Chemical Properties of Rotenone (CAS 83-79-4)

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

InChI Key

JUVIOZPCNVVQFO-UHFFFAOYSA-N

Formula

C23H22O6

SMILES

C=C(C)C1Cc2c(ccc3c2OC2COc4cc(OC)c(OC)cc4C2C3=O)O1

Molecular Weight¹

394.42

CAS

83-79-4

Other Names

• (-)-Rotenone
• (-)-cis-Rotenone
• (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-8,9-dimethoxy-2-(1-methylethenyl)-,(2R,6aS,12aS)-
• (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6a«alpha»H)-one, 1,2,12,12a«alpha»-tetrahydro-2«alpha»-isopropenyl-8,9-dimethoxy-
• (2R,2«alpha»,6a«alpha»,12a«alpha»)-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
• (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
• 1,2,12,12a-tetrahydro-2-isopropenyl-8,9-dimethoxy[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)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
• 2,6a,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(1H)-one
• 2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-H]chromen-6(6ah)-one, (6R,-(6a«alpha»,12a«alpha»)-
• 5'«beta»-Rotenone
• Barbasco
• Cenol garden dust
• Chem fish
• Chem-Mite
• Cube extract
• Cube root
• Cube-Pulver
• Cubor
• Curex flea duster
• Dactinol
• Deril
• Derrin
• Derris
• Derris (insecticide)
• Derris root
• Dri-kil
• ENT 133
• Extrax
• Fish-Tox
• Foliafume E.C.
• Green Cross Warble Powder
• Green cross warble
• Haiari
• Liquid Derris
• Mexide
• NCI-C55210
• Nicouline
• Noxfire
• Noxfish
• Nusyn-noxfish
• Paraderil
• Pb-nox
• Powder and root
• Prenfish
• Prentox
• Pro-nox fish
• Ro-Ko
• Ronone
• Rotacide E.C.
• Rotefive
• Rotefour
• Rotenon
• Rotenona
• Rotenox
• Rotessenol
• Rotocide
• Synpren
• Tubatoxin
• Tubotoxin
• [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-(2«alpha»,6a«alpha»,12a«alpha»)]-

• C_p,gas : Ideal gas heat capacity (J/mol×K).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
• log₁₀WS : Log10 of Water solubility in mol/l.
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• I_np : Non-polar retention indices.
• T_boilr : Boiling point at reduced pressure (K).
• T_fus : Normal melting (fusion) point (K).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ΔfusH°	28.46	kJ/mol	Experimental Phase Equilibrium Data for Rotenone in Supercritical Carbon Dioxide
log10WS	[-4.42; -4.42]
log10WS	-4.42		Aq. Solubility Prediction
log10WS	-4.42		Estimated Solubility
logPoct/wat	3.703		Crippen Calculated Property
McVol	281.450	ml/mol	McGowan Calculated Property
Inp	[3242.00; 3242.00]
Inp	3242.00		NIST
Inp	3242.00		NIST
Tfus	[438.20; 443.90]	K
Tfus	443.90	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Tfus	438.20 ± 0.20	K	NIST

Cheméo can also estimate Normal Boiling Point Temperature, Critical Temperature, Critical Pressure, Critical Volume, Enthalpy of formation at standard conditions, Enthalpy of vaporization at standard conditions, Standard Gibbs free energy of formation, Acentric Factor, Ionization energy for this compound, but they fall outside the models' validated range, so they are not shown here. Open the prediction tool to compute them on demand.

Temperature Dependent Properties

Pressure Dependent Properties

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[403.47; 955.75]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			-1.40500e+01
Coefficient B			1.80296e+00
Coefficient C			-1.06566e-03
Coefficient D			2.32500e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	403.47	J/mol×K	273.00	Calculated Property
Cp,gas	500.72	J/mol×K	353.78	Calculated Property
Cp,gas	587.28	J/mol×K	434.56	Calculated Property
Cp,gas	663.89	J/mol×K	515.33	Calculated Property
Cp,gas	731.28	J/mol×K	596.11	Calculated Property
Cp,gas	790.20	J/mol×K	676.89	Calculated Property
Cp,gas	841.37	J/mol×K	757.67	Calculated Property
Cp,gas	885.52	J/mol×K	838.44	Calculated Property
Cp,gas	923.41	J/mol×K	919.22	Calculated Property
Cp,gas	955.75	J/mol×K	1000.00	Calculated Property

Similar Compounds

Find more compounds similar to Rotenone.

Mixtures

• Carbon dioxide + Rotenone + Water

Sources

• Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) ChEDL chemicals 1.5.2, from Bradley, J.-C.; Williams, A.; Lang, A. Jean-Claude Bradley Open Melting Point Dataset. Figshare, 2014 (CC0).
• Cheméo Relay (1.0, beta) Beta: served but experimental, data-limited and below our cross-validation release bar; the Joback value is recommended where available.
• Crippen Method
• Experimental Phase Equilibrium Data for Rotenone in Supercritical Carbon Dioxide
• Joback Method
• Aqueous Solubility Prediction Method
• Estimated Solubility Method
• McGowan Method
• NIST Webbook

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Calculated This icon marks a calculated value or equation: a prediction, not a measurement.
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