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 InfoCard 100.006.757 Edit this at Wikidata
EC 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 checkY
    Key: WEEGYLXZBRQIMU-UHFFFAOYSA-N checkY
  • 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
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)
−116.3×10−6 cm3/mol
Pharmacology
R05CA13 (WHO)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H304, H315, H317, H319, H411
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).

Eucalyptol (also called cineole) is a monoterpenoid colorless liquid, and a bicyclic ether.[1] It has a fresh camphor-like odor and a spicy, cooling taste.[1] It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil.[2][3] Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.[4]

In 1870, F. S. Cloez identified and ascribed the name "eucalyptol" to the dominant portion of Eucalyptus globulus oil.[2]

  1. ^ a b "Eucalyptol". PubChem, US National Library of Medicine. 22 April 2023. Retrieved 28 April 2023.
  2. ^ a b Boland, D. J.; Brophy, J. J.; House, A. P. N. (1991). Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing. Melbourne: Inkata Press. p. 6. doi:10.1002/ffj.2730070209. ISBN 0-909605-69-6.
  3. ^ "GCMS – Gas Chromatography Mass Spectrometry Analysis" (PDF). New Direction Aromatics. Archived (PDF) from the original on 28 October 2020. Retrieved 7 December 2022.
  4. ^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.