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 and Quantified
Creation Date2012-09-11 17:42:13 UTC
Update Date2019-07-23 06:08:27 UTC
HMDB IDHMDB0031306
Secondary Accession Numbers
  • HMDB31306
Metabolite Identification
Common Name3-Hydroxy-4,5-dimethyl-2(5H)-furanone
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.
Structure
Data?1563862107
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
4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanoneHMDB
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-oneHMDB
SautaloneHMDB
SotolonHMDB
SotoloneHMDB
Chemical FormulaC6H8O3
Average Molecular Weight128.1259
Monoisotopic Molecular Weight128.047344122
IUPAC Name3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one
Traditional Namesotolon
CAS Registry Number28664-35-9
SMILES
CC1OC(=O)C(O)=C1C
InChI Identifier
InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3
InChI KeyUNYNVICDCJHOPO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyk 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-7fdd65bce51735b71d12JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i0-9700000000-43cc2ff6f95044077419JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-9300000000-4d5cfb96c51ba990b353JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi0-9200000000-3e0b5f2cf3a4e88018faJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9000000000-ac732b4b21400d1500e7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-26b4264da2affe2f394bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-eb2c54bf2d77e47495b9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0api-9000000000-1a81a14f56906486c81cJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified5.99 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified12.60 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.99 - 226 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Not SpecifiedMaple syrup urine disease details
Associated Disorders and Diseases
Disease References
Maple syrup urine disease
  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. [PubMed:10234605 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003360
KNApSAcK IDNot Available
Chemspider ID56569
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62835
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:10234605 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .