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Showing Compound (R)-4-Hexyl-gamma-butyrolactone (FDB018947)

Record Information
Version1.0
Creation date2010-04-08 22:14:02 UTC
Update date2025-11-19 02:15:53 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 gamma-hexyl-gamma-butyrolactone or 4-hydroxydecanoic acid g-lactone, 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 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. Based on a literature review a significant number of articles have been published on xi-5-Hexyldihydro-2(3H)-furanone.
CAS Number107797-26-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
(+)-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 RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-9100000000-5c41e313dc97eb12ddd52015-03-01View Spectrum
GC-MS4-Hexyl-gamma-butyrolactone, non-derivatized, GC-MS Spectrumsplash10-000i-9000000000-4b166790a11e7c302d92Spectrum
GC-MS4-Hexyl-gamma-butyrolactone, non-derivatized, GC-MS Spectrumsplash10-000i-9000000000-4b166790a11e7c302d92Spectrum
Predicted GC-MS4-Hexyl-gamma-butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ap3-9100000000-b00c7215590a3d9b2e9dSpectrum
Predicted GC-MS4-Hexyl-gamma-butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-0900000000-d70fbbe72766763b45e22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052s-4900000000-0e9fb29ea39a5db8b46d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-052s-4900000000-ca7c24e9577963b4e53e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-d70fbbe72766763b45e22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-052s-4900000000-0e9fb29ea39a5db8b46d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-290b1fa859383e242f932015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-9800000000-93589434f6ecccc40d352015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d48426fb0e1a4c1a49a72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-63a514b1d1c53dbcbd662015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-2900000000-d4ee5269c414e9f521f42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-9b6a92e807e7ae4e5fd52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-efbd93a1a83feefc94df2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-175297cb580811c14bb12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-9db65c438d4cb8beba4f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fu-9500000000-c1c23158375af766301b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9100000000-032097fa4e962fbd80562021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-15c616405145e21bbc242021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID12285
ChEMBL IDCHEMBL365740
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