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Showing Compound 1,8-Cineole (FDB014616)

Record Information
Version1.0
Creation date2010-04-08 22:11:22 UTC
Update date2019-11-26 03:10:28 UTC
Primary IDFDB014616
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,8-Cineole
DescriptionOccurs in eucalyptus, lavender, sage and many other oils. Flavouring ingredient Eucalyptol is a natural organic compound which is a colorless liquid. It is a cyclic ether and a monoterpenoid.; Eucalyptol is an organic compound which is a colorless liquid. It is a cyclic ether and a monoterpene.; Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fraction. Eucalyptol was given GRAS (Generally Recognized As Safe) status by the Flavor and Extract Manufacturer's Association FEMA, 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 are rather limited. Following the accidental exposure of human beings, 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 flavor. (PMID: 12048025, Fitoterapia. 2002 Jun;73(3):269-75); In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is claimed that it is added to improve the flavor.; It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. 1,8-Cineole is found in many foods, some of which are common thyme, caraway, sunflower, and pot marjoram.
CAS Number470-82-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
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
Chemical FormulaC10H18O
IUPAC name1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
InChI IdentifierInChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
InChI KeyWEEGYLXZBRQIMU-UHFFFAOYSA-N
Isomeric SMILESCC12CCC(CC1)C(C)(C)O2
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS1,8-Cineole, non-derivatized, GC-MS Spectrumsplash10-000x-9200000000-f7ec56dac2ebea83be0eSpectrum
Predicted GC-MS1,8-Cineole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-3900000000-207d29106cfe3c54c018Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9500000000-9dc534a13d795eb1b96c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-c05885d0e60c65af2adf2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003u-9000000000-217a9576a252e64568252012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-87fbd679809c90a3eb192017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-aa8e8e9cd53dad3b120e2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0900000000-5296316e735fc49999bf2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b403942017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b403942017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-da51d6a18dbcbda3b1682017-06-28View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID2656
ChEMBL IDCHEMBL485259
KEGG Compound IDC09844
Pubchem Compound ID2758
Pubchem Substance IDNot Available
ChEBI ID27961
Phenol-Explorer IDNot Available
DrugBank IDDB03852
HMDB IDHMDB04472
CRC / DFC (Dictionary of Food Compounds) IDJSX85-C:JSX85-C
EAFUS ID1324
Dr. Duke ID1,8-CINEOL|CINEOLE|1,8-CINEOLE|CINEOL
BIGG IDNot Available
KNApSAcK IDC00000136
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID470-82-6
GoodScent IDrw1056361
SuperScent ID2758
Wikipedia IDEucalyptol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.