(-)-α-丁香

(-)-α-丁香用途

α-Thujone 是一种从西方金钟柏精油中分离出来的单萜,具有有效的抗肿瘤活性。α-Thujone 是 GABAA 受体的可逆调节剂,在抑制 GABA 诱导的电流时,α-Thujone 的 IC50 为 21 μM。α-Thujone 诱导 ROS 依赖性细胞毒性,还诱导细胞凋亡 (apoptosis ) 和自噬 (autophagy)。α-Thujone 具有抗伤害,杀虫和驱虫活性,并且很容易穿透血脑屏障。

(-)-α-丁香名称

[ CAS 号 ]:
546-80-5

[ 中文名 ]:
(-)-α-侧柏酮

[ 英文名 ]:
α-Thujone

[中文别名 ]:

[英文别名 ]:

Thujon
l-Thujone
Tanacetone
6-Ketosabinane
(-)-alpha-thujone

(-)-α-丁香生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> 细胞凋亡

研究领域 >> 癌症

研究领域 >> 感染

信号通路 >> 自噬 >> 自噬

信号通路 >> 跨膜转运 >> GABA受体

研究领域 >> 神经疾病

信号通路 >> 神经信号通路 >> GABA受体

[参考文献]

[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.

(-)-α-丁香物理化学性质

[ 密度 ]:
0.914 g/mL at 20ºC(lit.)

[ 沸点 ]:
84-86ºC17 mm Hg(lit.)

[ 熔点 ]:
181ºC

[ 分子式 ]:
C₁₀H₁₆O

[ 分子量 ]:
152.23300

[ 闪点 ]:
148 °F

[ 精确质量 ]:
152.12000

[ PSA ]:
17.07000

[ LogP ]:
2.25760

[ 外观性状 ]:
无色或近乎于无色液体带有一种像薄荷醇的气味

[ 折射率 ]:
n20/D 1.450

[ 储存条件 ]:
-20°C，密闭，干燥

(-)-α-丁香MSDS

详细MSDS(安全技术说明书)

(-)-α-丁香毒性和生态

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

(-)-α-丁香安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 风险声明 (欧洲) ]:
R22

[ 安全声明 (欧洲) ]:
23-26-36/37/39-45

[ 危险品运输编码 ]:
UN 2810 6.1/PG 3

[ RTECS号 ]:
XO9625000

(-)-α-丁香文献

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...

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