Showing Compound Card for 2-Acetylfuran (CDB005818)

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Record Information
Version1.0
Created at2020-04-27 16:59:37 UTC
Updated at2021-01-04 18:49:23 UTC
CannabisDB IDCDB005818
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Acetylfuran
Description2-Acetylfuran, also known as 2-furylethanone is an acetylated derivative of furan in which the acetyl group positioned on C-2 of the furan ring. 2-Acetylfuran belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 2-Acetylfuran is one of two isomers of acetylfuran wherein the acetyl group is substituted at two positions (the 2- and 3- positions) of furan ring. 2-Acetylfuran exists as a clear, colorless crystals that melt at 30 degrees Celsius. 2-Acetylfuran was first obtained in 1914 via the reaction of the methyl Grignard reagent on 2-furonitrile ( Ref:DOI ). It is produced industrially via the Friedel–Crafts acylation of furan with acetic anhydride. 2-Acetylfuran has a sweet, almond, cocoa and balsamic aroma and a sweet, nutty, milky taste. It is used as a flavoring ingredient and as a perfuming agent. 2-Acetylfuran is also used as an intermediate in the production of pharmaceuticals such as the second-generation cephalophosphorin antibiotic known as cefuroxime. 2-Acetylfuran is found naturally in a few different foods, such as roasted almond, asparagus, cooked apple, cooked beef, beer, blueberries, brandy, bread, cherries, chestnuts, cocoa, coffee, mustard, peaches, peanuts, pineapple, plums, popcorn, pork, potatoes, raisins, rum, sesame seeds, strawberries, tamarind, tea, wine, kohlrabis, corn, yellow bell peppers, and cauliflowers. This could make 2-acetylfuran a potential biomarker for the consumption of these foods. 2-Acetylfuran is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2-Furanyl)-1-ethanoneChEBI
1-(2-Furanyl)-ethanoneChEBI
1-(2-Furanyl)ethanoneChEBI
1-(2-Furyl)ethanoneChEBI
2-Furyl methyl ketoneChEBI
2-FurylethanoneChEBI
AcetylfuranChEBI
Furyl methyl ketoneChEBI
Methyl 2-furyl ketoneChEBI
1-(2-Furanyl)-ethanone (2-acetylfuran)HMDB
1-(2-Furanyl)ethanone (acetylfuran)HMDB
1-(2-Furanyl)ethanone, 9ciHMDB
1-(Furan-2-yl)ethanoneHMDB
2-AcetofuroneHMDB
2-Acetyl-furanHMDB
2-AcetylfuraneHMDB
a-Furyl methyl ketoneHMDB
FEMA 3163HMDB
Ketone, 2-furyl methylHMDB
Chemical FormulaC6H6O2
Average Molecular Weight110.11
Monoisotopic Molecular Weight110.0368
IUPAC Name1-(furan-2-yl)ethan-1-one
Traditional Nameacetylfuran
CAS Registry Number1192-62-7
SMILES
CC(=O)C1=CC=CO1
InChI Identifier
InChI=1S/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
InChI KeyIEMMBWWQXVXBEU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl alkyl ketones
Alternative Parents
Substituents
  • Aryl alkyl ketone
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

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Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP0.52Not Available
Predicted Properties
PropertyValueSource
logP0.73ALOGPS
logP0.59ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)14.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.21 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.85 m³·mol⁻¹ChemAxon
Polarizability10.9 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)splash10-0002-9200000000-02caa47cd67aaabc5a452015-03-01View Spectrum
GC-MS2-Acetylfuran, non-derivatized, GC-MS Spectrumsplash10-0002-9100000000-626116be3c33a62f5993Spectrum
GC-MS2-Acetylfuran, non-derivatized, GC-MS Spectrumsplash10-01ow-9200000000-39cadbe5f909cbb066e3Spectrum
GC-MS2-Acetylfuran, non-derivatized, GC-MS Spectrumsplash10-0002-9100000000-626116be3c33a62f5993Spectrum
GC-MS2-Acetylfuran, non-derivatized, GC-MS Spectrumsplash10-01ow-9200000000-39cadbe5f909cbb066e3Spectrum
Predicted GC-MS2-Acetylfuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01p6-9100000000-6196177f86bc1367abbfSpectrum
Predicted GC-MS2-Acetylfuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Acetylfuran, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5900000000-d233a631e1c9df3d54e82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9700000000-91ffe1670f8da4e6cc4f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8bd4ecfbf7f0251b0da02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-96c0bfd0a7b470f5436d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9700000000-47ef7fef4ff9fe443aea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-fd81c21f4fe0ae36b25c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-9400000000-5488e53621f4e2c864582021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-3ea8732d7b56741cba4a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b25aa8dca4484c86c9082021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9200000000-ddae71262428d03ad2942021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4f6867f4e1fd0f185b942021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a7e5d9120b0b8d7f7abe2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033127
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011128
KNApSAcK IDC00029371
Chemspider ID13849
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Acetylfuran
METLIN IDNot Available
PubChem Compound14505
PDB IDNot Available
ChEBI ID59983
References
General ReferencesNot Available