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
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