Rotenone

Title: Rotenone
CAS Registry Number: 83-79-4
CAS Name: [2R-(2a,6aa,12aa)]-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
Trademarks: Canex (Mallinckrodt Vet.); Noxfire (AgrEvo)
Molecular Formula: C23H22O6
Molecular Weight: 394.42
Percent Composition: C 70.04%, H 5.62%, O 24.34%
Literature References: Principal insecticidal constituent of derris root, cubé, etc. Powerful inhibitor of mitochondrial electron transport. Isoln from Lonchocarpus nicou (Aubl.) DC., Leguminosae: Geoffrey, Ann. Inst. Colon. Marseille 2, 1 (1895). Review of structure: La Forge et al., Chem. Rev. 12, 181 (1933); Butenandt, McCartney, Ann. 494, 17 (1932); King, Annu. Rep. Prog. Chem. 29, 186 (1932). Absolute configuration: Büchi et al., J. Chem. Soc. 1961, 2843; Nakazaki, Arakawa, Bull. Chem. Soc. Jpn. 34, 1246 (1961); Begley et al., Chem. Commun. 1975, 850. NMR spectrum: Crombie, Lown, ibid. 1962, 775. Total synthesis: Miyano et al., Agric. Biol. Chem. 25, 673 (1961); Miyano, J. Am. Chem. Soc. 87, 3958 (1965). Alternate synthesis: Crombie et al., J. Chem. Soc. Perkin Trans. 1 1973, 1277, eidem, Chem. Commun. 1979, 1142; I. Sasaki, K. Yamashita, Agric. Biol. Chem. 43, 137 (1979). Synthesis of stereoisomers: Unai, Yamamoto, ibid. 37, 897 (1973). Toxicology: Santi, Toth, Farmaco Ed. Sci. 20, 270 (1965). Toxicity data: J.-I. Fukami et al., Science 155, 713 (1967). Review: H. Fukami, M. Nakajima in Naturally Occurring Insecticides, M. Jacobson, D. G. Crosby, Eds. (Dekker, New York, 1971) pp 71-97; S. B. Soloway, Environ. Health Perspect. 14, 109-117 (1976); T. J. Haley, J. Environ. Pathol. Toxicol. 1, 315-337 (1978).
Properties: Orthorhombic, six-sided plates from trichloroethylene, mp 165-166° (dimorphic form, mp 185-186°). [a]D20 -228° (c = 2.22 in benzene). uv spectra: Büchi et al., loc. cit. Practically insol in water. Sol in alcohol, acetone, carbon tetrachloride, chloroform, ether, and many other organic solvents. Dec upon exposure to light and air. Colorless solns in organic solvents oxidize upon exposure and become yellow, orange and then deep red and may deposit crystals of dehydrorotenone and rotenonone which are toxic to insects. LD50 i.p. in mice: 2.8 mg/kg (Fukami); in rats (mg/kg): 132 orally; 6 i.v. (Soloway).
Melting point: mp 165-166°; mp 185-186°
Optical Rotation: [a]D20 -228° (c = 2.22 in benzene)
Toxicity data: LD50 i.p. in mice: 2.8 mg/kg (Fukami); in rats (mg/kg): 132 orally; 6 i.v. (Soloway)
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; numbness of mucous membranes; nausea, vomiting, abdominal pain; muscle tremors, incontinence, clonic convulsions, stupor. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 274. Inhalation may cause severe pulmonary irritation. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 366-368.
Use: Pesticide.
Therap-Cat-Vet: Ectoparasiticide.
Rotraxate Rottlerin Roxarsone Roxatidine Acetate Roxithromycin

Rotenone
Skeletal formula
Space-filling model
Identifiers
CAS number 83-79-4 YesY
PubChem 6758
ChemSpider 6500 N
UNII 03L9OT429T YesY
KEGG C07593 YesY
MeSH Rotenone
ChEBI CHEBI:28201 N
ChEMBL CHEMBL429023 N
Jmol-3D images Image 1
Properties
Molecular formula C23H22O6
Molar mass 394.41
Appearance Colorless to red
Density 1.27 g/cm3 @ 20 °C
Melting point 165−166 °C
Boiling point 210−220 °C at 0.5 mmHg
Solubility Soluble in ether and acetone, slightly soluble in ethanol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Rotenone is an odourless, colourless, crystalline ketonic chemical compound used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the seeds and stems of several plants, such as the jicama vine plant; and the roots of several members of Fabaceae.