You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 02:09:15 UTC
Update Date2020-11-09 23:29:51 UTC
HMDB IDHMDB0040594
Secondary Accession Numbers
  • HMDB40594
Metabolite Identification
Common Name(±)-Furaneol
Description(±)-Furaneol, also known as HDMF or furaneol, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group (±)-Furaneol is an extremely weak basic (essentially neutral) compound (based on its pKa) (±)-Furaneol is a sweet, almond, and candy tasting compound. Outside of the human body, (±)-Furaneol is found, on average, in the highest concentration within pineapples (±)-Furaneol has also been detected, but not quantified in, several different foods, such as cereals and cereal products, fruits, nuts, and pulses. This could make (±)-furaneol a potential biomarker for the consumption of these foods.
Structure
Data?1563863566
Synonyms
ValueSource
2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuranChEBI
2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-oneChEBI
2,5-Dimethyl-4-hydroxy-3(2H)-furanoneChEBI
4-Hydroxy-2,5-dimethyl-3(2H)-furanoneChEBI
4-Hydroxy-2,5-dimethyl-furan-3(2H)-oneChEBI
Dimethylhydroxy furanoneChEBI
FuraneolChEBI
HDMFChEBI
Pineapple ketoneChEBI
Furaneol, (R)-isomerHMDB
4-HDMFHMDB
AlletoneHMDB
Furaneol, (S)-isomerHMDB
Chemical FormulaC6H8O3
Average Molecular Weight128.1259
Monoisotopic Molecular Weight128.047344122
IUPAC Name4-hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one
Traditional Namefuraneol
CAS Registry NumberNot Available
SMILES
CC1OC(C)=C(O)C1=O
InChI Identifier
InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
InChI KeyINAXVXBDKKUCGI-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
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point77 - 78 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility446 g/LALOGPS
logP-0.33ALOGPS
logP0.21ChemAxon
logS0.54ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.29 m³·mol⁻¹ChemAxon
Polarizability12.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-8c4cb8aa573b16fcfb70Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adu-9600000000-2c6fe7e0e944a33c5cc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-2a171214e5cd4706888fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3900000000-31e666e61cc7b8411876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054p-9000000000-af02647aeeb779640073Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-357e93488390a2976c9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-602820cb95c6f5aecaaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-4e8ccb8034b60b5362d0Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020380
KNApSAcK IDNot Available
Chemspider ID18218
KEGG Compound IDNot Available
BioCyc IDCPD-10198
BiGG IDNot Available
Wikipedia LinkFuraneol
METLIN IDNot Available
PubChem Compound19309
PDB IDNot Available
ChEBI ID76247
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.. .