ChemicalBook > CAS DataBase List > Rotenone

Rotenone

Rotenone Structure
Rotenone
  • CAS No.83-79-4
  • Chemical Name:Rotenone
  • CBNumber:CB6397762
  • Molecular Formula:C23H22O6
  • Formula Weight:394.42
  • MOL File:83-79-4.mol
Rotenone Property
  • Melting point: :159-164 °C (lit.)
  • Boiling point: :210-220 °C/0.5 mmHg (lit.)
  • alpha  :-115 º (C=1.4 IN CHLOROFORM)
  • Density  :1.1917 (rough estimate)
  • refractive index  :1.4593 (estimate)
  • storage temp.  :Keep in dark place,Inert atmosphere,Room temperature
  • Water Solubility  :15 mg l-1 (100 °C)
  • form  :White to off-white solid
  • Merck  :14,8271
  • BRN  :6773081
  • Stability: :Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies.
  • InChIKey :JUVIOZPCNVVQFO-HBGVWJBISA-N
  • EWG's Food Scores :1-2
  • FDA UNII :03L9OT429T
  • NIST Chemistry Reference :Rotenone(83-79-4)
  • EPA Substance Registry System :Rotenone (83-79-4)
  • Pesticides: Freedom of Information Act (FOIA) :Rotenone
Safety
  • Hazard Codes  :T,N
  • Risk Statements  :25-36/37/38-50/53
  • Safety Statements  :22-24/25-36-45-60-61
  • RIDADR  :UN 2811 6.1/PG 3
  • WGK Germany  :3
  • RTECS  :DJ2800000
  • HazardClass  :6.1(b)
  • PackingGroup  :III
  • HS Code  :29329990
  • Hazardous Substances Data :83-79-4(Hazardous Substances Data)
  • Toxicity :LD50 i.p. in mice: 2.8 mg/kg (Fukami); in rats (mg/kg): 132 orally; 6 i.v. (Soloway)
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H301-H315-H319-H335-H410
  • Precautionary statements P261-P273-P301+P310-P305+P351+P338-P501-P280-P301+P310+P330-P337+P313-P391
Rotenone Price More Price(12)
  • Brand: Sigma-Aldrich
  • Product number: 557368
  • Product name : Rotenone - CAS 83-79-4 - Calbiochem
  • Purity: A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I (NADH-CoQ reductase) of the respiratory chain.
  • Packaging: 1 g
  • Price: $85.65
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 557368
  • Product name : Rotenone
  • Purity: 
  • Packaging: 1gm
  • Price: $86
  • Updated: 2019/12/02
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 45656
  • Product name : Rotenone
  • Purity: PESTANAL , analytical standard
  • Packaging: 250mg
  • Price: $22.3
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: R0090
  • Product name : Rotenone
  • Purity: 
  • Packaging: 5G
  • Price: $120
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: R0090
  • Product name : Rotenone
  • Purity: 
  • Packaging: 25G
  • Price: $414
  • Updated: 2021/03/22
  • Buy: Buy

Rotenone Chemical Properties,Usage,Production

  • Description The principal source of rotenone is the tuber root of Derris elliptica; however, it is also extracted from the roots of Derris mallaccensis, Lonchocarpus utilis, and Lonchocarpus uruca. Rotenone is both a stomach and contact poison for arthropods. Its fast knockdown action is attributed to decreasing the availability of nicotinamide adenine dinucleotide to serve as a cofactor in various biochemical pathways including the Krebs cycle, thereby inhibiting the mitochondrial respiratory enzymes.
  • Chemical Properties Rotenone is a colorless to red odorless crystalline solid; a white crystalline solid when pure; oxidation will cause yellowing to bright red coloring. Odorless.
    Rotenone
    Rotenone is related to isoflavonoid compounds derived from the roots of Derris spp., Lonchocarpus spp., and Tephrosia spp., found primarily in Southeast Asia, South America, and East Africa. The isolated compound is an odorless, colorless to red crystalline solid. It is insoluble in water and has a very low vapor pressure (U.S. EPA, 2007; HSDB, 2012a).
  • Uses Rotenone is used for the control of aphids, thrips, suckers and other insects in fruit and vegetable cultivation. It is also used for control in buildings, for the control of lice, ticks and warble fly on animals and as a piscicide for the management of fish populations.
  • Uses Rotenone is an broad spectrum insecticide that occurs naturally in seeds and stems of several plants. Rotenone was first registered in 1947 and is currently used exclusively to kill fish (U.S. EPA, 2007). In 2006, registrants voluntarily canceled all livestock, residential and home owner uses, domestic pet uses, and all other uses except for piscicide uses. Currently the main uses include fish management strategies to remove nonnative fish species from lakes, ponds, or streams and in catfish aquaculture prior to stocking ponds with with fry to remove undesirable fish species (U.S. EPA, 2006d).
    Rotenone has been historically used by native people to paralyze fish for capture and consumption. Outside the United States, the compound is still used to control insects in fruit and vegetable cultivation and for control of fire ants and mosquito larvae in pond water (HSDB, 2012a).
  • Uses Insecticide; lotion for chiggers; emulsion for scabies.
  • 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).
  • 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. .
  • Hazard Toxic by ingestion, overexposure can be fatal, irritant to skin, eyes and upper respiratory tract. Central nervous system impairment. Ques- tionable carcinogen.
  • Health Hazard Rotenone is an irritant and affects the nervous system, causing convulsions.
  • Fire Hazard Flash point data for ROTENONE are not available; however, ROTENONE is probably combustible.
  • Agricultural Uses Insecticide, Acaracide, Veterinary medicine: The use of rotenone as a pesticide to kill invasive fish species is currently the only allowable use of this pesticide. Rotenone is a selective, nonspecific botanical insecticide with some acaricidal properties, and has been used in agriculture to control insects on vine fruit, flowers and vegetables. Registered for use in the U.S.A U.S. EPA restricted Use Pesticide (RUP) due to acute inhalation, acute oral, and aquatic toxicity. Agricultural and residential uses and all food uses were voluntarily cancelled in 2006[83]. In 2006, registrants requested voluntarily cancellation of all livestock, residential and home owner uses, domestic pet uses, and all other uses except for pesticide uses. In 2011 the use of this pesticide chemical was linked to Parkinson’s disease. Not listed for use in EU countries.
  • Trade name ACME® Rotenone; AROL GORDON DUST®; BARBASCO®; BONIDE CUKE AND MELON DUST®; CENOL GARDEN DUST®; CHEM FISH®; CHEM-MITE®; CUBE®; CUBE EXTRACT®; CUBEPULVER®; CUBEROL®; CUBE ROOT®; CUBOR®; CUREX FLEA DUSTER®; DACTINOL®; DERIL®; DERRIN®; DERRIS®; DRI-KIL®; ENT-133®; EXTRAX®; FISH-TOX®; GREEN CROSS WARBLE POWDER®; HAIARI®; LIQUID DERRIS®; MEXIDE®; NICOULINE®; NOXFIRE®; NOXFISH®; PARADERIL®; POWDER AND ROOT®; PRENTOX®; PRO-NOX FISH®; RO-KO®; RONONE®; ROTACIDE®; ROTEFIVE®; ROTEFOUR®; ROTESSENOL®; SINID®; TOX-R®; TUBATOXIN®
  • 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.
  • Potential Exposure A potential danger to those involved in extraction from derris root, formulation or application of this insecticide. Rotenone is used as a pharmaceutical and veterinary drug.
  • Carcinogenicity In human lymphocyte culture assays rotenone did not increase the frequency of chromosomal aberrations or sister chromatid exchanges but did cause an increase in the frequency of binucleated micronuclei and a delay in cell cycle.
  • Environmental Fate Rotenone released to the atmosphere will exist as particulates due to the extremely low vapor pressure. Particulate-phase rotenone will be removed from the atmosphere by wet and dry deposition and may be degraded by direct photolysis. It is mobile to moderately mobile in soil and sediment and volatilization from soil surfaces is not expected to occur to any extent. If released to water, rotenone generally degrades quickly through abiotic (hydrolytic and photolytic) mechanisms, with half-lives of a few days to several weeks or longer depending on water temperature (U.S. EPA, 2007; HSDB, 2012a).
    Rotenone has a relatively low potential for bioconcentration in aquatic organisms (Bioconcentration Factor (BCF) < 30X) (U.S. EPA, 2007).
  • Metabolic pathway By hepatic microsomal incubations from rainbow trout with 14C-rotenone, three major and several minor metabolites of rotenone are observed, the major ones being identified as rotenolone and two epimeric forms of 6' ,7' -dihydroxyrotenone.
  • Shipping UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
  • Degradation Rotenone is racemised in base to less insecticidal compounds and it is decomposed on exposure to light and air (PM). Photochemical degradation in methanol of seven rotenoids isolated from Tephrosa villosa (Krupadanam et al., 1978) resulted generally in much decomposition but rotenone was relatively stable under the conditions used. When the compound was used as an insecticidal spray it was converted by light and air into dehydro-rotenone (2) and rotenonone (3). These structures are shown in Scheme 1.
  • Toxicity evaluation Rotenone inhibits the electron transport chain by blocking transport between the flavoprotein and the ubiquinone. The oxidation of pyruvate in rat mitochondria is virtually completely blocked by rotenone in vitro (<1 mmol l-1 concentration). Cell death occurs by apoptosis due to excess generation of free radicals. In addition, rotenone causes a definite anesthetic effect when it comes in contact with nerve axons. Death appears to occur due to depression of the respiratory center.
    Rotenone is toxic to insects, humans, animals, and fish. Rotenone exerts selective toxicity, as it is highly toxic to fish because of its rapid absorption from the GI tract in comparison to mammalian species in which it is poorly absorbed. The selective toxicity of rotenone in insects and fish versus mammals can also be explained based on the metabolism of this compound. Rotenone converts to highly toxic metabolites in large quantities in insects and fish, while it converts to nontoxic metabolites in mammals.
  • Incompatibilities Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and alkalies.
  • Waste Disposal Rotenone is decomposed by light and alkali to less insecticidal products. It is readily detoxified by the action of light and air. It is also detoxified by heating; 2 hours @ 100 ? C results in 76% decomposition. Oxidation products are probably nontoxic. Incineration has been recommended as a disposal procedure. Burial with lime would also present minimal danger to the environ- ment . In accordance with 40CFR165, follow recommen- dations for the disposal of pesticides and pesticide containers. Must be disposed properly by following pack- age label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Rotenone Preparation Products And Raw materials
Raw materials
Preparation Products
Global(267)Suppliers
  • Supplier:
    Hangzhou FandaChem Co.,Ltd.
  • Tel:008615858145714
  • Fax:+86-571-56059825
  • Email:fandachem@gmail.com
  • Country:CHINA
  • ProdList:8909
  • Advantage:55
  • Supplier:
    ATK CHEMICAL COMPANY LIMITED
  • Tel:+86 21 5161 9050/ 5187 7795
  • Fax:+86 21 5161 9052/ 5187 7796
  • Email:ivan@atkchemical.com
  • Country:CHINA
  • ProdList:26751
  • Advantage:60
  • Supplier:
    career henan chemical co
  • Tel:+86-371-86658258
  • Fax:
  • Email:sales@coreychem.com
  • Country:CHINA
  • ProdList:29954
  • Advantage:58
  • Supplier:
    Accela ChemBio Inc.
  • Tel:(+1)-858-699-3322
  • Fax:(+1)-858-876-1948
  • Email:info@accelachem.com
  • Country:United States
  • ProdList:19969
  • Advantage:58
  • Supplier:
    Xi'an Kono chem co., Ltd.,
  • Tel:13289246953 029-86107037
  • Fax:
  • Email:info@konochemical.com
  • Country:CHINA
  • ProdList:3000
  • Advantage:58
  • Supplier:
    Chongqing Chemdad Co., Ltd
  • Tel:+86-13650506873
  • Fax:
  • Email:sales@chemdad.com
  • Country:CHINA
  • ProdList:37282
  • Advantage:58
83-79-4, RotenoneRelated Search:
  • (-)-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)]-
  • [1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6ah)-one,1,2,12,12a-tetrahydr
  • [1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6ah)-one,1,2,12,12a-tetrahydro
  • [2r-(2alpha,6aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methyl
  • [2theta-(2alpha,6aalpha,12aalpha)]--9-dimethoxy-2-(1-methylethenyl)-
  • 1,2,12,12aalpha-tetrahydro-2a-isopropenyl-8,9-dimethoxy[1]benzopyrano[3,4-b]fu
  • 1,2,12,12a-tetrahydro-2-isopropenyl-8,9-dimethoxy[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)-[1]benzopyrano[3,4-b]f
  • 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
  • Rotenone(Barbasco)
  • Rotenone - CAS 83-79-4 - Calbiochem
  • 2,6a,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(1H)-one
  • 2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-H]chromen-6(6ah)-one
  • 4-b]furo[2,3-h][1]benzopyran-6(6aH)-one,1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-,[[1]Benzopyrano[3
  • 5’-beta-rotenone
  • 5’beta-rotenone
  • 5'beta-Rotenone
  • 9-dimethoxy--2-alpha-isopropenyl-
  • 9-dimethoxy-etrahydro-2alpha-isopropenyl-
  • Barbasco
  • Derris resins
  • Derris root
  • derris(insecticide)
  • derrisextract,e.c.(2.5%)
  • Dri-kil
  • ENT 133
  • ent133
  • ethenyl)[1]benzopyrano[3,4-b]furo[2,3-h]benzopyran-6(6ah)-one
  • Extrax
  • Fish-Tox
  • Foliafume
  • foliafumee.c.
  • FS derris
  • gerane
  • Green cross warble
  • Green Cross Warble Powder
  • greencrosswarblepowder
  • Haiari
  • Hydrogenated rotenone
  • Liquid Derris
  • liquidderris
  • Mexide
  • NCI-C55210
  • nekoe
  • Nicouline
  • Noxfish
  • Nusyn
  • Nusyn-noxfish
  • o-8,9-dimethoxy-2-(1-methylethenyl)-,[2r-(2.alpha.,6a.alpha.,12a.alpha)]
  • Paraderil
  • Pb-nox