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(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Rotenone

CAS: 83-79-4

Molecular Formula: C23H22O6

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  5. (2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Names and Identifiers

Name Rotenone
Synonyms Rotenone
tubatoxin
(-)-cis-rotenone
(2r-(2alpha,6aalpha,12aalpha))--9-dimethoxy-2-(1-methylethenyl)-
(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6alphah)-one,1,2,12,12aalpha-t
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
(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
(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
(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
(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(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(6aalphaH)-one, 1,2,12,12aalpha-tetrahydro-2alpha-isopropenyl-8,9-dimethoxy-
(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
EINECS 201-501-9
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-HBGVWJBISA-N

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Physico-chemical Properties

Molecular FormulaC23H22O6
Molar Mass394.42
Density1.1917 (rough estimate)
Melting Point159-164 °C (lit.)
Boling Point210-220 °C/0.5 mmHg (lit.)
Specific Rotation(α)-115 º (C=1.4 IN CHLOROFORM)
Flash Point244.7°C
Water Solubility15 mg l-1 (100 °C)
Vapor Presure1.45E-12mmHg at 25°C
AppearanceWhite to off-white solid
ColorWhite to Light yellow to Light orange
Merck14,8271
BRN6773081
Storage ConditionKeep in dark place,Inert atmosphere,Room temperature
StabilityStable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies.
Refractive Index1.4593 (estimate)
Physical and Chemical PropertiesThe pure product is colorless orthogonal six-sided Flake crystal. Decomposition of light and air. Soluble in acetone, carbon tetrachloride, ethanol, acetic acid, chloroform, ether and other organic solvents, almost insoluble in water. The solution showed photo-oxidation to yellow, orange to deep red, and deposition of dehydrorotenone and rotenedione crystals. The relative density was 1.27. Melting point 165-166°C. Boiling Point 210-220°C(0.67kPa), 185-186°C (double crystal form). Moderate toxicity, rats oral half lethal dose 132mg/kg.
rotenone is a mitochondrial inhibitor, can inhibit mitochondrial electron transfer, is a commonly used insecticide, Rotenone into the worm body inhibit mitochondrial respiratory chain, leading to pests appear Dyspnea and convulsions and other respiratory system disorders, he died of paralysis due to delayed movement.
UseAs an agricultural insecticide, it can also control human and animal ectoparasites and be used for biochemical research.

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Risk and Safety

Risk CodesR25 - 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 DescriptionS22 - 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. 
UN IDsUN 2811 6.1/PG 3
WGK Germany3
RTECSDJ2800000
HS Code29329990
Hazard Class6.1(b)
Packing GroupIII
ToxicityLD50 i.p. in mice: 2.8 mg/kg (Fukami); in rats (mg/kg): 132 orally; 6 i.v. (Soloway)

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Nature

Open Data Verified Data
  • colorless crystal, melting point 1 63 ℃, 1 81 ℃ (double crystal), vapor pressure <1mPa( 20 ℃). From the molecular structure, there are different optical isomers, natural products are levorotatory, optical rotation (benzene)- 255., It will be racemized in case of alkali. Easy oxidation, in light, air, water, alkaline conditions will accelerate the oxidation, and lose insecticidal activity, dry conditions more stable. Difficult to dissolve in water (10 mg/L,1 00 ℃), also difficult to dissolve in ether, alcohol, petroleum ether and carbon tetrachloride, soluble in acetone, carbon disulfide, ethyl acetate and chloroform.
  • dosage form single dose 2.5%, 7.5% rotenone cream, 3. 5%, 4% hypertonic rotenone EC; 18%, 21% sinomenine · fish Endo EC, 1. 3%, 2.5%, 7.5% Cyanogen · fish Vine EC, 25% amine · fish Vine EC, 25% enemy · fish Vine EC, 1. 8% avix, 5% pyrethrins, etc.
Last Update：2024-01-02 23:10:35

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Preparation Method

Open Data Verified Data

in the root of 15 genera of legume, the most important species are the genus of the genus of the genus of the genus of the genus of the genus and the genus of the genus of the genus of the genus, the main species are the Derris (fur) china, Derris chinensis, Peru spindle nut Bean (Lonch-ocarpus utilis) and Brazil spindle nut Bean (Loncho-carpus urucu). Can be directly processed into powder, can also be processed into powder extract, water, emulsifiable concentrate use.

Last Update：2022-01-01 11:18:12

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Use

Open Data Verified Data

rotenone is a selective plant-derived insecticide/acaricide that inhibits glutamate dehydrogenase in nerve and muscle tissue, acting as a contact and gastric poison. The insecticidal spectrum is wide, and it is effective for many kinds of pests, such as Lepidoptera, Hemiptera, Coleoptera, Diptera, Hymenoptera, ptera, tick and mite. In the light of rotenone easily oxidized to hydrorotenone and lost insecticidal activity. Mainly used for vegetables, fruit trees, tea trees, flowers and other crops to control a variety of aphids, mites, shrimp, melon flies, blue Spodoptera exigua, Spodoptera litura, thrips, yellow stripe jumping nail, yellow gourd, twenty-eight star, tea worms, tea geometrid, can also be used to control health pests, such as mosquitoes, flies, fleas, lice and so on.

Last Update：2022-01-01 11:18:12

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Safety

Open Data Verified Data
  • The acute oral LD50 of rats is 132-1500mg/kg, the acute oral LD50 of mice is 350mg/kg, and the acute percutaneous LD50 of rabbits is 940mg/kg. Rotenone is moderately toxic to humans and animals, highly toxic to aquatic organisms such as fish and silkworm, and low toxic to bees.
  • 2.5% rotenone emulsion is packed in iron drum; Powder is 250g × 30 packs/piece (carton); Crude oil is packed in iron drum, 180kg/barrel; Crystal powder is packed in vacuum plastic bag 2kg. This product should be stored in a cool, dry and ventilated place.
Last Update：2022-01-01 11:18:13

(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one - Reference Information

NIST chemical information information provided by: webbook.nist.gov (external link)
EPA chemical substance information information provided by: ofmpeb.epa.gov (external link)
Overview Rotenone (Rotenone) and Rotenone compounds are derived from the leguminous plants of the genus rotenum, A class of selective insecticidal active substances extracted from plants such as synbiotic genus, caulis spatholobi, poisonous fish bean and sphenoid, which can inhibit nerve tissue and muscle tissue, in which rotenone is the most toxic.
The resources of rotenone are very rich. At present, it has been found that 68 legumes contain rotenone, and more than 74 kinds of rotenone compounds. The genus rotenone is found in tropical and subtropical regions and grows widely in Southeast Asia. In South China, such as Guizhou, it is rich in wild and cultivated rotenone resources.
rotenone is unstable in nature, and is easy to be degraded by oxidation and photolysis. In general, its toxic components 5 a decomposition of 6 days, and the Sunshine of the summer, only 2 a 3 days. Rotenone is also easily degraded in soil and water. The half-life is only 3 A 1 days. Because rotenone has a short half-life, is easy to decompose and does not pollute the environment, it is widely used in crop pest management and fish pond cleaning all over the world. It is regarded as a natural low toxicity and efficient insecticide.
mechanism of action early studies have shown that the mechanism of action of rotenone is mainly to affect the respiration of insects, it mainly interacts with a component between NADH dehydrogenase and coenzyme Q. Rotenone inhibits the electron transport chain of the pest cell, thereby reducing the level of ATP in the organism, ultimately leaving the pest without energy supply, and then the action is delayed, paralysis and slow death. Mitochondria, NADH dehydrogenase, succinic acid, mannitol and other substances in many biological cells have some sensitivity to rotenone. Electron transport from NADPH to NADH in setatria cervi mitochondria is highly inhibited by rotenone. Also, the activity of the fumarate reductase system in the mitochondrial granules of the filarial parasite Setaria digitata is sensitive to rotenone. Rotenone and salicylhydroxamic acid can inhibit the electromotive force (EMT) of mitochondrial inner membrane of Trypanosoma brucei brucei, thus indirectly affecting the activity of NADH dehydrogenase; rotenone can also inhibit the activity of NADH to cytochrome C and NADH to coenzyme Q reductase in mitochondrial respiratory chain of Trypanosoma brucei brucei, and the inhibition rate is as high as 80% ~ 90%. Rotenone can inhibit the synthesis of mannitol in Cryptococcusneoformans cells, which may affect the activity of mannitol synthase, thus indirectly affecting the organism.
Application in recent years, the use of rotenone products showed an increasing trend year by year, among these products, 2.5%, 7.5% rotenone EC, 3.5% hypertonic rotenone EC, 5% pyrethrins • rotenone EC (pyrethrins + rotenone), 18% octanoic (phoxim + rotenone) and 1.3% Cyanogen · rotenum (fenvalerate + rotenone) for the control of aphids on cruciferous vegetables and tomatoes; 0.2% matrine aqueous + 1.8% rotenone emulsion tank mixture, 25% F. Rotenum (trichlorfon + rotenone), 1.3% F. F. (fenvalerate + rotenone) and 2.5% C. F. (fenvalerate + rotenone) are used to control rapeseed worm (Pierce rapae),7.5% Cyanogen • fish oil (fenvalerate + rotenone) and 1.8% avermectin • fish oil (abamectin + rotenone) for the control of diamondback moth (Plutella xylosterella),25% amine for the control of prynaspis yanonia on citrus, 21% sinomenine EC (Phoxim + rotenone) control of cotton on the cotton bollworm (heliothiazea). These products are mainly used as materials, most of which are complex products, and the control area is up to tens of millions of ha. Studies have shown that rotenone and other chemical or biological pesticides mixed with high efficiency, low toxicity, can effectively delay the resistance of pests, reduce environmental pollution, but also stimulate plant growth, no killing effect on natural enemies, it is conducive to promoting ecological balance.
shrimp pond using technology 1. Shrimp culture with 4% rotenone cream cleaning pond: rotenone 0.025mg/L can be used to poison the fish, while the shrimp can survive in 10mg/L of rotenone solution. Rotenone has a large area of destructive effects on fish and other organisms, so it is suitable for the culture of shrimp and other shrimp. The pond can be cleaned with 667m2 water surface and 1 m water depth. Rotenone can also be used as a capper with the catch of ornamental fish.
2, catch ornamental fish: many kinds of fish in the lethal concentration of rotenone solution (0.025mg/L) will quickly float on the water surface, at this time, if they are transferred to the methylene salt solution of 5-10mg/L concentration in time, these fish will immediately recover their vitality. The application of Rotenone can capture high-quality ornamental fish, this method is mainly used in some scientific research and academic research.
3, 5-7% rotenda root powder pond: 667m2 water surface 1 m deep without cubic meter with 6-8 grams of root powder.
toxicity and health hazards rotenone has strong neurotoxicity, which can cause convulsion after high dose ingestion, Coma, heart, liver, kidney and other organ failure. Rotenone is a medium toxicity, toxic to fish, the lethal dose of fish to human is 3.6~20g. Therefore, the user should be scientific and rational drug use, safety protection. In addition, a large number of medical studies have found that rotenone is cytotoxic and can inhibit the utilization of oxygen by the cell respiratory chain. Long-term low-dose injection can lead to the emergence of typical Lewy bodies in rat brain dopamine (DA) neurons, and there will be similar symptoms of Parkinson's disease. The stability of rotenone is poor and the duration of action is short, so people do not have the opportunity to contact for a long period of time.
note rotenone should not be used in combination with alkaline agents. This agent is highly toxic to domestic animals, fish and Silkworm. It is necessary to avoid the drift of the drug solution to the nearby pool and Mulberry. Red water in Liao A is easy to decompose, should be used with; Should be stored in A cool, dark place, avoid high temperature, exposure, away from fire. The safe harvest interval of cruciferous vegetables was 3 days.
Use used as an agricultural insecticide, also for controlling human and animal ectoparasites and for biochemical research.
inhibitors of mitochondrial electron transport
production method 1. Extraction of the roots of plants containing rotenone, such as plants of the genus rotenone, the genus Deram, the drunk fish bean meal or the plants of the genus cinerea, with an organic solvent, followed by concentration of the extract and filtration, provides a crystalline product.
category pesticide
toxicity grade highly toxic
Acute toxicity oral-rat LD50: 60 mg/kg; Oral-mouse LD50: 2.8 mg/kg
stimulation data eyes-rabbit 1% mild
flammability hazard characteristics flammable, spicy and irritating smoke
storage and transportation characteristics The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials
extinguishing agent dry powder, foam, sand
Occupational Standard TLV-TWA 5 mg/m3; Tel 10 mg/m3
toxic substance data information provided by: pubchem.ncbi.nlm.nih.gov (external link)
immediate life-threatening and health concentration 2,500 mg/m3
Last Update：2024-04-09 21:04:16
(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
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CAS: 83-79-4
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Hubei YoungXin Pharmaceutical Tech Co.,Ltd.
Spot supply
Product Name: Rotenone Visit Supplier Webpage Request for quotation
CAS: 83-79-4
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052 Click to send a QQ message
Wechat: 15671228036
Hefei TNJ Chemical Industry Co.,Ltd.
Product Name: Rotenone Request for quotation
CAS: 83-79-4
Tel: 0086-551-65418684
Email: sales@tnjchem.com
　　　　 info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840 Click to send a QQ message
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
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(2R,6aS,12aR)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
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