Showing Compound Card for p-Acetanisole (CDB000652)

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Record Information
Version1.0
Created at2020-03-19 00:49:05 UTC
Updated at2020-12-07 19:07:37 UTC
CannabisDB IDCDB000652
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namep-Acetanisole
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. p-Acetanisole is a volatile compound found in marijuana (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-AcetylanisoleChEBI
4-Methoxyphenyl methyl ketoneChEBI
AcetanisoleChEBI
1-(4-Methoxyphenyl)ethanoneChEMBL, HMDB
1-(4-Methoxyphenyl)-ethanoneHMDB
4'-Methoxy-acetophenoneHMDB
4-Methoxy-acetophenoneHMDB
4-MethoxyacetophenoneHMDB, MeSH
FEMA 2005HMDB
LinarodinHMDB
P-AcetylanisoleHMDB
P-MethoxyacetophenoneHMDB
P-MetoxyacetophenoneHMDB
Para-methoxyacetophenoneHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.17
Monoisotopic Molecular Weight150.0681
IUPAC Name1-(4-methoxyphenyl)ethan-1-one
Traditional NameP-methoxyacetophenone
CAS Registry Number100-06-1
SMILES
COC1=CC=C(C=C1)C(C)=O
InChI Identifier
InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
InChI KeyNTPLXRHDUXRPNE-UHFFFAOYSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point38 - 39 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP1.74Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-5900000000-aeafe190f2bb388caf112015-03-01View Spectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-0be5991ccb2021dc5422Spectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-1c868f73005d65c19187Spectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-002r-9700000000-e00e43b1125f4e22757aSpectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-b943a08390f9ab22ada1Spectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-0be5991ccb2021dc5422Spectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-1c868f73005d65c19187Spectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-002r-9700000000-e00e43b1125f4e22757aSpectrum
GC-MSp-Acetanisole, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-b943a08390f9ab22ada1Spectrum
Predicted GC-MSp-Acetanisole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-4900000000-c9f5be49882a00ded896Spectrum
Predicted GC-MSp-Acetanisole, 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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032570
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010502
KNApSAcK IDC00052720
Chemspider ID13835344
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7476
PDB IDNot Available
ChEBI ID86567
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]