Eucalyptol

Alias: 8-epoxy-p-Menthane; Cineole; NSC6171; 8-Cineole; NSC-617
Cat No.:V20852 Purity: ≥98%
Eucalyptol (1,8-epoxy-p-Menthane; Cineole; 1,8-Cineole; NSC-617) is an organic compound and a colorless liquid, acting an inhibitor of 5-HT3 receptor ,potassium channel, TNF-α and IL-1β.
Eucalyptol Chemical Structure CAS No.: 470-82-6
Product category: 5-HT Receptor
This product is for research use only, not for human use. We do not sell to patients.
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Product Description

Eucalyptol (1,8-epoxy-p-Menthane; Cineole; 1,8-Cineole; NSC-617) is an organic compound and a colorless liquid, acting an inhibitor of 5-HT3 receptor ,potassium channel, TNF-α and IL-1β. Eucalyptol's pleasant spicy aroma and taste make it a popular ingredient in flavorings, fragrances, and cosmetic products.

Biological Activity I Assay Protocols (From Reference)
Targets
5-HT3 Receptor; IL-1β; potassium channel
ln Vitro
Eucalyptol suppresses 5-HT-evoked currents in oocytes expressing 5-HT3 receptors with an IC50 of 258 µM[1]. Eucalyptol (Cin) treatment dramatically reduces the ROS level in a dose-dependent manner in Aβ25-35 treated cells. Eucalyptol treatment significantly decreases the NO level in Aβ25-35 treated cells in a dose dependent manner (p<0.05 and p<0.01). When compared to Aβ25-35 treated PC12 cells, eucalyptol treatment also significantly lowers the IL-1βlevel in Aβ25-35 treated cells in a dose-dependent manner (p<0.05 and p<0.01). In comparison to Aβ25-35 treated cells, eucalyptol also attenuates IL-6 levels in a dose-dependent manner (p<0.05 and p<0.01)[3].
ln Vivo
From day 7 to day 50 of treatment, the male and female rats treated with the highest doses of eucalyptol (CIN), 500 and 1000 mg/kg, exhibited a lower body weight than the control group. During the first week of treatment, the administration of Eucalyptol (500 and 1000 mg/kg) to male rats and 1000 mg/kg to female rats significantly reduces their body weight gain. However, male and female rats treated with all doses of the second week until the end of treatment experience an increase in body weight after this reduction. In comparison to the control group, male rats exhibited a significant increase of 6.93% in mean corpuscular volume (MCV) (Eucalyptol 1000 mg/kg) and a decrease of 6.74 and 6.67% in mean corpuscular hemoglobin concentration (MCHC) (Eucalyptol 500 and 1000 mg/kg) and mean platelet volume (MPV) of 10.40, 10.60, and 15.73% (Eucalyptol 100, 500, and 1000 mg/kg, respectively).
Cell Assay
The MTT dye-uptake method is used to determine the protective dose of cineole (eucalyptol). Briefly put, 96-well tissue culture plates are seeded with 1×104 cells per well, and the cells are allowed to adhere for 24 hours at 37°C in a CO2 incubator. For the specified amount of time, cells undergo differentiation. After that, the medium is switched out for one that contains eucalyptol (0 to 10 μM) in various experiments for a maximum of 24 hours. After adding 10 μL of tetrazolium bromide salt (5 mg/mL of stock in PBS) to 100 mL of cell suspension per well, the plate is incubated for 4 hours. The reaction mixture is carefully removed at the conclusion of the incubation period, and 200 μL of DMSO is pipetted up and down multiple times into each well until the content is homogenized. Using a microplate reader, the plates are read at 550 nm after being placed on a rocker shaker for 10 minutes at room temperature[3].
Animal Protocol
In this experiment, Swiss mice are employed. With free access to water, the animals are split into two groups of five at random and fast for the entire night. The other group is given a single oral dosage of 2000 mg/kg of eucalyptol, while the control group is given a 1% Tween-80 aqueous solution (0.1 mL/10 g). After receiving oral medication, the animals are observed every day for 14 days at 30, 60, 120, 180, and 240 minutes. Everyday data is gathered on behavioral shifts, weight, food and water intake, clinical indicators of toxicity, and death[4].
References

[1]. Noncompetitive Inhibition of 5-HT3 Receptors by Citral, Linalool, and Eucalyptol Revealed by Nonlinear Mixed-Effects Modeling. J Pharmacol Exp Ther. 2016 Mar;356(3):549-62.

[2]. Eucalyptol induces hyperexcitability and epileptiform activity in snail neurons by inhibiting potassium channels. Eur J Pharmacol. 2015 Oct 5;764:70-8.

[3]. 1,8-cineole (eucalyptol) mitigates inflammation in amyloid Beta toxicated PC12 cells: relevance to Alzheimer's disease. Neurochem Res. 2014 Feb;39(2):344-52.

[4]. Repeated-doses and reproductive toxicity studies of the monoterpene 1,8-cineole (eucalyptol) in Wistar rats. Food Chem Toxicol. 2016 Nov;97:297-306.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H18O
Molecular Weight
154.253
Exact Mass
154.14
Elemental Analysis
C, 77.87; H, 11.76; O, 10.37
CAS #
470-82-6
Appearance
Oily liquid
SMILES
CC1(C2CCC(O1)(CC2)C)C
InChi Key
WEEGYLXZBRQIMU-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
Chemical Name
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
Synonyms
8-epoxy-p-Menthane; Cineole; NSC6171; 8-Cineole; NSC-617
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ≥ 120 mg/mL (~778.0 mM)
H2O: ~33.3 mg/mL (~216.1 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 3.5 mg/mL (22.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 3.5 mg/mL (22.69 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 3.5 mg/mL (22.69 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.4830 mL 32.4149 mL 64.8298 mL
5 mM 1.2966 mL 6.4830 mL 12.9660 mL
10 mM 0.6483 mL 3.2415 mL 6.4830 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04703673 Completed Drug: Cineole
Drug: Nasal Decongestant
Rhinosinusitis Acute
Rhinosinusitis Chronic
Bronchitis
Engelhard Arzneimittel GmbH
& Co.KG
January 8, 2021 N/A
Biological Data
  • Electrophysiological characterization of the actions of citral (Cit), eucalyptol (Euc), and linalool (Lin) at 5-HT3 receptors. J Pharmacol Exp Ther . 2016 Mar;356(3):549-62.
  • Inhibition of the 5-HT3 receptor by citral, eucalyptol, or linalool. J Pharmacol Exp Ther . 2016 Mar;356(3):549-62.
  • Predicted binding locations for citral, eucalyptol, and linalool in a homology model of the human 5-HT3 receptor. J Pharmacol Exp Ther . 2016 Mar;356(3):549-62.
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