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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H18O
Molecular Weight 154.2493
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EUCALYPTOL

SMILES

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

InChI

InChIKey=WEEGYLXZBRQIMU-LUYSIGKXSA-N
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10?

HIDE SMILES / InChI

Molecular Formula C10H18O
Molecular Weight 154.2493
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20359267 | https://www.ncbi.nlm.nih.gov/pubmed/27771935 | https://www.ncbi.nlm.nih.gov/pubmed/27722047 | https://www.ncbi.nlm.nih.gov/pubmed/27251496 | https://www.ncbi.nlm.nih.gov/pubmed/19624838 | https://www.ncbi.nlm.nih.gov/pubmed/26207629

Eucalyptol is a natural organic compound with fresh mint-like smell and a spicy, cooling taste. Eucalyptol comprises up to 90 percent of the essential oil of some species of the generic product Eucalyptus oil, hence the common name of the compound. It is also found in camphor laurel, bay leaves, tea tree, mugwort, sweet basil, wormwood, rosemary, common sage, Cannabis sativa and other aromatic plant foliage. Eucalyptol with a purity from 99.6 to 99.8 percent can be obtained in large quantities by fractional distillation of eucalyptus oil. Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant, as well as an inactive ingredient in body powder. The typical concentrations of eucalyptol in cosmetic products have been reported to be 1.6% in perfume, 0.4% in soap, 0.1% in creams and lotions and 0.04% in detergents. Committee of Experts on Flavouring Substances of the Council of Europe (CEFS) proposed upper levels of 0.1 mg/kg in beverages and 5 mg/kg in food with the exception of 15 mg/kg in candy and confectionery and 50 mg/kg in alcoholic beverages. Eucalyptol 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Helixia Sinus

Approved Use

Unknown
Primary
Helixia Sinus

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
790.75 ng/mL
4 mL single, respiratory
dose: 4 mL
route of administration: Respiratory
experiment type: SINGLE
co-administered:
EUCALYPTOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
275 ng/mL
2 mL single, respiratory
dose: 2 mL
route of administration: Respiratory
experiment type: SINGLE
co-administered:
EUCALYPTOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
19 nM
1.02 mg single, oral
dose: 1.02 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EUCALYPTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
23076 ng × min/mL
4 mL single, respiratory
dose: 4 mL
route of administration: Respiratory
experiment type: SINGLE
co-administered:
EUCALYPTOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
104.6 min
4 mL single, respiratory
dose: 4 mL
route of administration: Respiratory
experiment type: SINGLE
co-administered:
EUCALYPTOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
19.9 min
2 mL single, respiratory
dose: 2 mL
route of administration: Respiratory
experiment type: SINGLE
co-administered:
EUCALYPTOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0%
EUCALYPTOL plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Other AEs: Nausea, stomach ach...
Other AEs:
Nausea
stomach ach
Heartburn
Sources:
AEs

AEs

AESignificanceDosePopulation
Heartburn
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Nausea
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
stomach ach
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
PubMed

PubMed

TitleDatePubMed
Essential oil composition and antimicrobial activity of three Zingiberaceae from S.Tomé e Príncipe.
2001 Aug
Metabolites of dietary 1,8-cineole in the male koala (Phascolarctos cinereus).
2001 Aug
Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes.
2001 Oct
Volatile oil comparison of cotyledon leaves of chemotypes of Melaleuca alternifolia.
2002 Feb
Correlation between chemical composition and antibacterial activity of essential oils of some aromatic medicinal plants growing in the Democratic Republic of Congo.
2002 Feb
Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis.
2002 Jul 24
In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology.
2002 Jul 8
Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line.
2002 Jul-Aug
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).
2002 May
Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil.
2003
Near infrared spectroscopy for cost effective screening of foliar oil characteristics in a Melaleuca cajuputi breeding population.
2003 Apr 23
Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth.
2003 Aug 27
Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil.
2003 Jun
Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.
2003 Mar 12
Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens.
2003 May 21
The effects of Eucalyptus terpenes on hepatic cytochrome P450 CYP4A, peroxisomal Acyl CoA oxidase (AOX) and peroxisome proliferator activated receptor alpha (PPARalpha) in the common brush tail possum (Trichosurus vulpecula).
2003 Oct
Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy.
2003 Oct
Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases.
2003 Sep 15
Effect of monoterpenes on lipid oxidation in maize.
2004 Jun
Chemical composition of the essential oils of two Alpinia species from Hainan Island, China.
2004 Mar-Apr
Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis.
2004 May
Patents

Sample Use Guides

In this double-blind, placebo-controlled multi-center-study we randomly assigned 242 patients with stable COPD to receive 200 mg of cineole or placebo 3 times daily as concomitant therapy for 6 months
Route of Administration: Oral
Cell viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. BEAS-2B cells were treated with 0.1, 1, 10 µg/mL 1.8-cineole (Eucalyptol) for 24 h, and then incubated with MTT (0.5 mg/mL) at 37°C for 4 h. The viable cell number was directly proportional to the production of formazan, which was dissolved in isopropanol and determined by measuring the absorbance at 570 nm using a microplate reader.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:12:51 GMT 2025
Edited
by admin
on Mon Mar 31 18:12:51 GMT 2025
Record UNII
RV6J6604TK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINEOLE
EP   INCI   MART.   WHO-DD  
INCI  
Preferred Name English
EUCALYPTOL
FCC   FHFI   HPUS   HSDB   II   INCI   MI   USAN   USP   USP-RS   VANDF  
USAN   INCI  
Official Name English
1,8-CINEOL
Common Name English
EUCALYPTOL [II]
Common Name English
CINEOLE [MART.]
Common Name English
1,8-CINEOLE
Common Name English
EUCALYPTOL [MI]
Common Name English
1,8-EPOXY-P-MENTHANE
Systematic Name English
EUCALYPTOLE
Common Name English
NSC-6171
Code English
EUCALYPTOL [USP IMPURITY]
Common Name English
TERPAN
Common Name English
CAJEPUTOL
Common Name English
EUCALYPTOL [HPUS]
Common Name English
EUCALYPTOL [USP MONOGRAPH]
Common Name English
EUCALY
Common Name English
Cineole [WHO-DD]
Common Name English
P-MENTHANE, 1,8-EPOXY-
Systematic Name English
EUCALYPTOL [USAN]
Common Name English
EUKALYPTOL
Common Name English
EUCALYPTOL [USP-RS]
Common Name English
2-OXA-1,3,3-TRIMETHYLBICYCLO(2.2.2)OCTANE
Systematic Name English
CINEOLE [EP MONOGRAPH]
Common Name English
EUCALYPTOL [VANDF]
Common Name English
EUCALYPTOL [FHFI]
Common Name English
P-CINEOLE
Common Name English
EUCALYPTOL [FCC]
Common Name English
1,3,3-TRIMETHYL-2-OXABICYCLO(2.2.2)OCTANE
Systematic Name English
FEMA NO. 2465
Code English
2-OXABICYCLO(2.2.2)OCTANE, 1,3,3-TRIMETHYL-
Systematic Name English
EUCAPUR
Common Name English
EUCALYPTOL [HSDB]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
WHO-VATC QR05CA13
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
JECFA EVALUATION EUCALYPTOL
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
NCI_THESAURUS C74536
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
WHO-ATC R05CA13
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
Code System Code Type Description
WIKIPEDIA
EUCALYPTOL
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
DAILYMED
RV6J6604TK
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
MERCK INDEX
m5208
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY Merck Index
RS_ITEM_NUM
1268900
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID4020616
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
CAS
470-82-6
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-431-5
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
RXCUI
21116
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY RxNorm
CHEBI
27961
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
DRUG CENTRAL
4259
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
HSDB
991
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
NSC
6171
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
PUBCHEM
2758
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
ChEMBL
CHEMBL485259
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
NCI_THESAURUS
C76772
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
FDA UNII
RV6J6604TK
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
SMS_ID
100000092061
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
EVMPD
SUB20486
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
MESH
C010087
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
JECFA MONOGRAPH
1243
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
DRUG BANK
DB03852
Created by admin on Mon Mar 31 18:12:51 GMT 2025 , Edited by admin on Mon Mar 31 18:12:51 GMT 2025
PRIMARY
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