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Identification
YMDB IDYMDB01697
Namegamma-Decalactone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
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).
Structure
Thumb
Synonyms
  • 2-Decalactone
  • 2(3H)-Furanone, 5-hexyldihydro-
  • 4-Decalactone
  • 4-Decanolide
  • 4-Hexyl-«
  • 4-Hexyl-4-butanolide
  • 4-Hydroxydecanoic acid lactone
  • 4-Hydroxydecanoic acid, «
  • 5-Hexyldihydro-2(3H)-furanone
  • 5-Hexyltetrahydro-2-furanone
  • Decan-4-olide
  • Decanoic acid, 4-hydroxy-, «
  • Decanolactone
  • Decanolide-1,4
  • Hydroxydecanoic acid «
  • gamma-Lactone decanoic acid
  • gamma-Decanolactone
  • gamma-Decalactone
CAS number706-14-9
WeightAverage: 170.2487
Monoisotopic: 170.13067982
InChI KeyIFYYFLINQYPWGJ-UHFFFAOYSA-N
InChIInChI=1S/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3
IUPAC Name5-hexyloxolan-2-one
Traditional IUPAC Namegamma-decalactone
Chemical FormulaC10H18O2
SMILESCCCCCCC1CCC(=O)O1
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
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP2.72 [HANSCH,C ET AL. (1995)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
ButteryFDB016224
CoconutFDB016224
FatFDB016224
FreshFDB016224
OilyFDB016224
PeachFDB016224
SweetFDB016224
WaxyFDB016224
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0037217
Pubchem Compound ID7710
Kegg IDNot Available
ChemSpider ID12285
FOODB IDFDB016224
Wikipedia IDNot Available
BioCyc IDNot Available