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MedKoo Cat#: 571222 | Name: Esfenvalerate
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Description:

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

Esfenvalerate is a common insecticide.

Chemical Structure

Esfenvalerate
Esfenvalerate
CAS#66230-04-4

Theoretical Analysis

MedKoo Cat#: 571222

Name: Esfenvalerate

CAS#: 66230-04-4

Chemical Formula: C25H22ClNO3

Exact Mass: 419.1288

Molecular Weight: 419.91

Elemental Analysis: C, 71.51; H, 5.28; Cl, 8.44; N, 3.34; O, 11.43

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 weeks
100mg USD 450.00 2 weeks
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Related CAS #
No Data
Synonym
Esfenvalerate; Asana; Halmark; A alpha; Fenvalerate (S,S)-isomer
IUPAC/Chemical Name
Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-, (S)-cyano(3-phenoxyphenyl)methyl ester, (alphaS)-
InChi Key
NYPJDWWKZLNGGM-RPWUZVMVSA-N
InChi Code
InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m1/s1
SMILES Code
O=C(O[C@H](C#N)C1=CC=CC(OC2=CC=CC=C2)=C1)[C@@H](C(C)C)C3=CC=C(Cl)C=C3
Appearance
Solid powder
Purity
>98% (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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 419.91 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: Ye X, Xiong K, Liu J. Comparative toxicity and bioaccumulation of fenvalerate and esfenvalerate to earthworm Eisenia fetida. J Hazard Mater. 2016 Jun 5;310:82-8. doi: 10.1016/j.jhazmat.2016.02.010. Epub 2016 Feb 6. PubMed PMID: 26900980. 2: Birolli WG, Alvarenga N, Seleghim MH, Porto AL. Biodegradation of the Pyrethroid Pesticide Esfenvalerate by Marine-Derived Fungi. Mar Biotechnol (NY). 2016 Aug;18(4):511-20. doi: 10.1007/s10126-016-9710-z. Epub 2016 Jul 6. PubMed PMID: 27381569. 3: Adelsbach TL, Tjeerdema RS. Chemistry and fate of fenvalerate and esfenvalerate. Rev Environ Contam Toxicol. 2003;176:137-54. Review. PubMed PMID: 12442505. 4: Tian K, Liu D, Yuan Y, Li M, Qiu X. CYP6B6 is involved in esfenvalerate detoxification in the polyphagous lepidopteran pest, Helicoverpa armigera. Pestic Biochem Physiol. 2017 May;138:51-56. doi: 10.1016/j.pestbp.2017.02.006. Epub 2017 Mar 1. PubMed PMID: 28456304. 5: Kunimatsu T, Yamada T, Ose K, Sunami O, Kamita Y, Okuno Y, Seki T, Nakatsuka I. Lack of (anti-) androgenic or estrogenic effects of three pyrethroids (esfenvalerate, fenvalerate, and permethrin) in the Hershberger and uterotrophic assays. Regul Toxicol Pharmacol. 2002 Apr;35(2 Pt 1):227-37. PubMed PMID: 12052007. 6: Bjergager MB, Hanson ML, Lissemore L, Henriquez N, Solomon KR, Cedergreen N. Synergy in microcosms with environmentally realistic concentrations of prochloraz and esfenvalerate. Aquat Toxicol. 2011 Jan 25;101(2):412-22. doi: 10.1016/j.aquatox.2010.11.004. Epub 2010 Nov 19. PubMed PMID: 21216352. 7: Rosa R, Bordalo MD, Soares AM, Pestana JL. Effects of the Pyrethroid Esfenvalerate on the Oligochaete, Lumbriculus variegatus. Bull Environ Contam Toxicol. 2016 Apr;96(4):438-42. doi: 10.1007/s00128-015-1718-y. Epub 2015 Dec 23. PubMed PMID: 26693935. 8: Jones MM, Robertson JL, Weinzierl RA. Susceptibility of oriental fruit moth (Lepidoptera: Tortricidae) to two pyrethroids and a proposed diagnostic dose of esfenvalerate for field detection of resistance. J Econ Entomol. 2011 Jun;104(3):1031-7. PubMed PMID: 21735926. 9: Xu L, Li D, Qin J, Zhao W, Qiu L. Over-expression of multiple cytochrome P450 genes in fenvalerate-resistant field strains of Helicoverpa armigera from north of China. Pestic Biochem Physiol. 2016 Sep;132:53-8. doi: 10.1016/j.pestbp.2016.01.003. Epub 2016 Jan 14. PubMed PMID: 27521913. 10: Wang B, Liu JJ, Wang Y, Fu L, Shen R, Yu Z, Wang H, Chen YH, Zhang C, Meng XH, Xu DX. Maternal Fenvalerate Exposure Induces Fetal Intrauterine Growth Restriction Through Disrupting Placental Thyroid Hormone Receptor Signaling. Toxicol Sci. 2017 Jun 1;157(2):377-386. doi: 10.1093/toxsci/kfx052. PubMed PMID: 28369636. 11: Varró P, Kovács M, Világi I. The insecticide esfenvalerate modulates neuronal excitability in mammalian central nervous system in vitro. Toxicol Lett. 2017 Feb 5;267:39-44. doi: 10.1016/j.toxlet.2016.12.012. Epub 2016 Dec 19. PubMed PMID: 28007640. 12: Brander SM, Mosser CM, Geist J, Hladik ML, Werner I. Esfenvalerate toxicity to the cladoceran Ceriodaphnia dubia in the presence of green algae, Pseudokirchneriella subcapitata. Ecotoxicology. 2012 Nov;21(8):2409-18. doi: 10.1007/s10646-012-0996-y. Epub 2012 Sep 14. PubMed PMID: 22975895. 13: Palmquist KR, Jepson PC, Jenkins JJ. Impact of aquatic insect life stage and emergence strategy on sensitivity to esfenvalerate exposure. Environ Toxicol Chem. 2008 Aug;27(8):1728-34. doi: 10.1897/07-499.1. Epub 2008 Feb 11. PubMed PMID: 18616381. 14: Palmquist KR, Jenkins JJ, Jepson PC. Effects of dietary esfenvalerate exposures on three aquatic insect species representing different functional feeding groups. Environ Toxicol Chem. 2008 Aug;27(8):1721-7. doi: 10.1897/07-501.1. Epub 2008 Feb 11. PubMed PMID: 18616382. 15: Bjergager MB, Hanson ML, Solomon KR, Cedergreen N. Synergy between prochloraz and esfenvalerate in Daphnia magna from acute and subchronic exposures in the laboratory and microcosms. Aquat Toxicol. 2012 Apr;110-111:17-24. doi: 10.1016/j.aquatox.2011.12.001. Epub 2011 Dec 24. PubMed PMID: 22245628. 16: Palmquist KR, Jenkins JJ, Jepson PC. Clutch morphology and the timing of exposure impact the susceptibility of aquatic insect eggs to esfenvalerate. Environ Toxicol Chem. 2008 Aug;27(8):1713-20. doi: 10.1897/07-491.1. Epub 2008 Feb 12. PubMed PMID: 18616380. 17: Lyu Z, Wang Q, Lu L, Xia X, Zhang L. [Research of fenvalerate induced neurodevelopmental toxicity by interfering with the action of estrogen]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2014 Jul;32(7):487-92. Chinese. PubMed PMID: 25182815. 18: Han Y, Yu W, Zhang W, Yang Y, Walsh T, Oakeshott JG, Wu Y. Variation in P450-mediated fenvalerate resistance levels is not correlated with CYP337B3 genotype in Chinese populations of Helicoverpa armigera. Pestic Biochem Physiol. 2015 Jun;121:129-35. doi: 10.1016/j.pestbp.2014.12.004. Epub 2014 Dec 8. PubMed PMID: 26047121. 19: Caglayan A, Kocer-Gumusel B, Erkekoglu P, Hincal F. The effects of fenvalerate on hepatic and cerebral xenobiotic metabolizing enzymes in selenium and/or iodine deficient rats. Iran J Basic Med Sci. 2016 Oct;19(10):1040-1048. PubMed PMID: 27872699; PubMed Central PMCID: PMC5110651. 20: Rodrigues AC, Gravato C, Quintaneiro C, Barata C, Soares AM, Pestana JL. Sub-lethal toxicity of environmentally relevant concentrations of esfenvalerate to Chironomus riparius. Environ Pollut. 2015 Dec;207:273-9. doi: 10.1016/j.envpol.2015.09.035. Epub 2015 Sep 25. PubMed PMID: 26412267.