Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2015-07-20 21:54:16 UTC
Primary IDFDB003360
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Hydroxy-4,5-dimethyl-2(5H)-furanone
DescriptionKey flavour compd. 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. (Wikipedia)
CAS Number28664-35-9
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxy-3-methyl-2-penten-4-olidebiospider
2-Hydroxy-3,4-dimethyl-2-buten-1,4-olidedb_source
2,3-Dimethyl-4-hydroxy-2,5-dihydrofuran-5-onebiospider
2(5H)-Furanone, 3-hydroxy-4,5-dimethyl-biospider
3-hydroxy-4,5-dimethyl-5H-furan-2-onebiospider
3-Hydroxy-4,5-dimethyl-furan-2(5H)-oneHMDB
3-Hydroxy-4,5-dimethylfuran-2(5H)-onebiospider
3-Hydroxy-4,5(R)-dimethyl-2(5H)-furanonebiospider
3,4-Dimethyl-2-hydroxy-2-butan-1,4-olidemanual
4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanonebiospider
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-onebiospider
4,5-Dimethyl-3-hydroxy-2(5H)-furanonebiospider
Furan-2(5H)-one, 3-hydroxy-4,5-dimethyl-biospider
Sautalonemanual
Sotolonbiospider
Sotolonedb_source
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
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 KeyInChIKey=UNYNVICDCJHOPO-UHFFFAOYSA-N
Isomeric SMILESCC1OC(=O)C(O)=C1C
Average Molecular Weight128
Monoisotopic Molecular Weight128
Classification
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
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 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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-7fdd65bce51735b71d12View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i0-9700000000-43cc2ff6f95044077419View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-9300000000-4d5cfb96c51ba990b353View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi0-9200000000-3e0b5f2cf3a4e88018faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9000000000-ac732b4b21400d1500e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-26b4264da2affe2f394bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3900000000-eb2c54bf2d77e47495b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0api-9000000000-1a81a14f56906486c81cView in MoNA
ChemSpider ID56569
ChEMBL IDNot Available
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
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.
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).