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4'-Methoxyacetophenone (FDB010502)

Record Information
Version1.0
Creation date2010-04-08 22:09:09 UTC
Update date2020-09-17 15:35:35 UTC
Primary IDFDB010502
Secondary Accession Numbers
  • FDB006573
Chemical Information
FooDB Name4'-Methoxyacetophenone
Descriptionp-Acetanisole also known as 4'-Methoxyacetophenone, 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. p-Acetanisole is an aromatic chemical compound with an aroma described as sweet, fruity, nutty, and similar to vanilla. In addition, Acetanisole can sometimes smell like butter or caramel. At room temperature p-Acetanisole is solid and has a white crystal-like structure. Once melted, the white crystals turn into a clear liquid. p-Acetanisole is a sweet, acacia, and anisic tasting compound. p-Acetanisole is found in the highest concentration in peppermints. p-Acetanisole has also been detected, but not quantified, in several different foods, such as alcoholic beverages, fruits, garden tomato, and herbs and spices. This could make p-Acetanisole a potential biomarker for the consumption of these foods. Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride. It is used as a cigarette additive, a fragrance, and a flavoring in food.
CAS Number100-06-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.07 g/LALOGPS
logP1.82ALOGPS
logP1.37ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)16.28ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.92 m³·mol⁻¹ChemAxon
Polarizability16.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O2
IUPAC name1-(4-methoxyphenyl)ethan-1-one
InChI IdentifierInChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
InChI KeyNTPLXRHDUXRPNE-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C(C)=O
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
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
  • Phenoxy compound
  • Methoxybenzene
  • Aryl alkyl ketone
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.98%; H 6.71%; O 21.31%DFC
Melting PointMp 38-39°DFC
Boiling PointBp15 138-139°DFC
Experimental Water SolubilityNot Available
Experimental logP1.74HANSCH,C ET AL. (1995)
Experimental pKapKa1 -4.81 (25°, H2SO4 aq.)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-5900000000-aeafe190f2bb388caf112015-03-01View Spectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-0be5991ccb2021dc5422Spectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-1c868f73005d65c19187Spectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-002r-9700000000-e00e43b1125f4e22757aSpectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-b943a08390f9ab22ada1Spectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-0be5991ccb2021dc5422Spectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-1c868f73005d65c19187Spectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-002r-9700000000-e00e43b1125f4e22757aSpectrum
GC-MSAcetoanisole, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-b943a08390f9ab22ada1Spectrum
Predicted GC-MSAcetoanisole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-4900000000-c9f5be49882a00ded896Spectrum
Predicted GC-MSAcetoanisole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0udi-0900000000-ab069ee93798f8739e172020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0udi-0900000000-6203f76f25d6e3c8be5c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0udi-0900000000-ad7a20071a6e1ac1c7a72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0pbc-5900000000-9849be577667954c8fc02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0006-9300000000-dcda3a9adc2e48dfdc3c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0006-9000000000-b4c802ba762cfa4d59da2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0006-9000000000-f254a40405a0263449a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-479b62bd5617988dda6f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-0900000000-ffc26e9e01000f0bfb822020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-c264202316aaf331d82d2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-861dd46badcb34e0f0722016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-38c20646c05816cc908b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-4900000000-0831cbb3d37aeb598b6d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2a2829588a725eaabaf12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-41c21874174fde2141cb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar3-8900000000-defe3e6768f83be656152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6x-9800000000-405d7d3603c0c8a729a22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-67646729036995c83f102021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-581faeebb3727fbecafc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0900000000-c9e4c29bb4ce1dc0381b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e8361658ecd5aff1745f2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider ID13835344
ChEMBL IDCHEMBL401912
KEGG Compound IDNot Available
Pubchem Compound ID7476
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32570
CRC / DFC (Dictionary of Food Compounds) IDFBR47-H:FBR44-E
EAFUS ID17
Dr. Duke IDP-METHOXY-ACETOPHENONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1000111
SuperScent ID7476
Wikipedia IDNot Available
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
butter
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
caramel
  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.
vanilla
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
hawthorn
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
anisic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsamic
  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.
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
MSDSNot Available
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).