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Record Information
Version1.0
Created at2006-08-13 19:29:25 UTC
Updated at2021-10-07 20:38:52 UTC
NP-MRD IDNP0000712
Secondary Accession NumbersNone
Natural Product Identification
Common NameEucalyptol
DescriptionEucalyptol is an organic compound that is a colourless 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 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 usually added to improve the flavour (PMID: 12048025 ).
Structure
Thumb
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
CineolHMDB
EucapurHMDB
TerpanHMDB
EucalyptolChEBI
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
Traditional Name1,8-cineole
CAS Registry Number470-82-6
SMILES
CC12CCC(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
InChI KeyWEEGYLXZBRQIMU-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Achillea santolinoidsKNApSAcK Database
Aegle marmelosPlant
Ageratina conyzoidesPlant
Ajania fruticulosaKNApSAcK Database
Allium sativumKNApSAcK Database
Alphinia galanga-
Alpinia officinarumKNApSAcK Database
Alpinia zerumbetKNApSAcK Database
Amorpha fruticosaKNApSAcK Database
Anemopsis californicaKNApSAcK Database
Anethum foeniculumPlant
Anthemis aciphyllaLOTUS Database
Anthemis aciphylla BOISS.var.discoidea BOISSKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Artemisia anethoidesKNApSAcK Database
Artemisia annuaKNApSAcK Database
Artemisia baldshuanicaLOTUS Database
Artemisia californicaKNApSAcK Database
Artemisia canaLOTUS Database
Artemisia cana ssp.viscidulaKNApSAcK Database
Artemisia herba-albaLOTUS Database
Artemisia maritima var. stechmanniaKNApSAcK Database
Artemisia tauricaLOTUS Database
Asarum heterotropoides var.mandsuricumKNApSAcK Database
Asarum sieboldiiKNApSAcK Database
Backhousia angustifoliaLOTUS Database
Baeckea frutescens-
Brassica hirtaKNApSAcK Database
Calamintha nepetaKNApSAcK Database
Calycanthus floridusKNApSAcK Database
Cananga odorataKNApSAcK Database
Canarium albumKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Centaurea atropurpureaKNApSAcK Database
Centaurea orientalisKNApSAcK Database
Chrysanthemum borealeKNApSAcK Database
Cinnamomum augustifoliumKNApSAcK Database
Cinnamomum camphoraKNApSAcK Database
Cinnamomum camphorataKNApSAcK Database
Cinnamomum fragransKNApSAcK Database
Cinnamomum illicioidesKNApSAcK Database
Cistus albidusKNApSAcK Database
Citrus aurantifoliaKNApSAcK Database
Citrus aurantiifoliaPlant
Citrus limonKNApSAcK Database
Citrus reticulataKNApSAcK Database
Conyza newiiKNApSAcK Database
Coridothymus capitatusKNApSAcK Database
Croton lechleri Mull.Arg.KNApSAcK Database
Csitus ladaniferus-
Cuminum cyminumPlant
Cuminum cyminum L.KNApSAcK Database
Curcuma aeruginosaKNApSAcK Database
Curcuma amanda RoxbKNApSAcK Database
Curcuma aromaticaKNApSAcK Database
Curcuma kwangsiensisKNApSAcK Database
Curcuma longaLOTUS Database
Curcuma manggaKNApSAcK Database
Curcuma phaeocaulisKNApSAcK Database
Curcuma wenyujinKNApSAcK Database
Curcuma xanthorrhizaKNApSAcK Database
Cymbopogon citratusKNApSAcK Database
Cyperus rotundusPlant
Cyperus rotundus L.KNApSAcK Database
Eucalyptus albaKNApSAcK Database
Eucalyptus bicostataKNApSAcK Database
Eucalyptus camaldulensisKNApSAcK Database
Eucalyptus cinereaKNApSAcK Database
Eucalyptus cineriaKNApSAcK Database
Eucalyptus citriodaraKNApSAcK Database
Eucalyptus citriodoraKNApSAcK Database
Eucalyptus degluptaKNApSAcK Database
Eucalyptus flocktoniaeLOTUS Database
Eucalyptus globulusKNApSAcK Database
Eucalyptus grandisKNApSAcK Database
Eucalyptus leucoxylonKNApSAcK Database
Eucalyptus macathuriiKNApSAcK Database
Eucalyptus macklianaKNApSAcK Database
Eucalyptus maideniKNApSAcK Database
Eucalyptus maideniiKNApSAcK Database
Eucalyptus microcorysKNApSAcK Database
Eucalyptus mitchellianaLOTUS Database
Eucalyptus nitensKNApSAcK Database
Eucalyptus oblongaLOTUS Database
Eucalyptus pellitaKNApSAcK Database
Eucalyptus radiataKNApSAcK Database
Eucalyptus resiniferaKNApSAcK Database
Eucalyptus robustaKNApSAcK Database
Eucalyptus salignaKNApSAcK Database
Eucalyptus sideroxylonKNApSAcK Database
Eucalyptus smithiiKNApSAcK Database
Eucalyptus spathulataLOTUS Database
Eucalyptus tereticornisKNApSAcK Database
Eucalyptus torellianaKNApSAcK Database
Eucalyptus viminalisKNApSAcK Database
Foeniculum vulgareKNApSAcK Database
Hedychium coronariumKNApSAcK Database
Helichrysum italicumKNApSAcK Database
Hesperis matronalisKNApSAcK Database
Isodon rubescensPlant
Laurus nobilisKNApSAcK Database
Laurus nobilis L.Plant
Lavandula angustifoliaKNApSAcK Database
Lavandula dentataKNApSAcK Database
Lavandula stoechasKNApSAcK Database
Leptospermum scopariumKNApSAcK Database
Lindera neesianaKNApSAcK Database
Lippia javanicaKNApSAcK Database
Lippia ukambensisKNApSAcK Database
Litsea pungensKNApSAcK Database
Malva sylvestrisLOTUS Database
Matricaria discoideaLOTUS Database
Matricaria matricarioidesLOTUS Database
Melaleuca alternifoliaLOTUS Database
Melaleuca leucadendraKNApSAcK Database
Melaleuca leucadendronKNApSAcK Database
Mentha arvensisPlant
Mentha arvensis L.KNApSAcK Database
Mentha piperitaLOTUS Database
Mentha piperita L.KNApSAcK Database
Mentha pulegiumPlant
Mentha pulegium L.KNApSAcK Database
Myrtus communisKNApSAcK Database
Nicotiana alataKNApSAcK Database
Nicotiana bonariensisKNApSAcK Database
Nicotiana langsdorffiiKNApSAcK Database
Nicotiana mutabilisKNApSAcK Database
Ocimum basilicumKNApSAcK Database
Ocimum kilimandscharicimKNApSAcK Database
Origanum vulgarePlant
Perilla frutescensLOTUS Database
Pinus halepensisKNApSAcK Database
Pinus sibiricaKNApSAcK Database
Piper nigrumKNApSAcK Database
Piper nigrum L.Plant
Plectranthus marrubioidesKNApSAcK Database
Psidium guajavaKNApSAcK Database
Quercus cocciferaKNApSAcK Database
Rabdosia rubescensKNApSAcK Database
Rosmarinus officinalisKNApSAcK Database
Salvia leucophyllaKNApSAcK Database
Salvia officinalisKNApSAcK Database
Salvia rosmarinusPlant
Santolina corsica Jordan et FourrKNApSAcK Database
Sideritis chamaedrifoliaLOTUS Database
Sideritis tragoriganumLOTUS Database
Sinapis albaPlant
Tanacetum macrophyllumKNApSAcK Database
Tanacetum vulgareKNApSAcK Database
Tarchonanthus camphoratusKNApSAcK Database
Tetradenia ripariaKNApSAcK Database
Thryptomene saxicolaLOTUS Database
Thymus eriocalyxKNApSAcK Database
Thymus piperellaKNApSAcK Database
Thymus pubescensKNApSAcK Database
Thymus vulgarisKNApSAcK Database
Thymus X-porlockKNApSAcK Database
Tipuana tipuKNApSAcK Database
Verbena officinalisPlant
Vitex trifoliaKNApSAcK Database
Xylopia aethiopicaKNApSAcK Database
Xylopia cayennensisKNApSAcK Database
Xylopia parvifloraKNApSAcK Database
Zanthoxylum armatumKNApSAcK Database
Zanthoxylum bungeanumKNApSAcK Database
Zanthoxylum decaryiKNApSAcK Database
Zingiber officinaleKNApSAcK Database
Species Where Detected
Species NameSourceReference
Fusarium culmorumKNApSAcK Database
Ganoderma lucidumKNApSAcK Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point1.5 °CNot Available
Boiling Point176.00 to 177.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3.5 mg/mL at 21 °CNot Available
LogP2.74Griffin, S., Wyllie, S. G., & Markham, J. (1999). Determination of octanol-water partition coefficient for terpenoids using reversed-phase high-performance liquid chromatography. Journal of Chromatography A, 864(2), 221-228.
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
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
Good Scents IDrw1056361
References
General References
  1. Giannakou SA, Dallas PP, Rekkas DM, Choulis NH: In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. Int J Pharm. 2002 Jul 8;241(1):27-34. [PubMed:12086718 ]
  2. Narishetty ST, Panchagnula R: Effect of L-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. J Control Release. 2005 Jan 20;102(1):59-70. [PubMed:15653134 ]
  3. Lim PF, Liu XY, Kang L, Ho PC, Chan YW, Chan SY: Limonene GP1/PG organogel as a vehicle in transdermal delivery of haloperidol. Int J Pharm. 2006 Mar 27;311(1-2):157-64. Epub 2006 Jan 31. [PubMed:16451823 ]
  4. Cornwell PA, Barry BW, Stoddart CP, Bouwstra JA: Wide-angle X-ray diffraction of human stratum corneum: effects of hydration and terpene enhancer treatment. J Pharm Pharmacol. 1994 Dec;46(12):938-50. [PubMed:7536240 ]
  5. Juergens UR, Engelen T, Racke K, Stober M, Gillissen A, Vetter H: Inhibitory activity of 1,8-cineol (eucalyptol) on cytokine production in cultured human lymphocytes and monocytes. Pulm Pharmacol Ther. 2004;17(5):281-7. [PubMed:15477123 ]
  6. Moghimi HR, Williams AC, Barry BW: Enhancement by terpenes of 5-fluorouracil permeation through the stratum corneum: model solvent approach. J Pharm Pharmacol. 1998 Sep;50(9):955-64. [PubMed:9811155 ]
  7. Kato T, Iijima H, Ishihara K, Kaneko T, Hirai K, Naito Y, Okuda K: Antibacterial effects of Listerine on oral bacteria. Bull Tokyo Dent Coll. 1990 Nov;31(4):301-7. [PubMed:2133450 ]
  8. Harper DS, Brogdon CL, Wu MM, Epelle U: A rapid method for evaluating microbicidal activity of dentifrice formulations against salivary bacteria ex vivo. J Clin Dent. 2000;11(4):89-93. [PubMed:11460277 ]
  9. Duisken M, Sandner F, Blomeke B, Hollender J: Metabolism of 1,8-cineole by human cytochrome P450 enzymes: identification of a new hydroxylated metabolite. Biochim Biophys Acta. 2005 Apr 15;1722(3):304-11. Epub 2005 Jan 17. [PubMed:15715982 ]
  10. De Vincenzi M, Silano M, De Vincenzi A, Maialetti F, Scazzocchio B: Constituents of aromatic plants: eucalyptol. Fitoterapia. 2002 Jun;73(3):269-75. [PubMed:12048025 ]
  11. Bastos VP, Gomes AS, Lima FJ, Brito TS, Soares PM, Pinho JP, Silva CS, Santos AA, Souza MH, Magalhaes PJ: Inhaled 1,8-cineole reduces inflammatory parameters in airways of ovalbumin-challenged Guinea pigs. Basic Clin Pharmacol Toxicol. 2011 Jan;108(1):34-9. doi: 10.1111/j.1742-7843.2010.00622.x. Epub 2010 Aug 16. [PubMed:20722639 ]