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Showing Compound 4-Hexyl-gamma-butyrolactone (FDB008393)

Record Information
Version1.0
Creation date2010-04-08 22:08:03 UTC
Update date2019-11-26 03:02:34 UTC
Primary IDFDB008393
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hexyl-gamma-butyrolactone
DescriptionXi-5-hexyldihydro-2(3h)-furanone, also known as 4-decanolide or gamma-decanolactone, is a member of the class of 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 practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Xi-5-hexyldihydro-2(3h)-furanone can be found in fruits, which makes xi-5-hexyldihydro-2(3h)-furanone a potential biomarker for the consumption of this food product.
CAS Number706-14-9
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
(±)-4-n-Hexylbutyrolactonemanual
(±)-gamma-Decalactonemanual
(±)-gamma-Decanolactonemanual
(RS)-gamma-Decalactonemanual
2-Decalactonemanual
4-Hydroxydecanoic acid lactone, 8CIdb_source
Decanolactonedb_source
g-Decalactonedb_source
g-Hexylbutyrolactonedb_source
gamma-Decanolidemanual
gamma-Hexylbutyrolactonemanual
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
Disposition

Biological location:

Source:

Role

Industrial application:

Biological role:

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 PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
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 IDNot Available
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 IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDDHQ01-E:DHQ01-E
EAFUS ID829
Dr. Duke IDGAMMA-DECALACTONE|GAMMA-DECANOLACTONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID706-14-9
GoodScent IDrw1012281
SuperScent ID12813
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 / Bioactivities
DescriptorIDDefinitionReference
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
Perfume48318 A fragrant substance with a biological role in attracting and repelling, having therapeutic applications in aromatherapy for mood enhancement and stress relief. Key medical uses include anxiety reduction, mood elevation, and pain management, with some fragrances exhibiting anti-anxiety and anti-depressant properties.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
peach
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy
  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.
buttery
  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.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).