Record Information
Version1.0
Creation date2010-04-08 22:14:02 UTC
Update date2015-07-21 06:32:10 UTC
Primary IDFDB018947
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-4-Hexyl-gamma-butyrolactone
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 ketone group on the carbon adjacent to the oxygen atom. xi-5-Hexyldihydro-2(3H)-furanone is an extremely weak basic (essentially neutral) compound (based on its pKa). 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.
CAS Number107797-26-2
Structure
Thumb
Synonyms
SynonymSource
4-Hexyl-4-butanolideHMDB
gamma-Lactone decanoic acidHMDB
4-DecanolideHMDB
Decan-4-olideHMDB
gamma-DecanolactoneHMDB
gamma-DecalactoneMeSH
(+)-gamma-Decalactonebiospider
(5R)-5-Hexyldihydro-2(3H)-furanonebiospider
(R)-4-Decanolidebiospider
(R)-4-Hexyl-gamma-butyrolactonemanual
(R)-4-N-Hexylbutyrolactonebiospider
(R)-5-Hexyldihydro-2(3H)-furanonedb_source
(R)-gamma-Decalactonebiospider
2(3H)-Furanone, 5-hexyldihydro-, (R)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.52ALOGPS
logP2.87ChemAxon
logS-3.1ALOGPS
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 RuleYesChemAxon
Chemical FormulaC10H18O2
IUPAC name5-hexyloxolan-2-one
InChI IdentifierInChI=1S/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3
InChI KeyIFYYFLINQYPWGJ-UHFFFAOYSA-N
Isomeric SMILESCCCCCCC1CCC(=O)O1
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.55%; H 10.66%; O 18.80%DFC
Melting PointNot Available
Boiling PointBp7.7 140-145°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +42.5 (c, 0.5 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-4b166790a11e7c302d92JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-4b166790a11e7c302d92JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ap3-9100000000-b00c7215590a3d9b2e9dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-0900000000-d70fbbe72766763b45e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052s-4900000000-0e9fb29ea39a5db8b46dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-290b1fa859383e242f93JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-9800000000-93589434f6ecccc40d35JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d48426fb0e1a4c1a49a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-63a514b1d1c53dbcbd66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-2900000000-d4ee5269c414e9f521f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-9b6a92e807e7ae4e5fd5JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-000i-9100000000-5c41e313dc97eb12ddd5JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID12285
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID12813
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37217
CRC / DFC (Dictionary of Food Compounds) IDDHQ01-E:LNK18-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1555311
SuperScent ID183870
Wikipedia IDNot Available
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
peach
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
strong
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  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