Name: ROTENONE
SKU: 83-79-4

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Basic Information

Molecular Structure:
CAS No.:	83-79-4
Name:	ROTENONE

Formula:	C₂₃H₂₂O₆
Molecular Weight:	394.424
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;
EINECS:	201-501-9
Density:	1.271 g/cm³
Melting Point:	159-164 °C
Boiling Point:	559.8 °C at 760 mmHg
Flash Point:	244.6 °C
Solubility:	0.2 mg/L at 20 °C in water
Appearance:	white or off-white powder
Hazard Symbols:	N,T
Risk Codes:	25-36/37/38-50/53
Safety:	22-24/25-36-45-60-61
Transport Information:	UN 2811 6.1/PG 3
PSA:	63.22000
LogP:	3.70330

Synthetic route

: 23355-70-6
(6aS,12aS,5'R)-rotenone enol acetate

: 83-79-4
rotenone

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	83%

: 186581-53-3, 908094-01-9
diazomethane

: 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

Conditions	Yield
In diethyl ether	59%

: 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

Conditions	Yield
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

Conditions	Yield
With pyridine; thionyl chloride at 0℃; for 0.5h;	40%

: 123000-20-4
(6aS,12aR,5'R)-(trans)-(+)-rotenone

: 83-79-4
rotenone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; chloroform for 2h;

: 123000-19-1
(6aR,12aS,5'R)-rotenone

: 83-79-4
rotenone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; chloroform
With hydrogenchloride In methanol; chloroform epimerisation;

: 509-96-6
12a-hydroxyrotenone

: 83-79-4
rotenone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Raw Materials

3466-09-9

Downstream Products

3466-23-7

3466-09-9

522-17-8

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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.

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

Analytical Methods

For occupational chemical analysis use NIOSH: Rotenone, 5007.

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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History

Standards and Recommendations

Analytical Methods

Specification