Rotenone

Base Information

• Chemical Name: Rotenone
• CAS No.: 83-79-4
• Deprecated CAS: 12679-58-2
• Molecular Formula: C23H22O6
• Molecular Weight: 394.424
• Hs Code.: 29329990
• European Community (EC) Number: 201-501-9
• ICSC Number: 0944
• NSC Number: 26258,8505
• UN Number: 2588
• UNII: 03L9OT429T
• DSSTox Substance ID: DTXSID6021248
• Nikkaji Number: J108.000H
• Wikipedia: Rotenone
• Wikidata: Q412388
• NCI Thesaurus Code: C76087
• Pharos Ligand ID: WW3JW45N3PU1
• Metabolomics Workbench ID: 22653
• ChEMBL ID: CHEMBL429023
• Mol file: 83-79-4.mol

Synonyms:Rotenone

Chemical Property of Rotenone

Chemical Property:

• Appearance/Colour: white or off-white powder
• Vapor Pressure: 1.45E-12mmHg at 25°C
• Melting Point: 159-164 °C
• Refractive Index: 1.591
• Boiling Point: 559.8 °C at 760 mmHg
• Flash Point: 244.6 °C
• PSA: 63.22000
• Density: 1.271 g/cm³
• LogP: 3.70330
• Storage Temp.: Store at RT
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥77.6 mg/mL in DMSO
• Water Solubility.: 15 mg l-1 (100 °C)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 394.14163842
• Heavy Atom Count: 29
• Complexity: 664
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Rotenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,T
• Hazard Codes: T,N
• Statements: 25-36/37/38-50/53
• Safety Statements: 22-24/25-36-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC
• Isomeric SMILES: CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. This may result in convulsions and respiratory depression.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the kidneys and liver.
• Description: The principal source of rotenone is the tuber root of Derris elliptica; however, it is also extracted from the roots of Derris mallaccensis, Lonchocarpus utilis, and Lonchocarpus uruca. Rotenone is both a stomach and contact poison for arthropods. Its fast knockdown action is attributed to decreasing the availability of nicotinamide adenine dinucleotide to serve as a cofactor in various biochemical pathways including the Krebs cycle, thereby inhibiting the mitochondrial respiratory enzymes. Rotenone is a classical inhibitor of complex I of the mitochondrial electron transport chain, inhibiting NADH/DB oxidoreductase and NADH oxidase with IC50 values of 28.8 and 5.1 nM, respectively. In substantia nigra pars compacta neurons, it activates ATP-sensitive potassium channels and increases the production of reactive oxygen species (ROS) in the mitochondria, effects that are decreased by the antioxidant trolox . In rodents, rotenone induces dopaminergic cell death in the substantia nigra, formation of cytoplasmic inclusions similar to Lewy bodies, oxidative damage to proteins, and parkinsonian symptoms of bradykinesia and rigidity. In a rat model of Parkinson’s disease, chronic rotenone administration of 1.5 and 2.5 mg/kg per day for two months reduces tyrosine hydroxylase levels in the posterior striatum and prefrontal cortex, induces catalepsy, and decreases spontaneous locomotion and exploration in the open field test. Formulations containing rotenone have been used as insecticides and piscicides.
• 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. Rotenone is an broad spectrum insecticide that occurs naturally in seeds and stems of several plants. Rotenone was first registered in 1947 and is currently used exclusively to kill fish (U.S. EPA, 2007). In 2006, registrants voluntarily canceled all livestock, residential and home owner uses, domestic pet uses, and all other uses except for piscicide uses. Currently the main uses include fish management strategies to remove nonnative fish species from lakes, ponds, or streams and in catfish aquaculture prior to stocking ponds with with fry to remove undesirable fish species (U.S. EPA, 2006d). Rotenone has been historically used by native people to paralyze fish for capture and consumption. Outside the United States, the compound is still used to control insects in fruit and vegetable cultivation and for control of fire ants and mosquito larvae in pond water (HSDB, 2012a). Insecticide; lotion for chiggers; emulsion for scabies.

Technology Process of Rotenone

There total 52 articles about Rotenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

(6aS,12aS,5'R)-rotenone enol acetate (23355-70-6) → rotenone (83-79-4)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Heating;

Reference yield: 59.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (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 (34487-52-0) → rotenone (83-79-4)

Guidance literature:

In diethyl ether;

Reference yield: 50.0%

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 (30462-22-7) → rotenone (83-79-4) + Isorotenone (549-22-4)

Guidance literature:

With Burgess Reagent; In toluene; for 0.5h; Reflux;

DOI:10.1002/anie.201609253

upstream raw materials:

diazomethane

(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

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

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

Downstream raw materials:

(2R,6aS,12aS)-2-(2-Chloro-1-methyl-1-phenylselanyl-ethyl)-8,9-dimethoxy-1,2,12,12a-tetrahydro-6aH-chromeno[3,4-b]furo[2,3-h]chromen-6-one

6a,12a-dehydrorotenone

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

(S)-5-((3aR,9bS)-7,8-Dimethoxy-3a,9b-dihydro-4H-chromeno[4,3-d]isoxazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Refernces

• 1、 Nakatani,Matsui. "Interconversion between Rotenone and Dalpanol". . p. 601 - 602. Retrieved 1977.
• 2、 Nakamura, Kayo,Ohmori, Ken,Suzuki, Keisuke. "Stereocontrolled Total Syntheses of (?)-Rotenone and (?)-Dalpanol by 1,2-Rearrangement and SNAr Oxycyclizations". . p. 182 - 187. Retrieved 2016/12/30.
• 3、 -. "Rotanone Analogs: Method of Preparation and Use". . . Retrieved 2009/06/27.