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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:22:45 UTC
Update Date2019-07-23 06:23:02 UTC
HMDB IDHMDB0037133
Secondary Accession Numbers
  • HMDB37133
Metabolite Identification
Common NameLinaloyl oxide
DescriptionLinaloyl oxide, also known as fema 3735, 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. Linalool creates a synergistic effect with the codling moth's pheromone called codlemone, which increases attraction of males. Linaloyl oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Linaloyl oxide is found, on average, in the highest concentration within limes. Linaloyl oxide has also been detected, but not quantified in, several different foods, such as alcoholic beverages, citrus, evergreen blackberries, fruits, and tea. This could make linaloyl oxide a potential biomarker for the consumption of these foods. Over 200 species of plants produce linalool, mainly from the families Lamiaceae (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), and Rutaceae (citrus fruits), but also birch trees and other plants, from tropical to boreal climate zones, including fungi. Linalool is used as a scent in 60% to 80% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions. Linalool is used in some mosquito-repellent products; however, the EPA notes that "a preliminary screen of labels for products containing [l]inalool (as the sole active ingredient) indicates that efficacy data on file with the Agency may not support certain claims to repel mosquitos."LavandulaCinnamomum tamalaCannabis sativaCannabis indicaOcimum basilicumSolidago Meyen, Solidago chilensisArtemisia vulgaris (mugwort)Humulus lupulusLinalool can be absorbed by inhalation of its aerosol and by oral intake or skin absorption, potentially causing irritation, pain and allergic reactions. Each enantiomer evokes different neural responses in humans, so are classified as possessing distinct scents. Both enantiomeric forms are found in nature:. It has other names such as β-linalool, linalyl alcohol, linaloyl oxide, allo-ocimenol, and 3,7-dimethyl-1,6-octadien-3-ol. In higher plants, linalool, as other monoterpenoids, is produced from isopentenyl pyrophosphate via the universal isoprenoid intermediate geranyl pyrophosphate, through a class of membrane-bound enzymes named monoterpene synthases.
Structure
Data?1563862982
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility0.02 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fwl-9300000000-bd4fe33bbcf6d0369e1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-f9ecba55ccee79339306Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-9100000000-6c84d3d773b31f16dde0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nf-9000000000-afc9e9075bde776980faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-e8e599e465eea0fbfb0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-7900000000-00f419898f3a112d466eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06ds-9100000000-3350510ed9b6aae9292bSpectrum
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 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.. .