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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H18O
Molecular Weight 154.2497
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EUCALYPTOL

SMILES

CC1(C)[C@@]2([H])CCC(C)(CC2)O1

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

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
PubMed

PubMed

TitleDatePubMed
Biotransformation of 1,8-cineole by human liver microsomes.
2001
In vitro activity of tea tree oil against Candida albicans mycelial conversion and other pathogenic fungi.
2001 Aug
Toxicity, feeding deterrence, and effect of activity of 1,8-cineole from Artemisia annua on progeny production of Tribolium castanaeum (Coleoptera: Tenebrionidae).
2001 Aug
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
1,8-cineol, a food flavoring agent, prevents ethanol-induced gastric injury in rats.
2001 Feb
Ambulation-promoting effect of peppermint oil and identification of its active constituents.
2001 Jul-Aug
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Comparison of eucalyptus camaldulensis Dehn. oils from Mozambique as obtained by hydrodistillation and supercritical carbon dioxide extraction.
2001 May
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
2001 Nov
Seasonal changes in the composition of the essential oil extract of East Mediterranean sage (Salvia libanotica) and its toxicity in mice.
2001 Oct
Effect of passive and iontophoretic skin pretreatments with terpenes on the in vitro skin transport of piroxicam.
2001 Oct 23
Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and beta-pinene by in vitro cultures.
2001 Sep
Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals.
2002 Dec
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
Microsomal metabolism and enzyme kinetics of the terpene p-cymene in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus) and rat.
2002 May
Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches.
2003 Apr 9
Essential oils produced by in vitro shoots of sage (Salvia officinalis L.).
2003 Apr 9
Effect of the volatile constituents isolated from Thymus albicans, Th. mastichina, Th. carnosus and Thymbra capitata in sunflower oil.
2003 Dec
Erythema multiforme due to contact with weeds: a recurrence after patch testing.
2003 Jan
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.
2003 Jun
Monoterpenoid accumulation in 1,8-cineole, terpinolene and terpinen-4-ol chemotypes of Melaleuca alternifolia seedlings.
2003 Mar
Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.
2003 Mar 12
Composition and antimicrobial activity of Achillea clavennae L. essential oil.
2003 Nov
Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities.
2003 Nov 19
Chemical composition and biological activity of Nepeta parnassica oils and isolated nepetalactones.
2003 Sep-Oct
Evaluation of toxic/protective effects of the essential oil of Salvia officinalis on freshly isolated rat hepatocytes.
2004 Aug
Characteristics, clinical effect profile and tolerability of a nasal spray preparation of Artemisia abrotanum L. for allergic rhinitis.
2004 Jan
Antifungal activity of Thymus oils and their major compounds.
2004 Jan
Transformation of terpenes using a Picea abies suspension culture.
2004 Jan 22
Antinociceptive profile of 2-phenylselenenyl-1,8-cineole in mice.
2004 Jun
Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt.
2004 Mar
Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis.
2004 May
Flavor release and perception in hard candy: influence of flavor compound-compound interactions.
2004 May 5
Ovicidal and adulticidal activity of Eucalyptus globulus leaf oil terpenoids against Pediculus humanus capitis (Anoplura: Pediculidae).
2004 May 5
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.
Name Type Language
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
EP   INCI   MART.   WHO-DD  
INCI  
Official 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
CINEOLE [WHO-DD]
Common Name English
EUCALYPTOLE
Common Name English
CINEOLE [INCI]
Common Name English
NSC-6171
Code English
TERPAN
Common Name English
CAJEPUTOL
Common Name English
EUCALYPTOL [HPUS]
Common Name English
EUCALYPTOL [USP MONOGRAPH]
Common Name English
EUCALY
Common Name English
EUCALYPTOL [INCI]
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
EUCALYPTOL [USP]
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 Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
WHO-VATC QR05CA13
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
JECFA EVALUATION EUCALYPTOL
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
NCI_THESAURUS C74536
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
WHO-ATC R05CA13
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
Code System Code Type Description
WIKIPEDIA
EUCALYPTOL
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
MERCK INDEX
M5208
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY Merck Index
EPA CompTox
470-82-6
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
CAS
470-82-6
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-431-5
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
RXCUI
21116
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
4259
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
HSDB
991
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
PUBCHEM
2758
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL485259
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
NCI_THESAURUS
C76772
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
FDA UNII
RV6J6604TK
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
EVMPD
SUB20486
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
MESH
C010087
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
USP_CATALOG
1268900
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB03852
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY