Eucalyptol

Identification

Name
Eucalyptol
Accession Number
DB03852  (EXPT00969)
Type
Small Molecule
Groups
Nutraceutical
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
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Rosatra Synergy for treatment of Acne RosaceaOil.7 g/50gTopicalPhytopia Co., Ltd.2016-02-29Not applicableUs
International/Other Brands
Soledum
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Advanced AntisepticEucalyptol (.042 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L) + Thymol (.064 mL/100L)MouthwashOralWakfern Food Corporation2010-11-24Not applicableUs
Advanced AntisepticEucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.06 kg/100L) + Thymol (.064 kg/100L)MouthwashOralDemoulas Supermarkets, Inc.2010-07-22Not applicableUs
Advanced Antiseptic CitrusEucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L) + Thymol (.042 mL/100L)MouthwashOralDrug Mart1991-06-15Not applicableUs
Advanced Antiseptic CitrusEucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L) + Thymol (.042 mL/100L)MouthwashOralH.E.B.2010-10-15Not applicableUs
Advanced CitrusEucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.06 kg/100L) + Thymol (.064 kg/100L)MouthwashOralWalmart Stores2010-07-22Not applicableUs
Advanced Citrus AntisepticEucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.06 mL/100L) + Thymol (.064 mL/100L)MouthwashOralPublix Supermarkets, Inc.2001-05-03Not applicableUs
Alsirub OntEucalyptol (2.5 %) + Menthol (4 %) + Methyl salicylate (7.5 %)OintmentTopicalAlsi Cie Ltee1977-12-312003-05-21Canada
Amber Mouth RinseEucalyptol (.92 mg/mL) + Menthol (.42 mg/mL) + Methyl salicylate (.6 mg/mL) + Thymol (.64 mg/mL)LiquidOralFilo America2013-07-30Not applicableUs
Amber Mouth Wash - LiqEucalyptol (0.092 %) + Menthol (0.042 %) + Thymol (0.064 %)LiquidDentalPerrigo International1996-10-091999-08-06Canada
Amber Mouthwash - LiqEucalyptol (0.092 %) + Menthol (0.042 %) + Thymol (0.064 %)LiquidDentalPerrigo International1996-06-301999-08-06Canada
Categories
UNII
RV6J6604TK
CAS number
470-82-6
Weight
Average: 154.2493
Monoisotopic: 154.135765198
Chemical Formula
C10H18O
InChI Key
WEEGYLXZBRQIMU-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[[email protected]@]12CC[[email protected]@H](CC1)C(C)(C)O2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral, rat LD50: 2480 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not 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
KEGG Drug
D04115
KEGG Compound
C09844
PubChem Compound
2758
PubChem Substance
46506161
ChemSpider
21111689
ChEBI
27961
ChEMBL
CHEMBL1231862
PharmGKB
PA449555
IUPHAR
2464
Guide to Pharmacology
GtP Drug Page
HET
CNL
Wikipedia
Eucalyptol
ATC Codes
R05CA13 — Cineole
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Download (74.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentCoughing1
4CompletedPreventionNeonatal Infections1
4CompletedTreatmentAggressive Periodontitis1
Not AvailableRecruitingTreatmentPeriodontitis / Type 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not 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)
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0536-9200000000-aa52695ff4a2c1313e0b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organoheterocyclic compounds
Sub Class
Oxanes
Direct Parent
Oxanes
Alternative Parents
Oxacyclic compounds / Dialkyl ethers / Hydrocarbon derivatives
Substituents
Oxane / Oxacycle / Ether / Dialkyl ether / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aliphatic heteropolycyclic compound
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cineole (CHEBI:27961 )

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:28