Es-fenvalerate - analytical standard, ≥99% , CAS No.66230-04-4

CAS: 66230-04-4 Cat. No.: E109868 Molecular Weight: 419.9 Beilstein Registry Number: 4275674 EC Number: 613-911-9

GRADE & PURITY Analytical standard, ≥99%

Synonyms

(S)-Cyano(3-phenoxyphenyl)methyl (S)-2-(4-chlorophenyl)-3-methylbutanoate | A alpha | CY15763700 | A835377 | Asana | Fenvalerate alpha | S 5602 A alpha | (S-(R*,R*))-Cyano(3-phenoxyphenyl)methyl 4-chloro-2-(1-methylethyl)benzeneacetate | OMS 3023 | Esfenv

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

(S)-Cyano(3-phenoxyphenyl)methyl (S)-2-(4-chlorophenyl)-3-methylbutanoate | A alpha | CY15763700 | A835377 | Asana | Fenvalerate alpha | S 5602 A alpha | (S-(R*, R*))-Cyano(3-phenoxyphenyl)methyl 4-chloro-2-(1-methylethyl)benzeneacetate | OMS 3023 | Esfenv

Specifications & Purity

analytical standard, ≥99%

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC(C)C(C1=CC=C(C=C1)Cl)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3
• IUPAC Name: [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate
• InChIKey: NYPJDWWKZLNGGM-RPWUZVMVSA-N
• 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/t23-,24+/m1/s1
• Isomeric SMILES: CC(C)[C@@H](C1=CC=C(C=C1)Cl)C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3
• RTECS: CY1576367
• Molecular Weight: 419.9
• Beilstein: 4275674
• Reaxy-Rn: 2025982
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2025982&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrethroids
• Alternative Parents: Diphenylethers Diarylethers Benzyloxycarbonyls Phenylpropanes Phenoxy compounds Phenol ethers Chlorobenzenes Aryl chlorides Carboxylic acid esters Nitriles Monocarboxylic acids and derivatives Organopnictogen compounds Organic oxides Carbonyl compounds Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Pyrethroid skeleton - Diphenylether - Diaryl ether - Benzyloxycarbonyl - Phenylpropane - Phenoxy compound - Phenol ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Carboxylic acid ester - Nitrile - Carbonitrile - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Organohalogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organochloride - Aromatic homomonocyclic compound
• Description: 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: Pyrethroid insecticides - Pyrethroid pesticides

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

Discover Target: NFKB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Glycine max (342 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trichoplusia ni (986 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Lipe Hormone-sensitive lipase (209 Activities)

Discover Target: Lipe

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Helicoverpa zea (137 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Spodoptera exigua (540 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

Discover Target: Nr1i2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Boil Point(°C): 151-167°C
• Melt Point(°C): 59°C
• Molecular Weight: 419.900 g/mol
• XLogP3: 6.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 419.129 Da
• Monoisotopic Mass: 419.129 Da
• Topological Polar Surface Area: 59.300 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 586.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jiyuan Liu, Yifan Li, Pei Wang, Yalin Zhang, Zhen Tian.  (2023)  High-efficiency removal of pyrethroids using a redesigned odorant binding protein.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:37913660] [10.1016/j.jhazmat.2023.132856]

2. Yu Shi, Qingqing Liu, Wenjie Lu, Jing Yuan, Yihua Yang, John Oakeshott, Yidong Wu.  (2023)  Divergent amplifications of CYP9A cytochrome P450 genes provide two noctuid pests with differential protection against xenobiotics.  PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,  120  (37): (e2308685120).  [PMID:37669374] [10.1073/pnas.2308685120]

3. Kai Tian, Jing Feng, Jiang Zhu, Jiagao Cheng, Mei Li, Xinghui Qiu.  (2021)  Pyrethrin-resembling pyrethroids are metabolized more readily than heavily modified ones by CYP9As from Helicoverpa armigera.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:34119216] [10.1016/j.pestbp.2021.104871]

4. Xiaozhou Li, Tianyue Yang, Youtao Song, Jinghai Zhu, Deli Wang, Wei Li.  (2018)  Surface-enhanced Raman spectroscopy (SERS)-based immunochromatographic assay (ICA) for the simultaneous detection of two pyrethroid pesticides.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2018.11.112]

5. Wang Huidong, Shi Yu, Wang Lu, Liu Shuai, Wu Shuwen, Yang Yihua, Feyereisen René, Wu Yidong.  (2018)  CYP6AE gene cluster knockout in Helicoverpa armigera reveals role in detoxification of phytochemicals and insecticides.  Nature Communications,  9  (1): (1-8).  [PMID:30446639] [10.1038/s41467-018-07226-6]

6. Weiping Wang, Hualing Zhu, Shumin Cui, Jigen Miao, Jianrong Chen.  (2014)  Ultrasound-assisted dispersive liquid–liquid microextraction based on solidification of floating organic droplets coupled with gas chromatography for the determination of pesticide residues in water samples.  Analytical Methods,  6  (10): (3388-3394).  [PMID:] [10.1039/C3AY42331J]

7. Cui Shumin, Chen Qianxia, Wang Weiping, Miao Jigen, Wang Aijun, Chen Jianrong.  (2013)  Ultra-Preconcentration and Determination of Multiple Pesticide Residues in Water Samples Using Ultrasound-Assisted Dispersive Liquid–Liquid Microextraction and GC-FID.  CHROMATOGRAPHIA,  76  (11): (671-678).  [PMID:] [10.1007/s10337-013-2441-7]

8. Qiang Yang, Xin Zhou, Jiayu Wang, Jie Hu, Xiupei Yang, Lianfang Chen.  (2025)  MOF/COF hybrid adsorbents enable rapid and efficient pyrethroid extraction from eggplant via pH-salt-independent DSPE-HPLC for food safety analysis.  FOOD CHEMISTRY,      [PMID:40876161] [10.1016/j.foodchem.2025.146064]

9. Yu Shi, Ruixiao Ji, Jiaqiong Li, Minghong Du, Liyu Liu, Yating Guo, Yidong Wu.  (2025)  Mutation and Overexpression of CYP9A9a Confer High-Level Esfenvalerate Resistance in Spodoptera exigua.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41204635] [10.1021/acs.jafc.5c11971]