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Topic summary

Eucalyptol

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
3D model (JSmol)
105109 5239941 ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.006.757EC Number
  • 207-431-5
131076
KEGG
UNII
  • 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
  • O2C1(CCC(CC1)C2(C)C)C
Properties C10H18OMolar mass154.253 g·mol Density0.9225g/cm Melting point2.9 °C (37.2 °F; 276.0 K) Boiling point176–177 °C (349–351 °F; 449–450 K) −116.3×10 cm/molPharmacology R05CA13 (WHO) Hazards GHS labelling: DangerH226, H304, H315, H317, H319, H411P210, 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).

Eucalyptol (also called cineole) is a monoterpenoid colorless liquid, and a bicyclicether. 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.

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

Wikipedia source