CAS 584-79-2|allethrin
Introduction：Basic information about CAS 584-79-2|allethrin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | allethrin | ||
|---|---|---|---|
| CAS Number | 584-79-2 | Molecular Weight | 302.408 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 386.8±42.0 °C at 760 mmHg |
| Molecular Formula | C19H26O3 | Melting Point | 51ºC |
| MSDS | ChineseUSA | Flash Point | 166.0±27.9 °C |
| Symbol | GHS07, GHS09 | Signal Word | Warning |
Names
| Name | allethrin |
|---|---|
| Synonym | More Synonyms |
allethrin BiologicalActivity
| 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 >>ApoptosisResearch 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
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)
- 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)
Safety Information
| Symbol | GHS07, GHS09 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H332-H410 |
| Precautionary Statements | P273-P501 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn:Harmful;N:Dangerousfortheenvironment; |
| Risk Phrases | R20/22;R50/53 |
| Safety Phrases | S36-S60-S61-S36/37-S24/25-S23 |
| RIDADR | UN 3082 |
| RTECS | GZ1925000 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
Articles29
More Articles| A permethrin/allethrin mixture induces genotoxicity and cytotoxicity in human peripheral blood lymphocytes. J. Toxicol. Environ. Health A 78(1) , 7-14, (2015) Two pyrethroids, permethrin and allethrin, are often combined for large-scale use in public health programs to control vector-borne diseases. In this study, the genotoxic potential of a commercial for... | |
| [Evaluation of effectiveness of several repellents against mosquito bites available at the Polish market]. Przegl. Epidemiol. 66(3) , 479-85, (2012) 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... | |
| Recurrent tonic-clonic seizures and coma due to ingestion of Type I pyrethroids in a 19-month-old patient. Clin. Toxicol. (Phila.) 51(6) , 497-500, (2013) Pyrethroids are synthetic pyrethrin analogues that induce sodium-channel depolarization and hyperexcitation. Severe pyrethroid poisoning is manifested by a "Tremor Syndrome" (Type I cyano-agents) or a... |
Synonyms
| MFCD00045443 |
| Chrysanthemumic acid ester of (±)-allethrolone |
| (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate |
| 1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate |
| EINECS 209-542-4 |
| Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester |
| 3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate |
| Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, 2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl ester |
| Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, trans-(+)- |
| (±)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (±)-cis-trans-chrysanthemate |
| 3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropancarboxylat |
| Allethrin |
| UNII:0X03II877M |
| 3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate |
| 2,2-Diméthyl-3-(2-méthyl-1-propèn-1-yl)cyclopropanecarboxylate de 2-méthyl-4-oxo-3-(2-propèn-1-yl)-2-cyclopentén-1-yle |
| (1Ξ)-2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl (1Ξ,3Ξ)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate |
| 2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate |
| (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS,3RS |
| 2-Methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate |
| 2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate |
