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Showing Compound 3-Hydroxy-4,5-dimethyl-2(5H)-furanone (FDB003360)

Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2025-11-18 22:51:16 UTC
Primary IDFDB003360
Secondary Accession Numbers
  • FDB007346
Chemical Information
FooDB Name3-Hydroxy-4,5-dimethyl-2(5H)-furanone
Description3-Hydroxy-4,5-dimethyl-2(5H)-furanone belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone is a strong, extremely sweet, and burnt tasting compound. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), robusta coffees (Coffea canephora), fenugreeks (Trigonella foenum-graecum), herbs and spices, and evergreen blackberries (Rubus laciniatus). This could make 3-hydroxy-4,5-dimethyl-2(5H)-furanone a potential biomarker for the consumption of these foods. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone, with regard to humans, has been linked to the inborn metabolic disorder maple syrup urine disease. Based on a literature review very few articles have been published on 3-Hydroxy-4,5-dimethyl-2(5H)-furanone.
CAS Number28664-35-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,3-Dimethyl-4-hydroxy-2,5-dihydrofuran-5-oneHMDB
2-Hydroxy-3,4-dimethyl-2-buten-1,4-olideHMDB
2-Hydroxy-3-methyl-2-penten-4-olideHMDB
3,4-Dimethyl-2-hydroxy-2-butan-1,4-olideHMDB
3-Hydroxy-4,5(R)-dimethyl-2(5H)-furanoneHMDB
3-Hydroxy-4,5-dimethyl-5H-furan-2-oneHMDB
3-Hydroxy-4,5-dimethyl-furan-2(5H)-oneHMDB
3-Hydroxy-4,5-dimethylfuran-2(5H)-oneHMDB
4,5-Dimethyl-3-hydroxy-2(5H)-furanoneHMDB, MeSH
4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanoneHMDB
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-oneHMDB
SautaloneHMDB
SotolonHMDB
SotoloneHMDB, MeSH
2(5H)-Furanone, 3-hydroxy-4,5-dimethyl-biospider
3-hydroxy-4,5-dimethyl-5H-furan-2-onebiospider
Furan-2(5H)-one, 3-hydroxy-4,5-dimethyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility218 g/LALOGPS
logP-0.14ALOGPS
logP0.68ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.92 m³·mol⁻¹ChemAxon
Polarizability12.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H8O3
IUPAC name3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one
InChI IdentifierInChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3
InChI KeyUNYNVICDCJHOPO-UHFFFAOYSA-N
Isomeric SMILESCC1OC(=O)C(O)=C1C
Average Molecular Weight128.1259
Monoisotopic Molecular Weight128.047344122
Classification
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid derivative
  • 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.25%; H 6.29%; O 37.46%DFC
Melting PointNot Available
Boiling PointNot Available
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-MS3-Hydroxy-4,5-dimethyl-2(5H)-furanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-7fdd65bce51735b71d12Spectrum
Predicted GC-MS3-Hydroxy-4,5-dimethyl-2(5H)-furanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i0-9700000000-43cc2ff6f95044077419Spectrum
Predicted GC-MS3-Hydroxy-4,5-dimethyl-2(5H)-furanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Hydroxy-4,5-dimethyl-2(5H)-furanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-9300000000-4d5cfb96c51ba990b3532016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi0-9200000000-3e0b5f2cf3a4e88018fa2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9000000000-ac732b4b21400d1500e72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-26b4264da2affe2f394b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-eb2c54bf2d77e47495b92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0api-9000000000-1a81a14f56906486c81c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-5900000000-a9b9f4b7467f05d32c852021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aos-9100000000-15b07a7cfd09c718a1882021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8bba3e142b490d9cfb122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-32e912844db31429eab02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9000000000-186c5ec73109434e3baa2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-7185ebac9651271eeeee2021-09-23View Spectrum
NMRNot Available
ChemSpider ID56569
ChEMBL IDCHEMBL3185688
KEGG Compound IDNot Available
Pubchem Compound ID62835
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31306
CRC / DFC (Dictionary of Food Compounds) IDCWG65-S:CWG65-S
EAFUS ID994
Dr. Duke IDSOTOLONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID28664-35-9
GoodScent IDrw1029011
SuperScent ID62835
Wikipedia IDSotolon
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
cotton candy
  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
spice
  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
maple
  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.
celery
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fennel
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
caramel
  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.
tobacco
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
smoky
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
seedy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
extremely sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
strong
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
burnt
  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.
coffee
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cottoncandy
  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
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).