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MedKoo Cat#: 592100 | Name: Allethrin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

The allethrins are a group of related synthetic compounds used in insecticides.

Chemical Structure

Allethrin
CAS#584-79-2

Theoretical Analysis

MedKoo Cat#: 592100

Name: Allethrin

CAS#: 584-79-2

Chemical Formula: C19H16O3

Exact Mass: 302.1882

Molecular Weight: 302.41

Elemental Analysis: C, 75.46; H, 8.67; O, 15.87

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 400.00 2 Weeks
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Related CAS #
No Data
Synonym
Allethrin; Allylcinerine; NSC 11782; NSC11782; NSC-11782; RU 27436; RU27436; RU-27436
IUPAC/Chemical Name
3-Allyl-4-methyl-2-oxo-3-cyclopenten-1-yl ester of 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid
InChi Key
XAQVCWAIAWPMMQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H26O3/c1-7-8-13-12(4)10-15(17(13)20)22-18(21)16-14(9-11(2)3)19(16,5)6/h7,9,14-16H,1,8,10H2,2-6H3
SMILES Code
O=C(C1C(C)(C)C1/C=C(C)\C)OC2C(C(CC=C)=C(C)C2)=O
Appearance
An oil
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 302.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jalouli M, Mofti A, Elnakady YA, Nahdi S, Feriani A, Alrezaki A, Sebei K, Bizzarri M, Alwasel S, Harrath AH. Allethrin Promotes Apoptosis and Autophagy Associated with the Oxidative Stress-Related PI3K/AKT/mTOR Signaling Pathway in Developing Rat Ovaries. Int J Mol Sci. 2022 Jun 7;23(12):6397. doi: 10.3390/ijms23126397. PMID: 35742842; PMCID: PMC9224321. 2: Srivastava AK, Srivastava PK, Al-Khedhairy AA, Musarrat J, Shukla Y. Retraction notice to "Allethrin-induced genotoxicity and oxidative stress in Swiss albino mice" [MUTGEN 747 (1) (2012) 22-28]. Mutat Res Genet Toxicol Environ Mutagen. 2020 Jan;849:503116. doi: 10.1016/j.mrgentox.2019.503116. Epub 2020 Jan 29. PMID: 32087847. 3: Bhatt P, Huang Y, Rene ER, Kumar AJ, Chen S. Mechanism of allethrin biodegradation by a newly isolated Sphingomonas trueperi strain CW3 from wastewater sludge. Bioresour Technol. 2020 Feb 24;305:123074. doi: 10.1016/j.biortech.2020.123074. Epub ahead of print. PMID: 32146283. 4: Na HG, Kim YD, Choi YS, Bae CH, Song SY. Allethrin and prallethrin stimulates MUC5AC expression through oxidative stress in human airway epithelial cells. Biochem Biophys Res Commun. 2018 Sep 3;503(1):316-322. doi: 10.1016/j.bbrc.2018.06.022. Epub 2018 Jun 12. PMID: 29885834. 5: Srivastava AK, Srivastava PK, Al-Khedhairy AA, Musarrat J, Shukla Y. Allethrin-induced genotoxicity and oxidative stress in Swiss albino mice. Mutat Res. 2012 Aug 30;747(1):22-28. doi: 10.1016/j.mrgentox.2012.03.003. Epub 2012 Mar 20. Retraction in: Mutat Res Genet Toxicol Environ Mutagen. 2020 Jan;849:503116. PMID: 22475934. 6: Madhubabu G, Yenugu S. Allethrin toxicity causes reproductive dysfunction in male rats. Environ Toxicol. 2017 Jun;32(6):1701-1710. doi: 10.1002/tox.22394. Epub 2017 Feb 9. PMID: 28181402. 7: Huang Y, Chen WJ, Li J, Ghorab MA, Alansary N, El-Hefny DE, El-Sayyad GS, Mishra S, Zhang X, Bhatt P, Chen S. Novel mechanism and degradation kinetics of allethrin using Bacillus megaterium strain HLJ7 in contaminated soil/water environments. Environ Res. 2022 Nov;214(Pt 3):113940. doi: 10.1016/j.envres.2022.113940. Epub 2022 Aug 8. PMID: 35952736. 8: Castillo G, Barrios-Arpi L, Ramos-Gonzalez M, Vidal P, Gonzales-Irribarren A, Ramos-Cevallos N, Rodríguez JL. Neurotoxicity associated with oxidative stress and inflammasome gene expression induced by allethrin in SH-SY5Y cells. Toxicol Ind Health. 2022 Dec;38(12):777-788. doi: 10.1177/07482337221089585. Epub 2022 Sep 8. PMID: 36074087. 9: Bhatt P, Rene ER, Kumar AJ, Zhang W, Chen S. Binding interaction of allethrin with esterase: Bioremediation potential and mechanism. Bioresour Technol. 2020 Nov;315:123845. doi: 10.1016/j.biortech.2020.123845. Epub 2020 Jul 15. PMID: 32707504. 10: Bhatt P, Zhang W, Lin Z, Pang S, Huang Y, Chen S. Biodegradation of Allethrin by a Novel Fungus Fusarium proliferatum Strain CF2, Isolated from Contaminated Soils. Microorganisms. 2020 Apr 20;8(4):593. doi: 10.3390/microorganisms8040593. PMID: 32325934; PMCID: PMC7232317. 11: Sayono S, Mudawamah PL, Meikawati W, Sumanto D. Effect of D-Allethrin Aerosol and Coil to the Mortality of Mosquitoes. J Arthropod Borne Dis. 2019 Sep 30;13(3):259-267. PMID: 31879666; PMCID: PMC6928380. 12: Gupta G, Chaitanya RK, Golla M, Karnati R. Allethrin toxicity on human corneal epithelial cells involves mitochondrial pathway mediated apoptosis. Toxicol In Vitro. 2013 Dec;27(8):2242-8. doi: 10.1016/j.tiv.2013.09.011. Epub 2013 Sep 19. PMID: 24055895. 13: Madhubabu G, Yenugu S. 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. doi: 10.1002/tox.21864. Epub 2013 Apr 18. PMID: 23595975. 14: Narahashi T. Mode of action of DDT and allethrin on nerve: cellular and molecular mechanisms. Residue Rev. 1969;25:275-88. doi: 10.1007/978-1-4615-8443-8_21. PMID: 4307950. 15: Ravula AR, Yenugu S. Pyrethroid based pesticides - chemical and biological aspects. Crit Rev Toxicol. 2021 Feb;51(2):117-140. doi: 10.1080/10408444.2021.1879007. Epub 2021 Apr 6. PMID: 33821762. 16: Ramos-Chavez LA, Sordo M, Calderon-Aranda E, Castañeda-Saucedo E, Ostrosky- Wegman P, Moreno-Godinez ME. A permethrin/allethrin mixture induces genotoxicity and cytotoxicity in human peripheral blood lymphocytes. J Toxicol Environ Health A. 2015;78(1):7-14. doi: 10.1080/15287394.2015.956025. PMID: 25424543. 17: Madhubabu G, Yenugu S. Allethrin induces oxidative stress, apoptosis and calcium release in rat testicular carcinoma cells (LC540). Toxicol In Vitro. 2014 Dec;28(8):1386-95. doi: 10.1016/j.tiv.2014.07.008. Epub 2014 Jul 27. PMID: 25072698. 18: Darugar V, Vakili M, Manzur ME, Brandán SA. Structural and vibrational investigation of Cis-Trans isomers of potent insecticide allethrin. J Mol Model. 2022 Aug 22;28(9):268. doi: 10.1007/s00894-022-05272-y. PMID: 35995874. 19: Chen CD, Chin AC, Lau KW, Low VL, Lee HL, Lee PKY, Azidah AA, Sofian-Azirun M. Bioefficacy Evaluation of Commercial Mosquito Coils Containing Metofluthrin, d-Allethrin, d-Trans Allethrin, and Prallethrin Against Aedes albopictus (Diptera: Culicidae) in Malaysia. J Med Entomol. 2018 Oct 25;55(6):1651-1655. doi: 10.1093/jme/tjy130. PMID: 30085203. 20: Moya-Quiles MR, Muñoz-Delgado E, Vidal CJ. Interactions of the pyrethroid insecticide allethrin with liposomes. Arch Biochem Biophys. 1994 Jul;312(1):95-100. doi: 10.1006/abbi.1994.1285. PMID: 8031152.

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