CAS 546-80-5|α-Thujone

Introduction：Basic information about CAS 546-80-5|α-Thujone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. α-Thujone BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles29
7. Synonyms

Common Name	α-Thujone
CAS Number	546-80-5	Molecular Weight	152.23300
Density	0.914 g/mL at 20ºC(lit.)	Boiling Point	84-86ºC17 mm Hg(lit.)
Molecular Formula	C₁₀H₁₆O	Melting Point	181ºC
MSDS	ChineseUSA	Flash Point	148 °F
Symbol	GHS07	Signal Word	Warning

Names

Name	(-)-α-thujone
Synonym	More Synonyms

α-Thujone BiologicalActivity

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 >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorResearch Areas >>Neurological DiseaseSignaling 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.

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 >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorResearch Areas >>Neurological DiseaseSignaling 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
InChIKey	USMNOWBWPHYOEA-MRTMQBJTSA-N
SMILES	CC1C(=O)CC2(C(C)C)CC12

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

Articles29

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...

Synonyms

Thujon

l-Thujone

Tanacetone

6-Ketosabinane

Bicyclo[3.1.0]hexan-3-one,4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-

(-)-alpha-thujone

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