U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Evaluation of toxic/protective effects of the essential oil of Salvia officinalis on freshly isolated rat hepatocytes.
2004-08
Chemical composition of the essential oils of two Alpinia species from Hainan Island, China.
2004-07-10
Antinociceptive profile of 2-phenylselenenyl-1,8-cineole in mice.
2004-06
Effect of monoterpenes on lipid oxidation in maize.
2004-06
Flavor release and perception in hard candy: influence of flavor compound-flavor solvent interactions.
2004-05-05
Flavor release and perception in hard candy: influence of flavor compound-compound interactions.
2004-05-05
Ovicidal and adulticidal activity of Eucalyptus globulus leaf oil terpenoids against Pediculus humanus capitis (Anoplura: Pediculidae).
2004-05-05
Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis.
2004-05
Constraint of feeding by chronic ingestion of 1,8-cineole in the brushtail possum (Trichosurus vulpecula).
2004-04
Effects of a novel gaseous antioxidative system containing a rosemary extract on the oxidation induced by nitrogen dioxide and ultraviolet radiation.
2004-04
1,8-cineole (eucalyptol), a monoterpene oxide attenuates the colonic damage in rats on acute TNBS-colitis.
2004-04
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
2004-03-24
Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt.
2004-03
Inhibition of acetylcholinesterase by Tea Tree oil.
2004-03
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.
2004-02
Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry.
2004-01-23
Transformation of terpenes using a Picea abies suspension culture.
2004-01-22
Characteristics, clinical effect profile and tolerability of a nasal spray preparation of Artemisia abrotanum L. for allergic rhinitis.
2004-01
Chemical and biological evaluation of the essential oils of different Melaleuca species.
2004-01
Antifungal activity of Thymus oils and their major compounds.
2004-01
Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi.
2003-12
Effect of the volatile constituents isolated from Thymus albicans, Th. mastichina, Th. carnosus and Thymbra capitata in sunflower oil.
2003-12
Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities.
2003-11-19
Composition and antimicrobial activity of Achillea clavennae L. essential oil.
2003-11
Chemical composition and biological activity of Nepeta parnassica oils and isolated nepetalactones.
2003-10-28
Effect of nitrogen concentration of the nutrient solution on the volatile constituents of leaves of Salvia fruticosa Mill. in solution culture.
2003-10-22
Essential oils from Mediterranean lamiaceae as weed germination inhibitors.
2003-10-08
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).
2003-10
Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy.
2003-10
Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases.
2003-09-15
Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth.
2003-08-27
Preferred age for assessment of qualitative and quantitative characteristics of the essential oil of tea tree (Melaleuca alternifolia) seedlings prior to plantation establishment.
2003-07-16
Noninvasive glucose monitoring by back diffusion via skin: chemical and physical enhancements.
2003-07
Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth.
2003-06-18
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.
2003-06
Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil.
2003-06
Fragrance chemistry, nocturnal rhythms and pollination "syndromes" in Nicotiana.
2003-06
Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens.
2003-05-21
Antimicrobial and antioxidant activities of three Mentha species essential oils.
2003-05
Near infrared spectroscopy for cost effective screening of foliar oil characteristics in a Melaleuca cajuputi breeding population.
2003-04-23
Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches.
2003-04-09
Essential oils produced by in vitro shoots of sage (Salvia officinalis L.).
2003-04-09
Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.
2003-03-12
Antibacterial activity and chemical composition of essential oil of Chrysanthemum boreale.
2003-03
Monoterpenoid accumulation in 1,8-cineole, terpinolene and terpinen-4-ol chemotypes of Melaleuca alternifolia seedlings.
2003-03
Odor compound detection in male euglossine bees.
2003-01
Dietary influences on terpenoids sequestered by the biological control agent Oxyops vitiosa: effect of plant volatiles from different Melaleuca quinquenervia chemotypes and laboratory host species.
2003-01
Differential metabolism of 1,8-cineole in insects.
2003-01
Erythema multiforme due to contact with weeds: a recurrence after patch testing.
2003-01
Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil.
2003
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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