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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:32:52 UTC
Update Date2022-03-07 02:55:16 UTC
HMDB IDHMDB0037309
Secondary Accession Numbers
  • HMDB37309
Metabolite Identification
Common Name5-Hexyldihydro-4-methyl-2(3H)-furanone
Description5-Hexyldihydro-4-methyl-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 a floral tasting compound. 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. Based on a literature review very few articles have been published on 5-Hexyldihydro-4-methyl-2(3H)-furanone.
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point110.00 to 115.00 °C. @ 3.50 mm HgThe Good Scents Company Information System
Water Solubility148.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.987 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.34231661259
DarkChem[M-H]-141.72431661259
DeepCCS[M+H]+150.56130932474
DeepCCS[M-H]-147.7330932474
DeepCCS[M-2H]-184.7530932474
DeepCCS[M+Na]+160.04530932474
AllCCS[M+H]+145.432859911
AllCCS[M+H-H2O]+141.332859911
AllCCS[M+NH4]+149.232859911
AllCCS[M+Na]+150.332859911
AllCCS[M-H]-149.532859911
AllCCS[M+Na-2H]-150.632859911
AllCCS[M+HCOO]-152.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hexyldihydro-4-methyl-2(3H)-furanoneCCCCCCC1OC(=O)CC1C2163.1Standard polar33892256
5-Hexyldihydro-4-methyl-2(3H)-furanoneCCCCCCC1OC(=O)CC1C1460.3Standard non polar33892256
5-Hexyldihydro-4-methyl-2(3H)-furanoneCCCCCCC1OC(=O)CC1C1531.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9200000000-924e02732440d7c623762017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-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 - 5-Hexyldihydro-4-methyl-2(3H)-furanone 10V, Positive-QTOFsplash10-000i-1900000000-1413a9dbeed0a65d4c802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 20V, Positive-QTOFsplash10-0002-9500000000-9523b5be831d444b929a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 40V, Positive-QTOFsplash10-052f-9000000000-c9d45a73c9db0056b1ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 10V, Negative-QTOFsplash10-001i-0900000000-d9378f500bb33ce8d93e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 20V, Negative-QTOFsplash10-001r-2900000000-6649840c2fd85c99f4912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 40V, Negative-QTOFsplash10-000f-9300000000-b325ead0da3f70bcdeec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 10V, Negative-QTOFsplash10-001i-0900000000-bdf024d2f8d89dbc72d22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 20V, Negative-QTOFsplash10-001i-3900000000-4caf77c01e929a2100342021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 40V, Negative-QTOFsplash10-0006-9400000000-87b6b56908ce1a2d750b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 10V, Positive-QTOFsplash10-05mx-9600000000-36c28a294d46ecfc5bdb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 20V, Positive-QTOFsplash10-0a4l-9300000000-9bd6ca2644a3c08768cc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hexyldihydro-4-methyl-2(3H)-furanone 40V, Positive-QTOFsplash10-052f-9000000000-9da4b81015bda03f942a2021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1446901
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.. .