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Record Information
Version3.6
Creation Date2012-09-11 18:41:07 UTC
Update Date2016-02-11 02:21:17 UTC
HMDB IDHMDB33910
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetophenone
DescriptionAcetophenone is found in chicory. Acetophenone is a flavouring ingredient used in fruit flavours; leavening agent Acetophenone is a raw material for the synthesis of some pharmaceuticals and is also listed as an approved excipient by the U.S. FDA. In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes. Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone has been shown to exhibit anti-fungal function (PMID 11215330 ).
Structure
Thumb
Synonyms
ValueSource
AcetylbenzeneChEBI
Benzoyl methideChEBI
Methyl phenyl ketoneChEBI
Phenyl methyl ketoneChEBI
1-Phenyl-1-ethanoneHMDB
1-Phenyl-ethanoneHMDB
1-Phenylethan-1-oneHMDB
1-Phenylethanone (acetophenone)HMDB
1-Phenylethanone, 9ciHMDB
AcetofenonHMDB
AcetophenonHMDB
Acetyl-benzeneHMDB
AcetylbenzolHMDB
alpha-AcetophenoneHMDB
BenzoylmethideHMDB
DymexHMDB
FEMA 2009HMDB
HypnonHMDB
HypnoneHMDB
Ketone, methyl phenylHMDB
Methyl phenyl-ketoneHMDB
MethylphenylketoneHMDB
Nchem.180-comp5HMDB
PhenylHMDB
PhenylethanoneHMDB
PhenylmethylketoneHMDB
Chemical FormulaC8H8O
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
IUPAC Name1-phenylethan-1-one
Traditional Nameacetophenone
CAS Registry Number98-86-2
SMILES
CC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
InChI KeyInChIKey=KWOLFJPFCHCOCG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAcetophenones
Direct ParentAcetophenones
Alternative Parents
Substituents
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Drug
  • Food
Biofunction
  • Nutrient
  • anti-fungal
Application
  • Drug
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point20 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.13 mg/mL at 25 °CNot Available
LogP1.58Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 mg/mLALOGPS
logP1.65ALOGPS
logP1.53ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)16.1ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.46 m3·mol-1ChemAxon
Polarizability13.05 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-7c012935d15ff7510bb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-2aa01ede85e5b5caa8d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6900000000-d47a5846f1d60b451390View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ba5d67d7d79e78cf111eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-b904a793250c40e784a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-f72df069d2851aa2de2aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04619
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012106
KNApSAcK IDC00002685
Chemspider ID7132
KEGG Compound IDC07113
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetophenone
NuGOwiki LinkHMDB33910
Metagene LinkHMDB33910
METLIN IDNot Available
PubChem Compound7410
PDB IDAC0
ChEBI ID27632
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gul HI, Ojanen T, Vepsalainen J, Gul M, Erciyas E, Hanninen O: Antifungal activity of some mono, bis and quaternary Mannich bases derived from acetophenone. Arzneimittelforschung. 2001 Jan;51(1):72-5. [11215330 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.