Cineole

Modify Date: 2024-01-03 12:41:57

Cineole Structure
Cineole structure
Common Name Cineole
CAS Number 470-82-6 Molecular Weight 154.249
Density 0.9±0.1 g/cm3 Boiling Point 174.0±8.0 °C at 760 mmHg
Molecular Formula C10H18O Melting Point 1.5ºC
MSDS Chinese USA Flash Point 50.9±15.3 °C
Symbol GHS02
GHS02
Signal Word Warning

 Use of Cineole


Eucalyptol is an inhibitor of 5-HT3 receptor ,potassium channel, TNF-α and IL-1β.

 Names

Name 1,8-cineole
Synonym More Synonyms

 Cineole Biological Activity

Description Eucalyptol is an inhibitor of 5-HT3 receptor ,potassium channel, TNF-α and IL-1β.
Related Catalog
Target

5-HT3 Receptor

IL-1β

TNF-α

potassium channel

In Vitro Eucalyptol inhibits 5-HT-evoked currents in oocytes expressing 5-HT3 receptors with an IC50 of 258 µM[1]. Eucalyptol (Cin) treatment significantly decreases the ROS level in Aβ25-35 treated cells in a dose dependent manner. Eucalyptol treatment significantly decreases the NO level in Aβ25-35 treated cells in a dose dependent manner (p<0.05 and p<0.01). Eucalyptol treatment also significantly decreases IL-1βlevel in Aβ25-35 treated cells in a dose dependent manner (p<0.05 and p<0.01) as compare to Aβ25-35 treated PC12 cells. IL-6 level is also attenuated by Eucalyptol in dose dependent manner (p<0.05 and p<0.01) as compare to Aβ25-35 treated cells[3].
In Vivo Results show that male and female rats treated with Eucalyptol (CIN) at the highest doses, 500 and 1000 mg/kg, have shown lower body weight than control group from the 7th to 50th day of treatment. The administration of Eucalyptol significantly reduces body weight gain of male rats (Eucalyptol 500 and 1000 mg/kg) and female rats (Eucalyptol 1000 mg/kg) in the first week of treatment. However, this reduction is followed by an increase in body weight of rats males and females treated with all doses of the second week until the end of treatment. For male rats, there is a significant increase of 6.93% in mean corpuscular volume (MCV) (Eucalyptol 1000 mg/kg) and of 43.54 and 38.98% in the platelet count (Eucalyptol 500 and 1000 mg/kg, respectively) 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), when compare to the control group[4].
Cell Assay The protective dose of Eucalyptol (Cineole) is determined by MTT dye-uptake method. In brief, cells (1×104 per well) are seeded in 96-well tissue culture plates and allowed to adhere for 24 h in CO2 incubator at 37°C. Cells are differentiated for the indicated time period. Thereafter, the medium is replaced with the medium containing Eucalyptol (0 to 10 μM) in different experiments for a period up to 24 h. Tetrazolium bromide salt (5 mg/mL of stock in PBS) 10 μL/well is added in 100 mL of cell suspension and plate is incubated for 4 h. At the end of incubation period, the reaction mixture is carefully taken out and 200 μL of DMSO is added to each well by pipetting up and down several times until the content gets homogenized. The plates are kept on rocker shaker for 10 min at room temperature and then read at 550 nm using microplate reader[3].
Animal Admin Swiss mice are used in this experiment. The animals are randomly divided into two groups (n=5) and fasted overnight with free access to water. The group control receives a 1% Tween-80 aqueous solution (0.1 mL/10 g) and the other group is treated with Eucalyptol a single 2000 mg/kg dose by oral route. The animals are observed at 30, 60, 120, 180 and 240 min after oral treatment and daily for 14 days. Behavioral changes, weight, food and water consumption, clinical signs of toxicity or mortality are recorded daily[4].
References

[1]. Jarvis GE, et al. 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]. Zeraatpisheh Z, et al. Eucalyptol induces hyperexcitability and epileptiform activity in snail neurons by inhibiting potassium channels. Eur J Pharmacol. 2015 Oct 5;764:70-8.

[3]. Khan A, et al. 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.[3]

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

 Chemical & Physical Properties

Density 0.9±0.1 g/cm3
Boiling Point 174.0±8.0 °C at 760 mmHg
Melting Point 1.5ºC
Molecular Formula C10H18O
Molecular Weight 154.249
Flash Point 50.9±15.3 °C
Exact Mass 154.135757
PSA 9.23000
LogP 2.82
Vapour Pressure 1.6±0.3 mmHg at 25°C
Index of Refraction 1.461
Stability Stable. Flammable. Incompatible with acids, bases, strong oxidizing agents.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OS9275000
CHEMICAL NAME :
p-Menthane, 1,8-epoxy-
CAS REGISTRY NUMBER :
470-82-6
LAST UPDATED :
199710
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C10-H18-O
MOLECULAR WEIGHT :
154.28
WISWESSER LINE NOTATION :
T66 A B AOTJ B1 B1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2480 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - coma
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1070 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1500 mg/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
2250 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2 gm/kg
SEX/DURATION :
female 19-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
200 mg/L
REFERENCE :
EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 10(Suppl 10),1,1987 *** REVIEWS *** TOXICOLOGY REVIEW DPIRDU Dangerous Properties of Industrial Materials Report. (Van Nostrand Reinhold, 115 Fifth Ave., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 2(4),10,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 19540 No. of Facilities: 1103 (estimated) No. of Industries: 11 No. of Occupations: 23 No. of Employees: 5213 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 19540 No. of Facilities: 4397 (estimated) No. of Industries: 48 No. of Occupations: 57 No. of Employees: 83399 (estimated) No. of Female Employees: 20158 (estimated)

 Safety Information

Symbol GHS02
GHS02
Signal Word Warning
Hazard Statements H226
Precautionary Statements P210-P370 + P378
Personal Protective Equipment Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes Xi:Irritant
Risk Phrases R10;R37/38;R41
Safety Phrases S26-S39
RIDADR UN 1993
WGK Germany 2
RTECS OS9275000
Packaging Group III
Hazard Class 3.0

 Synthetic Route

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 Synonyms

2-Oxa-1,3,3-trimethylbicyclo(2.2.2)octane
eucalyptol (cineole)
Terpan
2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
2,2,4-trimethyl-3-oxabicyclo[2.2.2]octane
Eucapur
Zineol
Eukalyptol [Czech]
p-Menthane, 1,8-epoxy-
Eucalyptol
Eucalyptole
MFCD00167977
1,8-Cineol
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane,1,8-Cineole,1,8-Epoxy-p-menthane
EINECS 207-431-5
1,3,3-Trimethyl-2-oxabicyclo(2.2.2)octane
cineole
Cajeputol
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
1,8-cineole
1,8-Epoxy-p-menthane
limonene oxide
p-Cineole
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