Eucalyptol

Identification

Summary

Eucalyptol is a common ingredient in mouthwash and cosmetics derived naturally from the eucalyptus plant that is frequently used to to improve symptoms of airway mucus hypersecretion.

Brand Names

Listerine Antiseptic

Generic Name

Eucalyptol

DrugBank Accession Number

DB03852

Background

Eucalyptol is naturally produced cyclic ether and 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.

Type

Small Molecule

Groups

Experimental, Nutraceutical

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Eucalyptol (DB03852)

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Weight

Average: 154.2493
Monoisotopic: 154.135765198

Chemical Formula

C₁₀H₁₈O

Synonyms

• 1,8-cineol
• 1,8-Cineole
• 1,8-epoxy-p-menthane
• 1,8-oxido-p-menthane
• Cajeputol
• Cineole
• Eucalyptol
• Zineol

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Pharmacology

Indication

Not Available

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Prophylaxis of	Gingivitis		••• •••

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

• Eucalyptol
  • 2alpha-hydroxy-1,8-cineole
  • 3alpha-hydroxy-1,8-cineole

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Oral, rat LD50: 2480 mg/kg

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

Not Available

Products

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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Germ Free ARIA	Liquid	1.2 g/100mL	Topical	Omega Vision Co., Ltd.	2022-09-24	Not applicable
Rosatra Synergy for treatment of Acne Rosacea	Oil	0.7 g/50g	Topical	Phytopia Co., Ltd.	2016-02-29	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
365 Whole Foods Market Anticavity/Antigingivitis Mouthwash	Eucalyptol (0.92 mg/1mL) + Menthol (0.42 mg/1mL) + Methyl salicylate (0.6 mg/1mL) + Sodium fluoride (0.1 mg/1mL) + Thymol (0.64 mg/1mL)	Mouthwash	Dental	Whole Foods Market, Inc.	2022-01-31	Not applicable
365 Whole Foods Market Antigingivitis Mouthwash	Eucalyptol (0.92 mg/1mL) + Menthol (0.42 mg/1mL) + Methyl salicylate (0.6 mg/1mL) + Thymol (0.64 mg/1mL)	Mouthwash	Dental	Whole Foods Market, Inc.	2022-01-31	Not applicable
Advanced Antiseptic	Eucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L)	Mouthwash	Oral	Demoulas Super Markets, Inc	2010-07-22	Not applicable
Advanced Antiseptic	Eucalyptol (.042 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.064 mL/100L)	Mouthwash	Oral	Wakefern Food Corporation	2010-11-24	Not applicable
Advanced Antiseptic Citrus	Eucalyptol (.092 mL/100L) + Menthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.042 mL/100L)	Mouthwash	Oral	H E B	2010-10-15	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Antiseptic Rinse	Eucalyptol (.092 kg/100L) + Menthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L)	Mouthwash	Oral	Meijer	2006-08-08	Not applicable
Germ Free ARIA	Eucalyptol (1.2 g/100mL)	Liquid	Topical	Omega Vision Co., Ltd.	2022-09-24	Not applicable

Categories

ATC Codes

R05CA13 — Cineole

• R05CA — Expectorants
• R05C — EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS
• R05 — COUGH AND COLD PREPARATIONS
• R — RESPIRATORY SYSTEM

Drug Categories

• Agrochemicals
• Alcohols
• Anti-Infective Agents
• Antitussive Agents
• Central Nervous System Agents
• Compounds used in a research, industrial, or household setting
• Cosmetics
• Cough and Cold Preparations
• Cyclohexanes
• Cyclohexanols
• Cycloparaffins
• Diet, Food, and Nutrition
• Expectorants
• Fatty Alcohols
• Flavoring Agents
• Food
• Food Additives
• Food Ingredients
• Hexanols
• Insect Repellents
• Lipids
• Monoterpenes
• Mouthwashes
• Pesticides
• Pharmaceutic Aids
• Pharmaceutical Preparations
• Physiological Phenomena
• Protective Agents
• Respiratory System Agents
• Solvents
• Terpenes
• Toxic Actions

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds 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

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Oxacyclic compounds / Dialkyl ethers / Hydrocarbon derivatives

Substituents

Aliphatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Oxacycle / Oxane

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cineole (CHEBI:27961)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

RV6J6604TK

CAS number

470-82-6

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[C@@]12CC[C@@H](CC1)C(C)(C)O2

References

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. [Article]

External Links

KEGG Drug

D04115

KEGG Compound

C09844

PubChem Compound

2758

PubChem Substance

46506161

ChemSpider

21111689

RxNav

21116

ChEBI

27961

ChEMBL

CHEMBL1231862

PharmGKB

PA449555

Guide to Pharmacology

GtP Drug Page

PDBe Ligand

CNL

Wikipedia

Eucalyptol

PDB Entries

1t2b / 3be0 / 4fmx / 4fyz / 4l6g / 4l77 / 4lht

MSDS

Download (74.3 KB)

Clinical Trials

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Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Healthy Subjects (HS)	1
3	Unknown Status	Treatment	Cough	1
2	Recruiting	Prevention	Neisseria Gonorrhoeae Infection	1
Not Available	Completed	Not Available	Acute rhino-sinusitis / Bronchitis / Chronic Sinusitis	1
Not Available	Recruiting	Not Available	Community Acquired Pneumonia (CAP)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Ointment	Nasal
Liquid	Dental
Mouthwash	Oral
Mouthwash	Buccal
Lotion	Topical
Spray	Topical
Powder	Topical
Solution	Respiratory (inhalation)
Liquid	Topical
Cream	Topical
Mouthwash	Buccal; Oral
Liquid	Intramuscular
Suppository	Rectal
Capsule
Gel	Topical
Liquid	Topical	1.2 g/100mL
Ointment	Topical
Rinse	Oral
Lozenge	Oral
Solution	Topical
Mouthwash	Dental; Oral
Spray	Oral
Liquid	Oral
Emulsion	Topical
Oil	Topical	0.7 g/50g
Capsule	Oral
Oil	Topical
Mouthwash	Dental
Capsule, gelatin coated	Oral
Liquid	Respiratory (inhalation)
Solution	Oral

Prices

Not Available

Patents

Not Available

Properties

State

Liquid

Experimental Properties

Property	Value	Source
melting point (°C)	1.5 °C	PhysProp
boiling point (°C)	176.4 °C	PhysProp
water solubility	3500 mg/L (at 21 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	2.74	GRIFFIN,S ET AL. (1999)

Predicted Properties

Property	Value	Source
Water Solubility	0.0225 mg/mL	ALOGPS
logP	3.36	ALOGPS
logP	2.35	Chemaxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4.2	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	1	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	9.23 Å2	Chemaxon
Rotatable Bond Count	0	Chemaxon
Refractivity	45.86 m3·mol-1	Chemaxon
Polarizability	18.54 Å3	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.988
Blood Brain Barrier	+	0.9842
Caco-2 permeable	+	0.7609
P-glycoprotein substrate	Substrate	0.5435
P-glycoprotein inhibitor I	Non-inhibitor	0.6374
P-glycoprotein inhibitor II	Non-inhibitor	0.6455
Renal organic cation transporter	Non-inhibitor	0.7847
CYP450 2C9 substrate	Non-substrate	0.8132
CYP450 2D6 substrate	Non-substrate	0.7839
CYP450 3A4 substrate	Substrate	0.5962
CYP450 1A2 substrate	Non-inhibitor	0.7719
CYP450 2C9 inhibitor	Non-inhibitor	0.7571
CYP450 2D6 inhibitor	Non-inhibitor	0.95
CYP450 2C19 inhibitor	Non-inhibitor	0.658
CYP450 3A4 inhibitor	Non-inhibitor	0.9395
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9399
Ames test	Non AMES toxic	0.9574
Carcinogenicity	Non-carcinogens	0.7856
Biodegradation	Not ready biodegradable	0.8549
Rat acute toxicity	1.8144 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8743
hERG inhibition (predictor II)	Non-inhibitor	0.7089

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0f79-3900000000-207d29106cfe3c54c018
Mass Spectrum (Electron Ionization)	MS	splash10-0536-9200000000-aa52695ff4a2c1313e0b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0900000000-d481148e26447211338e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0900000000-a54b2adeda330d15fd27
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0900000000-e9c7c0e6b576a23d244c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0900000000-5deec8995c432ff9d8c3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0900000000-20548748424de9aa6d15
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052r-0900000000-f2f636a07e006bc2d898
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	138.77718	predicted	DeepCCS 1.0 (2019)
[M+H]+	133.3374801	predicted	DarkChem Lite v0.1.0
[M+H]+	141.17274	predicted	DeepCCS 1.0 (2019)
[M+Na]+	133.1899801	predicted	DarkChem Lite v0.1.0
[M+Na]+	147.40157	predicted	DeepCCS 1.0 (2019)

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Drug created at June 13, 2005 13:24 / Updated at September 28, 2021 21:54