Properties and Composition of Eucalyptol
- Eucalyptol is a monoterpenoid colorless liquid.
- It has a fresh camphor-like odor and a spicy, cooling taste.
- Eucalyptol is insoluble in water but miscible with organic solvents.
- It makes up about 70-90% of eucalyptus oil.
- Eucalyptol forms crystalline adducts with hydrohalic acids, -cresol, resorcinol, and phosphoric acid.

Uses of Eucalyptol
- Eucalyptol is used in flavorings, fragrances, and cosmetics due to its pleasant aroma and taste.
- It is used as a flavoring at low levels in various products, including baked goods, confectionery, meat products, and beverages.
- Eucalyptol is an ingredient in commercial mouthwashes.
- It has been used in traditional medicine as a cough suppressant.
- Eucalyptol was listed as one of the additives to cigarettes to improve flavor.

Toxicology of Eucalyptol
- Eucalyptol has a toxicity (LD50) of 2.48 grams per kg (rat).
- Ingestion in significant quantities can cause headache and gastric distress.
- If swallowed, it can enter the lungs and cause delirium, convulsions, or severe injury.
- Eucalyptol is difficult to remove from the lungs once inhaled.
- It can also cause nausea and vomiting if subsequently vomited.

Biosynthesis of Eucalyptol
- Eucalyptol is generated from geranyl pyrophosphate (GPP) which isomerizes to (-)-linalyl diphosphate (LPP).
- Ionization of the pyrophosphate, catalyzed by cineole synthase, produces eucalyptol.
- The process involves the intermediacy of alpha-terpinyl cation.
- Eucalyptol is found in various plant species, including eucalyptus, galangal, Spanish sage, damiana, pepperwood, and ginger.

Other Properties and Effects of Eucalyptol
- Eucalyptol exhibits insecticidal and insect repellent properties.
- It is attractive to males of various species of orchid bees, which use it to synthesize pheromones.
- Eucalyptol is used as bait to attract and collect orchid bees for study.
- The presence of cineole (eucalyptol) elevates territorial behavior in orchid bees.
- Eucalyptol has been studied for its fumigant insecticidal activity and repellent effect on insects.
- Eucalyptus essential oils have been found to have insecticidal effects.
- The chemistry and bioactivity of Eucalyptus essential oils have been extensively studied.
- There are multiple Eucalyptus species that have been studied for their essential oil composition.
- The essential oils of Alpinia and Hedychium species have been compared in research studies.
- Essential oils from other plant species have been investigated for their chemical composition and potential therapeutic properties.

Eucalyptol (Wikipedia)

Eucalyptol (also called cineole) is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.

Eucalyptol

Names
IUPAC name 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Other names 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.
Identifiers
CAS Number	470-82-6 Y
3D model (JSmol)	Interactive image
Beilstein Reference	105109 5239941
ChEBI	CHEBI:27961
ChEMBL	ChEMBL485259 Y
ChemSpider	2656 Y
DrugBank	DB03852 Y
ECHA InfoCard	100.006.757
EC Number	207-431-5
Gmelin Reference	131076
IUPHAR/BPS	2464
KEGG	D04115 Y
PubChem CID	2758
UNII	RV6J6604TK Y
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 Y Key: WEEGYLXZBRQIMU-UHFFFAOYSA-N Y 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
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
Pharmacology
ATC code	R05CA13 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H304, H315, H317, H319, H411
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

In 1870, F. S. Cloez identified and ascribed the name "eucalyptol" to the dominant portion of Eucalyptus globulus oil.