Cineol

2.74

log Kow = 2.74

EUCALYPTUS, BITTER-SWEET FLAVOR

Pungent, cooling, spicy taste

0.921 to 0.923 (NTP, 1992)

0.9267 g/cu cm at 20 °C

0.921-0.924

Colorless liquid or oil

Colorless mobile liquid

Colorless essential oil

Colorless liquid

Insoluble (<1 mg/ml at 68 °F) (NTP, 1992)

3500

In water, 3.50X10+3 mg/L at 21 °C

Miscible with ether, alcohol, chloroform, glacial acetic acid, and fixed or volatile oils

Soluble in alcohols, most fixed oils, glycerin, propylene glycol; 1:5 in 60% alcohol

Soluble in ethanol, ethyl ether; slightly soluble in carbon tetrachloride

349 to 351 °F at 760 mmHg (NTP, 1992)

176.4

176 °C

Specific gravity: 0.921-0.923 at 25 °C/25 °C; BP: 176-177 °C

176-177 °C

34.7 °F (NTP, 1992)

1.5

1.5 °C

1.9 [mmHg]

1.90 mm Hg at 25 °C

Index of refraction: 1.4586 at 20 °C/D

Index of refraction: 1.455-1.460 at 20 °C/D

1.454-1.460

This chemical does not meet GHS hazard criteria for 0.3% (8 of 2296) of reports.

Warning

H226 (98.7%): Flammable liquid and vapor [Warning Flammable liquids]；H317 (84.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P210, P233, P240, P241, P242, P243, P261, P272, P280, P302+P352, P303+P361+P353, P321, P333+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2296 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 8 of 2296 reports by companies.；There are 16 notifications provided by 2288 of 2296 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Chemical: 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 15-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13231

Eucalyptol: Does not have an individual approval but may be used under an appropriate group standard

SYMPTOMS: The symptoms associated with this compound include: epigastric burning with nausea and usually vomiting; vertigo; ataxia; muscle weakness; stupor; pallor; and sometimes - cyanosis, respiratory stridor and miosis. Delirium and occasionally convulsions may occur. Symptoms may be delayed for 24 hours, rarely.；ACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. (NTP, 1992)

Emergency treatment: Eucalyptus oil; In a series of 109 children, ingestion of 2-3 mL caused mild sedation while ingestion of >5 ml caused serious CNS depression or coma; [HSDB] After ingestion, causes CNS depression, vomiting, and increased risk for aspiration pneumonia; [Goldfrank, p. 625] Safe when used as a flavoring agent in food; [JECFA] An irritant; Effects in high-dose animal studies include changes in renal tubules; [MSDSonline]

Cineole is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Flam. Liq. 3 (98.7%)；Skin Sens. 1 (84.2%)

Flammable liquids - Category 3

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. (NTP, 1992)

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.

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.

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.

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. (NTP, 1992)

SRP: Recycle any unused portion of the material for its approved use or return it 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 it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:；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 tank car or highway tank 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. (ERG, 2024)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Infant rats express conditioned responses to an odor experienced prenatally as a chemosensory cue associated with moderate alcohol intoxication. This study examined postnatal intake of a chemosensory cue (cineole) that had been paired with alcohol's unconditioned effects. It also tested the interaction between prenatal association and postnatal conditioning with cineole and alcohol. Pregnant female rats intubated with cineole were given ethanol (EtOH).25 or 4.0 hr later. Other groups received only water or water paired with ethanol. During postnatal day 15 (PD15), infant consumption of cineole solution was assessed. After the cineole drinking test, pups were intubated with EtOH or water to assess infant conditioning. On PD16, all pups were tested for mouthing to milk alone or to a milk-cineole solution. Statistical analysis confirmed fetal associative conditioning attributable to the unconditioned effects of prenatal alcohol. Fetuses given explicit pairings of cineole and alcohol ingested less cineole on PD15 than control fetuses given a 4-hr interval between cineole and alcohol. On PD16, consumption of cineole was significantly increased by prenatal exposure to cineole. Teratogenic effects of this dose of prenatal alcohol did not affect postnatal associative or nonassociative behavior. Prenatal associative learning can be established through temporal contiguity between fetal chemosensory stimulation and alcohol's unconditioned properties. This associative memory survives to infancy and modulates intake patterns and behavioral reactivity to substances that were prenatally paired with alcohol intoxication.

Cineole was administered by gavage to three groups, each of ten male and ten female Wistar Han (TM): RCCHan(TM): WIST strain rats, for up to eleven weeks (including a two week pre-pairing phase, pairing, gestation and early lactation for females) at dose levels of 30, 300 and 600 mg/kg bw/day. A control group of ten males and ten females was dosed with vehicle alone (Arachis oil BP). Clinical signs, bodyweight change, dietary intake and water consumption were monitored during the study. Pairing of animals within each dose group was undertaken on a one male: one female basis within each treatment group on Day 5 of the study, with females subsequently being allowed to litter and rear their offspring to Day 5 of lactation. An additional pairing for high dose females that failed to achieve pregnancy was performed to fully assess mating performance and fertility. During the lactation phase, daily clinical observations were performed on all surviving offspring, together with litter size and offspring weights and assessment of surface righting reflex. Adult males were terminated on Day 52 of the study following the completion of the second pairing at 600 mg/kg bw/day. Females and offspring were terminated on day 5 post partum. Any female which did not produce a pregnancy (unless allocated to a further mating phase) was terminated on or after Day 25 post coitum. All animals were subjected to a gross necropsy examination and histopathological evaluation of reproductive tissues was performed. Additional male organ weight and detailed histopathological examination of the testes were performed to more fully assess male fertility. Adult response: Mortality: There were no unscheduled deaths in the study. Clinical observations: Transient post-dosing salivation was observed from Day 7 at 600 mg/kg bw/day and Day 13 at 300 mg/kg bw/day. This sign was observed regularly throughout the treatment period with all animals being affected at both dosages, although the incidence of

LC50; Species: Pimephales promelas (Fathead Minnow) age 28 days, length 19.1 mm, weight 0.097 g; Conditions: freshwater, flow through, 25.1 °C, pH 7.9, hardness 43.9 mg/L CaCO3, alkalinity 43.3 mg/L CaCO3, dissolved oxygen 6.9 mg/L; Concentration: 102000 ug/L for 96 hr (95% confidence limit: 95400-109000 ug/L) /99% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 220(SRC), determined from a log Kow of 2.74(2) and a regression-derived equation(3), indicates that 1,8-cineole is expected to have moderate mobility in soil(SRC). Volatilization of 1,8-cineole from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 1.9 mm Hg(4), and water solubility, 3.5X10+3 mg/L(5). 1,8-Cineole is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Biodegradation data in soil were not available(SRC, 2015).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 220(SRC), determined from a log Kow of 2.74(2) and a regression-derived equation(3), indicates that 1,8-cineole is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.1X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 1.9 mm Hg(5), and water solubility, 3.5X10+3 mg/L(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 13 hours and 8 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 30(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2015).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,8-cineole, which has a vapor pressure of 1.9 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cineole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 days, calculated from its rate constant of 1.11X10-11 cu cm/molecule-sec at 25 °C(3). 1,8-Cineole does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

1,8-Cineole was identified as a volatile odor component released from cooking full-fat and reduced fat frankfurters. Mean relative peaks (1 ng bromobenznene = 100) were 1290, 1830 and 1870 for 30%, 12% and 5% fat, respectively(1). The compound was present as 0.18% of volatiles identified from edible Korean chamchwi (Aster scaber)(2). Concentrations in mature and ripe guava (Psidium guajava Linn) fruit volatiles were 30,954 and 7,238 ug/kg, respectively(3).

IDENTIFICATION AND USE: Cineole is an essential oil that is used as a fragrance or flavoring agent in: foods, candies, pharmaceutical aid (flavor), cough drops, and personal care products. It has a history of being used as an expectorant and an antiseptic. HUMAN EXPOSURE AND TOXICITY: Cineole is the main constituent of eucalyptus oil, and it is mainly used as a mucolytic agent in inflammatory airway diseases. ANIMAL STUDIES: A study was performed to assess the ocular irritancy potential of eucalyptol to the isolated bovine cornea. The corneas treated with eucalyptol were clear post treatment and had cloudy areas post incubation. Eucalyptol was considered not to be an ocular corrosive or severe irritant. Cineole was administered by gavage to three groups, each of five male and five female rats, for twenty-eight consecutive days, at dose levels of 30, 300 and 600 mg/kg bw/day. For both sexes at 300 and 600 mg/kg bw/day, examination of the liver revealed a dosage dependent incidence of centrilobular hypertrophy of the hepatocytes; no other indicators of liver damage were apparent. Following the two week recovery period, hypertrophy of hepatocytes was no longer present at 600 mg/kg bw/day for either sex. 1,8-Cineole induced accumulation of protein droplets in proximal tubular epithelial cells in male rats. The renal changes were specific to the male rat and of no toxicological relevance to man. Eucalyptol was tested as a constituent of toothpaste in an oral long-term study with mice. Groups of 52 male mice were given 0, 8 and 32 mg/kg bw/day eucalyptol in toothpaste base by gavage for 80 weeks followed by an observation period between 16 and 24 weeks. No treatment-related effects on body weight, food consumption, survival, weight of adrenals, kidneys, liver, lungs or spleen, or on the microscopic appearance of brain, lungs, liver and kidneys or on tumor incidence was observed.

1.8-Cineole is considered a major monoterpene emitted by vegetation into the atmosphere; monoterpene emission rate estimates for 49 US tree genera range from 1 to 50 mg C-sq m/hr(1). The compound has been identified as an emission from agricultural and natural plant species present in California's Central Valley(2). 1,8-Cineole emission concentrations were 225, 280, 145, and 150 nmol/sq m-min from Eucalyptus camaldulensis, E globulus, E grandis and E viminalis, respectively, in southern Australia(3). 1,8-Cineole with limonene was emitted at rates of 10%, 1% and 1% of the total biogeneic volatile compounds identified from the leaves of Eucalyptus dunnii, E. saligna and E. citriodora, respectively, originating from Guaiba, Brazil collected during May and Jun 2000(4). Evaluation of ambient air around Eucalyptus globulus trees growing in Algiers City area, Algeria revealed 1,8-cineole present at 15.2% of total biogenic volatile emissions. It was not detected in emissions from Pinus halepensis or Cedrus atlantica trees(5). Emission rates of 1,8-cineole from forests in five geographical regions in Switzerland were monitored. Biogenic volatile organic compounds comprise 23% of total annual emissions in Switzerland. The Norway spruce (Picea abies) is the dominant tree at 49.1%; 1,8-cineole is a component of Norway spruce emissions(6). 1,8-Cineole was present at 8.54% of total emissions measured in 3 hours from a Mediterranean oak species Quercus ilex(7).

1,8-Cineole, with a fresh camphoraceous smell, has been identified as a volatile emission from Boletus erthropus, Paxillus involutus, Amanita rubescens, and Gomphidius glutinosus mushrooms at relative amounts of 8%, 6%, 1%, and 1% and 0.2%, respectively(1). 1,8-Cineole was identified at concentrations of in the volatiles of the essential oils of fresh lovage (Levisticum officinale) and ginger powder (Zingiber officianle). It was not identified in fresh celery (Apium graveolens), honeysuckle (Lonicera periclymenum) or apples (Malus domestica cv Golden Delicious)(2).

1,8-Cineole concentrations in plants(1).；Table: Top 40 Plants [Table#2657]

Cineole concentrations in plants(1). /Cineole/；Table: Top 40 Plants [Table#2658]

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of April 22, 2015: http://actor.epa.gov/dashboard/]

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=470-82-6]

1,8-Cineole was present in groundwater samples at 8, 5, and 1 ug/L at distances of 5, 19, and 39 meters, respectively, down gradient of a landfill in Vejen, Denmark(1). 1,8-Cineole was identified not quantified in the leachate plum from a landfill in Norman, OK sampled in November 1995 and April 1996(2). 1,8-Cineole was on average only 1% of the total post treatment odor faction from a municipal waste treatment plant in China(3).

The Koc of 1,8-cineole is estimated as 220(SRC), using a log Kow of 2.74(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,8-cineole is expected to have moderate mobility in soil. In soil infiltration studies using secondary effluent from Fort Polk, LA collected Nov 4-5 1980, 1,8-cineole, present at 0.091 ug/L, was not detected in column fluid effluents on the second inundation cycle(4).

Chemical: 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 15-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13231

Eucalyptol: Does not have an individual approval but may be used under an appropriate group standard

Cineole is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

R - Respiratory system；R05 - Cough and cold preparations；R05C - Expectorants, excl. combinations with cough suppressants；R05CA - Expectorants；R05CA13 - Cineole

QR - Respiratory system；QR05 - Cough and cold preparations；QR05C - Expectorants, excl. combinations with cough suppressants；QR05CA - Expectorants；QR05CA13 - Cineole

The biotransformation of 1,8-cineole was investigated using human liver microsomes. The metabolite was established as 2-exo-hydroxy-1,8-cineole. 1,8-cineole 2-hydroxylation catalyzed by human liver microsomes was found to be efficiently conducted.

Cineole was administered to male rats once daily by gastric intubation for 20 days. Urine was collected and major metabolites identified as methyl ester of 1,8-dihydroxy-10-carboxy p-methane, 2-hydroxy cineole and 3-hydroxy cineole.

Nature of non-conjugated metabolites of 1,8-cineole in urine and feces of brushtail possum yield p-cresol, 9-hydroxycineole and cineol-9-oic acid.

1,8-Cineole has known human metabolites that include 3alpha-hydroxy-1,8-cineole and 2alpha-hydroxy-1,8-cineole.

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.

Substances added to foods and medicine to improve the taste.

Substances causing insects to turn away from them or reject them as food.

Solutions for rinsing the mouth, possessing cleansing, germicidal, or palliative properties. (From Boucher&apos;s Clinical Dental Terminology, 4th ed)

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant &amp; Hackh&apos;s Chemical Dictionary, 5th ed)

Chief constituent of oil of eucalyptus; [Merck Index] Used in pharmaceuticals (cough syrups and expectorants); Also used as a flavoring agent, fragrance, disinfectant, and solvent; [HSDB] Eucalyptus oil contains up to 70% eucalyptol; [Goldfrank, p. 625]

Using Disinfectants or Biocides [Category: Clean]

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.

Reported uses (ppm):；Table: Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 1994) [Table#2660]

(1979) 2.78X10+8 GRAMS (EUCALYPTUS OIL)

(1981) 3.05X10+8 GRAMS (EUCALYPTUS OIL)

2023: 8,500,000 - <10,000,000 lb；2022: 8,500,000 - <10,000,000 lb；2021: 8,500,000 - <10,000,000 lb；2020: 10,000,000 - <25,000,000 lb

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-. Aggregated National Production Volume: < 500,000 pounds.[US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. 2-Oxabicyclo

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-. National Production Volume: 100,000 - 500,000 lb/yr.[USEPA/Pollution Prevention and Toxics; 2012 Chemical Data Reporting Database. 2-Oxabicyclo

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 it 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.

Technical-grade 1,8-cineole with a purity of 99.6 - 99.8% is produced in Spain in large quantities by fractional distillation of ... /Eucalyptus globulus Labill. (Family: Myrtaceae)/. A product essentially free from other products can be obtained by crystallization of cineole-rich eucalyptus oil fractions.

Grades: Technical; National Formulary.

Technical grade ... purity of 99.6 - 99.8%

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Denaturant; Tonic

Not Known or Reasonably Ascertainable；All Other Chemical Product and Preparation Manufacturing；Plastics Material and Resin Manufacturing；All Other Basic Organic Chemical Manufacturing；Food, beverage, and tobacco product manufacturing；Soap, Cleaning Compound, and Toilet Preparation Manufacturing

2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-: ACTIVE

1,8-cineole is produced only from natural sources as these are sufficiently inexpensive to make synthesis uneconomic. Originally, it 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 its taking over as the dominant source. ... Much of the oil is used per se and only about one-quarter of it 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.