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gamma-Heptalactone (YMDB16105)

Identification
YMDB IDYMDB16105
Namegamma-Heptalactone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDihydro-5-propyl-2(3H)-furanone, also known as (+/-)-4-heptanolide or 5-propyl-tetrahydro-furan-2-one, 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. Thus, dihydro-5-propyl-2(3H)-furanone is considered to be a fatty ester lipid molecule. Dihydro-5-propyl-2(3H)-furanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dihydro-5-propyl-2(3H)-furanone is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (+/-)-4-heptanolide
  • (+/-)-dihydro-5-propyl-2(3H)-furanone
  • (+/-)-gamma-propyl-gamma-butyrolactone
  • 1,4-Heptanolide
  • 4-Hydroxyheptanoic acid, gamma-lactone
  • 4-Propyl-4-hydroxybutanoic acid lactone
  • 5-Propyl-tetrahydro-furan-2-one
  • gamma-Heptalactone
  • gamma-Heptanolactone
  • gamma-Propiobutyrolactone
  • gamma-Propyl-gamma-butyrolactone
  • Heptan-4-olide
  • Heptanolide-4,1
  • 4-Propyl-g-butyrolactone
  • 4-Propyl-γ-butyrolactone
CAS numberNot Available
WeightAverage: 128.169
Monoisotopic: 128.083729628
InChI KeyVLSVVMPLPMNWBH-UHFFFAOYSA-N
InChIInChI=1S/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3
IUPAC Name5-propyloxolan-2-one
Traditional IUPAC Name5-propyloxolan-2-one
Chemical FormulaC7H12O2
SMILESCCCC1CCC(=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 Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.81 g/LALOGPS
logP1.42ALOGPS
logP1.53ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.85 m³·mol⁻¹ChemAxon
Polarizability14.17 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
CaramelFDB008341
CoconutFDB008341
FatFDB008341
FruitFDB008341
HayFDB008341
NutFDB008341
NuttyFDB008341
SweetFDB008341
TonkaFDB008341
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-c224bc120cc60670620fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-c224bc120cc60670620fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-d65f08c5431130e748caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-4900000000-98642a6f9598537ab510JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r9-9300000000-d38e27aabefbd271fd0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-ebcb66a25ad3f79fa256JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-705e0da057c614b37de1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9700000000-dc33ef926913eed12375JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f99153eb643bf57c921dJSpectraViewer
References
References:
  • Robinson AL, Ebeler SE, Heymann H, Boss PK, Solomon PS, Trengove RD. (2009). "Interactions between wine volatile compounds and grape and wine matrix components influence aroma compound headspace partitioning." J Agric Food Chem. 2009 Nov 11;57(21):10313-22.19845354
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0031681
Pubchem Compound ID7742
Kegg IDNot Available
ChemSpider ID7456
FOODB IDFDB008341
Wikipedia IDNot Available
BioCyc IDNot Available