Showing metabocard for Eucalyptol (BMDB0004472)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:31 UTC
Update Date2020-05-11 19:57:49 UTC
BMDB IDBMDB0004472
Secondary Accession Numbers
  • BMDB04472
Metabolite Identification
Common NameEucalyptol
DescriptionEucalyptol, also known as 1,8-cineol or cineole, 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. Thus, eucalyptol is considered to be an isoprenoid lipid molecule. Eucalyptol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,8-CineolKegg
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octaneKegg
CineoleKegg
1,8-CineoleHMDB
SoledumHMDB
1,8-Epoxy-p-menthaneHMDB
1,8-Oxido-p-menthaneHMDB
2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octaneHMDB
CajeputolHMDB
CINEOLHMDB
CNLHMDB
CucalyptolHMDB
EucalyptoleHMDB
EucapurHMDB
EukalyptolHMDB
Limonene oxideHMDB
p-CineoleHMDB
TerpanHMDB
Zedoary oilHMDB
ZineolHMDB
1,8 Epoxy p menthaneMeSH
1,8 CineolMeSH
1,8 CineoleMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
Traditional Nameeucalyptol
CAS Registry Number470-82-6
SMILES
CC12CCC(CC1)C(C)(C)O2
InChI Identifier
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
InChI KeyWEEGYLXZBRQIMU-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 heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point1.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.5 mg/mL at 21 °CNot Available
LogP2.74GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
logP3.36ALOGPS
logP2.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.86 m³·mol⁻¹ChemAxon
Polarizability18.54 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000x-9200000000-f7ec56dac2ebea83be0eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-3900000000-207d29106cfe3c54c018View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9500000000-9dc534a13d795eb1b96cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-c05885d0e60c65af2adfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003u-9000000000-217a9576a252e6456825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-87fbd679809c90a3eb19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-aa8e8e9cd53dad3b120eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0900000000-5296316e735fc49999bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b40394View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b40394View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-da51d6a18dbcbda3b168View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004472
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014616
KNApSAcK IDC00000136
Chemspider ID2656
KEGG Compound IDC09844
BioCyc IDCPD-4261
BiGG IDNot Available
Wikipedia LinkEucalyptol
METLIN ID7060
PubChem Compound2758
PDB IDNot Available
ChEBI ID584235
References
Synthesis ReferenceLana, Enio J. Leao; Rocha, Kelly A. da Silva; Kozhevnikov, Ivan V.; Gusevskaya, Elena V. Synthesis of 1,8-cineole and 1,4-cineole by isomerization of a-terpineol catalyzed by heteropoly acid. Journal of Molecular Catalysis A: Chemical (2006), 259(1-2), 99-102.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available