Structure via PubChem · Public domain (PubChem)
rotenone
Sign in to saveAlso known as 1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methyl-ethenyl)-[1]benzopyrano [3,4-b]furo[2,3-h][1] benzopyran-6(6aH)-one, [2R-(2alpha,6aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6aH)-one, barbasco, 5'beta-rotenone, canex, (-)-cis-rotenone, (-)-rotenone, noxfire
Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids. Rotenone is approved for use as a piscicide to remove alien fish species, see Uses. It has also been used as a broad-spectrum insecticide, but its use as an insecticide has been banned in many countries.
Chemical data
- Formula
- C23H22O6
- Molecular weight
- 394.4 g/mol
- IUPAC name
- (1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
- SMILES
- CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC
- InChIKey
- JUVIOZPCNVVQFO-HBGVWJBISA-N
- XLogP
- 4.1
- Polar surface area
- 63.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
8,173 papers- Rotenone: from modelling to implication in Parkinson's disease.Folia neuropathologica · 2019
- Mitochondrial complex I inhibitor rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production.The Journal of biological chemistry · 2003
- ROS Regulate Rotenone-induced SH-SY5Y Dopamine Neuron Death Through Ferroptosis-mediated Autophagy and Apoptosis.Molecular neurobiology · 2025
- Effect of Rotenone on the Neurodegeneration among Different Models.Current drug targets · 2024
- Using Rotenone to Model Parkinson's Disease in Mice: A Review of the Role of Pharmacokinetics.Chemical research in toxicology · 2021
via PubMed
Wikidata facts
- Mass
- 394.142
Show 11 more facts
- immediately dangerous to life or health
- 2500
- melting point
- 330
- chemical formula
- C₂₃H₂₂O₆
- NIOSH Pocket Guide ID
- 0548
- density
- 1.27
- vapor pressure
- 0.00004
- time-weighted average exposure limit
- 5
- canonical SMILES
- CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC
- isomeric SMILES
- CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC
- Commons category
- Rotenone
- boiling point
- 215
via Wikidata · CC0
~15 min read
Article
14 sectionsContents
- Discovery
- Uses
- Use as piscicide in fisheries management
- Rotenone degradation and ecosystem impact
- Notable administrations as piscicide
- Deactivation
- Use as insecticide
- Mechanism of action
- Presence in plants
- Mammalian toxicity
- Parkinson's disease
- See also
- References
- External links
Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids. Rotenone is approved for use as a piscicide to remove alien fish species, see Uses. It has also been used as a broad-spectrum insecticide, but its use as an insecticide has been banned in many countries.
== Discovery ==