Showing Compound Card for Eucalyptol (CDB000189)

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Record Information
Version1.0
Created at2020-03-18 23:28:05 UTC
Updated at2020-12-07 19:07:14 UTC
CannabisDB IDCDB000189
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEucalyptol
Description1,8-Cineole also known as Eucalyptol, belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-membered saturated aliphatic heterocycle, composed of one oxygen atom and five carbon atoms. Eucalyptol is an organic compound that is a colourless liquid. It is a cyclic ether and a monoterpenoid. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fractions. Eucalyptus oil is the oil extracted from the leaves of various Eucalyptus species. Eucalyptol oil is used for its aromatic properties and as an ingredient in pharmaceutical and industrial applications. Cineole-based eucalyptus oil is used as a flavouring at low levels (0.002%) in various products, including baked goods, confectionery, meat products, and beverages. Eucalyptol was given GRAS (Generally Recognized as Safe) status by the Flavor and Extract Manufacturer's Association FEMA in 1965 and is approved by the Food and Drug Administration for food use. 1,8-Dihydroxy-10-carboxy-p-menthane, 2-hydroxy-cineole, and 3-hydroxy-cineole are the main metabolites of eucalyptol. Toxicological data available on eucalyptol is rather limited. Following accidental exposure, death was reported in two cases after ingestion of 3.5-5 mL of essential eucalyptus oil, but a number of recoveries have also been described for much higher amounts of oil. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is added to improve the flavour (PMID: 12048025 ). Eucalyptol is found in many foods, some of which are common thyme, caraway, sunflower, and pot marjoram. Eucalyptol can also be found in the volatile fraction of Cannabis sativa (PMID: 26657499 ) and is likely a component of marijuana smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,3-TRIMETHYL-2-oxabicyclo[2.2.2]octaneChEBI
1,8-CineolChEBI
1,8-Epoxy-p-menthaneChEBI
1,8-Oxido-p-menthaneChEBI
CajeputolChEBI
CineoleChEBI
ZineolChEBI
1,8-CineoleHMDB
1,8-EucalyptolHMDB
2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octaneHMDB
EucaliptolHMDB
EucalyptoleHMDB
EucalytolHMDB
EukalyptolHMDB
p-CineoleHMDB
EucalyptolChEBI
CineolPhytoBank
EucapurPhytoBank
TerpanPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
Traditional Name1,8-cineole
CAS Registry Number470-82-6
SMILES
C[C@@]12CC[C@@H](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/t8-,10+
InChI KeyWEEGYLXZBRQIMU-WAAGHKOSSA-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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point1.5 °CNot Available
Boiling Point176–177 °CWikipedia
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0536-9200000000-aa52695ff4a2c1313e0b2015-03-01View Spectrum
Predicted GC-MSEucalyptol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-3900000000-207d29106cfe3c54c018Spectrum
Predicted GC-MSEucalyptol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9500000000-9dc534a13d795eb1b96c2020-03-10View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-c05885d0e60c65af2adf2020-03-10View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003u-9000000000-217a9576a252e64568252020-03-10View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-87fbd679809c90a3eb192017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-aa8e8e9cd53dad3b120e2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0900000000-5296316e735fc49999bf2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b403942017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b403942017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-da51d6a18dbcbda3b1682017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-9ea4da9bfdad90f3be7e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-085a10049717ea8e20df2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-085a10049717ea8e20df2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-0900000000-5cb534f49edce4797f2c2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 3A4CYP3A47q21.1P08684 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Sensi StarDetected and Quantified0.04 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.04 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0004472
DrugBank IDDB03852
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112393
KNApSAcK IDC00000136
Chemspider ID21111689
KEGG Compound IDC09844
BioCyc IDCPD-4261
BiGG IDNot Available
Wikipedia LinkEucalyptol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27961
References
General References
  1. De Vincenzi M, Silano M, De Vincenzi A, Maialetti F, Scazzocchio B: Constituents of aromatic plants: eucalyptol. Fitoterapia. 2002 Jun;73(3):269-75. doi: 10.1016/s0367-326x(02)00062-x. [PubMed:12048025 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]