r
rotenone
Chemical compound
Also known as 1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methyl-ethenyl)-[1]benzopyrano [3,4-b]furo[2,3-h][1] benzopyran-6(6aH)-one · [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 · barbasco · 5'beta-rotenone · canex · (-)-cis-rotenone
- Formula
- C₂₃H₂₂O₆
1
- C₂₃H₂₂O₆
- Mass
- 394.142 Da
1
- 394.142 Da
- Melting point
- 330°F
- Boiling point
- 215°C
- Density
- 1.27 g/cm³
Overview
Chemistry
All data
145 statements · 57% with external sources · numbers in brackets are citations
- Immediately dangerous to life or health
- 2,500 milligram per cubic metre
- Vapor pressure
- 4e-5 millimetre of mercury temperature: 68°F · criterion used: maximum
- Time-weighted average exposure limit
- 5 milligram per cubic metre applies to jurisdiction: United States · runtime: 10 h
- Canonical SMILES
- CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC
1
- 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
1
- CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC
- Part of
- response to rotenone subject has role: reactant
1
- cellular response to rotenone subject has role: reactant
1
- response to rotenone subject has role: reactant
- Found in taxon
- Pachyrhizus erosus
- Tephrosia purpurea
2
Sources- 1.Stated in Flavonoids of Tephrosia polyphylla
- 2.Stated in A new epoxyflavanone from tephrosia hamiltonii1
- Tephrosia vogelii
- Tephrosia pentaphylla
- Piscidia piscipula
7
Sources- 1.Stated in New Rotenoids from the Root Bark of Jamaican Dogwood (Piscidia erythrina L.)
- 2.Stated in Some New Constituents of Piscidia erythrina L.
- 3.Stated in Two isoflavones from Piscidia erythrina
- 4.Stated in Isoflavonoids from the Root Bark of Piscidia erythrina and a Note on the Structure of Piscidone
- 5.Stated in Fish Poisons from Ichthyomethia Piscipula. I
- 6.Stated in Über die Inhaltsstoffe vonPiscidia eryfhrina L
- Millettia ferruginea
1
- Tephrosia leiocarpa
1
- Derris trifoliata
5
Sources- 1.Stated in Cancer chemopreventive activity of rotenoids from Derris trifoliata
- 2.Stated in Flavonoids from Derris species
- 3.Stated in 7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoliata
- 4.Stated in Cytotoxic rotenoloids from the stems of Derris trifoliata
- 5.Stated in Two unusual rotenoid derivatives, 7a-O-methyl-12a-hydroxydeguelol and spiro-13-homo-13-oxaelliptone, from the seeds of Derris trifoliata
Show 35 moreShow less
- Derris malaccensis
- Millettia
1
- Mundulea chapelieri
- Derris elliptica
5
Sources- 1.Stated in Antifeedants in Cyperaceae: coumaran and quinones from Cyperus spp.
- 2.Stated in Flavonoids from Derris species
- 3.Stated in NMR investigations of rotenoids
- 4.Stated in Untersuchung ueber die Wurzel von Derris elliptica Benth. I.
- 5.Stated in Zur Kenntnis der Bestandteile einiger Derris-Arten
- Derris brevipes
1
- Millettia rubiginosa
1
- Lonchocarpus salvadorensis
- Tephrosia procumbens
- Amorpha fruticosa
2
Sources- 1.Stated in Enzymic oxidative modification of prenyl groups. The biosynthetic origins of the E-ring systems of rotenone and amorphigenin
- 2.Stated in Biosynthesis of rotenone and amorphigenin. Study of the origins of isopropenyl-substituted dihydrofuran E-rings using isotopically labelled late precursors
- Neorautanenia mitis
- Antheroporum pierrei
- Erycibe expansa
- Millettia pachycarpa
1
- Tephrosia interrupta
1
- Tephrosia linearis
1
- Millettia pachyloba
- Pachyrrhizus erosus
- Spatholobus parviflorus
1
- Tephrosia macropoda
1
- Tephrosia strigosa
1
- Tephrosia villosa
- Deguelia urucu
1
- Deguelia negrensis
1
- Tephrosia cinerea
- Lonchocarpus nicou
- Pachyrhizus tuberosus
- Arabidopsis thaliana
- Valeriana officinalis
- Lonchocarpus chiricanus
- Derris montana
- Lonchocarpus heptaphyllus
- Lonchocarpus utilis
3
Sources- 1.Stated in Lonchocarpene, a Stilbene, and Lonchocarpusone, an Isoflavone: Two New Pyranopolyphenols from Lonchocarpus nicou Roots
- 2.Stated in Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents
- 3.Stated in Anticancer action of cubé insecticide: Correlation for rotenoid constituents between inhibition of NADH:ubiquinone oxidoreductase and induced ornithine decarboxylase activities
- Derris
- Tephrosia candida
- Lonchocarpus
- Stereoisomer of
- (1S,6S,13R)-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
- (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)-, (2S-(2alpha,6aalpha,12aalpha))-
- Epirotenone, (-)-
- Epirotenone
On other databases
51 identifiers linking rotenone across the web's reference databases
- CAMEO Chemicals ID20997
- CAS Registry Number83-79-4
- ChEBI ID28201
- ChEMBL IDCHEMBL429023
- ChemSpider ID6500
- Dewey Decimal Classification615.952
- DrugBank IDDB11457
- DSSTOX compound identifierDTXCID901248
- DSSTox substance IDDTXSID6021248
- EC number201-501-9
- ECHA Substance Infocard ID100.001.365
- Encyclopædia Britannica Online IDscience/rotenone
- Encyclopedia of China (Third Edition) ID (2026)1G2I2
- Encyclopedia of China (Third Edition) old ID (2021)414062
- Freebase ID/m/02jxhm
- GND ID4834738-3
- Gran Enciclopèdia Catalana IDrotenona
- Gran Enciclopèdia Catalana ID (former scheme)0140177
- Great Norwegian Encyclopedia IDrotenon
- HCIS ID2385
- HSDB ID1762
- Human Metabolome Database IDHMDB0034436
- ICSC ID0944
- InChIInChI=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
- InChIKeyJUVIOZPCNVVQFO-HBGVWJBISA-N
- KEGG IDC07593
- KNApSAcK IDC00002568
- LIPID MAPS IDLMPK12060007
- MassBank accession IDMSBNK-MPI_for_Chemical_Ecology-CE000116
- MeSH descriptor IDD012402
- MeSH tree codeD03.383.663.283.266.450.400.843
- Microsoft Academic ID (discontinued)2778389096
- NSC number8505
- OpenAlex IDC2778389096
- OSHA Occupational Chemical Database ID718
- PDB ligand ID970
- PesticideInfo chemical IDPRI5581
- PM20 ware ID232771
- Probes And Drugs IDPD002240
- PubChem CID6758
- Reaxys registry number99070
- Römpp online IDRD-18-01852
- RTECS numberDJ2800000
- RxNorm CUI1366666
- SPLASHsplash10-0002-0129000000-cc8a296246aa7e1b7fec
- SureChEMBL ID42253
- UMLS CUIC0035871
- UniChem compound ID128707
- UNII03L9OT429T
- WordNet 3.1 Synset ID15037045-n
- ZVG number35460