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Showing Compound Furaneol (FDB020380)

Record Information
Version1.0
Creation date2010-04-08 22:14:59 UTC
Update date2019-11-26 03:18:51 UTC
Primary IDFDB020380
Secondary Accession Numbers
  • FDB016215
Chemical Information
FooDB NameFuraneol
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. Based on a literature review a significant number of articles have been published on (±)-Furaneol.
CAS Number3658-77-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
(±)-Furaneolmanual
COE 536manual
FEMA 3174manual
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
Chemical FormulaC6H8O3
IUPAC name4-hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one
InChI IdentifierInChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
InChI KeyINAXVXBDKKUCGI-UHFFFAOYSA-N
Isomeric SMILESCC1OC(C)=C(O)C1=O
Average Molecular Weight128.1259
Monoisotopic Molecular Weight128.047344122
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.25%; H 6.29%; O 37.46%DFC
Melting PointMp 77-78°DFC
Boiling PointSubl.1 85° (bath)DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSxi-Furaneol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-8c4cb8aa573b16fcfb70Spectrum
Predicted GC-MSxi-Furaneol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adu-9600000000-2c6fe7e0e944a33c5cc9Spectrum
Predicted GC-MSxi-Furaneol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-2a171214e5cd4706888fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3900000000-31e666e61cc7b8411876Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054p-9000000000-af02647aeeb779640073Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-357e93488390a2976c9dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-602820cb95c6f5aecaaeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-4e8ccb8034b60b5362d0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-f04fe270624eef9c155bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9000000000-996faea12712159d1b18Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-0c6cf150442af99bad61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-7900000000-afb6007af0c955aff56bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avl-9000000000-61679df963f1143460b0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mp-9000000000-67eb08c0013c727e892eSpectrum
NMRNot Available
ChemSpider ID18218
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID19309
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40594
CRC / DFC (Dictionary of Food Compounds) IDFWS46-C:MRR03-Y
EAFUS ID1743
Dr. Duke ID2,5-DIMETHYL-4-HYDROXY-3(2H)-FURANONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID3658-77-3
GoodScent IDrw1000931
SuperScent ID19309
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
caramel
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grape
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
strawberry
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
almond
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cotton
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
candy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sugar
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).