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.

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Physical Properties

Property	Value	Unit	Source
Δ_fusH°	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
logP_oct/wat	3.703		Crippen Calculated Property
McVol	281.450	ml/mol	McGowan Calculated Property
I_np	[3242.00; 3242.00]
I_np	3242.00		NIST
I_np	3242.00		NIST
T_fus	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

Property	Value	Unit	Temperature (K)	Source
C_p,gas	[962.69; 1033.36]	J/mol×K	[1019.17; 1270.91]

C_p,gas	962.69	J/mol×K	1019.17	Joback Calculated Property
C_p,gas	976.99	J/mol×K	1061.13	Joback Calculated Property
C_p,gas	990.14	J/mol×K	1103.08	Joback Calculated Property
C_p,gas	1002.25	J/mol×K	1145.04	Joback Calculated Property
C_p,gas	1013.42	J/mol×K	1187.00	Joback Calculated Property
C_p,gas	1023.76	J/mol×K	1228.95	Joback Calculated Property
C_p,gas	1033.36	J/mol×K	1270.91	Joback Calculated Property
Δ_fusH	35.64	kJ/mol	437.90	NIST

Pressure Dependent Properties

Property	Value	Unit	Pressure (kPa)	Source
T_boilr	488.20	K	0.07	NIST

Similar Compounds

Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5«alpha»,6«alpha»)-, bis(trifluoroacetate) (ester).

Guanosine, N-trimethylsilyl-, 2',3',5'-tris(trimethylsilyl) ether.

Normorphine, N-trimethylsilyl-, bis(trimethylsilyl) ether.

Triazolo[4,5-d]pyrimidin-7-ol,3h-v-, 5-amino-3-(2',3'-o-isopropylidene-beta-d-ribofuranosyl)-, 5'-diphenyl phosphate (keto form).

Crinan-11-ol, 1,2-didehydro-3-methoxy-, (3«beta»,5«alpha»,11R,13«beta»,19«alpha»)-.

Find more compounds similar to Rotenone.

Mixtures

Carbon dioxide + Rotenone + Water

Sources

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