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F1428

Sigma-Aldrich

Fenvalerate

≥97%

Sinónimos:

α-Cyano-3-phenoxybenzyl α-(4-chlorophenyl)­iso­valerate

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About This Item

Fórmula empírica (notación de Hill):
C25H22ClNO3
Número de CAS:
51630-58-1
Peso molecular:
419.90
Beilstein/REAXYS Number:
2025982
MDL number:
MFCD00055324
UNSPSC Code:
12352200
PubChem Substance ID:
329799681
NACRES:
NA.77

Quality Level

200

assay

≥97%

storage temp.

−20°C

SMILES string

CC(C)C(C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1)c3ccc(Cl)cc3

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

InChI key

NYPJDWWKZLNGGM-UHFFFAOYSA-N

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General description

Fenvalerate an ester molecule, exists in four stereoisomers with two chiral centers.

Application

Fenvalerate has been used to study the effect of Fen exposure on reproductive functions.

Biochem/physiol Actions

Fenvalerate has good insecticidal potential and is less toxic to animals. It might cause endocrine disruption and reproductive dysfunction in humans. Metabolism of fenvalerate includes oxidation, ester cleavage and conjugation reaction. It is stable at pH 5 and 7, while it gets hydrolyzed at pH 9. In rat models it is found to hinder the action of mitochondrial enzymes.
Fenvalerate is a type II semi-synthetic pyrethrin, which acts as a potent inhibitor of calcineurin (protein phosphatase 2B). This inhibitory action results in cellular hyperexcitability by causing non-mutated calcium channels to remain open for an extended period of time allowing an abundance of Ca2+ to enter the cell.
Piretroide de tipo II. Potente inhibidor de la calcineurina (proteína fosfatasa 2B).

Preparation Note

Fenvalerate has been reported to be soluble in DMSO, ethanol, and acetone.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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Effects of fenvalerate exposure on semen quality among occupational workers
Lifeng T, et al.
Contraception, 73(1), 92-96 (2006)
Fenvalerate-induced oxidative damage in rat tissues and its attenuation by dietary sesame oil
Prasanthi K, et al.
Food And Chemical Toxicology, 43(2), 299-306 (2005)
Paternal fenvalerate exposure influences reproductive functions in the offspring
Xia D, et al.
Reproductive Sciences, 20(11), 1308-1315 (2013)
Metabolic Pathways of Agrochemicals: Insecticides and fungicides, 659-659 (1998)
Saskia Knillmann et al.
Ecotoxicology (London, England), 21(4), 1039-1049 (2012-02-09)
Xenobiotics alter the balance of competition between species and induce shifts in community composition. However, little is known about how these alterations affect the recovery of sensitive taxa. We exposed zooplankton communities to esfenvalerate (0.03, 0.3, and 3 μg/L) in
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