Identification
NameEucalyptol
Accession NumberDB03852  (EXPT00969)
TypeSmall Molecule
GroupsNutraceutical
Description

Eucalyptol is a natural organic compound which is a colorless liquid. It is a cyclic ether and a monoterpenoid. Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant. It controls airway mucus hypersecretion and asthma via anti-inflammatory cytokine inhibition. Eucalyptol is an effective treatment for nonpurulent rhinosinusitis. Eucalyptol reduces inflammation and pain when applied topically. It kills leukaemia cells in vitro.

Structure
Thumb
Synonyms
1,8-cineol
1,8-Cineole
1,8-epoxy-p-menthane
1,8-oxido-p-menthane
cajeputol
cineol
cineole
Cucalyptol
Eucapur
Zineol
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Rosatra Synergy for Treatment Of Acne RosaceaOil.7 g/50gTopicalPhytopia Co., Ltd.2016-02-29Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
SoledumNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Advanced AntisepticMouthwashOralWakfern Food Corporation2010-11-24Not applicableUs
Advanced Antiseptic CitrusMouthwashOralH.E.B.2010-10-15Not applicableUs
Advanced CitrusMouthwashOralWalmart Stores2010-07-22Not applicableUs
Advanced Citrus AntisepticMouthwashOralPublix Supermarkets, Inc.2001-05-03Not applicableUs
Alsirub OntOintmentTopicalAlsi Cie Ltee1977-12-312003-05-21Canada
Amber Mouth RinseLiquidOralFilo America2013-07-30Not applicableUs
Amber Mouth Wash - LiqLiquidDentalPerrigo International1996-10-091999-08-06Canada
Amber Mouthwash - LiqLiquidDentalPerrigo International1996-06-301999-08-06Canada
Anitseptic Mouth RinseMouthwashOralPharmacy Vlaue Alliance Llc2003-08-19Not applicableUs
AntisepticMouthwashOralTarget Corporation.1996-07-15Not applicableUs
Antiseptic Blue Mint MouthwashLiquidOralFore Supply, Inc2017-06-05Not applicableUs
Antiseptic Lil Drug Store ProductsLiquidOralLil' Drug Store Products, Inc.2014-12-01Not applicableUs
Antiseptic Mouth RinseMouthwashOralWalgreens2007-03-30Not applicableUs
Antiseptic Mouth Rinse - LiqLiquidDentalPerrigo International1996-08-151999-08-06Canada
Antiseptic MouthrinseMouthwashOralWalmart Stores1989-11-11Not applicableUs
Antiseptic RinseMouthwashOralMeijer2006-08-08Not applicableUs
AntispeticMouthwashOralWalgreen2013-09-10Not applicableUs
Antispetic Mouth RinseMouthwashOralOnpoint, Inc2010-07-16Not applicableUs
Aurora Blue MintMouthwashBuccalAPOLLO HEALTH AND BEAUTY CARE2016-06-13Not applicableUs
Aurora Fresh BurstMouthwashBuccalAPOLLO HEALTH AND BEAUTY CARE2016-06-13Not applicableUs
Balminil CamphorubOintmentTopicalRougier Pharma Division Of Ratiopharm Inc1998-01-052003-09-22Canada
Balminil Nasal OintmentOintmentNasalRougier Pharma Division Of Ratiopharm Inc1995-12-312003-09-22Canada
Being Well AntisepticMouthwashOralSave A Lot Food Stores, Ltd.2014-10-03Not applicableUs
BiocenceLotionTopicalBio Germ Protection Llc2012-10-26Not applicableUs
BorasolPowderTopicalLaboratorios Dr. Collado, C x A.2013-01-01Not applicableUs
Buenos Dias De Personna Citrus FlavourMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Buenos Dias De Personna Cool MintMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Buenos Dias De Personna MintMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Buenos Dias De Personna OriginalMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Cal Mo Dol OntOintmentTopicalHerbes Universelles Inc.1980-12-312009-07-15Canada
Calmomusc LiqLiquidTopicalCardinaux Enrg Les Produits Naturels1989-12-312000-07-07Canada
Camocare Pain Relieving CreamCreamTopicalAbkit Inc.1995-12-312002-08-22Canada
Camphorated Ointment CompoundOintmentTopicalRougier Pharma Division Of Ratiopharm Inc1982-12-312003-09-22Canada
CarboseptolOintmentTopicalHerbes Universelles Inc.1966-12-312009-07-15Canada
Cool Mint Antiseptic MouthwashMouthwashBuccal; OralScott Chemical Canada1996-12-311998-09-09Canada
Creo Grippe Enfants SupSuppositoryRectalProduits Marc O (1987) Inc., Division Of Technilab Inc.1984-12-311999-09-17Canada
Creo Grippe Sup AdultesSuppositoryRectalProduits Marc O (1987) Inc., Division Of Technilab Inc.1992-12-301999-09-17Canada
Demo Cineol InjLiquidIntramuscularSabex Inc1951-12-311998-08-12Canada
Demo-cineol Adultes/adultsSuppositoryRectalSandoz Canada Incorporated1986-12-31Not applicableCanada
Demo-cineol Enfants/childrenSuppositoryRectalSandoz Canada Incorporated1977-12-31Not applicableCanada
Discount Drug Mart Blue Mint MouthwashLiquidOralDiscount Dollar Mart2014-05-06Not applicableUs
Discount Drug Mart Original Flavor MouthwashLiquidOralDiscount Drug Mart2014-05-06Not applicableUs
Discount Drug Mart Spring Mint MouthwashLiquidOralDiscount Drug Mart2014-05-06Not applicableUs
Equate Tartar Control PlusLiquidOralWalmart Stores2017-01-05Not applicableUs
Family Dollar Antiseptic Mouth RinseMouthwashOralFamily Dollar2011-05-16Not applicableUs
Family Dollar Antiseptic Mouth Rinse Blue MintMouthwashOralFamily Dollar Services2011-05-16Not applicableUs
Family Dollar Antiseptic Mouth Rinse Spring MintMouthwashOralFamily Dollar2011-05-16Not applicableUs
Green Mint Mouth RinseLiquidOralFilo America2013-07-30Not applicableUs
Handy Solutions Cool Mint Listerine Antiseptic MouthwashMouthwashOralNavajo Manuracturing Company2013-08-21Not applicableUs
Handy Solutions Listerine Antiseptic MouthwashMouthwashOralNavajo Manuracturing Company2013-08-21Not applicableUs
Hyvee Antiseptic Blue MintLiquidOralHyvee2015-04-08Not applicableUs
Hyvee Antiseptic MintLiquidOralHyvee2014-03-21Not applicableUs
Hyvee Antiseptic OriginalLiquidOralHyvee2013-09-12Not applicableUs
Hyvee Blue MintLiquidOralHyvee2014-03-19Not applicableUs
Hyvee Health Cool Blue Sugar FreeMouthwashOralHyvee2016-03-08Not applicableUs
Hyvee Health Green Mint Sugar FreeMouthwashOralHyvee2016-03-08Not applicableUs
Inarub CrmCreamTopicalFrega Inc.1979-12-312008-02-13Canada
Infraline LiqLiquidTopicalRolmex International Inc.1963-12-311997-08-08Canada
Jack and Jill RubOintmentTopicalW.K. Buckley Ltd.1954-12-311999-07-19Canada
Keloid Healer Synergy for Treatment Of KeloidsOilTopicalPhytopia Co., Ltd.2016-04-01Not applicableUs
Kiro-rubOintmentTopicalCentre De Recherches En Medication Naturelle Inc.1999-07-052001-07-01Canada
Larynsol LozLozengeOralHerbes Universelles Inc.1979-12-312009-07-15Canada
Listerine Advanced With Tartar Protection Antiseptic CitrusMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2013-10-112016-10-13Us
Listerine AntisepticMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-02-21Not applicableUs
Listerine Cool Mint AntisepticMouthwashOralJohnson & Johnson2012-02-21Not applicableUs
Listerine Freshburst AntisepticMouthwashOralJohnson & Johnson2012-02-21Not applicableUs
Listerine Naturals Antiseptic - Herbal MintMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2013-12-15Not applicableUs
Listerine Ultraclean Antiseptic Arctic MintMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-07-03Not applicableUs
Listerine Ultraclean Antiseptic Cool MintMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-07-09Not applicableUs
Listerine Ultraclean Antiseptic Fresh CitrusMouthwashOralJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2012-07-10Not applicableUs
Marco Rub Camphorated OntOintmentTopicalProduits Marc O (1987) Inc., Division Of Technilab Inc.1993-01-191999-09-17Canada
Marcs Blue MintLiquidOralAPOLLO HEALTH AND BEAUTY CARE2014-02-13Not applicableUs
Marcs OriginalLiquidOralAPOLLO HEALTH AND BEAUTY CARE2014-02-13Not applicableUs
Marcs Spring MintLiquidOralAPOLLO HEALTH AND BEAUTY CARE2014-02-13Not applicableUs
Mastic DentMouthwashDental; OralChia Gi Ltd2005-11-22Not applicableUs
Mouth RinseMouthwashOralKroger1989-11-11Not applicableUs
Onguent Camphre Menthol AlsiOintmentTopicalAlsi Cie Ltee1980-12-311998-07-03Canada
Oral Care AntisepticMouthwashOralRite Aid1990-10-15Not applicableUs
Oral Dent AmberMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Oral Dent Blue MintMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Oral Dent CitrusMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Oral Dent Fresh MintMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Oral-dent Blue MintMouthwashOralInternational Cosmetic Limited2013-01-10Not applicableUs
Original AntisepticMouthwashOralPublix1991-06-11Not applicableUs
Pastilles ValdaLozengeOralLabs Valda1981-12-311997-08-01Canada
Peppermint Mouth RinseLiquidOralFilo America2013-07-30Not applicableUs
Phytorub OntOintmentTopicalPhyto Health Corporation1978-12-312004-08-30Canada
Pommade Au The Des BoisEmulsionTopicalLab Valmo EnregistrÉ, Division Of Technilab Inc.1986-12-311999-09-17Canada
Quality Choice AmberLiquidOralChain Drug Marketing Association2015-09-13Not applicableUs
Quality Choice Blue MintLiquidOralChain Drug Marketing Association2015-09-13Not applicableUs
Quality Choice Sprng MintLiquidOralChain Drug Marketing Association2015-09-13Not applicableUs
Rhino-vaccinOintmentNasalRougier Pharma Division Of Ratiopharm Inc1951-12-312009-08-04Canada
RinseMouthwashOralWalgreen1990-05-15Not applicableUs
Royal Mouthwash Fresh and Clean Original MintLiquidOralFilo America2013-09-17Not applicableUs
Shaping With Workout - Loose Skin RevitalizerOilTopicalPhytopia Co., Ltd.2016-04-01Not applicableUs
Shaping Without WorkoutOilTopicalPhytopia Co., Ltd.2016-04-01Not applicableUs
Slim Booster With Natural Slimming ActivatorsOilTopicalPhytopia Co., Ltd.2016-04-01Not applicableUs
Smart Sense Blue MintLiquidOralKmart Corporation2013-05-13Not applicableUs
Smart Sense CitrusLiquidOralKmart Corporation2013-05-09Not applicableUs
Smart Sense Iceberg BlueLiquidOralKmart Corporation2013-04-22Not applicableUs
Smart Sense Original FlavorLiquidOralKmart Corporation2013-05-13Not applicableUs
Smart Sense Spring MintLiquidOralKmart Corporation2013-05-13Not applicableUs
Soft Mint Listerine AntisepticMouthwashDentalJohnson & Johnson Healthcare Products, Division Of Mc Neil Ppc, Inc.2010-02-05Not applicableUs
Tartar ControlMouthwashOralWestern Family2010-09-23Not applicableUs
Tartar Control PlusMouthwashOralWalgreen2013-10-10Not applicableUs
Thermo Rub OntOintmentTopicalRolmex International Inc.1973-12-312008-07-09Canada
Valda PastillesLozengeOralBayer Inc Consumer Care1995-12-312007-08-02Canada
Valda Pastilles Lemon FlavouredLozengeOralLabs Valda1992-12-311996-09-10Canada
Vaporisateur MedicamenteLiquidRespiratory (inhalation)Alsi Cie Ltee1979-12-312003-05-21Canada
Categories
UNIIRV6J6604TK
CAS number470-82-6
WeightAverage: 154.2493
Monoisotopic: 154.135765198
Chemical FormulaC10H18O
InChI KeyWEEGYLXZBRQIMU-WAAGHKOSSA-N
InChI
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10+
IUPAC Name
(1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
SMILES
C[C@@]12CC[C@@H](CC1)C(C)(C)O2
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

Oral, rat LD50: 2480 mg/kg

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. 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 ]
External Links
ATC CodesR05CA13 — Cineole
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (74.3 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentCoughing1
4CompletedPreventionNeonatal Infections1
4CompletedTreatmentAggressive Periodontitis1
Not AvailableRecruitingTreatmentPeriodontitis / Type 2 Diabetes Mellitus1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
LiquidDental
RinseOral
MouthwashOral
MouthwashBuccal
OintmentNasal
LotionTopical
SprayTopical
PowderTopical
LiquidTopical
CreamTopical
MouthwashBuccal; Oral
SuppositoryRectal
LiquidIntramuscular
LiquidOral
LozengeOral
OintmentTopical
MouthwashDental; Oral
EmulsionTopical
OilTopical.7 g/50g
OilTopical
MouthwashDental
LiquidRespiratory (inhalation)
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point (°C)1.5 °CPhysProp
boiling point (°C)176.4 °CPhysProp
water solubility3500 mg/L (at 21 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.74GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.0225 mg/mLALOGPS
logP3.36ALOGPS
logP2.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.86 m3·mol-1ChemAxon
Polarizability18.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.9842
Caco-2 permeable+0.7609
P-glycoprotein substrateSubstrate0.5435
P-glycoprotein inhibitor INon-inhibitor0.6374
P-glycoprotein inhibitor IINon-inhibitor0.6455
Renal organic cation transporterNon-inhibitor0.7847
CYP450 2C9 substrateNon-substrate0.8132
CYP450 2D6 substrateNon-substrate0.7839
CYP450 3A4 substrateSubstrate0.5962
CYP450 1A2 substrateNon-inhibitor0.7719
CYP450 2C9 inhibitorNon-inhibitor0.7571
CYP450 2D6 inhibitorNon-inhibitor0.95
CYP450 2C19 inhibitorNon-inhibitor0.658
CYP450 3A4 inhibitorNon-inhibitor0.9395
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9399
Ames testNon AMES toxic0.9574
CarcinogenicityNon-carcinogens0.7856
BiodegradationNot ready biodegradable0.8549
Rat acute toxicity1.8144 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8743
hERG inhibition (predictor II)Non-inhibitor0.7089
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0536-9200000000-aa52695ff4a2c1313e0bView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oxanes. These are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassOxanes
Direct ParentOxanes
Alternative ParentsOxacyclic compounds / Dialkyl ethers / Hydrocarbon derivatives
SubstituentsOxane / Oxacycle / Ether / Dialkyl ether / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptorscineole (CHEBI:27961 )
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:55