Rotenone

• Formula: C₂₃H₂₂O₆
• Molecular weight: 394.4172
• IUPAC Standard 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 Copy

  
• IUPAC Standard InChIKey: JUVIOZPCNVVQFO-UHFFFAOYSA-N Copy
• CAS Registry Number: 83-79-4
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: [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-(2α,6aα,12aα)]-; Cube-Pulver; Dactinol; Deril; Derrin; Derris; Derris (insecticide); Dri-kil; Liquid Derris; Nicouline; Noxfish; Paraderil; Ronone; Rotenon; (-)-Rotenone; 5'β-Rotenone; Rotocide; Tubatoxin; (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aαH)-one, 1,2,12,12aα-tetrahydro-2α-isopropenyl-8,9-dimethoxy-; Barbasco; Cenol garden dust; Chem-Mite; Cube extract; Cube root; Cubor; Curex flea duster; Derris root; Extrax; ENT 133; Fish-Tox; Green Cross Warble Powder; Haiari; Mexide; NCI-C55210; Powder and root; Pro-nox fish; Ro-Ko; Rotefive; Rotefour; Rotessenol; (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-α-isopropenyl-8,9-dimethoxy-; Chem fish; Prentox; Rotenona; Tubotoxin; (2R,2α,6aα,12aα)-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; Foliafume E.C.; Green cross warble; Noxfire; Nusyn-noxfish; Pb-nox; Prenfish; Rotacide E.C.; Synpren; 2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-H]chromen-6(6ah)-one, (6R,-(6aα,12aα)-; (-)-cis-Rotenone; Rotenox; (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,6aS,12aS)-; (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
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• Information on this page:
  • Phase change data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of fusion

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, custom temperature program

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Donnelly, Drewes, et al., 1990
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W., Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry, Thermochim. Acta, 1990, 167, 2, 155, https://doi.org/10.1016/0040-6031(90)80476-F . [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Donnelly, Drewes, et al., 1990, 2
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W., Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry, Thermochimica Acta, 1990, 167, 2, 155-187, https://doi.org/10.1016/0040-6031(90)80476-F . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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