Eucalyptol

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Eucalyptol
Names
IUPAC name
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Other names
1,8-Cineole
1,8-Epoxy-p-menthane
Properties
C10H18O
Molar mass 154.249 g/mol
Appearance Colorless liquid
Odor Mint or camphor-like
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)
0.35 g/100 ml (20 °C)
Solubility Miscible with glacial acetic acid, chloroform, diethyl ether, ethanol, glycerol, propylene glycol
Slightly soluble in CCl4
Vapor pressure 1.90 mm Hg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 49 °C (120 °F; 322 K)
Related compounds
Related compounds
Menthol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Eucalyptol is a natural organic compound that is a colorless liquid. It is a cyclic ether and a monoterpenoid.

Properties

Chemical

Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol and phosphoric acid. Formation of these adducts is useful for purification.

Physical

Eucalyptol is a clear viscous liquid, with a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with chloroform, diethyl ether and ethanol. The boiling point of this compound is 176 °C and the flash point is 49 °C.

Availability

Eucalyptol comprises up to 90% of eucalyptus oil's mass. Though not very cheap, it is a readily available source.

Purification can be achieved via fractional or vacuum distillation.

Preparation

It's much cheaper to extract the product from eucalyptus oil than synthesizing it from scratch.

Projects

Handling

Safety

Eucalyptol has low toxicity in small amounts. In higher-than-normal doses, eucalyptol is hazardous via ingestion, skin contact, or inhalation. It can have acute health effects on behavior, the respiratory tract, and the nervous system.

Storage

In closed bottles, away from light and air.

Disposal

No special disposal is required, as it's a naturally-occuring compound that has low toxicity.

Can be burned if desired.

References

Relevant Sciencemadness threads