Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:11:22 UTC
Update date2018-01-23 19:36:10 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
Synonyms
SynonymSource
CineoleKegg
1,8-CineolKegg
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octaneKegg
1,8-CineoleHMDB
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
SoledumHMDB
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane, 9CIdb_source
1,8-Epoxy-P-menthaneHMDB
4,7,7-trimethyl-8-oxabicyclo[2.2.2]octanebiospider
Cineolbiospider
Cyneoldb_source
Eucalyptoldb_source
FEMA 3658db_source
Terpanedb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting PointMp 1.5°DFC
Boiling PointBp 176-177°DFC
Experimental Water Solubility3.5 mg/mL at 21 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.74GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4550DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-3900000000-207d29106cfe3c54c018View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9500000000-9dc534a13d795eb1b96cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-c05885d0e60c65af2adfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003u-9000000000-217a9576a252e6456825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-87fbd679809c90a3eb19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-aa8e8e9cd53dad3b120eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0900000000-5296316e735fc49999bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b40394View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-99f5c9faaf8cf2b40394View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-da51d6a18dbcbda3b168View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
(-)-chronotropicDUKE
(-)-inotropicDUKE
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
allelopathicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anestheticDUKE
anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti bronchitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti catarrh52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cholinesterase37733 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).DUKE
anti fatigue52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti halitosicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti laryngitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
anti pharyngiticDUKE
anti plaqueDUKE
anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti rhinitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti sinusiticDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
candidicideDUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
cholereticDUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
convulsantDUKE
counterirritantDUKE
cytochrome-p450 inducerDUKE
decongestant77715 A drug used to relieve nasal congestion in the upper respiratory tract.DUKE
degranulantDUKE
dentifriceDUKE
edemagenicDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
gastroprotective55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
Gram(+)icide33282 A substance that kills or slows the growth of bacteria.DUKE
Gram(-)icide33282 A substance that kills or slows the growth of bacteria.DUKE
hepatotonicDUKE
herbicide24527 A substance used to destroy plant pests.DUKE
hypotensiveDUKE
inflammatoryDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
myorelaxantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
pediculicide38706 Substance used to treat lice (genus Pediculus) infestation.DUKE
perfume48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
rubefacientDUKE
secretogogueDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
spasmogenicDUKE
surfactant35195 A substance which lowers the surface tension of the medium in which it is dissolved, and/or the interfacial tension with other phases, and, accordingly, is positively adsorbed at the liquid/vapour and/or at other interfaces.DUKE
testosterone-hydroxylase inducerDUKE
transdermalDUKE
trichomonicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pepper
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
eucalyptus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.