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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:28 UTC
Update Date2019-07-23 06:08:12 UTC
HMDB IDHMDB0031178
Secondary Accession Numbers
  • HMDB31178
Metabolite Identification
Common Name2-Methyltetrahydrofuran-3-one
Description2-Methyltetrahydrofuran-3-one, also known as fema 3373 or tetrahydro-2-methyl-3-furanone, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. 2-Methyltetrahydrofuran-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-methyltetrahydrofuran-3-one has been detected, but not quantified in, coffee and coffee products. This could make 2-methyltetrahydrofuran-3-one a potential biomarker for the consumption of these foods. This compound has also been prepared in acceptable yield via oxidative hydroxylation of the 2-acetylbutyrolactone. Coffee furanone has also been prepared via the condensation of ethyl lactate and methyl acrylate in DMSO solution and (under phase transfer conditions) in ionic liquids. Coffee furnone was synthesized in 1963 by Wynberg via acid-catalyzed ring closure of β-alkoxy diazoketones. A related lactic acid synthesis was described as having the advantages of a simple process, high conversion rate, low pollution, and low cost. Coffee furanone is less odorous than furfuryl mercaptan, which with an odor threshold of 0.005 ppb was the first high impact aroma chemical, but has a very pleasant sweet caramel character, with some nuttiness. Coffee furanone (2-methyltetrahydrofuran-3-one) is a pleasant smelling liquid furan derivative which is a volatile constituent of the aroma complex of roasted coffee. The synthetic version of this natural flavorant and odorant is used in a variety of food and beverage applications, including coffee, nuts, cocoa, brandy, meat sauces and as a general food flavorant at a typical dosage (about 5-20 ppm), similar to the natural concentration (30 ppm) of coffee furanone in roasted coffee. Further approaches to the synthesis of coffee furanone involved the hydrolysis of the corresponding dithioketals and the oxidation of 2-methyltetrahydrofuran employing lithium hypochlorite in the presence of ruthenium catalysts.
Structure
Data?1563862092
Synonyms
ValueSource
FEMA 3373HMDB
Tetrahydro-2-methyl-3-furanoneHMDB
Coffee furanoneHMDB
Dihydro-2-methyl-3(2H)-furanoneHMDB
2-Methyl-2H-furan-3-oneHMDB
2-Methyl-3-ketotetrahydrofuranHMDB
2-Methyl-3-oxotetrahydrofuranHMDB
2-Methyldihydrofuran-3(2H)-oneHMDB
2-Methyldihydrofuran-3-oneHMDB
2-Methyloxolan-3-oneHMDB
2-Methyltetrahydrofuran-3-ketoneHMDB
Dihydro-2-methyl-3-furanoneHMDB
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name2-methyloxolan-3-one
Traditional Namecoffee furanone
CAS Registry Number3188-00-9
SMILES
CC1OCCC1=O
InChI Identifier
InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3
InChI KeyFCWYQRVIQDNGBI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Tetrahydrofuran
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility285 g/LALOGPS
logP-0.23ALOGPS
logP0.44ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.28 m³·mol⁻¹ChemAxon
Polarizability10.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-e3f8793e49d60fd01706Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-292e7d61f2837f8a2bdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-4900000000-edfea591ca0bfab8dc64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9000000000-068b28f9e446c64e3b11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-9dafb9e0683d4e36c353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-5c82778d6e8d3cd09ce1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9000000000-4516d0e13d4cac50eae8Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016567
KNApSAcK IDNot Available
Chemspider ID17494
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoffee furanone
METLIN IDNot Available
PubChem Compound18522
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .