Showing Compound Card for Benzyl acetophenone (CDB005749)

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Record Information
Version1.0
Created at2020-04-27 16:51:54 UTC
Updated at2021-01-04 18:49:13 UTC
CannabisDB IDCDB005749
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzyl acetophenone
Description1,3-Diphenyl-1-propanone, also known as hydrochalcone, dihydrochalcone or benzyl acetophenone, belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, 1,3-diphenyl-1-propanone is considered to be a flavonoid lipid molecule. 1,3-Diphenyl-1-propanone is a very hydrophobic molecule, practically insoluble in water, and neutral. The main natural source of dihydrochalcones are plants, in which they are biosynthesized by the phenylpropanoid pathway. The richest source of natural dihydrochalcones in diet are apples. In traditional medicine, dihydrochalcones have been used for the treatment of liver cirrhosis, hypertension, diabetes, malaria, yellow fever, breast cancer, gastroenteric and inflammatory disorders, and dengue fever (PMID: 31817526 ). 1,3-Diphenyl-1-propanone has been detected, but not quantified in, mushrooms. 1,3-Diphenyl-1-propanone is a constituent of marijuana (cannabis) smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3-Diphenyl-1-oxopropaneChEBI
Benzyl acetophenoneChEBI
beta-PhenylpropiophenoneChEBI
HydrochalconeChEBI
HydrocinnamophenoneChEBI
b-PhenylpropiophenoneGenerator
Β-phenylpropiophenoneGenerator
.omega.-benzyl acetophenoneHMDB
1, 3-Diphenyl-3-propanoneHMDB
1,3-Diphenyl-3-propanoneHMDB
2',4-Dihydroxy-alpha,beta-dihydrochalconeHMDB
2-Phenethyl phenyl ketoneHMDB
3-Phenyl-propiophenoneHMDB
3-PhenylpropiophenoneHMDB
BenzylacetophenoneHMDB
DihydrochalconeHMDB
Laquo omegaraquo -benzyl acetophenoneHMDB
Omega-benzyl acetophenoneHMDB
Phenethyl phenyl ketoneHMDB
Phenyl phenethyl ketoneHMDB
W-BenzylacetophenoneHMDB
Chemical FormulaC15H14O
Average Molecular Weight210.27
Monoisotopic Molecular Weight210.1045
IUPAC Name1,3-diphenylpropan-1-one
Traditional Namedihydrochalcone
CAS Registry Number1083-30-3
SMILES
O=C(CCC1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H14O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-10H,11-12H2
InChI KeyQGGZBXOADPVUPN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones 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 ParentRetro-dihydrochalcones
Alternative Parents
Substituents
  • Retro-dihydrochalcone
  • Alkyl-phenylketone
  • Butyrophenone
  • Phenylketone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point72 - 73 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.43ALOGPS
logP3.81ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)16.81ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.78 m³·mol⁻¹ChemAxon
Polarizability24.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSBenzyl acetophenone, non-derivatized, GC-MS Spectrumsplash10-0a4i-7930000000-932c5f7279d2b7703686Spectrum
GC-MSBenzyl acetophenone, non-derivatized, GC-MS Spectrumsplash10-0a4i-7930000000-932c5f7279d2b7703686Spectrum
Predicted GC-MSBenzyl acetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-7910000000-2ff89178c9c3eb7d8785Spectrum
Predicted GC-MSBenzyl acetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBenzyl acetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-03dl-8290000000-33e71a1f5cb5353bc2ad2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-b1705fdcb19173392fd12016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1910000000-d5f2c52fb0565d8415df2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900000000-88525d8ae195c0651d6d2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-5b057d0f9decb3eb21d62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0590000000-04d994e93740b2c50cfb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lfr-3900000000-757f5d7541e8ee5a86f72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2190000000-484043668f0e80cf605b2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-8940000000-f68242d0454815ca62b52021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5900000000-069075e13cc0d28a37ab2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-6eca0663b2d1b5b3602c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-2eb5534da0da9715f1ef2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3910000000-d2997154644a0445440d2021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032041
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008744
KNApSAcK IDC00007921
Chemspider ID58334
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydrochalcone
METLIN IDNot Available
PubChem Compound64802
PDB IDNot Available
ChEBI ID71231
References
General References
  1. Stompor M, Broda D, Bajek-Bil A: Dihydrochalcones: Methods of Acquisition and Pharmacological Properties-A First Systematic Review. Molecules. 2019 Dec 5;24(24). pii: molecules24244468. doi: 10.3390/molecules24244468. [PubMed:31817526 ]