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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:56 UTC
Update Date2020-07-08 16:44:48 UTC
HMDB IDHMDB0013785
Secondary Accession Numbers
  • HMDB13785
Metabolite Identification
Common NameFuran
DescriptionFuran is a member of the class of compounds known as furans. These are molecules containing a heterocyclic organic group consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system similar to benzene. Because of the aromaticity, furan is flat and lacks discrete double bonds. Furan is a colourless, flammable, highly volatile liquid with a boiling point close to room temperature (31°C). It is soluble in common organic solvents, including alcohol, ether, and acetone, but is insoluble in water. It has a strong ethereal odour. Furan is found in heat-treated (e.g. cooked, roasted, baked, pasteurized, and sterilized) commercial foods and is produced through thermal degradation of natural food constituents (PMID: 22641279 ). It can be found in roasted coffee, instant coffee, and processed baby foods (PMID: 22641279 ). In particular, the highest furan levels can be detected in coffee, with mean values between 42 and 3 660 ng/g for brewed coffee and roasted coffee beans. Furan can also be detected at levels between 0.2 and 3.2 ng/g in infant formula, from 22 to 24 ng/g in baked beans, from 13 to 17 ng/g in meat products, and from 23 to 24 ng/g in soups. In soy sauce, furan is detectable at 27 ng/g (PMID: 26483883 ). Research has indicated that coffee made in espresso makers and, above all, coffee made from capsules, contains more furan than that made in traditional drip coffee makers, although the levels are still within safe health limits. Various pathways have been reported for the formation of furan: (1) thermal degradation and/or thermal rearrangement of carbohydrates in the presence of amino acids, (2) thermal degradation of certain amino acids (aspartic acid, threonine, α-alanine, serine, and cysteine), (3) oxidation of ascorbic acid at higher temperatures, and (4) oxidation of polyunsaturated fatty acids and carotenoids (PMID: 26483883 ). Several studies have reported that furan formation occurs to a large extent during the Maillard reaction. The Maillard reaction involves the thermal degradation and rearrangement of carbohydrates (i.e. non-enzymatic browning reactions during food processing and cooking). Reducing hexoses often go through the Maillard reaction in the presence of amino acids and produce reactive intermediates such as 1-deoxy- and 3-deoxyosones, aldotetrose, and 2-deoxy-3-keto-aldotetrose. 2-Deoxy-3-keto-aldotetrose typically goes through retro-aldol cleavage leading to 3-deoxyosone which undergoes α-dicarbonyl cleavage, followed by oxidation and decarboxylation to form 2-deoxyaldotetrose, which is a direct precursor of furan. In addition to the formation of furan via carbohydrate degradation, furan can also be formed through thermal degradation of certain amino acids. Specifically, the amino acids that can form acetaldehyde and glycolaldehyde can produce furan by aldol condensation and cyclization (PMID: 26483883 ). Furan is toxic and may be carcinogenic. In particular, furan is a potent hepatotoxin and hepatocarcinogen in rodents, causing hepatocellular adenomas and carcinomas in rats and mice, and high incidences of cholangiocarcinomas in rats at doses ≥ 2 mg/kg (PMID: 22641279 ).
Structure
Data?1594226688
Synonyms
ValueSource
1,4-Epoxy-1,3-butadieneChEBI
Divinylene oxideChEBI
FuraneChEBI
OxacyclopentadieneChEBI
OxoleChEBI
TetroleChEBI
FurfuranHMDB
FurfuraneHMDB
Chemical FormulaC4H4O
Average Molecular Weight68.074
Monoisotopic Molecular Weight68.02621475
IUPAC Namefuran
Traditional Namefuran
CAS Registry Number110-00-9
SMILES
O1C=CC=C1
InChI Identifier
InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
InChI KeyYLQBMQCUIZJEEH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds 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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Indirect biological role:

Environmental role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-85.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 mg/mL at 25 °CNot Available
LogP1.34Not Available
Predicted Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP1.24ALOGPS
logP1.11ChemAxon
logS-0.63ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.57 m³·mol⁻¹ChemAxon
Polarizability6.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-4c50652f33a401ab3caeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-d007e0256578ac930b22Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-4c50652f33a401ab3caeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9000000000-d007e0256578ac930b22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-511af11e910184693aa1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-fd05695071ee559e9be4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-208e5dd03db999e390ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-351aa9d338efe69d31efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-acebecda0e70274875b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-1df91dbb0164452d0fd1Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kr-9000000000-3bddc12b5a8dd3ca188dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast 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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7738
KEGG Compound IDC14275
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFuran
METLIN IDNot Available
PubChem Compound8029
PDB IDNot Available
ChEBI ID35559
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Moro S, Chipman JK, Wegener JW, Hamberger C, Dekant W, Mally A: Furan in heat-treated foods: formation, exposure, toxicity, and aspects of risk assessment. Mol Nutr Food Res. 2012 Aug;56(8):1197-211. doi: 10.1002/mnfr.201200093. Epub 2012 May 29. [PubMed:22641279 ]
  2. Seok YJ, Her JY, Kim YG, Kim MY, Jeong SY, Kim MK, Lee JY, Kim CI, Yoon HJ, Lee KG: [Not Available]. Toxicol Res. 2015 Sep;31(3):241-53. doi: 10.5487/TR.2015.31.3.241. [PubMed:26483883 ]