You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-11 20:57:17 UTC
Update Date2016-02-11 02:44:04 UTC
HMDB IDHMDB35907
Secondary Accession NumbersNone
Metabolite Identification
Common NameLinalyl oxide
DescriptionLinalyl oxide is found in citrus. Linalyl oxide is isolated from Citrus paradisi (grapefruit), Thea sinensis (tea) and many other sources. Linalyl oxide is a flavouring ingredient.This is the furanoid form of linalool oxide; there are 4 possible stereo-isomers. Linalyl oxide belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain.
Structure
Thumb
Synonyms
ValueSource
2,6-Dimethyl-3,6-oxido-7-octen-2-olHMDB
2-(5-Methyl-5-vinyltetrahydro-2-furanyl)-2-propanolHMDB
2-(tetrahydro-5-Methyl-5-vinyl-2-furyl)propan-2-olHMDB
2-Methyl-2-vinyl-5-(1-hydroxy-1-methylethyl)tetrahydrofuranHMDB
2-Methyl-2-vinyl-5-(2-hydroxy-2-propyl)tetrahydrofuranHMDB
5-(1-Hydroxy-1-methylethyl)-2-methyl-2-vinyltetrahydrofuranHMDB
5-ethenyltetrahydro-a,a,5-Trimethyl-2-furanmethanol, 9ciHMDB
5-ethenyltetrahydro-alpha,alpha,5-Trimethyl-2-furanmethanolHMDB
alpha,alpha,5-Trimethyl-5-vinyltetrahydrofurfuryl alcoholHMDB
FEMA 3746HMDB
Furan linalool oxideHMDB
Linalool 3,6-oxideHMDB
Linalool oxideHMDB
tetrahydro-2-Methyl-5-(1-hydroxy-1-methylethyl)-2-vinylfuranHMDB
tetrahydro-alpha,alpha,5-Trimethyl-5-vinylfuran-2-methanolHMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name2-(5-ethenyl-5-methyloxolan-2-yl)propan-2-ol
Traditional Namelinalool oxide
CAS Registry Number60047-17-8
SMILES
CC(C)(O)C1CCC(C)(O1)C=C
InChI Identifier
InChI=1/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3
InChI KeyInChIKey=BRHDDEIRQPDPMG-UHFFFAOYNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxolanes
Sub ClassNot Available
Direct ParentOxolanes
Alternative Parents
Substituents
  • Tertiary alcohol
  • Oxolane
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Flavoring Agent
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.43Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.5 mg/mLALOGPS
logP1.51ALOGPS
logP1.67ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.32ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.04 m3·mol-1ChemAxon
Polarizability19.52 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-fd06f861f85ceeb7374aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl9-7900000000-6e140039d1c0b3a27f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-9100000000-374ae141a9cf1649d95dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-b79259e5d9b5eade7756View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1900000000-7c8bf5a1a274d134abd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsr-9400000000-9c5bb820e778e45b7d36View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014692
KNApSAcK IDC00010335
Chemspider ID20938
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB35907
Metagene LinkHMDB35907
METLIN IDNot Available
PubChem Compound22310
PDB IDNot Available
ChEBI 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.