Eucalyptol

Eucalyptol
Compound Structure:
Synonyms: Eucalyptol;Cineole;1,8-Cineole;470-82-6;1,8-Cineol;Cajeputol;1,8-Epoxy-p-menthane;Eucalyptole;Eucapur;Zineol;Terpan;Cineole ;1, 8-Cineole;p-Cineole;1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane;1,8-Oxido-p-menthane;Eukalyptol;CINEOL;Cucalyptol
Compound ID: NMPC-755
PubChem ID:

2758

Molecular Formula: C10H18O
Canonical SMILES: CC1(C2CCC(O1)(CC2)C)C
InChIKey: WEEGYLXZBRQIMU-UHFFFAOYSA-N
About the compound:

Eucalyptol, also known as cineole, is a naturally occurring cyclic ether and monoterpenoid. As a key component in many mouthwashes and cough suppressants, eucalyptol is recognized for its ability to control airway mucus hypersecretion and asthma through the inhibition of anti-inflammatory cytokines. It is also an effective treatment for nonpurulent rhinosinusitis and has been found to reduce inflammation and pain when applied topically. Additionally, eucalyptol has demonstrated effectiveness in killing leukemia cells in vitro. This monoterpenoid appears as a colorless liquid and is a bicyclic ether with a fresh, camphor-like odor and a spicy, cooling taste. It is insoluble in water but miscible with organic solvents. Eucalyptol constitutes approximately 70–90% of eucalyptus oil. It forms crystalline adducts with various substances like hydrohalic acids, o-cresol, resorcinol, and phosphoric acid, a process useful in its purification. Eucalyptol is utilized in flavorings, fragrances, and cosmetics due to its pleasant aroma and taste. In very low concentrations (0.002%), it is used as a flavoring agent in baked goods, confectionery, meat products, and beverages. A 1994 report from top cigarette companies listed eucalyptol as one of 599 additives in cigarettes, purportedly to enhance flavor. In commercial mouthwashes, eucalyptol serves as an active ingredient and has been traditionally used as a cough suppressant. Interestingly, eucalyptol is also attractive to males of various orchid bee species, which collect the chemical to create pheromones. This compound is used as bait in research studies to attract and observe these bees. Studies, like one with Euglossa imperialis, a nonsocial orchid bee species, have shown that cineole (eucalyptol) increases territorial behavior and specifically attracts male bees. These males often leave their territories to forage for substances like cineole, which are believed to be crucial in attracting females and synthesizing pheromones.

GHS Hazard Statements

H226 (99.03%): Flammable liquid and vapor [Warning Flammable liquids]

H317 (84.33%): May cause an allergic skin reaction [Warning Sensitization, Skin]

First Aid

Eyes: If contact lenses are present, remove them. Flush the eyes with water or saline for 20-30 minutes while seeking medical advice. Avoid using ointments or medications without a physician's guidance and transport the victim to a hospital immediately after flushing, even if there are no immediate symptoms.

Skin: Immediately rinse the affected skin with water, removing any contaminated clothing. Wash the skin thoroughly with soap and water. If symptoms like redness or irritation appear, contact a physician immediately and be prepared to go to a hospital.

Inhalation: Leave the area of exposure immediately and breathe fresh air. If symptoms like wheezing or coughing occur, seek medical attention and be ready to transport the victim to a hospital. Rescuers should wear appropriate respiratory protection, preferably a Self-Contained Breathing Apparatus.

Ingestion: Do not induce vomiting. If the victim is conscious and not having seizures, give them water to dilute the chemical and call for medical help immediately. If the victim is unconscious or convulsing, ensure their airway is clear, position them on their side with their head lower than their body, and do not give anything by mouth. Be prepared to transport them to a hospital as advised (NTP, 1992).

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

154.25 g/mol

XLogP3

2.5

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

0

Exact Mass

154.135765193 g/mol

Monoisotopic Mass

154.135765193 g/mol

Topological Polar Surface Area

9.2Ų

Heavy Atom Count

11

Formal Charge

0

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

Physical Description

1,8-cineol is a colorless liquid with a camphor-like odor. Spicy cooling taste. (NTP, 1992)

Boiling Point

349 to 351 °F at 760 mmHg (NTP, 1992)

Melting Point

1.5°C

Density

0.921 to 0.923 (NTP, 1992)

Solubility 

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

Vapor Pressure

1.9 [mmHg]

Source: PubChem

Source Species: Ficus exasperata
Zingiber officinale
Eucalyptus cloeziana
Securidata longependuculat
Brachystegia eurycoma
Acalypha segetalis
Eucalyptus torelliana
Centratherum punctatum
Murraya Koenigii
Pyrenacantha staudtii
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