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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:09:49 UTC
Update Date2019-07-23 06:20:20 UTC
HMDB IDHMDB0036096
Secondary Accession Numbers
  • HMDB36096
Metabolite Identification
Common Name1,4-Cineole
Description1,4-Cineole, also known as isocineole or p-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 an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862820
Synonyms
ValueSource
1,4-Epoxy-p-menthaneKegg
1,4-CineolHMDB
1-Isopropyl-4-methyl-7-oxabicyclo(2.2.1)heptaneHMDB
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptaneHMDB
1-Isopropyl-4-methylbicyclo[2.2.1]heptaneHMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo(2.2.1)heptaneHMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptaneHMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane, 9ciHMDB
7-Oxabicyclo(2.2.1)heptane, 1-isopropyl-4-methyl- (6ci)HMDB
IsocineoleHMDB
IsocinepleHMDB
p-CineoleHMDB
p-Menthane, 1,4-epoxyHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
Traditional Name1,4-cineol
CAS Registry Number470-67-7
SMILES
CC(C)C12CCC(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
InChI KeyRFFOTVCVTJUTAD-UHFFFAOYSA-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 Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point1 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.97Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
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
Polarizability18.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ox-9300000000-b9a5b5d2f98cced31647Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01xx-9500000000-a318fb72cb983bf328bdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ox-9300000000-b9a5b5d2f98cced31647Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01xx-9500000000-a318fb72cb983bf328bdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-4900000000-bdc12e60fcbd39f1835cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-dddd2f9cdd5cb5b07319Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-dceb1fb237319528cf1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2900000000-571ee3b396093a239686Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-f31d792cd2a066e8f6d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-3d49e541e98afbae6fdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zmr-2900000000-d8a5501eed1b480a13e2Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014936
KNApSAcK IDC00010825
Chemspider ID9702
KEGG Compound IDC16909
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10106
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.