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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:32:52 UTC
Update Date2019-07-23 06:23:28 UTC
HMDB IDHMDB0037309
Secondary Accession Numbers
  • HMDB37309
Metabolite Identification
Common Name5-Hexyldihydro-4-methyl-2(3H)-furanone
Description5-Hexyldihydro-4-methyl-2(3H)-furanone, also known as 3-methyl-4-decanolide or 5-hexyl-4-methyldihydro-2(3H)-furanone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 5-Hexyldihydro-4-methyl-2(3H)-furanone is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hexyldihydro-4-methyl-2(3H)-furanone is a floral tasting compound. Outside of the human body, 5-hexyldihydro-4-methyl-2(3H)-furanone has been detected, but not quantified in, citrus. This could make 5-hexyldihydro-4-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods.
Structure
Data?1563863008
Synonyms
ValueSource
3-Methyl-4-decanolideHMDB
5-Hexyl-4-methyldihydro-2(3H)-furanoneHMDB
5-Hexyldihydro-4-methyl-(4R-cis)-2(3H)-furanoneHMDB
5-Hexyldihydro-4-methyl-trans-(.+-.)-2(3H)-furanoneHMDB
5-Hexyldihydro-4-methylfuran-2(3H)-oneHMDB
cis-4-Hydroxy-3-methyldecanoic acid lactoneHMDB
trans-4-Hydroxy-3-methyldecanoic acid lactoneHMDB
Chemical FormulaC11H20O2
Average Molecular Weight184.2753
Monoisotopic Molecular Weight184.146329884
IUPAC Name5-hexyl-4-methyloxolan-2-one
Traditional Nametrans-3-methyl-4-decanolide
CAS Registry Number67663-01-8
SMILES
CCCCCCC1OC(=O)CC1C
InChI Identifier
InChI=1S/C11H20O2/c1-3-4-5-6-7-10-9(2)8-11(12)13-10/h9-10H,3-8H2,1-2H3
InChI KeyXNRLAEXLQFIKEY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP3.61ALOGPS
logP3.23ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity52.13 m³·mol⁻¹ChemAxon
Polarizability22.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9200000000-924e02732440d7c62376Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-1413a9dbeed0a65d4c80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9500000000-9523b5be831d444b929aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-c9d45a73c9db0056b1aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-d9378f500bb33ce8d93eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-2900000000-6649840c2fd85c99f491Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9300000000-b325ead0da3f70bcdeecSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016328
KNApSAcK IDNot Available
Chemspider ID96085
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound106756
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .