5b6b22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0940000000-0158cdbb6c513255d6422017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-b035f10818fdd63572bd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-f2dbf3782664618f2b302017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-0f0f84985a536e6e36492017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-2910000000-7c5af61c772ec555bbf92017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference