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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 02:09:15 UTC
Update Date2023-02-21 17:28:25 UTC
HMDB IDHMDB0040594
Secondary Accession Numbers
  • HMDB40594
Metabolite Identification
Common Name(±)-Furaneol
Description(±)-Furaneol, also known as furaneol or HDMF, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group (±)-Furaneol is a sweet, almond, and candy tasting compound (±)-Furaneol is found, on average, in the highest concentration within pineapples (Ananas comosus) (±)-Furaneol has also been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, fruits, nuts, and pulses. This could make (±)-furaneol a potential biomarker for the consumption of these foods (±)-Furaneol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on (±)-Furaneol.
Structure
Data?1677000504
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)-isomerMeSH, HMDB
4-HDMFMeSH, HMDB
AlletoneMeSH, HMDB
Furaneol, (S)-isomerMeSH, HMDB
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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point77 - 78 °CNot Available
Boiling Point215.53 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility18500 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.076 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+128.35830932474
DeepCCS[M-H]-125.28530932474
DeepCCS[M-2H]-162.13730932474
DeepCCS[M+Na]+137.01230932474
AllCCS[M+H]+127.332859911
AllCCS[M+H-H2O]+122.532859911
AllCCS[M+NH4]+131.732859911
AllCCS[M+Na]+133.032859911
AllCCS[M-H]-123.132859911
AllCCS[M+Na-2H]-125.232859911
AllCCS[M+HCOO]-127.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-FuraneolCC1OC(C)=C(O)C1=O2023.5Standard polar33892256
(??)-FuraneolCC1OC(C)=C(O)C1=O976.0Standard non polar33892256
(??)-FuraneolCC1OC(C)=C(O)C1=O1021.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-Furaneol,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)C(C)O11150.9Semi standard non polar33892256
(??)-Furaneol,1TMS,isomer #2CC1=C(O)C(O[Si](C)(C)C)=C(C)O11269.3Semi standard non polar33892256
(±)-Furaneol,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)O11318.3Semi standard non polar33892256
(±)-Furaneol,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)O11383.6Standard non polar33892256
(??)-Furaneol,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)O11410.3Semi standard non polar33892256
(??)-Furaneol,1TBDMS,isomer #2CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C)O11540.6Semi standard non polar33892256
(±)-Furaneol,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C)O11791.2Semi standard non polar33892256
(±)-Furaneol,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C)O11808.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Furaneol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-8c4cb8aa573b16fcfb702016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Furaneol GC-MS (1 TMS) - 70eV, Positivesplash10-0adu-9600000000-2c6fe7e0e944a33c5cc92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Furaneol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 10V, Positive-QTOFsplash10-004i-1900000000-2a171214e5cd4706888f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Positive-QTOFsplash10-004i-3900000000-31e666e61cc7b84118762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Positive-QTOFsplash10-054p-9000000000-af02647aeeb7796400732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 10V, Negative-QTOFsplash10-004i-0900000000-357e93488390a2976c9d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Negative-QTOFsplash10-004i-1900000000-602820cb95c6f5aecaae2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Negative-QTOFsplash10-0a4i-9100000000-4e8ccb8034b60b5362d02016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 10V, Negative-QTOFsplash10-004i-2900000000-f04fe270624eef9c155b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Negative-QTOFsplash10-006x-9000000000-996faea12712159d1b182021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Negative-QTOFsplash10-0a4l-9000000000-0c6cf150442af99bad612021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 10V, Positive-QTOFsplash10-004i-7900000000-afb6007af0c955aff56b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Positive-QTOFsplash10-0avl-9000000000-61679df963f1143460b02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Positive-QTOFsplash10-05mp-9000000000-67eb08c0013c727e892e2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDC00052712
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 IDNot Available
Good Scents IDrw1000931
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.. .