Record Information
Version1.0
Creation date2010-04-08 22:10:24 UTC
Update date2019-11-27 17:23:17 UTC
Primary IDFDB012860
Secondary Accession Numbers
  • FDB012861
Chemical Information
FooDB Name5,6-Dihydro-6-pentyl-2H-pyran-2-one
Description5,6-Dihydro-6-pentyl-2H-pyran-2-one, also known as 5-hydroxy-2-decenoic acid D-lactone or C-10 massoia lactone, belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. 5,6-Dihydro-6-pentyl-2H-pyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 5,6-Dihydro-6-pentyl-2H-pyran-2-one is a sweet, coconut, and creamy tasting compound. 5,6-Dihydro-6-pentyl-2H-pyran-2-one has been detected, but not quantified in, fruits. This could make 5,6-dihydro-6-pentyl-2H-pyran-2-one a potential biomarker for the consumption of these foods.
CAS Number54814-64-1
Structure
Thumb
Synonyms
SynonymSource
(R)-5,6-Dihydro-6-pentyl-2H-pyran-2-oneHMDB
2-Decen-5-olideHMDB
5,6-Dihydro-6-pentyl-(6R)-2H-pyran-2-oneHMDB
5,6-Dihydro-6-pentyl-(R)-2H-pyran-2-oneHMDB
5,6-Dihydro-6-pentyl-(theta)-2H-pyran-2-oneHMDB
5-Hydroxy-2-decenoic acid D-lactoneHMDB
5-Hydroxy-2-decenoic acid delta-lactoneHMDB
5-Hydroxy-2-decenoic acid lactoneHMDB
5-Hydroxy-2-decenoic acid laquo deltaraquo -lactoneHMDB
5-Hydroxy-2-decenoic acid, delta-lactoneHMDB
5-Hydroxy-2-decenoic acid, lactoneHMDB
C-10 Massoia lactoneHMDB
CocolactoneHMDB
FEMA 3744HMDB
Massoia lactoneHMDB
MassoilactoneHMDB
Massoy lactoneHMDB
2H-Pyran-2-one, 5,6-dihydro-6-pentyl-biospider
2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (6R)-biospider
2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (R)-biospider
2H-Pyran-2-one, 5,6-dihydro-6-pentyl-, (theta)-biospider
5-hydroxy-2-decenoic acid «delta»-lactonebiospider
5-Hydroxy-2-decenoic acid d-lactonedb_source
5-hydroxy-2-decenoic acid lactonebiospider
5-hydroxy-2-decenoic acid, lactonebiospider
5,6-Dihydro-6-pentyl-2H-pyran-2-one, (R)-biospider
C-10 massoia lactonebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.12ALOGPS
logP3.1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)17.28ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.75 m³·mol⁻¹ChemAxon
Polarizability19.6 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O2
IUPAC name6-pentyl-5,6-dihydro-2H-pyran-2-one
InChI IdentifierInChI=1S/C10H16O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h5,8-9H,2-4,6-7H2,1H3
InChI KeyNEDIAPMWNCQWNW-UHFFFAOYSA-N
Isomeric SMILESCCCCCC1CC=CC(=O)O1
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
Classification
Description belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentDihydropyranones
Alternative Parents
Substituents
  • Dihydropyranone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • 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

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.39%; H 9.59%; O 19.02%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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9200000000-4838fa181a658e937981View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-1900000000-38a27e29eba97dd46ed4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9400000000-079af338b6c63fdba27fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9000000000-6bdc9ad8f20b1cc6ee7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-1cddb2d1bcb26b9ce888View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-4900000000-5d0c17343ae1fcb5b046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-06a261e45e734d2f0c9bView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID39914
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHMN79-T:HMN79-T
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID54814-64-1
GoodScent IDrw1038011
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 / BioactivitiesNot Available
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. 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.
creamy
  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.
herbal
  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