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1,8 CINEOLE
CAS Number: 470-82-6
EC Number: 207-431-5
Chemical formula: C10H18O
Molar mass: 154.249 g/mol
Eucalyptol is a monoterpenoid.
A colorless liquid, Eucalyptol is a bicyclic ether.
Eucalyptol has a fresh mint-like smell and a spicy, cooling taste.
Eucalyptol is insoluble in water, but miscible with organic solvents.
Eucalyptol makes up 90% of eucalyptus oil.
Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid.
Formation of these adducts is useful for purification.
In 1870, F. S. Cloez identified and ascribed the name "eucalyptol" to the dominant portion of Eucalyptus globulus oil.
Eucalyptol is naturally produced cyclic ether and monoterpenoid.
Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant.
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.
Eucalyptol kills leukaemia cells in vitro.
Eucalyptol, also frequently called 1,8-cineol, is the primary constituent of oil.
Eucalyptol is also found in tea tree (Melaleuca alternifolia) oil.
(e.g., wormwood and sagebrush), and even Cannabis sativa.
French chemist François Stanislas Cloez isolated eucalyptol from Eucalyptus globulus in 1870.
Another Eucalyptusspecies, E. cloeziana, was named in his honor.
Eucalyptol is an ingredient in many spices used to prepare the turkey day meal: bay leaf, cardamom, rosemary, and sage, to name a few.
Eucalyptol is a contributor to the wonderful aroma of holiday cooking.
Eucalyptol is also used as a flavor ingredient in oral hygiene products and cough suppressants.
Eucalyptol is safe to ingest in small quantities, but Eucalyptol is toxic in larger doses.
In 1981, M. Verma and C. E. Meloan found that eucalyptol in bay leaves is an effective cockroach repellent.
Eucalyptol is a saturated monoterpene.
Eucalyptol is a volatile oil with medicinal values naturally found in eucalyptus oil.
Eucalyptol is a isoprenoid with 2-isoprene subunits (C10).
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.
Eucalyptol 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.
Eucalyptus Oil Natural 80% Eucalyptol is a colorless or pale yellow liquid having a characteristic aromatic somewhat camphoraceous odor and a pungent, spicy, cooling taste.
Eucalyptol is ideal for use in the personal care industry.
Eucalyptol is an organic compound that is a colourless liquid.
Eucalyptol is a cyclic ether and a monoterpene.
Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fraction.
Eucalyptol was given GRAS (Generally Recognized As Safe) status by the Flavor and Extract Manufacturer's Association FEMA, 1965 and is approved by the Food and Drug Administration for food use.
1,8-Dihydroxy-10-carboxy-p-menthane, 2-hydroxy-cineole, and 3-hydroxy-cineole are the main metabolites of eucalyptol.
Toxicological data available on eucalyptol are rather limited.
Following accidental exposure, death was reported in two cases after ingestion of 3.5-5 mL of essential eucalyptus oil, but a number of recoveries have also been described for much higher amounts of oil.
In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes.
Eucalyptol is usually added to improve the flavour.
This clear oily liquid can be extracted from plant matter, including cannabis, and used in various ways.
Often found in plants like wormwood and sagebrush, along with spices like cardamom, rosemary, bay leaves, and sage, this essential oil has a refreshing, minty flavor when consumed orally.
And of course, the most similar sounding plant with plentiful eucalyptol is the eucalyptus tree, the staple diet of Australia’s favorite koala.
Eucalyptol is an aromatic chemical, usually appearing as a clear liquid with a herbal eucalyptus odour.
Eucalyptol is naturally present as an organic compound in the essential oils of many plants, including tea tree, rosemary and sage.
Eucalyptol is the chief component of eucalyptus (Eucalyptus globulus) oil, and is used as a component of many fragrances, food and medicine flavourings for Eucalyptol potent aroma and minty-cooling flavour.
Eucalyptol is naturally present as a component of many of the essential oils we use as fragrances for our products.
Although this molecule is found in nature, Eucalyptol can still have a negative effect on some people who may be sensitive to Eucalyptol on their skin.
Physical Description of Eucalyptol:
1,8-cineol is a colorless liquid with a camphor-like odor.
Spicy cooling taste.
Health Benefits/Uses of Eucalyptol:
Along with Eucalyptol natural presence in many ingredients that add lots of flavor to food, eucalyptol oil is often used to add a minty and refreshing aftertaste to products like mouthwash and cough drops.
Eucalyptol also makes up about 90 percent of the formula known as eucalyptus oil, often used as apharmaceutical, antiseptic, repellent, flavoring, and fragrance additive.
What many might not know, however, is that eucalyptol oil can be used as an effective treatment for a laundry list of medical ailments with very few side effects.
Researchers and clinical trials have shown that doses of eucalyptol offer a range of health benefits.
Eucalyptol can:
Help to relieve sinus and nasal congestion.
Improve breathing issues like asthma.
Be somewhat productive at relieving pain.
Show potential as an anti-inflammatory and antiseptic.
Improve cognitive function in older people when used consistently.
For example, this double-blind, randomized, placebo-controlled study showed that Eucalyptol safe and effective to use eucalyptol oils orally to treat rhinosinusitis, a common sinus infection.
Treating a common infection with natural and accessible ingredients is a significant step forward for safe, affordable, and effective treatments that are divorced from the big pharma system.
Another research article showed that eucalyptus oil inhalation had a measurable effect on pain and inflammation for those recovering from knee replacement operations—this terpene’s potential as an anti-inflammatory and large amounts of eucalyptol present in eucalyptus oil.
A recent 2020 study showed that eucalyptol profoundly affected Japanese nursing home residents’ cognitive function when inhaled over set periods.
What’s even more interesting about this study is that the residents showed improved function in testing even when they inhaled small enough oil doses to not even detect that Eucalyptol had been dosed.
While the clinical research on eucalyptol is still in Eucalyptol early stages, the medical potential of this terpene is clear.
Eucalyptol is already used in medicinal products to treat bronchitis, sinusitis, chronic rhinitis, asthma, and rhinosinusitis.
Early animal research has shown Eucalyptol potential to improve long-term memory function in people of all ages and even suppress the growth of cancer cells.
Since everyone is different and has different health ailments, Eucalyptol essential to consult with your certified cannabis doctor and general practitioner before starting or ending any ongoing treatments you’re currently using to manage symptoms.
Applications of Eucalyptol:
Eucalyptol undergoes pyrolysis to yield p-cymene and hydrogen gas.
Eucalyptol can be used in the synthesis of mosquito repellents and herbicides.
Eucalyptol may be used as a reference standard for the determination of the analyte in:
Melon fruits by headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry.
Chrysanthemum flower by pressurized hot water extraction (PHWE) followed by headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry.
Pharmaceutical formulations by full evaporation technique extraction followed by capillary gas chromatography and ion-trap detection.
External analgesic pharmaceutical formulations by densitometric HPTLC analysis.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique.
Contact Technical Service for further support.
Eucalyptol has been used as reference standard in densitometric HPTLC analysis for the determination of Eucalyptol from external analgesic pharmaceutical formulations.
Uses of Eucalyptol:
Because of Eucalyptol pleasant, spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics.
Cineole-based eucalyptus oil is used as a flavouring at low levels (0.002%) in various products, including baked goods, confectionery, meat products, and beverages.
In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes.
Eucalyptol is claimed to be added to improve the flavor.
Eucalyptol is an ingredient in commercial mouthwashes, and has been used in traditional medicine as a cough suppressant.
Chief constituent of oil of eucalyptus.
Used in pharmaceuticals (cough syrups and expectorants).
Also used as a flavoring agent, fragrance, disinfectant, and solvent.
Eucalyptus oil contains up to 70% eucalyptol.
Industrial Processes with risk of exposure:
Fragrance and flavoring agent in foods, candies, cough drops, personal car products.
Pharmaceutical aid (flavor).
Pharmaceuticals (cough syrups, expectorants), flavoring, perfumery
Essential oils such as eucalyptol reduce plaque-related gingivitis.
Other Uses of Eucalyptol:
Eucalyptol exhibits insecticidal and insect repellent properties.
In contrast, eucalyptol is one of many compounds that are attractive to males of various species of orchid bees, which gather the chemical to synthesize pheromones; Eucalyptol is commonly used as bait to attract and collect these bees for study.
One such study with Euglossa imperialis, a nonsocial orchid bee species, has shown that the presence of cineole (also eucalyptol) elevates territorial behavior and specifically attracts the male bees.
Eucalyptol was even observed that these males would periodically leave their territories to forage for chemicals such as cineole, thought to be important for attracting and mating with females, to synthesize pheromones.
Therapeutic Uses of Eucalyptol:
Cineole has mucolytic, bronchodilating and anti-inflammatory properties and reduces the exacerbation rate in patients suffering from COPD, as well as ameliorates symptoms in patients suffering from asthma and rhinosinusitis.
Based on these effects, we therefore postulated the hypothesis that patients with acute bronchitis would also benefit from therapy with Cineole.
As part of a double-blind, placebo-controlled, multi-center-study, a total of 242 patients with confirmed acute bronchitis was randomly selected to participate.
Over a period of 10 days, all patients were administered 3 x 200 mg of Cineole, or a respective placebo, per day.
The primary outcome measure was a Bronchitis Sum Score, which summarizes the relevant symptoms of acute bronchitis.
After 4 days of treatment Eucalyptol was notable, that the patient group treated with Cineole, showed significantly more improvements of the bronchitis-sum-score than those of the placebo group (p?=?0.0383).
The statistical significant difference of the individual outcome measures was especially underlined by the frequency of cough fits by p?=?0.0001 after 4 days.
The effects of Cineole in the treatment of acute bronchitis were clearly measurable and could be proven after a treatment period of merely 4 days.
This study corroborates the fact that Cineole actively and significantly reduces cough frequency after four days.
The clinical effects of mucolytics in patients with chronic obstructive pulmonary disease (COPD) are discussed controversially.
Cineole is the main constituent of eucalyptus oil and mainly used in inflammatory airway diseases as a mucolytic agent.
We hypothesized that Eucalyptol known mucolytic, bronchodilating and anti-inflammatory effects as concomitant therapy would reduce the exacerbation rate and show benefits on pulmonary function tests as well as quality of life in patients with COPD.
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 during winter-time.
The frequency, duration and severity of exacerbations were combined as primary outcome measures for testing as multiple criteria.
Secondary outcome measures included changes of lung function, respiratory symptoms and quality of life as well as the single parameters of the exacerbations.
Baseline demographics, lung function and standard medication of both groups were comparable.
During the treatment period of 6 months the multiple criteria frequency, severity and duration of exacerbations were significantly lower in the group treated with cineole in comparison to placebo.
Secondary outcome measures validated these findings.
Improvement of lung function, dyspnea and quality of life as multiple criteria were statistically significant relative to placebo.
Adverse events were comparable in both groups.
Concomitant therapy with cineole reduces exacerbations as well as dyspnea and improves lung function and health status.
This study further suggests cineole as an active controller of airway inflammation in COPD by intervening in the pathophysiology of airway inflammation of the mucus membrane.
Industry Uses of Eucalyptol:
Odor agents
Consumer Uses of Eucalyptol:
Air care products
Cleaning and furnishing care products
Laundry and dishwashing products
Non-TSCA use
Personal care products
Plastic and rubber products not covered elsewhere
Methods of Manufacturing of Eucalyptol:
By fractional distillation (170-180 °C) from those essential oils containing high levels of eucalyptol, such as Eucalyptus globulus (approx 60%), and subsequent separation of the product by congealing the distillate.
By fractionally distilling eucalyptus oil followed by freezing.
The oil is imported from Spain, Portugal, and Austria.
1,8-Cineole is extracted exclusively from eucalyptus oils with a high 1,8-cineole content.
Various processes are used to separate Eucalyptol from the other terpenes, for example, treatment with H2SO4 in the cold, distillation in the presence of phenols, such as cresols or resorcinol, which form loose addition compounds, or by addition to beta-naphthol.
1,8-Cineole can also be enriched by rectification.
The yield is increased by gasification in the presence of a chromium-nickel catalyst.
A product essentially free from other products can be obtained by crystallization of cineole-rich eucalyptus oil fractions.
General Manufacturing Information of Eucalyptol:
Industry Processing Sectors:
All other chemical product and preparation manufacturing
Plastic material and resin manufacturing
Soap, cleaning compound, and toilet preparation manufacturing
1,8-cineole is produced only from natural sources as these are sufficiently inexpensive to make synthesis uneconomic.
Originally, Eucalyptol was produced from Cajeput oil, but the discovery of Eucalyptus globulus, the oil of which contains up to 95% 1,8-cineole, in 1788 led to the first commercial production from that source in 1854 in Australia, and then to Eucalyptol taking over as the dominant source.
Much of the oil is used per se and only about one-quarter of Eucalyptol is distilled to produce pure cineole.
The chief constituent of oil of eucalyptus; also found in essential oils of laurel, rosemary, and many other aromatic plants.
Pharmacology and Biochemistry of Eucalyptol:
MeSH Pharmacological Classification:
Flavoring Agents:
Substances added to foods and medicine to improve the taste.
Insect Repellents:
Substances causing insects to turn away from them or reject them as food.
Solvents:
Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar.
Anti-Infective Agents:
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Mouthwashes:
Solutions for rinsing the mouth, possessing cleansing, germicidal, or palliative properties.
Antitussive Agents:
Agents that suppress cough.
They act centrally on the medullary cough center.
EXPECTORANTS, also used in the treatment of cough, act locally.
Handling and Storage of Eucalyptol:
Nonfire Spill Response:
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material.
Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal.
Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution.
Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures and away from mineral acids and bases.
Storage Conditions of Eucalyptol:
Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature -20 °C.
First Aid of Eucalyptol:
EYES: First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.
INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital.
Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.
INGESTION: DO NOT INDUCE VOMITING.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.
Be prepared to transport the victim to a hospital if advised by a physician.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.
DO NOT INDUCE VOMITING.
IMMEDIATELY transport the victim to a hospital.
Fire Fighting of Eucalyptol:
Fires involving this compound should be controlled with a dry chemical, carbon dioxide, foam or Halon extinguisher.
Fire Fighting Procedures of Eucalyptol:
Advice for firefighters; Wear self-contained breathing apparatus for firefighting if necessary.
Use water spray to cool unopened containers.
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Isolation and Evacuation of Eucalyptol:
As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions.
LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet).
FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
Cleanup Methods of Eucalyptol:
Personal precautions, protective equipment and emergency procedures: Use personal protective equipment.
Avoid breathing vapors, mist or gas.
Remove all sources of ignition.
Beware of vapors accumulating to form explosive concentrations.
Vapors can accumulate in low areas.
Environmental precautions: Prevent further leakage or spillage if safe to do so.
Do not let product enter drains; Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.
Disposal Methods of Eucalyptol:
Recycle any unused portion of the material for Eucalyptol approved use or return Eucalyptol to the manufacturer or supplier.
Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations.
If Eucalyptol is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Preventive Measures of Eucalyptol:
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
List of plants that contain eucalyptol:
Aframomum corrorima
Artemisia tridentata
Cannabis
Cinnamomum camphora, camphor laurel (50%)
Eucalyptus cneorifolia
Eucalyptus dives
Eucalyptus dumosa
Eucalyptus globulus
Eucalyptus goniocalyx
Eucalyptus horistes
Eucalyptus kochii
Eucalyptus leucoxylon
Eucalyptus largiflorens
Eucalyptus oleosa
Eucalyptus polybractea
Eucalyptus radiata
Eucalyptus rossii
Eucalyptus sideroxylon
Eucalyptus smithii
Eucalyptus staigeriana
Eucalyptus tereticornis
Eucalyptus viridis
Hedychium coronarium, butterfly lily
Helichrysum gymnocephalum
Kaempferia galanga, galangal, (5.7%)
Laurus nobilis, bay laurel, (45%)
Melaleuca alternifolia, tea tree, (0–15%)
Salvia lavandulifolia, Spanish sage (13%)
Turnera diffusa, damiana
Umbellularia californica, pepperwood (22.0%)
Zingiber officinale, ginger
Identifiers of Eucalyptol:
CAS Number: 470-82-6
Beilstein Reference: 105109 5239941
ChEBI: CHEBI:27961
ChEMBL: ChEMBL485259
ChemSpider: 2656
DrugBank: DB03852
ECHA InfoCard: 100.006.757
EC Number: 207-431-5
Gmelin Reference: 131076
IUPHAR/BPS : 2464
KEGG: D04115
PubChem CID: 2758
UNII: RV6J6604TK
CompTox Dashboard (EPA): DTXSID4020616
InChI:
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
Key: WEEGYLXZBRQIMU-UHFFFAOYSA-N
InChI=1/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
Key: WEEGYLXZBRQIMU-UHFFFAOYAY
SMILES: O2C1(CCC(CC1)C2(C)C)C
Properties of Eucalyptol:
Chemical formula: C10H18O
Molar mass: 154.249 g/mol
Density: 0.9225 g/cm3
Melting point: 2.9 °C (37.2 °F; 276.0 K)
Boiling point: 176–177 °C (349–351 °F; 449–450 K)
Magnetic susceptibility (χ): −116.3×10−6 cm3/mol
Molecular Weight: 154.25
XLogP3: 2.5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 154.135765193
Monoisotopic Mass: 154.135765193
Topological Polar Surface Area: 9.2 Ų
Heavy Atom Count : 11
Complexity: 164
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Pharmacology of Eucalyptol:
ATC code: R05CA13 (WHO)
Names of Eucalyptol:
IUPAC name of Eucalyptol:
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Other names of Eucalyptol:
1,8-Cineole
1,8-Epoxy-p-menthane
cajeputol
1,8-epoxy-p-menthane, 1,8-oxido-p-menthane
eucalyptole
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
cineol
cineole.
Synonyms of Eucalyptol:
Eucalyptol
cineole
1,8-Cineole
470-82-6
1,8-Cineol
Cajeputol
Zineol
1,8-Epoxy-p-menthane
Eucalyptole
Eucapur
Terpan
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
p-Cineole
1,8-Oxido-p-menthane
Eukalyptol
EUCALYPTUS OIL
CINEOL
Cucalyptol
Soledum
Eukalyptol
Eucalyptol (natural)
Zedoary oil
2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
p-Menthane, 1,8-epoxy-
FEMA No. 2465
Cineole (VAN)
8000-48-4
NCI-C56575
UNII-RV6J6604TK
2-Oxabicyclo(2.2.2)octane, 1,3,3-trimethyl-
NSC 6171
1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octane
2-Oxa-1,3,3-trimethylbicyclo(2.2.2)octane
Cineole (Eucalyptol)
NSC6171
NSC-6171
2,2,4-trimethyl-3-oxabicyclo[2.2.2]octane
2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane
MFCD00167977
RV6J6604TK
CNL
4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
CHEBI:27961
NCGC00091666-01
NCGC00091666-04
DSSTox_CID_616
DSSTox_RID_75692
DSSTox_GSID_20616
(1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
Eucalyptus citriodora oil
Eucalyptol 1000 microg/mL in Methanol
CAS-470-82-6
SMR000471853
CCRIS 3727
HSDB 991
Eucalyptol [USAN:USP]
EINECS 207-431-5
Terpane
Cyneol
Eucaly
BIDD:ER0481
AI3-00578
Eucalyptol,(S)
Eucalyptol (USP)
1.8-cineole
Eucalyptol, 99%
Eucalyptol, Ph Helv
p-Menthane,8-epoxy-
cineole (1,8-)
WLN: T66 A B AOTJ B1 B1 F1
1,8-Cineol-[d3]
Spectrum2_000221
Spectrum3_000683
Spectrum4_001747
Spectrum5_000704
bmse000523
EC 207-431-5
SCHEMBL19622
SCHEMBL41020
BSPBio_002405
KBioGR_002194
MLS001050089
MLS001066338
DivK1c_000333
SPECTRUM1500294
SPBio_000261
Eucalyptol, analytical standard
CHEMBL485259
GTPL2464
CHEMBL1231862
CHEMBL1397305
DTXSID4020616
SCHEMBL13554591
SCHEMBL17836873
HMS501A15
KBio1_000333
KBio3_001625
NINDS_000333
HMS2271P04
Pharmakon1600-01500294
ZINC967566
HY-N0066
Tox21_111161
Tox21_202090
Tox21_302902
5750AF
BDBM50459887
CCG-36080
NSC760388
Acylated oxime isatin derivative, 19
AKOS015903223
AKOS016034339
AKOS037514637
Tox21_111161_1
CCG-266254
CS-8146
DB03852
LMPR0102090019
NSC-760388
IDI1_000333
Eucalyptol, tested according to Ph.Eur.
NCGC00091666-02
NCGC00091666-03
NCGC00091666-05
NCGC00095774-01
NCGC00178671-01
NCGC00256479-01
NCGC00259639-01
AC-20234
Eucalyptol, natural, >=99%, FCC, FG
LS-13868
NCI60_005108
1,3-Trimethyl-2-oxabicyclo[2.2.2]octane
2-Oxa-1,3-trimethylbicyclo[2.2.2]octane
DB-070775
2-Oxabicyclo[2.2.2]octane,3,3-trimethyl-
FT-0607033
FT-0626369
1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane
A15662
C09844
D04115
AB01563262_01
Q161572
SR-01000763816
SR-01000763816-2
W-106080
1,8-Cineole, primary pharmaceutical reference standard
Cineole, European Pharmacopoeia (EP) Reference Standard
Eucalyptol, certified reference material, TraceCERT(R)
F0001-1260
Eucalyptol, United States Pharmacopeia (USP) Reference Standard
Eucalyptol (cineole), Pharmaceutical Secondary Standard; Certified Reference Material
(±)-Eucalyptol
1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octane
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
1,3,3-Triméthyl-2-oxabicyclo[2.2.2]octane
1,8-Cineol
1,8-cineole
207-431-5
2-Oxa-1,3,3-trimethylbicyclo(2.2.2)octane
2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
470-82-6
Eucalyptol
Eucalyptole
Eukalyptol
Eukalyptol
p-Cineole
p-Menthane, 1,8-epoxy-
1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane
1,8-epoxy-p-menthane
1,8-oxido-p-menthane
105109
1216822-66-0
2,2,4-trimethyl-3-oxabicyclo[2.2.2]octane
2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane
2-Oxabicyclo(2.2.2)octane, 1,3,3-trimethyl-
4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
cajeputol
Cineole
CNL
Eucapur
Eukalyptol
Limonene oxide
MFCD00167977
T66 A B AOTJ B1 B1 F1
Terpan
Zineol
