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ROTENONE

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ROTENONE Basic information

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:
394.41718
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
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ROTENONE Chemical Properties

Melting point:
159-164 °C(lit.)
Boiling point:
210-220 °C0.5 mm Hg(lit.)
alpha 
-115 º (C=1.4 IN CHLOROFORM)
Density 
1.1917 (rough estimate)
refractive index 
1.4593 (estimate)
storage temp. 
Store at RT
form 
White to off-white solid
Water Solubility 
15 mg l-1 (100 °C)
Merck 
14,8271
BRN 
6773081
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)
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Safety Information

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)

MSDS

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ROTENONE Usage And Synthesis

Chemical Properties

white or off-white powder

Chemical Properties

Rotenone is a colorless to red odorless crystal- line solid; a white crystalline solid when pure; oxidation will cause yellowing to bright red coloring. Odorless.

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

acaricide, ectoparasiticide, antineoplastic, mitochondrial poison

Uses

Rotenone is an broad spectrum insecticide that occurs naturally in seeds and stems of several plants.

Uses

Pesticide.

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.

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.

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.

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

ROTENONESupplier

Wuhan Haizheng Industry & Trade Development Co. Ltd Gold
Tel
027-8866 0053/88660577/88660578
Email
pb@whhz.cn
Raw material medicin reagent co.,Ltd Gold
Tel
025-57798860
Email
sales@njromanme.com
J & K SCIENTIFIC LTD.
Tel
400-666-7788 +86-10-82848833
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
+86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-62670440(Beijing)
Email
sh@meryer.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
86-21-50328103 * 801、802、803、804 Mobile:18930552037
Email
3bsc@sina.com