CAS Number584-79-2
SynonymsMFCD00045443; Chrysanthemumic acid ester of (±)-allethrolone; 1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; EINECS 209-542-4; (±)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (±)-cis-trans-chrysanthemate; Allethrin; (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS,3RS
Molecular FormulaC19H26O3
Molecular Weight302.41
Purity98%
Density1.1±0.1 g/cm3
Boiling Point386.8±42.0 °C at 760 mmHg
Melting Point51ºC
AppearanceA clear amber viscous liquid
EINECS209-542-4
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 584-79-2 |
| Catalog No. | 2A-9009110 |
| Chinese Name | 富右旋反式烯丙菊酯 |
| Synonyms | MFCD00045443; Chrysanthemumic acid ester of (±)-allethrolone; 1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; EINECS 209-542-4; (±)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (±)-cis-trans-chrysanthemate; Allethrin; (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS,3RS |
| Molecular Formula | C19H26O3 |
| Molecular Weight | 302.41 |
| Purity | 98 |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 386.8±42.0 °C at 760 mmHg |
| Melting Point | 51ºC |
| Appearance | A clear amber viscous liquid |
| Storage Condition | Store separately, ventilate and dry at low tempera |
| Packaging | III |
| Application | The pyrethroid insecticide allethrin is a major mosquito repellent. Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular cancer cells (LC540). Allethrin induces BCL-2, c |
| EINECS | 209-542-4 |
| PubChem ID | 329754522 |
| MDL Number | MFCD00045443 |
| SMILES | C\C(C)=C/C1C(C(=O)OC2CC(=O)C(CC=C)=C2C)C1(C)C |
| InChI | 1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3 |
| InChI Key | ZCVAOQKBXKSDMS-UHFFFAOYSA-N |
| Beilstein/REAXYS | 2294836 |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/9110_1_584_79_2.pdf |
| Bioactivity | Allethrin, a pyrethroid insecticide is a major mosquito repellent agent. Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular carcinoma cells (LC540). Allethrin induces BCL-2, caspase-3 activation and release of intracellular calcium[1]. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer In Vitro Allethrin (0.001-250 μM) induces cytotoxicity and oxidative stress. Allethrin is cytotoxic to isolated Leydig cells and testicular cancer cells. Cytotoxicity is due to free radical generation and altered antioxidant status[1]. Morphological analyses of LC540 cells treated with Allethrin (125 μM) reveals the presence of apoptotic bodies[1]. Allethrin (125 μM) induces BCL-2, caspase-3 activation and release of intracellular calcium[1]. Allethrin (IC50≈85 μM) is toxic to human corneal epithelial (HCE) cells causing death through mitochondrial pathway[2]. Cell Cytotoxicity Assay[1] Cell Line: LC540 cells (derived from rat Leydig cell tumor) Concentration: 0.001-250 μM Incubation Time: 24 hours Result: At low concentrations did not display appreciable cell killing activity up to 50 μM when incubated for 24 h. At concentrations above 100 μM, cell killing was observed. Based on the results obtained, the IC50 was 125 μM. Apoptosis Analysis[1] Cell Line: LC540 cells Concentration: 125 μM Incubation Time: 24 hours Result: Revealed the presence of apoptotic bodies. The percentage of cells displaying early apoptotic features increased significantly. Western Blot Analysis[1] Cell Line: LC540 cells Concentration: 125 μM Incubation Time: 0, 3, 6, 9, 12, 24 hours Result: BCL-2, pro-Caspase-3 and PARP-1 protein expression decreased significantly with an increase in cleaved PARP-1 levels. In Vivo Adult male rats are treated orally with Allethrin (25, 50, 100, and 150 mg/kg; every day for 60 days). Lipid peroxidation is increased in the caput, cauda, and testes. Nitric oxide production is increased in the caput, but unaltered in the cauda and testes. The activities of catalase, glutathione peroxidase (GPx), glutathione-S-transferase (GST), and superoxide dismutase (SOD) are decreased in the caput and cauda[3]. Animal Model: Male Wistar rats aged 90 days[3] Dosage: 25, 50, 100, and 150 mg/kg Administration: Orally administered every day for 60 days Result: Increased levels of LPO products were observed in the caput, cauda, and testes of allethrin treated rats. In the caput, increased levels of NO was observed at all the doses tested, when compared with the vehicle treated control. Significant increase in catalase activity was observed in the cauda obtained from 50, 100, and 150 mg/kg. GPx activity was significantly increased in the caput obtained from 150 mg/kg treated rats. In the cauda, it was found to be increased significantly in the 50 and 100 mg/kg treated groups. In contrast, the activity of GPx activity was significantly decreased in the testes of rats treated with 150 mg/kg. GST activity was found to be increased significantly in a dose dependent manner in the caput and cauda of allethrin treated rats. In the caput, significant increase in the activity of SOD was observed in the 150 mg/kg body treated rats. In the cauda and testes, treatment resulted in increase of SOD activity at all the doses tested. References [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. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 386.8±42.0 °C at 760 mmHg Melting Point 51ºC Molecular Formula C19H26O3 Molecular Weight 302.408 Flash Point 166.0±27.9 °C Exact Mass 302.188202 PSA 43.37000 LogP 4.92 Vapour Pressure 0.0±0.9 mmHg at 25°C Index of Refraction 1.515 InChIKey ZCVAOQKBXKSDMS-UHFFFAOYSA-N SMILES C=CCC1=C(C)C(OC(=O)C2C(C=C(C)C)C2(C)C)CC1=O |
| Use of | Allethrin, a pyrethroid insecticide is a major mosquito repellent agent. Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular carcinoma cells (LC540). Allethrin induces BCL-2, caspase-3 activation and release of intracellular calcium[1]. Properties Articles29 Name allethrin Synonym More Synonyms allethrin Biological Activity Description Allethrin, a pyrethroid insecticide is a major mosquito repellent agent. Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular carcinoma cells (LC540). Allethrin induces BCL-2, caspase-3 activation and release of intracellular calcium[1]. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer References [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. Chemical & Physical Properties Molecular Formula C19H26O3 Exact Mass 302.188202 PSA 43.37000 Index of Refraction 1.515 InChIKey ZCVAOQKBXKSDMS-UHFFFAOYSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 3082 International Maritime Danger Regulations: 3082 International Air Transport Danger Regulations: 3082 14.2 Names specified by the United Nations (UN) European land transport hazard regulations: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (Allethrin) IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (Allethrin) International air transport hazard regulations: Environmentally hazardous substance, liquid, n.o.s. (Allethrin) 14.3 Transport hazard categories European land transport Dangerous Regulations: 9 International sea transport Dangerous Regulations: 9 International air transport Dangerous Regulations: 9 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Dangerous Regulations: Yes International Maritime Transport Dangerous Regulations Maritime Pollutants: Yes International Air Transport Dangerous Regulations: Yes 14.6 Special reminder to users further information Dangerous goods are individually packaged, with liquids exceeding 5 liters or solids exceeding 5 kilograms. The outer packaging of each independent package and the combined independent inner package must have EHS on it. Identification (according to European ADR Regulation 2.2.9.1.10, IMDG Regulation 2.10.3), |
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