This compound belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
External Descriptors
cyhalothrin
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
449.800 g/mol
XLogP3
6.100
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
7
Exact Mass
449.101 Da
Monoisotopic Mass
449.101 Da
Topological Polar Surface Area
59.300 Ų
Heavy Atom Count
31
Formal Charge
0
Complexity
736.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
3
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
Calculadoras de soluciones
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Application Protocols
No vendor-validated immunoassay or cell-biology application protocols are associated with this item. For analytical use, general practices include:
Stock preparation: dissolve to 1–10 mg/mL in HPLC-grade acetonitrile or isooctane; vortex/sonicate as needed.
Working solutions: prepare serial dilutions in the same solvent; for LC, mix with water just prior to injection to final organic content compatible with the method.
Calibration: use matrix-matched standards and internal standards to correct for recovery/ion-suppression.
Containers: amber, low-adsorption vials; pre-rinse with solvent to minimize wall losses.
These are general, literature-informed suggestions and not product-specific validated methods.
Biological Roles
General (literature; for research context only)
Mode of action: Type II pyrethroid; stabilizes the open state of voltage-gated sodium channels (VGSCs) in arthropod neurons, causing repetitive firing and knockdown. The γ-enantiomer displays higher potency than the racemate due to stereoselective binding.
Selectivity: enhanced insecticidal activity with comparatively lower mammalian potency linked to metabolic detoxification and sodium-channel isoform differences; nonetheless, laboratory exposure requires caution.
Metabolism: biotransformed by esterases and cytochrome P450s to yield phenoxybenzoic acids and alcohols; conjugation (e.g., glucuronidation) facilitates excretion (species-dependent).
Ecotoxicology: very toxic to aquatic invertebrates and fish; strong sorption to sediments/organic matter due to high hydrophobicity results in low water-column persistence but potential sediment residues.
Research uses informed by biology
Comparative pharmacology across insect VGSC mutants (kdr variants) to model resistance.
Biomarker studies of detoxification enzymes (e.g., P450s, GSTs, carboxylesterases) in exposed organisms.
Environmental risk assessments examining chronic/acute endpoints in non-target species.
Note: No medical or clinical use is implied; for laboratory research only.
Buffer Applications
Not typically used to prepare or modify aqueous buffers. The compound’s extremely low water solubility and base-labile ester function make it unsuitable for buffer formulations. For analytical workflows, prepare organic stock solutions (e.g., acetonitrile) and only mix with aqueous buffers as part of LC mobile phases immediately prior to use.
Green Alternatives
Perspective: gamma-Cyhalothrin is a halogenated, highly hydrophobic pyrethroid with significant aquatic toxicity. While there is no direct “green” drop-in replacement for its specific mode-of-action studies, greener choices can be made around solvents, matrices, and analytical workflows.
Greener handling choices
Solvent selection: prefer acetonitrile or ethyl acetate over dichloromethane or chlorinated solvents when method performance allows.
Miniaturization: apply microextraction (µSPE, SPME) and QuEChERS to reduce solvent volumes for residue analysis.
Waste reduction: consolidate standards, use ampouled single-use aliquots, and adopt rigorous inventory control to minimize expired materials.
Comparison (illustrative; literature-based)
Dichloromethane vs ethyl acetate: EtOAc offers lower toxicity and environmental impact, with sufficient solvency for pyrethroids in many procedures.
Hexane vs heptane/isooctane: higher-boiling alkanes reduce VOC emissions; balance against GC detector/method requirements.
Trade-offs
Less hazardous solvents may slightly impact extraction recoveries or chromatographic resolution; revalidate methods when swapping solvents.
Light- and base-sensitivity necessitate amberware and neutral to mildly acidic conditions regardless of solvent choice.
Pharmaceutical Uses
This product is not used as a pharmaceutical excipient or active for clinical applications. In laboratory settings, formulation principles from agrochemical science can be informative for research-only delivery studies:
Solubilization approaches (research context): emulsifiable concentrates, microencapsulation, or cyclodextrin inclusion complexes to disperse highly hydrophobic actives in aqueous media.
Stability considerations: avoid alkaline excipients; protect from light; use antioxidants only if compatible with the analytical or toxicology objectives.
No pharmacopeial status or excipient grade is claimed for this item; refer to CoA/Spec Sheet for any available analytical grade information.
Physical Properties
Item-specific properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Literature and general reference values (typical for gamma-/lambda-cyhalothrin; for guidance only)
Physical state: typically a viscous liquid or low-melting solid depending on isomer composition (literature).
Melting point: often reported in the 40–50 °C range for enriched isomers; racemates may show broader/variable MP (literature).
Boiling point: decomposes before boiling at atmospheric pressure; distillation not recommended (literature).
Solubility: very low in water (often <5 µg/L at 20–25 °C); readily soluble in organic solvents such as acetone, acetonitrile, dichloromethane, hexane, toluene, and methanol (literature).
Log Kow: high, typically ~6–7, indicating strong hydrophobicity and sorption to organic matter (literature).
Vapor pressure: low (sub-mPa at 20–25 °C), contributing to persistence on surfaces (literature).
Notes for practitioners
Expect strong adsorption to glass and plastics at trace levels; pre-rinse containers with the working solvent and consider silanized glassware for analytical work.
For quantitative analysis, prepare stocks in HPLC-grade acetonitrile or hexane and avoid aqueous diluents except as final mobile-phase mixtures.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grades for this compound type (general)
Analytical/Reference standard grade: Emphasizes isomeric purity (γ-enantiomeric excess), trace-impurity profiling, and stability in common analytical solvents (e.g., acetonitrile, hexane). Useful for residue analysis, method validation, and calibration curves.
Technical/agrochemical grade: Often a mixture with defined isomer ratios and broader impurity limits; not typically suitable for quantitative laboratory residue work.
Stabilization: Some pyrethroids are offered with trace stabilizers or in ampouled solutions to minimize photolysis/adsorption; any stabilizer or solution matrix would be explicitly listed on the CoA if applicable.
What to check on receipt
Confirm the isomeric designation (γ-isomer) and any stated enantiomeric excess or optical rotation (if provided on CoA).
Verify purity by GC-FID/GC–MS or LC–MS and check for common degradants (hydrolysis products, phenoxybenzoic acid derivatives) per your method needs.
Review storage and retest dates; high-hydrophobic actives can adsorb to container walls, impacting apparent concentration at low levels.
Reaction and Applications
This compound is primarily used as an active standard or research analyte rather than as a synthetic reagent.
Research applications (general)
Analytical chemistry: calibration standards for GC-ECD/GC–MS and LC–MS/MS in food, environmental, and surface residue monitoring; recovery studies in QuEChERS and SPE method development.
Environmental fate and transport: sorption/partitioning studies in soils and sediments; photolysis/hydrolysis kinetics; bioaccumulation modeling due to high log Kow.
Toxicology and neurobiology: reference modulator for insect voltage-gated sodium channels (VGSCs) and for comparative assays against other Type II pyrethroids.
Resistance research: comparator in metabolic and target-site resistance (kdr) studies in vector-control programs.
Practical notes
Prepare concentrated stocks (e.g., 1–10 mg/mL) in HPLC-grade acetonitrile or hexane; store aliquots in amber vials to limit adsorption and photodegradation.
Avoid strong base and prolonged exposure to aqueous buffers; ester hydrolysis yields phenoxybenzoic acid and related products, complicating quantitation.
For mass spectrometry, common transitions target the phenoxybenzyl fragments; validate collision energies and source conditions for your instrument.
Reaction Conditions
As a research analyte, gamma-Cyhalothrin is not commonly subjected to synthetic transformations during routine use. The following literature-guided conditions pertain to stability and analytical handling rather than preparative reactions.
Hydrolysis (literature guidance)
Base-catalyzed: accelerated in aqueous methanol or buffer pH > 9 at ambient temperature; half-lives decrease sharply with increasing pH. Avoid basic eluents/prolonged exposure.
Acidic: comparatively stable under mildly acidic conditions (pH 4–6), but strong acids can promote transesterification/cleavage in alcoholic media.
Photolysis
UV exposure can induce degradation; use amber glassware and minimize light during sample prep and storage.
Chromatography
GC: nonpolar columns (e.g., 5% phenyl–95% dimethylpolysiloxane); injector temps moderate to avoid on-column degradation; ECD or MS detection.
LC–MS/MS: reversed-phase C18 with ACN–water (0.1% formic acid) gradients; monitor characteristic phenoxybenzyl fragments. Validate dwell times and collision energies per instrument.
Extraction and cleanup
QuEChERS or SPE with C18/PSA/graphitized carbon black, depending on matrix. Hexane/acetone or ACN partitioning is common for residues.
These conditions are general references; optimize for your matrix and instrumentation.
Safety and Handling
Authority note: Always consult the SDS for definitive safety and regulatory information for this specific item.
Item-specific hazard fields from Product Data
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
Literature-based hazard profile for pyrethroids (general guidance, not item specification)
Likely hazards: harmful if swallowed, skin/eye irritant, skin sensitizer; may cause transient paresthesia on skin contact; very toxic to aquatic life with long-lasting effects.
Typical GHS for similar actives: Acute Tox. 4; Skin Sens. 1; Aquatic Acute 1; Aquatic Chronic 1 (literature examples).
Handling and PPE
Use in a fume hood; avoid inhalation and skin contact. Wear lab coat, nitrile gloves (double-glove for extended work), and splash goggles. Change gloves frequently due to high lipophilicity.
Prevent environmental release; collect wastes/contaminated disposables as halogenated-organic pesticide waste per local regulations.
Incompatibilities and stability
Avoid strong oxidizers, strong bases (can promote ester hydrolysis), and prolonged UV exposure (photolysis possible). Store away from food/feed areas.
First aid (general)
Skin: wash with soap and cool water; remove contaminated clothing.
Eyes: rinse with water for ≥15 min; seek medical attention if irritation persists.
Ingestion/inhalation: seek medical advice; provide SDS. Do not induce vomiting unless instructed by medical personnel.
Good solvents: acetonitrile, acetone, ethyl acetate, dichloromethane, toluene, hexane/isooctane, methanol (less preferred for long-term due to potential transesterification under basic conditions).
Poor solvents: water (very low solubility); strong protic/basic aqueous media will lead to hydrolysis over time.
Use-case guidance
Analytical standards: acetonitrile or isooctane/hexane are typical for GC/LC residue methods; ACN-water mobile phases are common for LC with minimal pre-exposure time to high-pH eluents.
Preparative work: nonpolar solvents (toluene, heptane) for crystallization or adsorption studies; DCM/EtOAc for extractions/partitions.
Comparison tips
Acetonitrile vs methanol: ACN offers better solubility and lower viscosity in LC; methanol is acceptable but avoid basic modifiers.
Hexane/isooctane for GC: reduces matrix effects and is compatible with ECD or MS detectors; store ampouled to minimize losses to adsorption/volatilization from vials.
Adsorption management
Precondition vials with solvent and consider amber glass to mitigate photolysis; add small amounts of nonionic surfactant only if method permits (analytical validation required).
Storage and Reconstitution
Item-specific storage from Product Data
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature; for handling in the lab)
Light sensitivity: store in amber glass containers, tightly sealed. Protect from prolonged UV/strong light.
Stability: avoid alkaline conditions and moisture ingress; consider storing concentrated solutions in dry acetonitrile, hexane, or isooctane.
Aliquoting: prepare small, single-use aliquots to minimize adsorption losses and repeat freeze–thaw cycles (if refrigerated). Room-temperature storage is acceptable per item data; refrigeration (2–8 °C) can further reduce degradation in solution if compatible with your workflows.
Reconstitution and solution prep
Solid or neat material: dissolve to a known concentration in HPLC-grade acetonitrile or hydrocarbon solvent; record exact mass and solvent lot.
Aqueous use: avoid except as final LC mobile-phase mixtures; do not store aqueous solutions.
Shelf-life
Not specified for this item; refer to CoA/Spec Sheet. Periodically verify concentration/purity by GC/LC, especially for trace-level work.
Research use only: Not for human or animal diagnostic/therapeutic use.
Structure and Identity
Brief description: gamma-Cyhalothrin is a single-enantiomer Type II pyrethroid insecticide; structurally, it is an α-cyano-3-phenoxybenzyl ester of a substituted cyclopropanecarboxylic acid bearing a chlorotrifluoromethyl vinyl substituent.
Item-specific identifiers (from Product Data)
CAS: 76703-62-3
InChIKey: 469163 (as provided; note this appears truncated vs. standard 27-character format)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature identifiers and composition (for reference only; not item specifications)
Typical molecular formula (literature): C23H19ClF3NO3
Stereochemistry: one or more stereogenic centers in the cyclopropane/carbinyl region; γ-isomer denotes a defined absolute configuration responsible for enhanced biological potency compared with the racemate.
2D description: a 3-phenoxyphenyl moiety linked via a benzylic carbon bearing a cyano group to an ester oxygen; the carbonyl connects to a di-substituted cyclopropane that also bears a chlorotrifluoromethyl-vinyl substituent.
Synthetic Utility
gamma-Cyhalothrin is typically a target molecule rather than a building block. Nevertheless, understanding its synthetic construction is valuable for stereochemical and impurity-control studies.
General retrosynthesis (literature)
Disconnection at the ester: α-cyano-3-phenoxybenzyl alcohol (or corresponding halide) coupled with a substituted cyclopropanecarboxylic acid (or acid chloride) delivers the ester.
Stereocontrol: the γ-isomer arises from enantioselective cyclopropanation and/or resolution at the cyclopropane and benzylic centers. Chiral auxiliaries or asymmetric Simmons–Smith variants have been explored for related pyrethroids.
Transformation studies (research)
Hydrolysis: base-catalyzed cleavage yields phenoxybenzoic acid derivatives and the cyclopropane acid—useful for marker analysis and metabolite identification.
Reductive/oxidative pathways: controlled transformations enable synthesis of labeled internal standards (e.g., 13C/2H at the benzylic carbon) for LC–MS.
Practical notes
For impurity profiling, prepare reference esters and corresponding alcohol/acid fragments; analyze by GC/LC with orthogonal detectors (ECD, MS).
Target Specificity
Not an antibody or biological targeting reagent. No antigen, epitope, clone, isotype, or species reactivity applies to this chemical standard. For biological mode-of-action context, see the Biological Roles section.
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