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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:42:13 UTC
Update Date2023-02-21 17:20:18 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?1677000018
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 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
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point25.00 to 29.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point93.00 to 95.00 °C. @ 2.00 mm HgThe Good Scents Company Information System
Water Solubility222800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.296 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+125.58730932474
DeepCCS[M-H]-122.24830932474
DeepCCS[M-2H]-159.57530932474
DeepCCS[M+Na]+134.46630932474
AllCCS[M+H]+127.632859911
AllCCS[M+H-H2O]+123.032859911
AllCCS[M+NH4]+132.032859911
AllCCS[M+Na]+133.332859911
AllCCS[M-H]-123.532859911
AllCCS[M+Na-2H]-125.632859911
AllCCS[M+HCOO]-128.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-4,5-dimethyl-2(5H)-furanoneCC1OC(=O)C(O)=C1C2173.0Standard polar33892256
3-Hydroxy-4,5-dimethyl-2(5H)-furanoneCC1OC(=O)C(O)=C1C1029.3Standard non polar33892256
3-Hydroxy-4,5-dimethyl-2(5H)-furanoneCC1OC(=O)C(O)=C1C1088.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-4,5-dimethyl-2(5H)-furanone,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)OC1C1211.5Semi standard non polar33892256
3-Hydroxy-4,5-dimethyl-2(5H)-furanone,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)OC1C1468.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-7fdd65bce51735b71d122016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone GC-MS (1 TMS) - 70eV, Positivesplash10-05i0-9700000000-43cc2ff6f950440774192017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 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 - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Positive-QTOFsplash10-0udi-9300000000-4d5cfb96c51ba990b3532016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Positive-QTOFsplash10-0zi0-9200000000-3e0b5f2cf3a4e88018fa2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Positive-QTOFsplash10-0zfr-9000000000-ac732b4b21400d1500e72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Negative-QTOFsplash10-004i-3900000000-26b4264da2affe2f394b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Negative-QTOFsplash10-004i-3900000000-eb2c54bf2d77e47495b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Negative-QTOFsplash10-0api-9000000000-1a81a14f56906486c81c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Positive-QTOFsplash10-004i-5900000000-a9b9f4b7467f05d32c852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Positive-QTOFsplash10-0aos-9100000000-15b07a7cfd09c718a1882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Positive-QTOFsplash10-0a4i-9000000000-8bba3e142b490d9cfb122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Negative-QTOFsplash10-004i-1900000000-32e912844db31429eab02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Negative-QTOFsplash10-00dl-9000000000-186c5ec73109434e3baa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Negative-QTOFsplash10-052f-9000000000-7185ebac9651271eeeee2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB003360
KNApSAcK IDC00050420
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1029011
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.. .