Record Information
Version1.0
Creation date2011-05-19 22:28:04 UTC
Update date2018-01-25 19:45:29 UTC
Primary IDFDB021845
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Octyl-gamma-butyrolactone
DescriptionXi-dihydro-5-octyl-2(3h)-furanone 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. Thus, xi-dihydro-5-octyl-2(3h)-furanone is considered to be a fatty ester lipid molecule. Xi-dihydro-5-octyl-2(3h)-furanone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Xi-dihydro-5-octyl-2(3h)-furanone can be found in a number of food items such as green vegetables, fruits, citrus, and milk and milk products, which makes xi-dihydro-5-octyl-2(3h)-furanone a potential biomarker for the consumption of these food products.
CAS Number57084-18-1
Structure
Thumb
Synonyms
SynonymSource
g-DodecalactoneGenerator
Γ-dodecalactoneGenerator
(+/-)-4-Dodecanolidebiospider
(+/-)-4-Hydroxy-4-octylbutanoic acid lactonebiospider
(+/-)-4-Hydroxydodecanoic acid lactonebiospider
(+/-)-Dihydro-5-octyl-2(3H)-furanonebiospider
(+/-)-Dihydro-5-octylfuran-2(3H)-onebiospider
(+/-)-Gamma-dodecalactonebiospider
(+/-)-Gamma-dodecanolactonebiospider
(+/-)-Gamma-octyl-gamma-butyrolactonebiospider
(±)-4-n-Octylbutyrolactonemanual
(±)-gamma-Dodecalactonemanual
(RS)-gamma-Dodecalactonemanual
4-Dodecanolidedb_source
4-Hydroxydodecanoic acid g-lactonedb_source
4-Octyl-gamma-butyrolactonemanual
5-Octyltetrahydro-2-furanonemanual
Dihydro-5-octyl-2(3H)-furanonedb_source
Dodecan-4-olidemanual
FEMA 2400db_source
g-Dodecanolactonedb_source
gamma-Dodecalactonemanual
gamma-Dodecanolactonemanual
gamma-Laurolactonemanual
gamma-Octyl-gamma-butyrolactonemanual
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP4.38ALOGPS
logP3.76ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity56.86 m³·mol⁻¹ChemAxon
Polarizability24.64 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H22O2
IUPAC name5-octyloxolan-2-one
InChI IdentifierInChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-11-9-10-12(13)14-11/h11H,2-10H2,1H3
InChI KeyWGPCZPLRVAWXPW-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCC1CCC(=O)O1
Average Molecular Weight198.3019
Monoisotopic Molecular Weight198.161979948
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 Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.68%; H 11.18%; O 16.14%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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-a490bf6e0f9a2e81e23bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-a490bf6e0f9a2e81e23bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052k-9300000000-3ddd88b82fbfb964968dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-0900000000-3e3f211faf7df77e4fd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03ka-3900000000-866d2e766f25ce0139e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0532-8900000000-c6acb00eee2158e2b0b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-b80e0c21587047764241View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-6900000000-ceb73688984a25ad4a3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-99819aa65436ef25e84cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-a311c565b7c81229943bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-1900000000-372f957627fa56c4d61dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-6676502e703119655e8bView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID16821
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDDGR30-K:DGR30-K
EAFUS ID1071
Dr. Duke IDGAMMA-DODECALACTONE
BIGG IDNot Available
KNApSAcK IDC00030347
HET IDNot Available
Flavornet ID2305-05-7
GoodScent IDrw1013371
SuperScent ID16821
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
sweet
  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. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruit
  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
flower
  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
musty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peach
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
metallic
  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.
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).