烯丙菊酯_MSDS_用途_密度_烯丙菊酯CAS号【584-79-2】

拟除虫菊酯杀虫剂丙烯菊酯是一种主要的驱蚊剂。丙烯菊酯诱导大鼠睾丸癌细胞氧化应激、凋亡和钙释放(LC540)。丙烯菊酯诱导BCL-2、caspase-3激活和细胞内钙释放[1]。

[ 描述 ]:

拟除虫菊酯杀虫剂丙烯菊酯是一种主要的驱蚊剂。丙烯菊酯诱导大鼠睾丸癌细胞氧化应激、凋亡和钙释放(LC540)。丙烯菊酯诱导BCL-2、caspase-3激活和细胞内钙释放[1]。

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> 细胞凋亡

研究领域 >> 癌症

[体外研究]

丙烯菊酯(0.001-250μM)诱导细胞毒性和氧化应激。丙烯菊酯对分离的睾丸间质细胞和睾丸癌细胞具有细胞毒性。细胞毒性是由于自由基的产生和抗氧化状态的改变[1]。用丙烯菊酯(125μM)处理的LC540细胞的形态学分析显示存在凋亡小体[1]。丙烯菊酯(125μM)诱导BCL-2、caspase-3激活和细胞内钙释放[1]。丙烯菊酯(IC50)≈85μM)对人类角膜上皮(HCE)细胞有毒,通过线粒体途径导致死亡[2]。细胞毒性试验[1]细胞系：LC540细胞(来源于大鼠睾丸间质细胞肿瘤)浓度：0.001-250μM培养时间：24小时结果：在低浓度下,培养24小时后,在50μM以下未显示明显的细胞杀伤活性。在浓度高于100μM时,观察到细胞杀伤。根据获得的结果,IC50为125μM。凋亡分析[1]细胞系：LC540细胞浓度：125μM培养时间：24小时结果：显示存在凋亡小体。显示早期凋亡特征的细胞百分比显著增加。Western Blot分析[1]细胞系：LC540细胞浓度：125μM培养时间：0,3,6,9,12,24小时结果：随着PARP-1水平的升高,BCL-2、pro-Caspase-3和PARP-1蛋白表达显著降低。

[体内研究]

成年雄性大鼠口服丙烯菊酯(25、50、100和150 mg/kg；每天60天)。头、尾和睾丸的脂质过氧化增加。头颅的一氧化氮生成增加,但尾部和睾丸的一氧化氮生成没有变化。头和尾的过氧化氢酶、谷胱甘肽过氧化物酶(GPx)、谷胱甘肽-S-转移酶(GST)和超氧化物歧化酶(SOD)活性降低[3]。动物模型：90天龄雄性Wistar大鼠[3]剂量：25、50、100和150 mg/kg给药：每天口服给药,持续60天结果：在丙烯菊酯处理的大鼠的头、尾和睾丸中观察到LPO产物水平增加。在caput中,与溶媒处理的对照组相比,在所有试验剂量下观察到NO水平升高。在50、100和150 mg/kg的剂量下,在尾部观察到过氧化氢酶活性显著增加。从150 mg/kg处理的大鼠获得的caput中,GPx活性显著增加。在尾侧,发现50和100 mg/kg治疗组的钙含量显著增加。相比之下,150 mg/kg剂量组大鼠睾丸中的GPx活性显著降低。在丙烯菊酯处理的大鼠的头和尾中发现GST活性以剂量依赖的方式显著增加。在caput中,150 mg/kg体重的大鼠体内的SOD活性显著增加。在尾部和睾丸中,治疗导致所有受试剂量的SOD活性增加。

[参考文献]

[1]. Golla Madhubabu, et al. Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular carcinoma cells (LC540). Toxicol In Vitro. 2014 Dec;28(8):1386-95.

[2]. Geetika Gupta, et al. Allethrin toxicity on human corneal epithelial cells involves mitochondrial pathway mediated apoptosis. Toxicol In Vitro. 2013 Dec;27(8):2242-8.

[3]. Golla Madhubabu, et al. Allethrin induced toxicity in the male reproductive tract of rats contributes to disruption in the transcription of genes involved in germ cell production. Environ Toxicol. 2014 Nov;29(11):1330-45.

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
386.8±42.0 °C at 760 mmHg

[ 熔点 ]:
51ºC

[ 分子式 ]:
C₁₉H₂₆O₃

[ 分子量 ]:
302.408

[ 闪点 ]:
166.0±27.9 °C

[ 精确质量 ]:
302.188202

[ PSA ]:
43.37000

[ LogP ]:
4.92

[ 外观性状 ]:
一种透明琥珀色的粘性液体

[ 蒸汽压 ]:
0.0±0.9 mmHg at 25°C

[ 折射率 ]:
1.515

[ 储存条件 ]:
通风低温干燥,与库房食品原料分开存放

详细MSDS(安全技术说明书)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GZ1925000

CHEMICAL NAME :: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo- 3-(2-propenyl)-2-cyclopenten-1-yl ester

CAS REGISTRY NUMBER :: 584-79-2

LAST UPDATED :: 199707

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C19-H26-O3

MOLECULAR WEIGHT :: 302.45

WISWESSER LINE NOTATION :: L5V BUTJ B2U1 C1 DOV- BL3TJ A1 A1 C1UY1&1

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 :: 685 mg/kg

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

TYPE OF TEST :: LCLo - Lowest published lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 13800 mg/m3/4H

TOXIC EFFECTS :: Behavioral - tremor Behavioral - excitement

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2500 mg/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 :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4 mg/kg

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

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 680 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 370 mg/kg

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

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/m3

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

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1200 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 38 mg/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 :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 4290 mg/kg

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

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 11332 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - excitement

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 11200 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: 2030 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 21 gm/kg/12W-I

TOXIC EFFECTS :: Liver - changes in liver weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Metabolism (Intermediary) - other proteins

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 1900 ug/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 66,277,1979 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2264 No. of Facilities: 202 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 1366 (estimated)

[ 符号 ]:

GHS07, GHS09

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302-H332-H410

[ 警示性声明 ]:
P273-P501

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn:Harmful;N:Dangerousfortheenvironment;

[ 风险声明 (欧洲) ]:
R20/22;R50/53

[ 安全声明 (欧洲) ]:
S36-S60-S61-S36/37-S24/25-S23

[ 危险品运输编码 ]:
UN 3082

[ RTECS号 ]:
GZ1925000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

1.制备方法：以菊酸乙酯为起始原料，经皂化、酸化、酰氯化，再经酯化而得：所得产品是八种异构体的混合物，原药质量指标为异构体总含量≥90.0%。原料消耗定额：菊酸乙酯（95.6%）840kg/t、液碱630kg/t、三氯化磷1110kg/t、丙烯醇酮550kg/t。

2.烯丙醇酮的制备以2-甲基呋喃为原料，经维氏反应制得5-甲基糠醛，经格利雅反应（2→3），糠醛转位反应（3→4）和异构化反应（4→5）制得烯丙醇酮的工业新方法。

格氏反应采用连续工艺，较间歇法易控制温度，镁也无需活化，生产装置也简单，糠醛转位反应以水为溶剂，严格控制反应pH值，收率可达70%；羟基环戊酮的异构化是与含水三氯乙醛作用，随之经三乙胺处理（或在水溶液中与碱作用，或用铝进行反应）。

3.富右旋反式菊酸的制备采用（±）顺反菊酸乙酯水解得到相应的菊酸，然后在转化催化剂存在下，于120℃反应２犺，转位得（±）富反式菊酸（顺／反＝10/90），再经－5℃冷冻结晶得（±）反式菊酸（顺／反＝2/98）。用右旋拆分剂，－5℃冷冻结晶，过滤，稀盐酸洗涤滤液，分出水层，油层洗至中性，减压蒸馏拆分（＋）-反-菊酸和（－）-反-菊酸。

4.富右旋反式烯丙菊酯的合成（＋）-反-菊酸与酰氯化剂（PCl3或SOCl2）作用得（＋）-反-菊酰氯。在吡啶和甲苯存在下，烯丙醇酮与（＋）-反-菊酰氯作用生成目的产物，其中右旋反式体含量80%以上。（－）反菊酸经旋化得（±）及菊酸。

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BACKGROUND. Mosquitoes are blood-sucking insects, nuisance to humans and animals. Their bites cause itching and allergic reactions. These insects are also vectors of several viruses, bacteria and para...

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