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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:22:45 UTC
Update Date2023-02-21 17:25:36 UTC
HMDB IDHMDB0037133
Secondary Accession Numbers
  • HMDB37133
Metabolite Identification
Common NameLinaloyl oxide
DescriptionLinaloyl oxide belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Linaloyl oxide is found, on average, in the highest concentration within limes (Citrus aurantiifolia). Linaloyl oxide has also been detected, but not quantified in, several different foods, such as red tea, herbal tea, green tea, teas (Camellia sinensis), and alcoholic beverages. This could make linaloyl oxide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Linaloyl oxide.
Structure
Data?1677000336
Synonyms
ValueSource
2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyranChEBI
2,2,6-Trimethyl-6-vinyltetrahydropyranChEBI
2,6,6-Trimethyl-2-ethenyltetrahydro-2H-pyranChEBI
2,6,6-Trimethyl-2-ethenyltetrahydropyranChEBI
2,6,6-Trimethyl-2-vinyltetrahydropyranChEBI
2-Ethenyltetrahydro-2,6,6-trimethyl-2H-pyranChEBI
2-Vinyltetrahydro-2,6,6-trimethyl-2H-pyranChEBI
Linalool 3,7-oxideChEBI
Tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyranChEBI
2,2,6-Trimethyl-6-vinyl-tetrahydropyranHMDB
2,6,6-Trimethyl-2-ethenyltetrahydro-2-pyranHMDB
2,6,6-Trimethyl-2-vinyl-tetrahydropyraneHMDB
2-ethenyltetrahydro-2,6,6-Trimethylpyran, 9ciHMDB
Dehydroxylinalool oxide aHMDB
FEMA 3735HMDB
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name2-ethenyl-2,6,6-trimethyloxane
Traditional Name2-ethenyl-2,6,6-trimethyloxane
CAS Registry Number7392-19-0
SMILES
CC1(C)CCCC(C)(O1)C=C
InChI Identifier
InChI=1S/C10H18O/c1-5-10(4)8-6-7-9(2,3)11-10/h5H,1,6-8H2,2-4H3
InChI KeyNETOHYFTCONTDT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxanes
Sub ClassNot Available
Direct ParentOxanes
Alternative Parents
Substituents
  • Oxane
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.35ALOGPS
logP2.74ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.68 m³·mol⁻¹ChemAxon
Polarizability18.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.71431661259
DarkChem[M-H]-131.38831661259
DeepCCS[M+H]+140.73230932474
DeepCCS[M-H]-136.90430932474
DeepCCS[M-2H]-174.60830932474
DeepCCS[M+Na]+150.14730932474
AllCCS[M+H]+131.332859911
AllCCS[M+H-H2O]+126.832859911
AllCCS[M+NH4]+135.532859911
AllCCS[M+Na]+136.732859911
AllCCS[M-H]-137.932859911
AllCCS[M+Na-2H]-139.632859911
AllCCS[M+HCOO]-141.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Linaloyl oxideCC1(C)CCCC(C)(O1)C=C1216.4Standard polar33892256
Linaloyl oxideCC1(C)CCCC(C)(O1)C=C954.6Standard non polar33892256
Linaloyl oxideCC1(C)CCCC(C)(O1)C=C965.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Linaloyl oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fwl-9300000000-bd4fe33bbcf6d0369e1f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linaloyl oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 10V, Positive-QTOFsplash10-0a4i-2900000000-f9ecba55ccee793393062016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 20V, Positive-QTOFsplash10-001j-9100000000-6c84d3d773b31f16dde02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 40V, Positive-QTOFsplash10-05nf-9000000000-afc9e9075bde776980fa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 10V, Negative-QTOFsplash10-0udi-1900000000-e8e599e465eea0fbfb0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 20V, Negative-QTOFsplash10-0udi-7900000000-00f419898f3a112d466e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 40V, Negative-QTOFsplash10-06ds-9100000000-3350510ed9b6aae9292b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 10V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 20V, Negative-QTOFsplash10-0udi-5900000000-67bec87194434c0dda412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 40V, Negative-QTOFsplash10-0udi-6900000000-aee78cdcdb533177a9bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 10V, Positive-QTOFsplash10-05o3-9100000000-6d42ee439d476a67a5ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 20V, Positive-QTOFsplash10-001l-9000000000-f3188b3d77123058e5542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linaloyl oxide 40V, Positive-QTOFsplash10-0gb9-9000000000-62fa83c27d8c6fac30d62021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB016128
KNApSAcK IDNot Available
Chemspider ID455792
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLinalool
METLIN IDNot Available
PubChem Compound522514
PDB IDNot Available
ChEBI ID132848
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .