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Acetophenone (FDB012106)

Record Information
Version1.0
Creation date2010-04-08 22:09:59 UTC
Update date2020-09-17 15:34:39 UTC
Primary IDFDB012106
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetophenone
DescriptionAcetophenone, also known as 1-phenylethanone or acetylbenzene, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. The chemical formula of acetophenone is C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is used as a flavouring ingredient for fruit flavours and as a leavening agent. Acetophenone is also the starting material for the synthesis of some pharmaceuticals and is listed as an approved excipient by the U.S. FDA. Acetophenone is currently listed as a Group D carcinogen indicating that it does not produce carcinogenic effects in humans. 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 found in many foods, some of which are chicory, spearmint, watermelon, rocket salad, and pepper (spice), apple, cheese, apricot, banana, beef, and cauliflower.
CAS Number98-86-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP1.65ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.1ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.46 m³·mol⁻¹ChemAxon
Polarizability13.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O
IUPAC name1-phenylethan-1-one
InChI IdentifierInChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
InChI KeyKWOLFJPFCHCOCG-UHFFFAOYSA-N
Isomeric SMILESCC(=O)C1=CC=CC=C1
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
Classification
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Aryl alkyl ketone
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 79.97%; H 6.71%; O 13.32%DFC
Melting PointMp 20°DFC
Boiling PointBp5 67°DFC
Experimental Water Solubility6.13 mg/mL at 25 oCSOUTHWORTH,GR & KELLER,JL (1986)
Experimental logP1.58HANSCH,C ET AL. (1995)
Experimental pKapKa1 -6.4 (25°, H2SO4 aq.)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.03DFC
Refractive Indexn20D 1.5342DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-9700000000-224496fb4a326cb28b65Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-9800000000-5d4a6da80c6c3c5f5fbbSpectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-8900000000-72a8572391def7a73d00Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0pdi-9600000000-d687340f90f63f7dc2dbSpectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0pdi-9500000000-3f26e145dcae1ef98802Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-558d4c95783742599522Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0adi-9700000000-6f2471f8e98524af3f5bSpectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0fr2-1900000000-a41b0cedd919c67e41f4Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-9700000000-224496fb4a326cb28b65Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-9800000000-5d4a6da80c6c3c5f5fbbSpectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-8900000000-72a8572391def7a73d00Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0pdi-9600000000-d687340f90f63f7dc2dbSpectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0pdi-9500000000-3f26e145dcae1ef98802Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-558d4c95783742599522Spectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0adi-9700000000-6f2471f8e98524af3f5bSpectrum
GC-MSAcetophenone, non-derivatized, GC-MS Spectrumsplash10-0fr2-1900000000-a41b0cedd919c67e41f4Spectrum
Predicted GC-MSAcetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pi0-9700000000-60050b91c62443766d21Spectrum
Predicted GC-MSAcetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-7c012935d15ff7510bb22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-2aa01ede85e5b5caa8d82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6900000000-d47a5846f1d60b4513902015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ba5d67d7d79e78cf111e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-b904a793250c40e784a32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-f72df069d2851aa2de2a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-9fe47ad4ae02d8640b562021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-5900000000-bb7919a9d31b496bf4412021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fbc-9100000000-9e7d314dd7e6128835bc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9200000000-9aee9a6157b9ef0e6d582021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-66cb89e73dbfd10f01172021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a1759373fa5762f762e42021-09-24View Spectrum
NMRNot Available
ChemSpider ID7132
ChEMBL IDCHEMBL274467
KEGG Compound IDC07113
Pubchem Compound ID7410
Pubchem Substance IDNot Available
ChEBI ID27632
Phenol-Explorer IDNot Available
DrugBank IDDB04619
HMDB IDHMDB33910
CRC / DFC (Dictionary of Food Compounds) IDHDG06-B:HDG06-B
EAFUS ID26
Dr. Duke IDACETOPHENONE|METHYL-PHENYLKETONE
BIGG IDNot Available
KNApSAcK IDC00002685
HET IDAC0
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID98-86-2
GoodScent IDrw1000131
SuperScent ID7410
Wikipedia IDAcetophenone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hypnoticDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
soporificDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
must
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
flower
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
almond
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
hawthorne
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
hawthorn
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mimosa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acacia
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
chemical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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
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References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).