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
CAS Number	470-82-6 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	105109 5239941
ChEBI	CHEBI:27961;
ChEMBL	ChEMBL485259 ;
ChemSpider	2656 ;
DrugBank	DB03852 ;
ECHA InfoCard	100.006.757
EC Number	207-431-5;
Gmelin Reference	131076
IUPHAR/BPS	2464;
KEGG	D04115 ;
PubChem CID	2758;
UNII	RV6J6604TK ;
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 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;
	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

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]

^ ^a ^b "Eucalyptol". PubChem, US National Library of Medicine. 22 April 2023. Retrieved 28 April 2023.
^ ^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.
^ "GCMS – Gas Chromatography Mass Spectrometry Analysis" (PDF). New Direction Aromatics. Archived (PDF) from the original on 28 October 2020. Retrieved 7 December 2022.
^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3-527-30673-2.

[pubchem-1] "Eucalyptol". PubChem, US National Library of Medicine. 22 April 2023. Retrieved 28 April 2023.

[wiener-2] 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 978-3-527-30673-2.

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