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Deltamethrin

CAT: 0804-HY-B1971-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-B1971-02Size:10 mM - 1 mL
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Description
Deltamethrin (Decamethrin) is an orally active synthetic pyrethroid insecticide. Deltamethrin induces oxidative stress and results in inflammation and apoptosis via inhibiting Nrf2/HO-1 pathway. Deltamethrin has an anticancer effect by inducing apoptosis. Deltamethrin can be used extensively in pest control[1][2][3][4][5][6].
CAS Number
52918-63-5
Product Name Alternative
Decamethrin
UNSPSC
12352005
Hazard Statement
H301+H331
Target
Apoptosis; Bcl-2 Family; Calcium Channel; Caspase; Endogenous Metabolite; Interleukin Related; NF-κB
Type
Reference compound
Related Pathways
Apoptosis; Immunology/Inflammation; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/deltamethrin.html
Concentration
10mM
Purity
99.93
Solubility
DMSO : 100 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C([C@H]1C(C)(C)[C@H]1/C=C(Br)\Br)O[C@H](C#N)C2=CC=CC(OC3=CC=CC=C3)=C2
Molecular Formula
C22H19Br2NO3
Molecular Weight
505.20
Precautions
H301+H331
References & Citations
[1]Lu Q, et al. Deltamethrin toxicity: A review of oxidative stress and metabolism [J]. Environmental research, 2019, 170: 260-281.|[2]Chi C C, et al. Effect of the pesticide, deltamethrin, on Ca2+ signaling and apoptosis in OC2 human oral cancer cells [J]. Drug and Chemical Toxicology, 2014, 37 (1) : 25-31.|[3]Kumar A, et al. Deltamethrin induced an apoptogenic signalling pathway in murine thymocytes: exploring the molecular mechanism [J]. Journal of Applied Toxicology, 2014, 34 (12) : 1303-1310.|[4]Rehman H, et al. The modulatory effect of deltamethrin on antioxidants in mice [J]. Clinica Chimica Acta, 2006, 369 (1) : 61-65.|[5]Hossain M M, et al. Neuromechanical effects of pyrethroids, allethrin, cyhalothrin and deltamethrin on the cholinergic processes in rat brain [J]. Life sciences, 2005, 77 (7) : 795-807|[6]Yang X, et al. The heart as a target for deltamethrin toxicity: Inhibition of Nrf2/HO-1 pathway induces oxidative stress and results in inflammation and apoptosis [J]. Chemosphere, 2022, 300: 134479.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
Bax; Bcl-2; Caspase 3; IL-1

Chemical Information

Deltamethrin

Deltamethrin is a cyclopropanecarboxylate ester obtained by formal condensation between 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol. It is the active insecticide of the proinsecticide tralomethrin. It has a role as an antifeedant, an agrochemical, an EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor, a calcium channel agonist and a pyrethroid ester insecticide. It is a nitrile, an aromatic ether, an organobromine compound and a cyclopropanecarboxylate ester. It is functionally related to a cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid.

CAS Number52918-63-5
PubChem CID40585
IUPAC Nametrans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Molecular FormulaC22H19Br2NO3
Molecular Weight505.2
XLogP6.2
Topological Polar Surface Area59.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Heavy Atom Count28
Formal Charge0
Complexity643
SMILES
CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Br)Br)C
InChI
InChI=1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1
InChIKey
OWZREIFADZCYQD-NSHGMRRFSA-N
Chemical Structure
2D Structure
2D structure of Deltamethrin
CAS: 52918-63-5
CID: 40585
Formula: C22H19Br2NO3
MW: 505.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight505.2
XLogP36.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass504.97112
Monoisotopic Mass502.97317
Topological Polar Surface Area59.3 Ų
Heavy Atom Count28
Formal Charge0
Complexity643
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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