55332-38-2

Usage

Uses

Used in Environmental Monitoring:
Esfenvalerate free acid metabolite is used as a bioindicator for [the purpose of monitoring pesticide contamination]. Its presence in environmental samples can signify prior use of esfenvalerate, allowing for the assessment of pesticide exposure and potential ecological impacts.
Used in Agricultural Practices:
In the agricultural industry, Esfenvalerate free acid metabolite is used as a reference point for [the purpose of understanding the impact of pesticide use on crops and the environment]. By tracking the levels of this metabolite, farmers and researchers can make informed decisions about the application of esfenvalerate and other pesticides, aiming to minimize their environmental footprint and ensure sustainable agricultural practices.
Used in Regulatory Compliance:
Esfenvalerate free acid metabolite is utilized as a regulatory tool for [ensuring compliance with environmental safety standards]. By monitoring the levels of this metabolite, regulatory bodies can enforce guidelines and restrictions on the use of esfenvalerate, protecting both human health and the environment from potential risks associated with pesticide exposure.
Used in Research and Development:
In the scientific community, Esfenvalerate free acid metabolite is employed as a research subject for [investigating the mechanisms of pesticide degradation and its environmental fate]. Understanding how this metabolite behaves in various ecosystems can contribute to the development of safer and more effective pest control strategies, as well as inform the design of new pesticides with reduced environmental impact.

Upstream product

• 2012-81-9 3-Methyl-2-(4'-chlorophenyl)-butyronitrile 
• 74408-48-3 2-(4-Chlorophenyl)-3-methylbutyraldehyde 
• 51630-58-1 FENVALERATE 
• 66230-04-4 esfenvalerate 
• 33131-40-7 2-(4-chlorophenyl)-3-methylcrotonic acid 
• 124932-02-1 (S)-2-(4-Chloro-phenyl)-3-methyl-butyric acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 2012-74-0 2-(4-chlorophenyl)-3-methylbutyric acid 
• 306974-39-0 (S)-3-methyl-2-(4-chlorophenyl)butan-1-ol 
• 18713-58-1 1-(4-chlorophenyl)-2-methylpropan-1-one 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 69741-69-1 2-(4-chlorophenyl)-3-methylbutyramide 
• 73591-05-6 (-)-CPA-(-)-PEA salt 
• 71656-96-7 (+)-CPA-(-)-PEA salt 
• 124931-85-7 (4-Chloro-phenyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 

Downstream Products

• 51631-50-6 2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride 
• 63640-09-5 (R)-2-(4-chlorophenyl)-3-methylbutyric acid 
• 69741-69-1 2-(4-chlorophenyl)-3-methylbutyramide 
• 131691-16-2 2-(4-Chloro-phenyl)-3-methyl-butyric acid 2-oxo-2H-chromen-4-yl ester 
• 131691-17-3 6-chlorocoumarin-4-yl α-isopropyl-4-chlorophenylacetate 
• 131691-10-6 2-(4-Chloro-phenyl)-3-methyl-butyric acid 2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl ester 
• 131691-14-0 flavone-7-yl α-isopropyl-4-chlorophenylacetate 
• 131691-15-1 2-(4-Chloro-phenyl)-3-methyl-butyric acid 3-methyl-4-oxo-2-phenyl-4H-chromen-7-yl ester 
• 73591-05-6 (-)-CPA-(-)-PEA salt 
• 71656-96-7 (+)-CPA-(-)-PEA salt 
• 74569-24-7 potassium α-isopropyl-4-chlorophenylacetate 
• 92742-11-5 p-chlorophenyl isopropyl ketene 
• 1208552-61-7 C₁₆H₁₇ClN₂O 
• 300851-67-6 4-chloro-α-(1-methylethyl)-N-2-thiazolylbenzeneacetamide 

Relevant academic research and scientific papers

Enantioselective extraction of fenvaleric acid enantiomers by two-phase (W/O) recognition chiral extraction

To establish an extraction method for fenvaleric acid (FA) enantiomers using l-iso-butyl-l-tartaric esters and hydroxypropyl-β-cyclodextrin (HP-β-CD) as chiral selector, the distribution of FA enantiomers was examined in methanol aqueous solution containing HP-β-CD and 1,2-dichloroethane organic solution containing l-iso-butyl-l-tartaric esters. The influences of the concentration of l-iso-butyl-l-tartaric esters and HP-β-CD, organic diluent, pH, extraction temperature and the concentration of methanol aqueous solution on the partition coefficient (k) and separation factor (α) of FA were investigated. The experiment results showed that the complex formed by l-iso-butyl-l-tartaric esters with S-enantiomer is stabler than that with R-enantiomer. With the increase of the concentration of l-iso-butyl-l-tartaric ester, k and α increased; With the increase of the concentration of HP-β-CD, k increased firstly, and then decreased, but α increased all the while, k was the highest when the concentration of HP-β-CD was 4 mmol L-1. 1,2-dichloroethane organic diluent was better than the others. With the increase of pH, k and α decreased; with further increasing concentration of methanol aqueous solution, k and α decreased, k and α were the highest when the concentration of methanol aqueous solution was 10%. The extraction temperature had a great influence on k and α, too.

Enantioselective Hydrogenation of Tetrasubstituted α,β-Unsaturated Carboxylic Acids Enabled by Cobalt(II) Catalysis: Scope and Mechanistic Insights

Chiral carboxylic acids are important compounds because of their prevalence in pharmaceuticals, natural products and agrochemicals. Asymmetric hydrogenation of α,β-unsaturated carboxylic acids has been widely recognized as one of the most efficient synthetic approaches to afford such compounds. Although related asymmetric hydrogenation of di- and trisubstituted unsaturated acids with noble metals is well established, asymmetric hydrogenation of challenging tetrasubstituted α,β-unsaturated carboxylic acids is rarely reported. We demonstrate enantioselective hydrogenation of cyclic and acyclic tetrasubstituted α,β-unsaturated carboxylic acids via cobalt(II) catalysis. This protocol showed broad substrate scope and gave chiral carboxylic acids in good yields with excellent enantiocontrol (up to 98 % yield and 99 % ee). Combined experimental and computational mechanistic studies support a CoII catalytic cycle involving migratory insertion and σ-bond metathesis processes. DFT calculations reveal that enantioselectivity may originate from the steric effect between the phenyl groups of the ligand and the substrate.

Manganese Catalyzed Hydrogenation of Enantiomerically Pure Esters

A manganese-catalyzed hydrogenation of esters has been accomplished with TONs up to 1000, using cheap, environmentally benign, potassium carbonate and simple alcohols as activator and solvent, respectively. The weakly basic conditions lead to good functional group tolerance and enable the hydrogenation of enantiomerically enriched α-chiral esters with essentially no loss of stereochemical integrity.

Soluble and functional expression of a recombinant enantioselective amidase from Klebsiella oxytoca KCTC 1686 in Escherichia coli and its biochemical characterization

A gene encoding an enantioselective amidase (KamH) was cloned from Klebsiella oxytoca KCTC 1686 and inserted into the EcoRI and HindIII sites of the vector pET-30a(+). When KamH with a peptide containing a His-tag and an enterokinase cleavage site was overexpressed in Escherichia coli, approximately half was found in the soluble fraction, but it lacked activity. After cleavage of the peptide by enterokinase, the enzyme activity was partly restored, reaching 420.2 ± 33.62 U/g dry cell weight (DCW). Another recombinant plasmid was constructed by inserting the KamH gene into the NdeI and EcoRI sites of pET-30a(+) to express KamH in its native form. The overexpressed amidase was found primarily in the soluble fraction and its maximum activity was 3613.4 ± 201.68 U/g DCW. This indicated that the peptide influenced not only soluble expression but also activity of KamH, perhaps by blocking the substrate-binding tunnel of KamH. Similar results were obtained with heterologously expressed amidases from Rhodococcus erythropolis MP50 and Agrobacterium tumefaciens d3. All of these amidases have an N-terminal α-helical domain. Therefore, amidases of this type may be functionally expressed in their native form. KamH hydrolyzed a range of aliphatic and aromatic amides and exhibited strict S-selectivity towards racemic amides.

Screening of by-products of esfenvalerate in aqueous medium using SBSE probe desorption GC-IT-MS technique

The pyrethroids, their metabolites and by-products have been recognized as toxic to environment and human health. Despite several studies about esfenvalerate toxicity and its detection in water and sediments, information about its degradation products is still scanty. In this work, esfenvalerate degradation products were obtained by chemical oxidation with hydrogen peroxide and their structure was elucidated using a procedure known as stir bar sorptive extraction (SBSE) probe desorption gas chromatography-ion trap mass spectrometry (GC-IT-MS) analysis. This procedure consists of the thermal desorption of analytes extracted from a SBSE stir bar introduced by a probe into a gas chromatograph (GC) coupled to an ion trap mass spectrometry (IT-MS) system. Based on IT-MS data, a degradation pathway of esfenvalerate is proposed with ten products of chemical oxidation of esfenvalerate that are fully identified. Among these compounds, 3-phenoxybenzoic acid and 3-phenoxybenzaldehyde were detected, reported as being environmental metabolites of some pyrethroids, with endocrine-disrupting activity.

The first synthetic agonists of FFA2: Discovery and SAR of phenylacetamides as allosteric modulators

Free fatty acid receptor 2 (FFA2) is a G-protein coupled receptor for which only short-chain fatty acids (SCFAs) have been reported as endogenous ligands. We describe the discovery and optimization of phenylacetamides as allosteric agonists of FFA2. These novel ligands can suppress adipocyte lipolysis in vitro and reduce plasma FFA levels in vivo, suggesting that these allosteric modulators can serve as pharmacological tools for exploring the potential function of FFA2 in various disease conditions.

Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols

A highly efficient asymmetric hydrogenation of racemic α-arylaldehydes via dynamic kinetic resolution has been developed by using [RuCl2(SDPs)(diamine)] complexes as catalysts, providing chiral primary alcohols in excellent enantioselectivities. Copyright

Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11

The pyrethroid pesticides residues on foods and environmental contamination are a public safety concern. Pretreatment with pyrethroid hydrolase has the potential to alleviate the conditions. For this purpose, a fungus capable of using pyrethroid pesticides as a sole carbon source was isolated from the soil and characterized as Aspergillus niger ZD11. A novel pyrethroid hydrolase from cell extract was purified 41.5-fold to apparent homogeneity with 12.6% overall recovery. It is a monomeric structure with a molecular mass of 56 kDa, a pl of 5.4, and the enzyme activity was optimal at 45°C and pH 6.5. The activities were strongly inhibited by Hg2+, Ag+, and p-chloromercuribenzoate, whereas less pronounced effects (5-10% inhibition) were observed in the presence of the remaining divalent cations, the chelating agent EDTA and phenanthroline. The purified enzyme hydrolyzed various insecticides with similar carboxylester. trans-Permethrin is the preferred substrate.

PROCESS FOR PREPARING (+)-2-(4-CHLOROPHENYL)-3-METHYL BUTANOIC ACID

The present invention relates to an environmentally benign process for preparation of (+)2-(4-chlorophenyl)-3-methyl butanoic acid (+ CPA) from its racemic acid, using optically active arylamines like (-) PEA in hydrophilic/hydrophobic organic solvents like butanol, propanol etc. as aqueous mixtures, separating the desired (+) CPA salt, mother liquor by filtration and refining the (+) CPA salt in the same solvent system as used for resolution, recovering the desired acid in high optical purity by extracting with aqueous mineral acid. The mother liquor is concentrated under vacuum and extracted with aqueous mineral acid to obtain undesired (-) CPA which was recovered and recycled after racemization. The aqueous mineral acid layer thus obtained is mixed with corresponding aqueous mineral acid layer obtained from (+) CPA recovery and extracted with aqueous caustic lie solution to recover the optically active amine used for resolution. Thus the method described effectively provides a process for recovery and recycle of the undesired (-) CPA, optically active amine, besides obtaining the desired (+) CPA in high optical purity.

A Rearrangement Route to Fenvaleric Acid

(±)-Fenvaleric acid 2, the key intermediate for the preparation of the pesticide esfenvalerate 1, was prepared by a novel sequence which first involves the Henry reaction of 2-methyl-1-nitropropane and 4-chlorobenzaldehyde. The nitroaldol reaction provided nitroalcohol 5 which was then reduced to the corresponding aminoalcohol 6. Submission of 6 to an aminopinacol rearrangement promoted by nitrous acid deamination then afforded aldehyde 8 through a 1,2-aryl shift. The product fenvaleric aldehyde 8 was then converted to the title compound 2 by a modified Jones oxidation.