4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE (CHEM005422)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:02:00 UTC
Update Date2016-11-09 01:09:32 UTC
Accession NumberCHEM005422
Identification
Common Name4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE
ClassSmall Molecule
DescriptionDescription: 3-Hydroxy-4,5-dimethyl-2(5H)-furanone or sotolone is key flavoring compound found in raw cane sugar, aged sake, coffee, fenugreek, lovage and wines. Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. In 1999 it was shown that sotolone is the cause of the odor found in patients with maple syrup urine disease (MSUD) - PMID 10234605. This compound was found in the urine of 7 MSUD patients but was undetectable in normal individuals. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone belongs to the family of Butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC6H8O3
Average Molecular Mass128.126 g/mol
Monoisotopic Mass128.047 g/mol
CAS Registry Number28664-35-9
IUPAC Name3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one
Traditional Namesotolon
SMILESCC1OC(=O)C(O)=C1C
InChI IdentifierInChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3
InChI KeyUNYNVICDCJHOPO-UHFFFAOYSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-7fdd65bce51735b71d12Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i0-9700000000-43cc2ff6f95044077419Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-9300000000-4d5cfb96c51ba990b353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi0-9200000000-3e0b5f2cf3a4e88018faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9000000000-ac732b4b21400d1500e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-26b4264da2affe2f394bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-eb2c54bf2d77e47495b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0api-9000000000-1a81a14f56906486c81cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-5900000000-a9b9f4b7467f05d32c85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aos-9100000000-15b07a7cfd09c718a188Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8bba3e142b490d9cfb12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-32e912844db31429eab0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9000000000-186c5ec73109434e3baaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-7185ebac9651271eeeeeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031306
FooDB IDFDB003360
Phenol Explorer IDNot Available
KNApSAcK IDC00050420
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID56569
ChEBI IDNot Available
PubChem Compound ID62835
Kegg Compound IDNot Available
YMDB IDYMDB01572
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Podebrad F, Heil M, Reichert S, Mosandl A, Sewell AC, Bohles H: 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease. J Inherit Metab Dis. 1999 Apr;22(2):107-14.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.