α-Thujone

Names

[ CAS No. ]:
546-80-5

[ Name ]:
α-Thujone

[Synonym ]:
Thujon
l-Thujone
Tanacetone
6-Ketosabinane
Bicyclo[3.1.0]hexan-3-one,4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-
(-)-alpha-thujone

Biological Activity

[Description]:

α-Thujone is a monoterpene isolated from Thuja occidentalis essential oil with potent anti-tumor activities. α-Thujone is a reversible modulator of the GABA type A receptor and the IC50 for α-Thujone is 21 μM in suppressing the GABA-induced currents. α-Thujone induces ROS accumulation-dependent cytotoxicity, also induces cell apoptosis and autophagy. α-Thujone has antinociceptive, insecticidal, and anthelmintic activity, and easily penetrates the blood-brain barrier[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[References]

[1]. Agus HH, et al. Involvement of Pca1 in ROS-mediated apoptotic cell death induced by alpha-thujone in the fission yeast (Schizosaccharomyces pombe). FEMS Yeast Res. 2020 Apr 29. pii: foaa022.

[2]. Pudełek M, et al. Therapeutic potential of monoterpene α-thujone, the main compound of Thuja occidentalis L. essential oil, against malignant glioblastoma multiforme cells in vitro. Fitoterapia. 2019 Apr;134:172-181.

[3]. Höld KM, et al. Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification. Proc Natl Acad Sci U S A. 2000 Apr 11;97(8):3826-31.

Chemical & Physical Properties

[ Density]:
0.914 g/mL at 20ºC(lit.)

[ Boiling Point ]:
84-86ºC17 mm Hg(lit.)

[ Melting Point ]:
181ºC

[ Molecular Formula ]:
C₁₀H₁₆O

[ Molecular Weight ]:
152.23300

[ Flash Point ]:
148 °F

[ Exact Mass ]:
152.12000

[ PSA ]:
17.07000

[ LogP ]:
2.25760

[ Index of Refraction ]:
n20/D 1.450

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XO9625000

CHEMICAL NAME :: 3-Thujanone, (1S,4R,5R)-(-)-

CAS REGISTRY NUMBER :: 546-80-5

LAST UPDATED :: 199701

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C10-H16-O

MOLECULAR WEIGHT :: 152.26

WISWESSER LINE NOTATION :: L35 EVTJ AY1&1 D1

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 :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FRXXBL French Demande Patent Document. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #2448856

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 120 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 65,275,1939

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2157 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 29,2,1940

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 362 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 29,2,1940

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 31 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 29,2,1940

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
23-26-36/37/39-45

[ RIDADR ]:
UN 2810 6.1/PG 3

[ RTECS ]:
XO9625000

Articles

Attempts to separate (-)-α-thujone, (+)-β-thujone epimers from camphor enantiomers by enantioselective HPLC with polarimetric detection.

J. Sep. Sci. 36(5) , 832-9, (2013)

In a first step, 26 chiral stationary phases (CSPs) have been screened for the separation of (-)-α-thujone, (+)-β-thujone epimers and camphor enantiomers by LC. The separations were monitored by a pol...

Long-term stability of thujone, fenchone, and pinocamphone in vintage preban absinthe.

J. Agric. Food Chem. 57(7) , 2782-5, (2009)

Research was conducted to ascertain whether analyses of vintage absinthe samples represent their original composition in the early 1900s. Absinthe stored in traditional green glass bottles and irradia...

Toxicokinetics of α-thujone following intravenous and gavage administration of α-thujone or α- and β-thujone mixture in male and female F344/N rats and B6C3F1 mice.

Toxicol. Appl. Pharmacol. 271(2) , 216-28, (2013)

Plants containing thujone have widespread use and hence have significant human exposure. α-Thujone caused seizures in rodents following gavage administration. We investigated the toxicokinetics of α-t...

Related Compounds

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