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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:21:34 UTC
Update Date2022-03-07 02:55:11 UTC
HMDB IDHMDB0037116
Secondary Accession Numbers
  • HMDB37116
Metabolite Identification
Common Namedelta-Decalactone
Descriptiondelta-Decalactone, also known as 5-decanolide or δ-amylvalerolactone, belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Thus, delta-decalactone is considered to be a fatty ester lipid molecule. delta-Decalactone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. delta-Decalactone is a sweet, apricot, and butter tasting compound. delta-Decalactone has been detected, but not quantified, in several different foods, such as coconuts, evergreen blackberries, bilberries, milk and milk products, and fats and oils. This could make delta-decalactone a potential biomarker for the consumption of these foods. A delta-lactone that is 5-valerolactone substituted by a pentyl group at position 6.
Structure
Data?1563862979
Synonyms
ValueSource
5-DecanolideChEBI
5-Hydroxydecanoic acid delta-lactoneChEBI
6-Pentyltetrahydro-2H-pyran-2-oneChEBI
6-PentylvalerolactoneChEBI
delta-AmylvalerolactoneChEBI
5-Hydroxydecanoate delta-lactoneGenerator
5-Hydroxydecanoate δ-lactoneGenerator
5-Hydroxydecanoic acid δ-lactoneGenerator
Δ-amylvalerolactoneGenerator
Δ-decalactoneGenerator
(+/-)-5-decanolideHMDB
(+/-)-6-pentyltetrahydro-2H-pyran-2-oneHMDB
(+/-)-delta-pentyl-delta-valerolactoneHMDB
5-Amyl-5-hydroxypentanoic acid lactoneHMDB
5-DecalactoneHMDB
5-Decanolide (laquo deltaraquo -decalactone)HMDB
5-Hydroxydecanoic acid lactoneHMDB
5-Hydroxydecanoic acid laquo deltaraquo -lactoneHMDB
5-Hydroxydecanoic lactoneHMDB
5-Pentyl-5-pentanolideHMDB
Amyl-delta-valerolactoneHMDB
Amyl-laquo deltaraquo -valerolactoneHMDB
D-DecalactoneHMDB
Decan-5-olideHMDB
Decanoic acid, 5-hydroxy-, laquo deltaraquo -lactoneHMDB
Decanolide-1,5HMDB
delta-DecanolactoneHMDB
delta-Pentyl-delta-valerolactoneHMDB
FEMA 2361HMDB
laquo deltaraquo -AmylvalerolactoneHMDB
laquo deltaraquo -DecalactoneHMDB
laquo deltaraquo -DecanolactoneHMDB
laquo deltaraquo -DecanolideHMDB
LT laquo deltaraquo GT -DecalactoneHMDB
tetrahydro-6-Pentyl-2H-pyran-2-oneHMDB
delta-DecalactoneChEBI
5-Pentyl-δ-valerolactoneGenerator
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name6-pentyloxan-2-one
Traditional Namedelta-decalactone
CAS Registry Number705-86-2
SMILES
CCCCCC1CCCC(=O)O1
InChI Identifier
InChI=1S/C10H18O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h9H,2-8H2,1H3
InChI KeyGHBSPIPJMLAMEP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassDelta valerolactones
Direct ParentDelta valerolactones
Alternative Parents
Substituents
  • Delta_valerolactone
  • Delta valerolactone
  • Oxane
  • 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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point-27.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point117.00 to 120.00 °C. @ 0.02 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP2.469 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP3.07ALOGPS
logP2.87ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.65 m³·mol⁻¹ChemAxon
Polarizability20.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.32331661259
DarkChem[M-H]-136.65731661259
DeepCCS[M+H]+144.47730932474
DeepCCS[M-H]-141.21530932474
DeepCCS[M-2H]-178.6230932474
DeepCCS[M+Na]+153.65630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
delta-DecalactoneCCCCCC1CCCC(=O)O12197.1Standard polar33892256
delta-DecalactoneCCCCCC1CCCC(=O)O11416.6Standard non polar33892256
delta-DecalactoneCCCCCC1CCCC(=O)O11518.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - delta-Decalactone EI-B (Non-derivatized)splash10-006y-9000000000-ac2a38db48be894bcefb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - delta-Decalactone EI-B (Non-derivatized)splash10-006y-9000000000-ac2a38db48be894bcefb2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - delta-Decalactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-054p-9200000000-4283f9517b8326841e442016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - delta-Decalactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - delta-Decalactone LC-ESI-QTOF , positive-QTOFsplash10-0udi-0900000000-3c39b7a149b7ba8485e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - delta-Decalactone LC-ESI-QTOF , positive-QTOFsplash10-052s-3900000000-42c0e919e06f752d329b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - delta-Decalactone 20V, Positive-QTOFsplash10-052s-3900000000-8e0e2851665ab93bd7582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - delta-Decalactone 10V, Positive-QTOFsplash10-0udi-0900000000-3c39b7a149b7ba8485e42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - delta-Decalactone 20V, Positive-QTOFsplash10-052s-3900000000-42c0e919e06f752d329b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 10V, Positive-QTOFsplash10-00di-0900000000-11bf82b4dc2d02619d9f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 20V, Positive-QTOFsplash10-001i-9300000000-779e83454acaf855ef9b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 40V, Positive-QTOFsplash10-052f-9000000000-e0b8ff2526444a9e77ea2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 10V, Negative-QTOFsplash10-016r-0900000000-68ca694b3df625447e8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 20V, Negative-QTOFsplash10-016r-4900000000-eee21863a417d6e9e7dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 40V, Negative-QTOFsplash10-0006-9100000000-c81b070c315fcda68fd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 10V, Negative-QTOFsplash10-014i-0900000000-efbd93a1a83feefc94df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 20V, Negative-QTOFsplash10-014i-1900000000-9934ee91f9331ff1917d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 40V, Negative-QTOFsplash10-0a4l-9500000000-1747d0a806f5cceb59022021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 10V, Positive-QTOFsplash10-00dl-9500000000-cb09dd4b56ab03241d2c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 20V, Positive-QTOFsplash10-052f-9200000000-761645e1c27bffca7a202021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Decalactone 40V, Positive-QTOFsplash10-052f-9000000000-625675dc767cf1aaf7522021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDFDB016109
KNApSAcK IDC00023985
Chemspider ID12282
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkΔ-Decalactone
METLIN IDNot Available
PubChem Compound12810
PDB IDNot Available
ChEBI ID87327
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1013411
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.. .