Structure via PubChem · Public domain (PubChem)
allethrin
Sign in to saveAlso known as 3-allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate, 3-allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemate, 3-allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylate, 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, Pynamin, (+/-)-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one ester, Allethrins
thumb|right|300px|Allethrin I (R = −CH3)Allethrin II (R = −COOCH3) The allethrins are a group of related synthetic compounds used in insecticides. They are classified as pyrethroids, i.e. synthetic versions of pyrethrin, a chemical with insecticidal properties found naturally in Chrysanthemum flowers. They were first synthesized in the United States by Milton S. Schechter in 1949. Allethrin was the first pyrethroid.
Chemical data
- Formula
- C19H26O3
- Molecular weight
- 302.4 g/mol
- IUPAC name
- (2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
- SMILES
- CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)CC=C
- InChIKey
- ZCVAOQKBXKSDMS-UHFFFAOYSA-N
- XLogP
- 4.8
- Polar surface area
- 43.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
327 papers- Allethrin Promotes Apoptosis and Autophagy Associated with the Oxidative Stress-Related PI3K/AKT/mTOR Signaling Pathway in Developing Rat Ovaries.International journal of molecular sciences · 2022
- Allethrin and prallethrin stimulates MUC5AC expression through oxidative stress in human airway epithelial cells.Biochemical and biophysical research communications · 2018
- Allethrin toxicity causes reproductive dysfunction in male rats.Environmental toxicology · 2017
- Allethrin-induced genotoxicity and oxidative stress in Swiss albino mice.Mutation research · 2012
- Novel mechanism and degradation kinetics of allethrin using Bacillus megaterium strain HLJ7 in contaminated soil/water environments.Environmental research · 2022
via PubMed
Wikidata facts
- Subclass of
- pyrethrin
- Mass
- 302.188
Show 7 more facts
- chemical formula
- C₁₉H₂₆O₃
- found in taxon
- Tanacetum partheniifolium
- canonical SMILES
- CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)CC=C
- Commons category
- Allethrins
- subject has role
- insecticide
- MCN code
- 2916.20.13
- different from
- Bioallethrin
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Chemical structure
- Toxicity
- Notes
- References
- External links
thumb|right|300px|Allethrin I (R = −CH3)Allethrin II (R = −COOCH3) The allethrins are a group of related synthetic compounds used in insecticides. They are classified as pyrethroids, i.e. synthetic versions of pyrethrin, a chemical with insecticidal properties found naturally in Chrysanthemum flowers. They were first synthesized in the United States by Milton S. Schechter in 1949. Allethrin was the first pyrethroid.
They are commonly used in ultra-low volume sprays for outdoor mosquito control, and in many household insecticides such as RAID, as well as mosquito coils.
Excerpted from Wikipedia’s “allethrin” article, available under the CC BY-SA 4.0 licence.