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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:43 UTC
Update Date2019-07-23 06:12:07 UTC
HMDB IDHMDB0032929
Secondary Accession Numbers
  • HMDB32929
Metabolite Identification
Common NameBenzofuran
DescriptionBenzofuran, also known as coumaron or 1-oxaindene, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Benzothiophene, an analog with a sulfur instead of the oxygen atom. Benzofuran is a drug. Benzofuran is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, benzofuran has been detected, but not quantified in, several different foods, such as alcoholic beverages, coffee and coffee products, herbs and spices, root vegetables, and tea. This could make benzofuran a potential biomarker for the consumption of these foods. This colourless liquid is a component of coal tar. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Benzofuran is a potentially toxic compound. For example, psoralen is a benzofuran derivative that occurs in several plants. Isobenzofuran, the isomer with oxygen in the adjacent position. Notable examples include:O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation. It is also obtained by dehydrogenation of 2-ethylphenol.
Structure
Data?1563862327
Synonyms
ValueSource
Benzo[b]furanChEBI
CoumaronChEBI
CoumaroneChEBI
CumaroneChEBI
1-BenzofuranHMDB
1-OxaindeneHMDB
1-OxideneHMDB
1-OxindeneHMDB
2,3-BenzofuranHMDB
Benzo(b)furanHMDB
BenzofurfuranHMDB
BZFHMDB
CumaronHMDB
BenzofuranChEBI
Chemical FormulaC8H6O
Average Molecular Weight118.1326
Monoisotopic Molecular Weight118.041864814
IUPAC Name1-benzofuran
Traditional Namebenzofuran
CAS Registry Number271-89-6
SMILES
O1C=CC2=C1C=CC=C2
InChI Identifier
InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
InChI KeyIANQTJSKSUMEQM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< -18 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.67Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP2.75ALOGPS
logP2.13ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.9 m³·mol⁻¹ChemAxon
Polarizability12.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9500000000-3d2e5f26beb578276710Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9500000000-3d2e5f26beb578276710Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-efdcea5ed8b525799ec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-bb3695060acd0d637949Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7900000000-9b6327284d187ad5caacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-20b4b4e88a2b2a09c04eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-f6b69baead38b400da70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9600000000-9853e0fb4ec328aab100Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-9700000000-e2e60a740f22f28eaf54Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04179
Phenol Explorer Compound IDNot Available
FooDB IDFDB010914
KNApSAcK IDNot Available
Chemspider ID8868
KEGG Compound IDC14512
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-benzofuran
METLIN IDNot Available
PubChem Compound9223
PDB IDNot Available
ChEBI ID35260
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wahab Khan M, Jahangir Alam M, Rashid MA, Chowdhury R: A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorg Med Chem. 2005 Aug 15;13(16):4796-805. [PubMed:15964760 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .