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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:27:23 UTC
Update Date2021-10-13 07:02:55 UTC
HMDB IDHMDB0037217
Secondary Accession Numbers
  • HMDB37217
Metabolite Identification
Common Namexi-5-Hexyldihydro-2(3H)-furanone
Descriptionxi-5-Hexyldihydro-2(3H)-furanone, also known as 4-hexyl-4-butanolide or gamma-lactone decanoic acid, 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 carboxy group on the carbon adjacent to the oxygen atom. xi-5-Hexyldihydro-2(3H)-furanone has been detected, but not quantified, in fruits. This could make XI-5-hexyldihydro-2(3H)-furanone a potential biomarker for the consumption of these foods.
Structure
Data?1563862995
Synonyms
ValueSource
4-DecanolideChEBI
4-Hexyl-gamma-butyrolactoneChEBI
4-Hydroxydecanoic acid gamma-lactoneChEBI
5-Hexyldihydro-2(3H)-furanoneChEBI
5-Hexyloxolan-2-oneChEBI
5-Hexyltetrahydro-2-furanoneChEBI
Decan-4-olideChEBI
gamma-DecanolactoneChEBI
gamma-Hexyl-gamma-butyrolactoneChEBI
gamma-N-DecalactoneChEBI
gamma-N-Hexyl-gamma-butyrolactoneChEBI
4-Hexyl-g-butyrolactoneGenerator
4-Hexyl-γ-butyrolactoneGenerator
4-Hydroxydecanoate g-lactoneGenerator
4-Hydroxydecanoate gamma-lactoneGenerator
4-Hydroxydecanoate γ-lactoneGenerator
4-Hydroxydecanoic acid g-lactoneGenerator
4-Hydroxydecanoic acid γ-lactoneGenerator
g-DecanolactoneGenerator
Γ-decanolactoneGenerator
g-Hexyl-g-butyrolactoneGenerator
Γ-hexyl-γ-butyrolactoneGenerator
g-N-DecalactoneGenerator
Γ-N-decalactoneGenerator
g-N-Hexyl-g-butyrolactoneGenerator
Γ-N-hexyl-γ-butyrolactoneGenerator
4-Hexyl-4-butanolideHMDB
gamma-Lactone decanoic acidHMDB
gamma-DecalactoneHMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name5-hexyloxolan-2-one
Traditional Namegamma-decalactone
CAS Registry NumberNot Available
SMILES
CCCCCCC1CCC(=O)O1
InChI Identifier
InChI=1S/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3
InChI KeyIFYYFLINQYPWGJ-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

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point114.00 to 116.00 °C. @ 0.50 mm HgThe Good Scents Company Information System
Water Solubility291.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.720The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP10(3.52) g/LALOGPS
logP10(2.87) g/LChemAxon
logS10(-3.1) g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.65 m³·mol⁻¹ChemAxon
Polarizability20.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.57531661259
DarkChem[M-H]-137.08931661259

Predicted Kovats Retention Indices

Not Available
Spectra
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 IDFDB016224
KNApSAcK IDC00023984
Chemspider ID12285
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Decalactone
METLIN IDNot Available
PubChem Compound12813
PDB IDNot Available
ChEBI ID145740
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012281
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.. .