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Rotenone

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Name

Rotenone

EINECS 201-501-9
CAS No. 83-79-4 Density 1.271 g/cm3
PSA 63.22000 LogP 3.70330
Solubility 0.2 mg/L at 20 °C in water Melting Point 159-164 °C
Formula C23H22O6 Boiling Point 559.8 °C at 760 mmHg
Molecular Weight 394.424 Flash Point 244.6 °C
Transport Information UN 2811 6.1/PG 3 Appearance white or off-white powder
Safety 22-24/25-36-45-60-61 Risk Codes 25-36/37/38-50/53
Molecular Structure Molecular Structure of 83-79-4 (ROTENONE) Hazard Symbols DangerousN,ToxicT
Synonyms

Rotenone(7CI);[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-(2a,6aa,12aa)]-;[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aaH)-one, 1,2,12,12aa-tetrahydro-2a-isopropenyl-8,9-dimethoxy-(8CI);(-)-Rotenone;(-)-cis-Rotenone;5'b-Rotenone;Cube-Pulver;Dactinol;Deril;Derrin;Derris;Derris (insecticide);Dri-kil;Liquid Derris;NSC 26258;NSC 8505;Nicouline;Noxfish;Paraderil;Rotenone;

Article Data 16

Rotenone Synthetic route

23355-70-6

(6aS,12aS,5'R)-rotenone enol acetate

83-79-4

rotenone

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;83%
34487-52-0

(2R,6aS,12aS)-8-hydroxy-9-methoxy-2-(prop-1-en-2-yl)-1,2,12,12a- tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

83-79-4

rotenone

Conditions
ConditionsYield
In diethyl ether59%
30462-22-7

2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

A

83-79-4

rotenone

B

549-22-4

Isorotenone

Conditions
ConditionsYield
With Burgess Reagent In toluene for 0.5h; Reflux;A 50%
B 13%
With Burgess Reagent In toluene for 0.5h; Inert atmosphere; Reflux;A 50%
B 13%
30462-22-7

2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

83-79-4

rotenone

Conditions
ConditionsYield
With pyridine; thionyl chloride at 0℃; for 0.5h;40%
123000-20-4

(6aS,12aR,5'R)-(trans)-(+)-rotenone

83-79-4

rotenone

Conditions
ConditionsYield
With hydrogenchloride In methanol; chloroform for 2h;
123000-19-1

(6aR,12aS,5'R)-rotenone

83-79-4

rotenone

Conditions
ConditionsYield
With hydrogenchloride In methanol; chloroform
With hydrogenchloride In methanol; chloroform epimerisation;
509-96-6

12a-hydroxyrotenone

83-79-4

rotenone

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride; zinc In water at 100℃; for 2.5h;20 mg
3466-09-9

6a,12a-dehydrorotenone

83-79-4

rotenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 31 mg / diisobutyaluminium hydride / toluene; tetrahydrofuran / 1 h / -78 °C
2: aq. HCl / methanol; CHCl3 / 2 h
View Scheme
Multi-step reaction with 2 steps
1: di-isobutylaluminium hydride
2: hydrogen chloride / methanol; CHCl3 / epimerisation
View Scheme
15130-81-1

(6aS,12aS,5′R)-rotenone-6′-norketone

A

83-79-4

rotenone

B

aqueous-alcoholic KOH-solution

aqueous-alcoholic KOH-solution

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / conc. H2SO4 / 3 h / Heating
2: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h
3: 83 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
23295-59-2, 23295-65-0

rotenone 6'-norketone enol acetate

A

83-79-4

rotenone

B

aqueous-alcoholic KOH-solution

aqueous-alcoholic KOH-solution

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h
2: 83 percent / conc. HCl / methanol / 2 h / Heating
View Scheme

Rotenone History

Emmanuel Geoffroy first isolated rotenone from a specimen of Rotenone (CAS NO.83-79-4), now called Lonchocarpus nicou, while traveling in French Guiana.He wrote about this research in his thesis, published posthumously in 1895 after his death from a parasitic disease.Researchers later determined that the substance which Geoffroy termed nicouline was identically rotenone.

Rotenone Standards and Recommendations

OSHA PEL: TWA 5 mg/m3
ACGIH TLV: TWA 5 mg/m3; Not Classifiable as a Human Carcinogen
DFG MAK: 5 mg/m3

Rotenone Analytical Methods

For occupational chemical analysis use NIOSH: Rotenone, 5007.

Rotenone Specification

The systematic name of Rotenone is (2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one. With the CAS registry number 83-79-4, it is also named as (-)-cis-Rotenone. The product's categories are Miscellaneous Natural Products; Alpha sort; Botanicals Pesticides & Metabolites; Q-ZAnalytical Standards; Botanicals Analytical Standards; Alphabetic; Insecticides; Pesticides; R; Mitochondrial Inhibitors; Cell Stress; Nitric Oxide and Cell Stress; Asymmetric Synthesis; Chiral Building Blocks; Complex Molecules, and the other registry number is 12679-58-2. Besides, it is white or off-white powder, which should be sealed in plastic bags in a cool, dry and ventilated place. It is stable, but light and air sensitive. In addition, its molecular formula is C23H22O6 and molecular weight is 394.42.

The other characteristics of Rotenonecan be summarized as:
(1)EINECS: 201-501-9; (2)ACD/LogP: 4.65; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 4.65; (5)ACD/LogD (pH 7.4): 4.65; (6)ACD/BCF (pH 5.5): 2007.36; (7)ACD/BCF (pH 7.4): 2007.36; (8)ACD/KOC (pH 5.5): 8046.68; (9)ACD/KOC (pH 7.4): 8046.68; (10)#H bond acceptors: 6; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 3; (13)Index of Refraction: 1.591; (14)Molar Refractivity: 104.92 cm3; (15)Molar Volume: 310.2 cm3; (16)Surface Tension: 45.3 dyne/cm; (17)Density: 1.271 g/cm3; (18)Flash Point: 244.6 °C; (19)Melting Point: 159-164 °C; (20)alpha: -115 °(c=1.4 in chloroform); (21)Water Solubility: 0.2 mg/L at 20 °C; (22)Enthalpy of Vaporization: 84.22 kJ/mol; (23)Boiling Point: 559.8 °C at 760 mmHg; (24)Vapour Pressure: 1.45E-12 mmHg at 25 °C.

Preparation of Rotenone:
This chemical can be prepared by extraction from the roots and stems of several tropical and subtropical plant species with organic solvents. And then concentrate extract liquor. At last, you would obtain this chemical after filtration and crystallization.

Uses of Rotenone: 
Rotenone:can be used as a broad-spectrum insecticide, piscicide, and pesticide. It is also used for studying of the biodiversity of marine fishes to collect cryptic, or hidden, fishes by fish researchers. And it has been used to reduce parasitic mites on chickens and other fowl in powdered form. Furthermore, it is used for the garden as an excellent organic pesticide dust.

Safety Information of Rotenone:
When you are using Rotenone, please be cautious about it as the following: it is toxic if swallowed. Please do not breathe dust. It is also irritating to eyes, respiratory system and skin. Youi should wear suitable protective clothing to avoid contact with skin and eyes. Moreover, this chemical is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. And this material and its container must be disposed of as hazardous waste. Please avoid release to the environment, and refer to special instructions / safety data sheets. Additionally, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C2c5ccc1O[C@@H](C(=C)\C)Cc1c5O[C@H]3[C@@H]2c4c(OC3)cc(OC)c(OC)c4
(2)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
(3)InChIKey: JUVIOZPCNVVQFO-HBGVWJBIBF

The toxicity data of Rotenone is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 650ug/kg (0.65mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
dog LDLo intravenous 650ug/kg (0.65mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
dog LDLo oral 300mg/kg (300mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
duck LD50 oral > 2gm/kg (2000mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
frog LDLo oral 4mg/kg (4mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
guinea pig LDLo intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 135, 1936.
guinea pig LDLo oral 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 135, 1936.
human LDLo oral 143mg/kg (143mg/kg) GASTROINTESTINAL: OTHER CHANGES "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 521, 1969.
man LDLo unreported 294mg/kg (294mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 2650ug/kg (2.65mg/kg)   Radiation Research. Vol. 91, Pg. 186, 1982.
mouse LD50 oral 2800ug/kg (2.8mg/kg)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 109, 1976.
pig LDLo oral 3700ug/kg (3.7mg/kg) BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of the American Veterinary Medical Association. Vol. 130, Pg. 410, 1957.
pigeon LDLo intravenous 1mg/kg (1mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LD50 skin > 1gm/kg (1000mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 5, 1978.
rabbit LDLo intramuscular 5mg/kg (5mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LDLo intravenous 350ug/kg (0.35mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LDLo oral 1600mg/kg (1600mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LDLo subcutaneous 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rat LCLo inhalation 500mg/m3/30M (500mg/m3)   Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat LD50 intraperitoneal 1600ug/kg (1.6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: COMA
Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat LD50 intravenous 200ug/kg (0.2mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat LD50 oral 60mg/kg (60mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
rat LD50 skin > 940mg/kg (940mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.
rat LD50 unreported 132mg/kg (132mg/kg)   Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes. Vol. 15, Pg. 929, 1980.
 

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