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F1428

Sigma-Aldrich

Fenvalerate

≥97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C25H22ClNO3
CAS Number:
51630-58-1
Molecular Weight:
419.90
Beilstein:
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.
Type II pyrethroid. Potent inhibitor of calcineurin (protein phosphatase 2B).

Preparation Note

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

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335,H410

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Metabolic Pathways of Agrochemicals: Insecticides and fungicides, 659-659 (1998)
Paternal fenvalerate exposure influences reproductive functions in the offspring
Xia D, et al.
Reproductive Sciences, 20(11), 1308-1315 (2013)
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)
Effects of fenvalerate exposure on semen quality among occupational workers
Lifeng T, et al.
Contraception, 73(1), 92-96 (2006)
Terrence L Adelsbach et al.
Reviews of environmental contamination and toxicology, 176, 137-154 (2002-11-22)
Fenvalerate is listed under Class IV of the U.S. Food and Drug Administration (USFDA) Surveillance Index Classification, indicating a low hazard potential to humans from both exposure and toxicological standpoints; thus, minimal monitoring is required (Reed 1981; Eisler 1992). To
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