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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:54:14 UTC
Update Date2019-07-23 06:12:44 UTC
HMDB IDHMDB0033182
Secondary Accession Numbers
  • HMDB33182
Metabolite Identification
Common Name2,5-Dimethylfuran
Description2,5-Dimethylfuran is a maillard product 2,5-Dimethylfuran has been identified as one of the components of cigar smoke with low cilatoxicity (ability to adversely affect the cilia in the respiratory tract that are responsible for removing foreign particles). Its blood concentration can be used as a biomarker for smoking. 2,5-Dimethylfuran, together with 2,5-hexanedione and 4,5-dihydroxy-2-hexanone, is one of the main metabolites of hexane in humans, which play a role in the mechanism for the neurotoxicity of hexane. A derivative of furan, 2,5-dimethylfuran is a heterocyclic compound of the formula C6H8O. While it may be abbreviated DMF, it should not be confused with dimethylformamide. Recent advances have increased its attractiveness as a biofuel.
Structure
Data?1563862364
Synonyms
ValueSource
2,5-Dimethyl-furanHMDB
2,5-DimethylfuraneHMDB
Chemical FormulaC6H8O
Average Molecular Weight96.1271
Monoisotopic Molecular Weight96.057514878
IUPAC Name2,5-dimethylfuran
Traditional Name2,5-dimethylfuran
CAS Registry Number625-86-5
SMILES
CC1=CC=C(C)O1
InChI Identifier
InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
InChI KeyGSNUFIFRDBKVIE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as heteroaromatic compounds. These are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.24Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.55 g/LALOGPS
logP2.17ALOGPS
logP1.51ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.87 m³·mol⁻¹ChemAxon
Polarizability11.09 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6w-9000000000-c4a1e868867e02296ecbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6w-9000000000-c4a1e868867e02296ecbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-5541d1a8919494d09a97JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-c1f5eca2bb55a34c6543JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-5506ccbd7d54899cdf5bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-e12a4cdc311091858f8cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-03aafe04d643341b91c1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-6c128c2cf7b062b9ad93JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ftb-9000000000-efa612ea3a77b76d3d8dJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-654fd33daad26ad7f6deJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000166 uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
details
UrineDetected but not Quantified Adult (>18 years old)FemaleBreast cancer details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011193
KNApSAcK IDNot Available
Chemspider ID11763
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,5-Dimethylfuran
METLIN IDNot Available
PubChem Compound12266
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .