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Merck
CN

F1428

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
UNSPSC Code:
12352200
NACRES:
NA.77
PubChem Substance ID:
329799681
MDL number:
MFCD00055324
Beilstein/REAXYS Number:
2025982

Key Documents

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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

SMILES string

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

InChI key

NYPJDWWKZLNGGM-UHFFFAOYSA-N

assay

≥97%

storage temp.

−20°C

Quality Level

200

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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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLCH3528
SLCG5665
SLCC8672
SLCB4666
SLBX3813

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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)
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)
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
Saskia Knillmann et al.
Global change biology, 19(5), 1598-1609 (2013-03-19)
Considerable research efforts have been made to predict the influences of climate change on species composition in biological communities. However, little is known about how changing environmental conditions and anthropogenic pollution can affect aquatic communities in combination. We investigated the
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