Record Information
Version1.0
Creation date2010-04-08 22:08:03 UTC
Update date2018-05-28 18:53:39 UTC
Primary IDFDB008395
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Pentyl-gamma-butyrolactone
DescriptionPresent in blackcurrant buds and berries, melon, papaya, pineapple, peaches, apricot, wheat bread, crispbread, wines, black tea and other foodstuffs. Flavouring agent. 4-Pentyl-gamma-butyrolactone is found in many foods, some of which are cereals and cereal products, white mustard, coconut, and alcoholic beverages.
CAS Number57084-16-9
Structure
Thumb
Synonyms
SynonymSource
g-NonanolideGenerator
Γ-nonanolideGenerator
(3H)-Dihydro-5-pentyl-2-furanonebiospider
1,4-Nonanolidedb_source
4-Hydroxynonanoic acid g-lactonedb_source
4-Hydroxynonanoic acid lactonebiospider
4-Pentyl-gamma-butyrolactonemanual
4-Pentylbutanolidebiospider
5-Pentyldihydro-2(3H)-furanonedb_source
5-Pentyldihydrofuran-2(3H)-onebiospider
Aldehyde C18 (misleading)db_source
Apricolindb_source
Cocos aldehyde (misleading)db_source
Dihydro-5-pentyl-2(3H)-furanonedb_source
FEMA 2781db_source
g-Amylbutyrolactonedb_source
g-Nonalactonedb_source
g-Pelargonolactonedb_source
Nonlactonbiospider
Prunolidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP2.41ALOGPS
logP2.42ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.05 m³·mol⁻¹ChemAxon
Polarizability18.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H16O2
IUPAC name5-pentyloxolan-2-one
InChI IdentifierInChI=1S/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3
InChI KeyOALYTRUKMRCXNH-UHFFFAOYSA-N
Isomeric SMILESCCCCCC1CCC(=O)O1
Average Molecular Weight156.2221
Monoisotopic Molecular Weight156.115029756
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 69.19%; H 10.32%; O 20.48%DFC
Melting PointNot Available
Boiling PointBoiling Pt : 136 oC at 1.28E+01 mm Hg
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-b49a9ba5068e6a6f37e2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-b49a9ba5068e6a6f37e2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9100000000-af0a79e6fed6da9b90e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-744435374457def1ad43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-9400000000-138d9d1b3adff2cc8bc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-2aef2660fd27b623a33aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-8a84aa8e2a9449a5fa56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-2900000000-f3ab54e2cccc6f3c6d41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-582e8883da5af41a1b0eView in MoNA
ChemSpider ID7424
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7710
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31531
CRC / DFC (Dictionary of Food Compounds) IDDHQ03-G:DHQ03-G
EAFUS ID2685
Dr. Duke IDGAMMA-NONALACTONE|NONAN-4-OLIDE
BIGG IDNot Available
KNApSAcK IDC00001318
HET IDNot Available
Flavornet ID104-61-0
GoodScent IDrw1000531
SuperScent IDNot Available
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
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
coconut
  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.
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
creamy
  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.
sweet
  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.
oily
  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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.