Rotenone

Rotenone

Names
IUPAC name (5′′R)-4′,5′-Dimethoxy-5′′-(prop-1-en-2-yl)-4′′,5′′-dihydrofuro[2′′,3′′:7,8]rotenan-4-one
Systematic IUPAC name (2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydro[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Other names Tubatoxin, Paraderil
Identifiers
CAS Number	83-79-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28201 N
ChEMBL	ChEMBL429023 N
ChemSpider	6500 N
ECHA InfoCard	100.001.365
KEGG	C07593 Y
MeSH	Rotenone
PubChem CID	6758
UNII	03L9OT429T Y
CompTox Dashboard (EPA)	DTXSID6021248
InChI InChI=1/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
SMILES CC(=C)[C@H]1Cc2c(O1)ccc3c2O[C@@H]4COc5cc(OC)c(OC)cc5[C@@H]4C3=O
Properties
Chemical formula	C23H22O6
Molar mass	394.423 g·mol−1
Appearance	Colorless to red crystalline solid[1]
Odor	odorless[1]
Density	1.27 g/cm3 @ 20 °C
Melting point	165 to 166 °C (329 to 331 °F; 438 to 439 K)
Boiling point	210 to 220 °C (410 to 428 °F; 483 to 493 K) at 0.5 mmHg
Solubility	Soluble in ether and acetone, slightly soluble in ethanol
Vapor pressure	<0.00004 mmHg (20°C)[1]
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	60 mg/kg (oral, rat) 132 mg/kg (oral, rat) 25 mg/kg (oral, rat) 2.8 mg/kg (oral, mouse)[2]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 mg/m3[1]
REL (Recommended)	TWA 5 mg/m3[1]
IDLH (Immediate danger)	2500 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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. When absorbed through the gills, rotenone disrupts cellular respiration in fish, leading to their death. Due to this, it has become a key tool in managing ecosystems affected by invasive or unwanted fish species, and as of 2024 there are no viable options that can replace its versatile value in fish removal actions. Rotenone has also been used as a broad-spectrum insecticide, but due to its high toxicity its use as an insecticide has been banned in some countries. Its value in ecosystem restoration is appreciated due to its rapid degradation, when exposed to light and warm temperatures, making it a temporary measure with minimal long-term environmental effects, see Rotenone and Ecosystem Impact.