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Related CAS#:
584-79-2 3972-20-1
28057-48-9 42534-61-2
497-92-7 870812-95-6
28434-00-6

584-79-2

584-79-2 structure
584-79-2 structure
  • Name: allethrin
  • Chemical Name: allethrin
  • CAS Number: 584-79-2
  • Molecular Formula: C19H26O3
  • Molecular Weight: 302.408
  • Catalog: Chemical pesticide Insecticide Pyrethroid insecticide
  • Create Date: 2018-07-10 14:56:43
  • Modify Date: 2024-01-03 08:09:42
  • 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].
Name allethrin
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
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
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.
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

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)
Symbol GHS07 GHS09
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)

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