Cineole

Eucalyptol

Names

IUPAC name

1,3,3-Trimethyl-2-oxabicyclo[2,2,2]octane

Other names

1,8-Cineole
1,8-Epoxy-p-menthane

Identifiers

CAS Number

470-82-6^Y

3D model (Jmol)

Interactive image

ChemSpider

2656^Y

DrugBank

DB03852^Y

ECHA InfoCard

100.006.757

IUPHAR/BPS

2464

KEGG

D04115^Y

PubChem CID

2758

UNII

RV6J6604TK^Y

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

C₁₀H₁₈O

154.249 g/mol

0.9225 g/cm³

1.5 °C (34.7 °F; 274.6 K)

Boiling point

176 to 177 °C (349 to 351 °F; 449 to 450 K)

Magnetic susceptibility (χ)

-116.3·10⁻⁶ cm³/mol

Pharmacology

ATC code

R05CA13 (WHO)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

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

Eucalyptol is also known by a variety of synonyms: 1,8-cineol, 1,8-cineole, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.

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

Eucalyptol comprises up to 90 percent of the essential oil of some species of the generic product Eucalyptus oil, hence the common name of the compound. It is also found in camphor laurel, bay leaves, tea tree, mugwort, sweet basil, wormwood, rosemary, common sage, Cannabis sativa and other aromatic plant foliage. Eucalyptol with a purity from 99.6 to 99.8 percent can be obtained in large quantities by fractional distillation of eucalyptus oil.

Although it can be used internally as a flavoring and medicine ingredient at very low doses, typical of many essential oils (volatile oils), eucalyptol is toxic if ingested at higher than normal doses.

Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with ether, ethanol, and chloroform. The boiling point is 176 °C and the flash point is 49 °C. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts are useful for purification.

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