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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:17:46 UTC
Update Date2019-07-23 06:16:06 UTC
HMDB IDHMDB0034452
Secondary Accession Numbers
  • HMDB34452
Metabolite Identification
Common 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. Outside of the human body, 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.
Structure
Data?1563862566
Synonyms
ValueSource
(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
Chemical FormulaC10H16O2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
IUPAC Name6-pentyl-5,6-dihydro-2H-pyran-2-one
Traditional Namemassoia lactone
CAS Registry Number54814-64-1
SMILES
CCCCCC1CC=CC(=O)O1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9200000000-4838fa181a658e937981Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-1900000000-38a27e29eba97dd46ed4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9400000000-079af338b6c63fdba27fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9000000000-6bdc9ad8f20b1cc6ee7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-1cddb2d1bcb26b9ce888Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-4900000000-5d0c17343ae1fcb5b046Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-06a261e45e734d2f0c9bSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012860
KNApSAcK IDNot Available
Chemspider ID36500
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound39914
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .