Rotenone
Also known as Dactinol, Paraderil, Tubatoxin
Key facts
What buyers check first
- Appearance
- Orthorhombic, six-sided plates from trichloroethylene
- Melting point
- 176 °C
- Boiling point
- 210 to 220
- Density
- 1.27 g/cm³
- Solubility
- 15 PPM IN WATER AT 100 °C. SHOWS RAPID RACEMIZATION ON ALKALI TREATMENT, CRYSTALLIZES WI…
- HS code
- 293299
- Category
- Insecticides and acaricides
- UN number
- UN 2588

What is Rotenone?
Plain description, key identifiers and synonyms
Rotenone is a member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica). It has a role as a piscicide, a phytogenic insecticide, a metabolite, a toxin, an antineoplastic agent and a mitochondrial NADH:ubiquinone reductase inhibitor. It is an organic heteropentacyclic compound and a member of rotenones.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- (1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
- CAS number
- 83-79-4 CAS number cross-checked
- EC number
- 201-501-9
- Molecular formula
- C23H22O6
- UNII
- 03L9OT429T
- MDL number
- MFCD09025614
- InChIKey
- JUVIOZPCNVVQFO-HBGVWJBISA-N
- InChI
- InChI=1S/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
- Canonical SMILES
- C=C(C)C1Cc2c(ccc3c2OC2COc4cc(OC)c(OC)cc4C2C3=O)O1
- 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
Synonyms
- Dactinol
- Paraderil
- Tubatoxin
- (-)-Rotenone
- Derrin
- Derris
- Nicouline
- (-)-cis-Rotenone
- Deril
- Liquid Derris
- Cube-Pulver
- Dri-Kil
- Rotocide
- Noxfire
- Ronone
- Rotenon
- Canex
- Rotefive
- Rotefour
- Rotessenol
- Tubotoxin
- Haiari
- Mexide
- Rotenox
- Cubor
Show all 39 synonymsShow fewer synonyms
- Chem-Mite
- Cenol garden dust
- Curex flea duster
- Synpren
- Gerane
- Ro-Ko
- Derris (insecticide)
- Pb-nox
- Rotenox 5EC
- 5'-beta-Rotenone
- Nekoe
- Green Cross Warble Powder
- Extrax
- Foliafume E.C.
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
| Appearance | Orthorhombic, six-sided plates from trichloroethyleneexp.Measured value |
|---|---|
| Odour | Odorlessexp.Measured value |
| Melting point | 176 °Cexp.Measured value |
| Boiling point | 210 to 220exp.Measured value |
| Density | 1.27 g/cm³exp.Measured value |
| Solubility | 15 PPM IN WATER AT 100 °C. SHOWS RAPID RACEMIZATION ON ALKALI TREATMENT, CRYSTALLIZES WITH SOLVENT OF CRYSTALLIZATION, CIS CONFIGURATION IS GENERALLY ACCEPTEDexp.Measured value |
| Vapour pressure | Less than 0.0075 mmHg at 68 °Fexp.Measured value |
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 394.42 g/molcalc.Computed value |
|---|---|
| Exact mass | 394.1416 Dacalc.Computed value |
| LogP (octanol/water) | 3.7calc.Computed value |
| Topological polar surface area | 63.22 Ųcalc.Computed value |
| Hydrogen bond donors | 0calc.Computed value |
| Hydrogen bond acceptors | 6calc.Computed value |
| Rotatable bonds | 3calc.Computed value |
| Heavy atoms | 29calc.Computed value |
| Rings | 5calc.Computed value |
| Aromatic rings | 2calc.Computed value |
| Fraction sp3 carbons | 0.35calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 3calc.Computed value |
| Lipinski rule of five | Passes (0 violations)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
Safety and hazards
GHS classification summary, not a safety data sheet
Hazard statements
- H301Toxic if swallowed.
- H315Causes skin irritation.
- H319Causes serious eye irritation.
- H335May cause respiratory irritation.
- H400Very toxic to aquatic life.
- H410Very toxic to aquatic life with long lasting effects.
Precautionary statements (21)
- P261Avoid breathing dust, fume, gas, mist, vapours or spray.
- P264Wash skin thoroughly after handling.
- P264 + P265Wash skin thoroughly after handling. Do not touch eyes.
- P270Do not eat, drink or smoke when using this product.
- P271Use only outdoors or in a well-ventilated area.
- P273Avoid release to the environment.
- P280Wear protective gloves, protective clothing, eye protection and face protection.
- P301 + P316If swallowed: Get emergency medical help immediately.
- P302 + P352If on skin: Wash with plenty of water.
- P304 + P340If inhaled: Remove person to fresh air and keep comfortable for breathing.
- P305 + P351 + P338If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
- P319Get medical help if you feel unwell.
- P321Specific treatment (see supplemental first aid instructions on the label).
- P330Rinse mouth.
- P332 + P317If skin irritation occurs: Get medical help.
- P337 + P317If eye irritation persists: Get medical help.
- P362 + P364Take off contaminated clothing. And wash it before reuse.
- P391Collect spillage.
- P403 + P233Store in a well-ventilated place. Keep container tightly closed.
- P405Store locked up.
- P501Dispose of contents and container in accordance with local regulations.
- UN number
- UN 2588
- Transport hazard class
- 6.1
- Packing group
- III
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Full safety data and first aidRotenone suppliers
Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings
- China, BeijingUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
- China, BaojiUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
- India, Kolkata ManufacturerUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
- United States, Schaumburg ManufacturerUnclaimed profileRotenoneGrade TechnicalPrice on request
- China, NantongUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
- China, BeijingUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
- China ManufacturerUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
- Price on request
- United States, Schaumburg ManufacturerUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
- China ManufacturerUnclaimed profileRotenoneGrade, purity and minimum order on requestPrice on request
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Where suppliers are based
64 suppliers in 11 countries
- United States27
- China20
- United Kingdom4
- Germany3
- Spain2
- Latvia2
- and 5 more countries
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Rotenone price
Indicative price range per kg from live supplier offers
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Uses and applications
What the substance is used for, by industry and function
EPA issued a notice of intent to suspend True Stop insecticide (EPA Registration Number 74343-1) on December 10, 2010.
Rotenone products are classified as Restricted Use Pesticides due to acute inhalation, acute oral, and aquatic toxicity.
All non-RUP (Restricted Use Pesticide) agricultural and residential uses, and all food uses were voluntarily cancelled in 2006.
Use classes: Insecticides, Veterinary substances, Acaricides, Insecticides.
Industries and functions
Pharmacological actions
- Insecticides
- Uncoupling Agents
Roles
- antineoplastic agent
- electron-transport chain inhibitor
- enzyme inhibitor
- insecticide
- metabolite
- mitochondrial NADH:ubiquinone reductase inhibitor
- mitochondrial respiratory-chain inhibitor
- pathway inhibitor
- pesticide
- pharmaceutical
- phytogenic insecticide
- piscicide
- poison
- respiratory-chain inhibitor
- toxin
Functional uses
- Biocide
Pharmacology
Rotenone is a naturally occurring organic heteropentacyclic compound and member of rotenones that is found in the roots of several plant species. It is a mitochondrial NADH:ubiquinone reductase inhibitor, toxin, and metabolite, and is used as an antineoplastic agent and insecticide. It is characterized as a colorless to brownish or a white to brownish-white crystalline solid that is odorless. Exposure occurs by inhalation, ingestion, or contact.
How it is made
Agitation of 100 g dichloromethane at 45 °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.
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.
Regulatory status
Inventories, regulations and trade controls that list this substance
Europe
- EU harmonised classification (CLP Annex VI)Index no: 650-005-00-2
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Rotenone is traded under.
Heterocyclic compounds with oxygen hetero-atom(s) only, other
- China28.9%
- Switzerland * partner reported12.7%
- Germany7.8%
- United States49.7%
- China11.9%
- India * partner reported3.3%
* Partner reported figures, a lower bound.
The HS code shown for Rotenone is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Frequently asked questions
Quick answers about Rotenone, based on the data on this page
What is Rotenone?
What is the CAS number of Rotenone?
What is the molecular formula and weight of Rotenone?
What is Rotenone used for?
Is Rotenone hazardous?
What is the HS code of Rotenone?
Where can I buy Rotenone?
Where can I buy Rotenone in India?
What is the price of Rotenone?
Guides for buyers
Practical guides that help when you source, ship or handle Rotenone
- Guide, SafetyHow to read a safety data sheet in 10 minutesA section by section method to pull the essentials out of any 16 section SDS: identity, hazards, composition, storage, PPE, properties, transport and emergency measures.Read
- Guide, Trade and logisticsShipping dangerous goods: UN numbers, classes and packing groupsHow the UN dangerous goods system works for chemicals, from the nine classes and UN numbers to packing groups, UN packaging marks, labels, documents and segregation.Read
- Guide, SafetyGHS pictograms, signal words and hazard statements explainedA practical guide to the nine GHS pictograms, the signal words Danger and Warning, H and P statements, and how to read a chemical label in seconds.Read
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