Rotenone(CAS No. 83-79-4)

Rotenone C23H22O6 (cas 83-79-4) Molecular Structure

83-79-4 Structure

Identification and Related Records

【Name】
Rotenone
【CAS Registry number】
83-79-4
【Synonyms】
(2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno(3,4-b)furo(2,3-h)chromen-6-one
tubatoxin
【EINECS(EC#)】
201-501-9
【Molecular Formula】
C23H22O6 (Products with the same molecular formula)
【Molecular Weight】
394.42
【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
【InChIKey】
JUVIOZPCNVVQFO-UHFFFAOYSA-N
【Canonical SMILES】
CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC
【Isomers smiles】
CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC
【MOL File】
83-79-4.mol

Chemical and Physical Properties

【Appearance】
white or off-white powder
【Density】
1.27(20℃)
【Melting Point】
159-164℃
【Boiling Point】
210-220℃ (0.5 mmHg)
【Refractive Index】
1.591
【Flash Point】
无意义
【Alpha】
-115 º (C=1.4 IN CHLOROFORM)
【Solubilities】
Sol in alcohol, acetone, carbon tetrachloride, chloroform, ether
Sol in acetic acid, acetone; sl sol in ethanol
15 PPM IN WATER AT 100 DEG C; SLIGHTLY SOL IN PETROLEUM OILS
SOL IN LIPIDS
Water solubility = 0.2 mg/l at 20 deg C
Soluble in ether, alcohol, acetone, and other organic solvents
【Color/Form】
ORTHORHOMBIC, SIX-SIDED PLATES FROM TRICHLOROETHYLENE
NEEDLES OR LEAVES (ALCOHOL, AQ ACETONE)
COLORLESS CRYSTALS
White crystals
Colorless to red, crystalline solid.
【Stability】
Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies.
【Storage temp】
Store at RT
【Spectral properties】
MAX ABSORPTION (ALCOHOL): 237 NM (LOG E= 4.15), 293.5 NM (LOG E= 4.25), 330.5 NM (LOG E= 3.80); SADTLER REFERENCE NUMBER: 373 (IR, PRISM)
Specific optical rotation: -228 deg at 20 deg C/D (concn by vol= 2.22 g in 100 ml benzene)
Specific optical rotation: -225.2 deg at 29.5 deg C/D (benzene)
Intense mass spectral peaks: 192 m/z (100%), 191 m/z (31%), 394 m/z (20%), 177 m/z (18%)
IR: 21008 (Sadtler Research Laboratories IR Grating Collection)
UV: 149 (Sadtler Research Laboratories Spectral Collection)
NMR: 16340 (Sadtler Research Laboratories Spectral Collection)
MASS: 5060 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
Strongly levorotatory in solution; specific rotation for D line 230 deg in benzene, 62 deg in ethylene dichloride.
【Computed Properties】
Molecular Weight:394.41718 [g/mol]
Molecular Formula:C23H22O6
XLogP3:4.1
H-Bond Donor:0
H-Bond Acceptor:6
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:394.141638
MonoIsotopic Mass:394.141638
Topological Polar Surface Area:63.2
Heavy Atom Count:29
Formal Charge:0
Complexity:664
Isotope Atom Count:0
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:6
Feature 3D Ring Count:5
Effective Rotor Count:4.2
Conformer Sampling RMSD:0.8
CID Conformer Count:4

Safety and Handling

【Hazard Codes】
T:Toxic;N:Dangerousfortheenvironment;
【Risk Statements】
R25;R36/37/38;R50/53
【Safety Statements 】
S22;S24/25;S36;S45;S60;S61
【HazardClass】
6.1(b)
【Safety】

Hazard Codes of Rotenone (CAS NO.83-79-4): ToxicT,DangerousN
Risk Statements: 25-36/37/38-50/53 
R25: Toxic if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 22-24/25-36-45-60-61 
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes. 
S36: Wear suitable protective clothing. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S60: This material and its container must be disposed of as hazardous waste. 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: DJ2800000
HazardClass: 6.1(b)
PackingGroup: III
Human poison by ingestion. Experimental poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. A skin and eye irritant. Acute poisoning causes numbness, nausea, vomiting, and tremors. Questionable carcinogen with experimental neoplastigenic, tumorigenic, and teratogenic data. Chronic exposure injures liver and kidneys. It is toxic to animals and very toxic to fish, but leaves no harmful residue on vegetable crops. When heated to decomposition it emits acrid smoke and irritating fumes. Used as an insecticide and as a fish poison.

 

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
Direct contact may cause irritation of the skin or conjunctiva.
【Cleanup Methods】
AQ SOLN OF ROTENONE WERE PERCOLATED THROUGH GLASS COLUMNS CONTAINING GRANULAR ACTIVATED CARBON. THE ABSORPTIVE CAPACITY OF THE ACTIVATED CARBON WAS 0.1 MG/G FOR ROTENONE.
1. Ventilate area of spill. 2. For small quantities, sweep onto paper or other suitable material, place in an appropriate container and burn in a safe place (such as a fume hood). Large quantities can be reclaimed; however, if this is not practical, dissolve in a flammable solvent (such as alc) and atomize in a suitable combustion chamber.
【Transport】
UN 2811
【Fire Potential】
Flammable if preheated.
【Formulations/Preparations】
Prentox Prenfish toxicant (5% rotenone); Prentox Synpren-Fish toxicant (2.5% rotenone and 2.5% piperonyl butoxide technical); Prentox, Rotenone Powder and Resins. Chem-Fish Synergized is 2.5% rotenone and 2.5% piperonyl butoxide; Chem-Fish Regular is 5%; Rotenone Resin (Blue Spruce) 45%; Rotenone Powder (Blue Spruce) at 5 to 7.5% pure. Rotenone Soln FK-11 (piperonyl butoxide 2.5% and rotenone 1.5%) (Fairfield American).
Formulations incl dusts of 0.75 to 1.5% concn, emulsifiable concentrates of 2 to 3% concn, wettable powder of 5% concn, soln of up to 5% concn, and resins of 30% concn intended for manufacture.
Grades: CP crystals; technical; also as extracts of derris and cube root.
Formulations include dusts of 0.75-5% concentration, crystalline preparations of 97% purity, and emulsified solution of up to 50% and resins of 42-45% concentration intended for manufacture.
... Noxfire (5% rotenone) tank mixed with Roussel Bio Corp piperonyl butoxide EC92% for insects which have become resistant to pyrethroid-based insecticides. Nusyn-Noxfish (2.5% rotenone/2.5% piperonyl butoxide technical). Foliafume E.C. (pyrethrins) ... PB-Nox (4.3% rotenone/8.6% piperonyl butoxide).
Dust, emulsifiable concentrate, wettable powder
【Reactivities and Incompatibilities】
Strong oxidizers, alkalis.
【Other Preventative Measures】
DO NOT REUSE EMPTY CONTAINER. DESTROY IT BY PERFORATING & CRUSHING. BURY OR DISCARD IN SAFE PLACE AWAY FROM WATER SUPPLIES.
Wear appropriate clothing to prevent repeated or prolonged skin contact. Wear eye protection to prevent any reasonable probability of eye contact. Employees should wash promptly when skin is wet or contaminated. Work clothing should be changed daily if it is possible that clothing is contaminated. Remove nonimpervious clothing promptly if wet or contaminated.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
【Protective Equipment and Clothing】
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Recommendations for respirator selection. Max concn for use: 50 mg/cu m. Respirator Class(es): Any chemical cartridge respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter. Any supplied-air respirator.
Recommendations for respirator selection. Max concn for use: 125 mg/cu m. Respirator Class(es): Any supplied-air respirator operated in a continuous flow mode. Any powered, air-purifying respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter.
Recommendations for respirator selection. Max concn for use: 250 mg/cu m. Respirator Class(es): Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter. Any powered, air-purifying respirator with a tight-fitting facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. Any supplied-air respirator that has a tight-fitting facepiece and is operated in a continuous-flow mode. Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece.
Recommendations for respirator selection. Max concn for use: 2500 mg/cu m. Respirator Class(es): Any supplied-air respirator operated in a pressure-demand or other positive-pressure mode.
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: Respirator Class(es): Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive pressure mode. Any supplied-air respirator with a full facepiece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode.
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Class(es): Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter. Any appropriate escape-type, self-contained breathing apparatus.
Wear rubber gloves for all handling ... Wear canister-type mask /if combustion occurs/. ... Self-contained breathing apparatus, rubber gloves, hats, suits, and boots must be worn /if extinguishing/.
【Specification】

white or off-white powder
Safety Statements:22-24/25-36-45-60-61
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
【Octanol/Water Partition Coefficient】
Log P = 4.10
【Disposal Methods】
1. By making packages of rotenone in paper or other flammable material and burning in a suitable combustion chamber. 2. By dissolving rotenone in a flammable solvent (such as alcohol) and atomizing in a suitable combustion chamber.
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

The current methods of extraction of rotenone and other natural insecticides from their plant sources are enhanced by mixing the known solvents such as dialkyl phthalates, dichloromethane, or trichlormethane at 10-70% with 30-90% of (C)8-20 aliphatic acid esters with (C)1-16 alkyls or alkenyls. Thus, agitation of 100 g dichloromethane at 45 deg for 0.5 hr, followed by removal of dichloromethane by distillation gave an extraction containing 14% rotenone plus 64% octyl stearate. The extraction was diluted to 7% rotenone and emulsified by a surfactant for spraying plants.
Pure crystalline rotenone is prepared by extracting powdered rotenone containing roots with a solvent, eg ether or carbon tetrachloride, and concentrating the solution to produce crystallization.
Produced in Malaysia from Derris elipitica roots and in South America from Lonchocarpus roots; white crystalline solid separated from the root by solvent extraction followed by crystallization.
U.S. Production

(1971) 1.4X10+7 GRAMS (CONSUMPTION)
(1974) 2.27X10+7 GRAMS (CONSUMPTION)
Consumption Patterns

21% USED ON CROPS; 78% USED ON LIVESTOCK; 1% FOR OTHER APPLICATIONS (1975)
【Sampling Procedures】
NIOSH Method 5007. Analyte: Rotenone. Matrix: Air. Sampler: Filter (1 um polytetrafluoroethylene membrane). Flow Rate: 1 to 3 liters/min. Sample Size: 100 liters. Shipment: Routine. Sample Stability: At least 7 days at 25 deg C in dark.

Biomedical Effects and Toxicity

【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.
【Pharmacological Action】
- Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
- Chemical agents that uncouple oxidation from phosphorylation in the metabolic cycle so that ATP synthesis does not occur. Included here are those IONOPHORES that disrupt electron transfer by short-circuiting the proton gradient across mitochondrial membranes.
【Therapeutic Uses】
Vet: acaricide, ectoparasiticide
MEDICATION: ANTIPROTOZOAL; MEDICATION (VET): GRUBICIDE; HAS BEEN USED FOR DEMODECTIC MANGE
/Former use/: Rotenone has been used topically for treatment of head lice, scabies, and other ectoparasites, but the dust is highly irritating to the eyes (potentially causing conjunctivitis), the skin (causing contact dermatitis), and to the upper respiratory tract (causing rhinitis) and throat (linked with pharyngitis).
【Biomedical Effects and Toxicity】
EXHALATION OF (14)CO2 WITHIN 50 HR AFTER ORAL OR IP DOSING OF 5'BETA-[3-METHOXY-(14)C]ROTENONE TO MICE & RATS RESPECTIVELY WAS 27 & 12.5%. /5'BETA-[3-METHOXY-(14)C]ROTENONE/
GI ABSORPTION IS PRESUMABLY SLOW & INCOMPLETE. ... FATS & OILS PROMOTE ABSORPTION.
One mechanism of detoxication of natural rotenone ... or one of its metabolites was found to be 3-O-demethylation, as indicated by recovery of 27 and 13% of the admin radiocarbon as 14C-labeled carbon dioxide within 50 hr after admin to mice and rats, respectively. Within the same period, the animals excreted 7-17% of the radioactivity in their urine ... In another study, 19.5 and 20.0% of the dose were recovered in the urine of mice and rats, respectively, within 24 hr after oral admin ... .

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
PHOTODECOMPOSITION PRODUCTS FORMED BY IRRADIATION OF ROTENONE...EXPOSED TO LIGHT ON GLASS SURFACES OR ON BEAN LEAVES: O-DEMETHYL ROTENONE; 6ALPHABETA, 12ALPHAALPHA-ROTENOLONE; DEHYDRO-ROTENONE; 6ALPHABETA, 12ALPHABETA-ROTENOLONE; ROTENONONE; 6',7'-EPOXYROTENONE; 6',7'-EPOXY-6ALPHABETA, 12ALPHABETA-ROTENOLONE.
The material deteriorates rapidly in sun, air, and water. Formulations lose their effectiveness within a week after application.
Rotenone is stable in the solid state but degradation is accelerated by the presence of organic solvents. Air and light are required. The rate of decomposition produced the yellow crystalline dehydrorotenone and rotenonone and a complex mixture of other oxidation products of rotenone.
The rate constant for the vapor-phase reaction of rotenone with photochemically-produced hydroxyl radicals has been estimated as 318X10-12 cu cm/molecule-sec at 25 deg(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 0.05 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). When exposed to light and air, rotenone undergoes hydroxylation at C-7, followed by dehydration to form dehydrorotenone. These reactions inactivate rotenone after 5 to 10 days of exposure to sunlight. In a study of photosensitizers, rotenone was found to be the most effective compound for enhancing the photochemical alteration of dieldrin to photodieldrin when applied to bean plants at levels as low as 0.3 ppm(4). In another study, irradiation of rotenone in oxygenated methanol solution with UV light yielded the following crystalline products: O-demethylrotenone, 6ab,-12ab-rotenolone, rotenonone, 4,5-dimethoxysalicylic acid, rissic acid, and tubaic acid(5).

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