Structure Database (LMSD)

Common Name
1,8-Cineol
Systematic Name
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Synonyms
  • Eucalyptol
  • 1,8-Epoxy-p-menthane
  • cajeputol
LM ID
LMPR0102090019
Formula
Exact Mass
Calculate m/z
154.135765
Status
Curated



Classification

Biological Context

Eucalyptol is a bicyclic monoterpene that has been found in Eucalyptus and other plants, including C. sativa and has diverse biological activities, including anti-inflammatory, decongestant, antinociceptive, and insect repellent properties.1,2,3,4,5 Eucalyptol (10 μM) inhibits TNF-α, IL-1β, IL-4, and IL-5 production by primary human lymphocytes stimulated by ionomycin and phorbol 12-myristate 13-acetate (PMA).2 It also decreases LPS-induced mucus production by primary human nasal turbinate slices when used at a concentration of 10 μM.3 Eucalyptol (400 mg/kg) decreases carrageenan-induced hind paw edema in rats and reduces the time spent licking the hind paw in a formalin-induced nociception test in mice.4 It inhibits A. aegypti mosquitoes from feeding on anesthetized gerbils when applied topically at a concentration of 10% and from laying eggs in an ovipositional bioassay when used at a concentration of 1% in standing water.5 Formulations containing eucalyptol have been used in mouthwash and cough suppressants.

This information has been provided by Cayman Chemical

References

1. Russo, E.B. Taming THC: Potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br. J. Pharmacol. 163(7), 1344-1364 (2011).
2. Juergens, U.R., Engelen, T., Racké, K., et al. Inhibitory activity of 1,8-cineol (eucalyptol) on cytokine production in cultured human lymphocytes and monocytes. Pulm. Pharmacol. Ther. 17(5), 281-287 (2004).
3. Sudhoff, H., Klenke, C., Greiner, J.F., et al. 1,8-Cineol reduces mucus-production in a novel human ex vivo model of late rhinosinusitis. PLoS One 10(7), e0133040 (2015).
5. Klocke, J.A., Darlington, M.V., and Balandrin, M.F. 1,8-Cineole (Eucalyptol), a mosquito feeding and ovipositional repellent from volatile oil of Hemizonia fitchii (Asteraceae). J. Chem. Ecol. 13(12), 2131-2141 (1987).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Eucalyptus (#3932)
Magnoliopsida (#3398)
ESSENTIAL OILS,
Encyclopedia of Analytical Science (Second Edition), 2005

String Representations

InChiKey (Click to copy)
WEEGYLXZBRQIMU-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
SMILES (Click to copy)
C12(C)CCC(CC1)C(C)(C)O2

Other Databases

Wikipedia
KEGG ID
HMDB ID
PubChem CID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 11
Rings 3
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 161.83
Topological Polar Surface Area 11.30
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 1
logP 3.32
Molar Refractivity 46.55

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Created at
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Updated at
20th Feb 2025