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-2-Â«alphaÂ»-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-
(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aÂ«alphaÂ»H)-one, 1,2,12,12aÂ«alphaÂ»-tetrahydro-2Â«alphaÂ»-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,2Â«alphaÂ»,6aÂ«alphaÂ»,12aÂ«alphaÂ»)-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»)-
2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-H]chromen-6(6ah)-one, (6R,-(6aÂ«alphaÂ»,12aÂ«alphaÂ»)-
5'«beta»-Rotenone
5'Â«betaÂ»-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»)]-
[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-(2Â«alphaÂ»,6aÂ«alphaÂ»,12aÂ«alphaÂ»)]-

C_p,gas : Ideal gas heat capacity (J/mol×K).
Δ_fG° : Standard Gibbs free energy of formation (kJ/mol).
Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
Δ_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
log₁₀WS : Log10 of Water solubility in mol/l.
logP_oct/wat : Octanol/Water partition coefficient.
McVol : McGowan's characteristic volume (ml/mol).
P_c : Critical Pressure (kPa).
I_np : Non-polar retention indices.
T_boil : Normal Boiling Point Temperature (K).
T_boilr : Boiling point at reduced pressure (K).
T_c : Critical Temperature (K).
T_fus : Normal melting (fusion) point (K).
V_c : Critical Volume (m³/kmol).
¹: Molecular weight from the IUPAC atomic weights tables.

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Physical Properties

Property	Value	Unit	Source
Δ_fG°	-19.59	kJ/mol	Joback Calculated Property
Δ_fH°_gas	-577.91	kJ/mol	Joback Calculated Property
Δ_fusH°	28.46	kJ/mol	Experim...
Δ_vapH°	97.06	kJ/mol	Joback Calculated Property
log₁₀WS	[-4.42; -4.42]
log₁₀WS	-4.42		Aq. Sol...
log₁₀WS	-4.42		Estimat...
logP_oct/wat	3.703		Crippen Calculated Property
McVol	281.450	ml/mol	McGowan Calculated Property
P_c	1675.53	kPa	Joback Calculated Property
I_np	3242.00		NIST
T_boil	1019.17	K	Joback Calculated Property
T_c	1270.91	K	Joback Calculated Property
T_fus	438.20 ± 0.20	K	NIST
V_c	1.067	m³/kmol	Joback Calculated Property

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

Find more compounds similar to Rotenone.

Mixtures

Carbon dioxide + Rotenone + Water

Sources

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