Showing Compound Card for 1,4-Cineole (CDB000188)

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Record Information
Version1.0
Created at2020-03-18 23:28:03 UTC
Updated at2020-11-18 16:34:54 UTC
CannabisDB IDCDB000188
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,4-Cineole
Description1,4-Cineole belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 1,4-Cineole is neutral compound. It is a colorless clear liquid with a minty, cooling piney, camphoraceous, eucalyptol-like odor and a flavor described as cooling, minty, menthol-like, green and herbal, with a terpy and camphoraceous nuance. 1,4-Cineole is found in highest concentrations in lavender spike water, juniper needle oil, cardamoms and limes. 1,4-Cineole has also been detected in evergreen grapes, grapefruit juice, lemon, orange, mandarins, blackberries, herbs and spices, roselles, and star anises ( Ref:DOI ). This could make 1,4-cineole a potential biomarker for the consumption of these foods. 1,4-Cineole is also found in cannabis plants (PMID:6991645 ) and in the essential oil of Rhododendron anthopogonoides (PMID: 22143541 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,4S)-1-Methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptaneChEBI
1,4-CineolChEBI
1,4-Epoxy-p-menthaneChEBI
1-Isopropyl-4-methyl-7-oxabicyclo(2.2.1)heptaneChEBI
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptaneChEBI
IsocineoleChEBI
IsocinepleChEBI
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1s,4s)-1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
Traditional Name(1s,4s)-1-isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane
CAS Registry Number470-67-7
SMILES
CC(C)[C@]12CC[C@](C)(CC1)O2
InChI Identifier
InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3/t9-,10+
InChI KeyRFFOTVCVTJUTAD-AOOOYVTPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Bicyclic monoterpenoid
  • Tetrahydrofuran
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.31ALOGPS
logP2.5ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.71 m³·mol⁻¹ChemAxon
Polarizability18.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28295867
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID80788
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Yang K, Zhou YX, Wang CF, Du SS, Deng ZW, Liu QZ, Liu ZL: Toxicity of Rhododendron anthopogonoides essential oil and its constituent compounds towards Sitophilus zeamais. Molecules. 2011 Aug 25;16(9):7320-30. doi: 10.3390/molecules16097320. [PubMed:22143541 ]