Product Name:	ROTENONE
Synonyms:	(-)-cis-rotenone;(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aalphaH)-one, 1,2,12,12aalpha-tetrahydro-2alpha-isopropenyl-8,9-dimethoxy-;(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-alpha-iospropenyl-8,9-dimethoxy-;(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-alpha-isopropenyl-8,9-dimethoxy-;(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6alphah)-one,1,2,12,12aalpha-t;(2r-(2alpha,6aalpha,12aalpha))--9-dimethoxy-2-(1-methylethenyl)-;(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;[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2alpha,6aalpha,12aalpha)]-
CAS:	83-79-4
MF:	C23H22O6
MW:	394.42
EINECS:	201-501-9
Product Categories:	Miscellaneous Natural Products;Alpha sort;BotanicalsPesticides&Metabolites;Q-ZAnalytical Standards;BotanicalsAnalytical Standards;Alphabetic;Insecticides;Pesticides;R;Mitochondrial Inhibitors;Cell Stress;Nitric Oxide and Cell Stress;Asymmetric Synthesis;Chiral Building Blocks;Complex Molecules;Inhibitors
Mol File:	83-79-4.mol

Melting point	159-164 °C(lit.)
Boiling point	210-220 °C0.5 mm Hg(lit.)
alpha	-115 º (C=1.4 IN CHLOROFORM)
storage temp.	Store at RT
Merck	14,8271
Stability:	Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies.
NIST Chemistry Reference	Rotenone(83-79-4)
EPA Substance Registry System	[1]Benzopyrano[3, 4-b]furo[2,3-h][1]benzopyran- 6(6aH)-one, 1,2,12,12a-tetrahydro-8,9- dimethoxy-2-(1-methylethenyl)-, (2R,6aS,12aS)-(83-79-4)

Chemical Properties	white or off-white powder
Uses	acaricide, ectoparasiticide, antineoplastic, mitochondrial poison
Uses	Rotenone is an broad spectrum insecticide that occurs naturally in seeds and stems of several plants.
Definition	ChEBI: A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy group (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).
Uses	Pesticide.
General Description	Colorless to brownish crystals or a white to brownish-white crystalline powder. Has neither odor nor taste.
Air & Water Reactions	ROTENONE decomposes upon exposure to light or air. Insoluble in water.
Reactivity Profile	ROTENONE is readily oxidized in the presence of alkalis. ROTENONE is incompatible with oxidizers. .
Fire Hazard	Flash point data for ROTENONE are not available; however, ROTENONE is probably combustible.
Biological Activity	Mitochondrial electron transport chain inhibitor (IC 50 = 1.7 - 2.2 μ M at complex I). Inhibits NADH oxidation by cardiac sarcoplasmic reticulum (IC 50 = 3.4 nM). Commonly used pesticide and induces Parkinsonism in animal models. Cell-permeable and brain penetrant.

ROTENONE

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