Rotenone

Overview IFRA Request a quote

  • Identifiers

    CAS number
    83-79-4

    Molecular formula
    C23H22O6

    SMILES
    CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Sweet 48.89%
    Spicy 46.19%
    Vanilla 35.48%
    Phenolic 30.56%
    Floral 28.58%
    Herbal 27.64%
    Powdery 27.49%
    Woody 27.27%
    Mint 26.87%
    Creamy 23.9%

     

    Flavor
    Bitter 93.77%
    Bland 20.52%
    Cedarleaf 19.22%
    Parsley 19.08%
    Lovage 18.73%
    Sweet-like 18.24%
    Ripe apricot 17.34%
    Red fruit 16.93%
    Eugenol 16.5%
    Basil 16.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.1

    pKa est.
    7.1 (neutral)

    Molecular weight
    394.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 329 to 331 °F (NTP, 1992)
    • 176 °C
    • MP: 185-186 °C /Dimophic Rotenone/
    • 163 °C
    • 165-166 °C
    • 329-331 °F
    • 330 °F

    Boiling point

    • 410 to 428 °F at 0.5 mmHg (NTP, 1992)
    • BP: 215 °C at 0.5 mm Hg
    • 410-428 °F
    • Decomposes

    Flash point

    • 211.4 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • SOLUBILITY: 15 PPM IN WATER AT 100 °C. SHOWS RAPID RACEMIZATION ON ALKALI TREATMENT; CRYSTALLIZES WITH SOLVENT OF CRYSTALLIZATION; CIS CONFIGURATION IS GENERALLY ACCEPTED
    • In water, 15 mg/L at 100 °C
    • Soluble in ethanol, acetone, benzene; slightly soluble in ether; very soluble in chloroform
    • SLIGHTLY SOLUBLE IN PETROLEUM OILS
    • SOL IN LIPIDS
    • Readily soluble in acetone, carbon disulfide, ethyl acetate and chloroform. Less readily soluble in diethyl ether, alcohols, petroleum ether and carbon tetrachloride.
    • In water 0.17 mg/L at 25 °C
    • 0.0002 mg/mL at 20 °C
    • Solubility in water: none
    • Insoluble

  • Synonyms

    • rotenone
    • 83-79-4
    • Dactinol
    • Paraderil
    • Barbasco
    • Tubatoxin
    • (-)-Rotenone
    • Derris
    • (-)-cis-Rotenone
    • Derrin
    • Nicouline
    • Rotocide
    • Noxfire
    • Ronone
    • Rotenon
    • Rotenox
    • Canex
    • Deril
    • Liquid Derris
    • Cube-Pulver
    • Dri-Kil
    • Rotessenol
    • Prentox
    • Rotefive
    • Rotefour
    • Tubotoxin
    • Cubor
    • Extrax
    • Haiari
    • Mexide
    • Chem-Mite
    • Pb-nox
    • Cenol garden dust
    • Curex flea duster
    • Gerane
    • Ro-Ko
    • Synpren
    • Derris (insecticide)
    • Caswell No. 725
    • Rotenox 5EC
    • Foliafume E.C.
    • 5'-beta-Rotenone
    • Green Cross Warble Powder
    • CCRIS 895
    • Rotenone [BSI:ISO]
    • Rotenone, dehydro
    • HSDB 1762
    • Rotacide E.C.
    • ENT 133
    • Rotenone, commercial
    • EPA Pesticide Chemical Code 071003
    • NCI-C55210
    • AI3-00133
    • NSC26258
    • EINECS 201-501-9
    • NSC 26258
    • Derris, JMAF
    • UNII-03L9OT429T
    • DTXSID6021248
    • CHEBI:28201
    • 03L9OT429T
    • ROTENONE [HSDB]
    • ROTENONE [ISO]
    • ROTENONE [MI]
    • NSC-26258
    • ROTENONE [MART.]
    • (1S,6R,13S)-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
    • 1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one
    • Rotenona
    • ROTENONE [GREEN BOOK]
    • Derris resins
    • MLS000738056
    • CHEMBL429023
    • DTXCID901248
    • (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-
    • (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one
    • (2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-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)benzopyran-6(6aH)-one
    • 1,2,12,12aalpha-Tetrahydro-2a-isopropenyl-8,9-dimethoxy(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one
    • 5'beta-Rotenone
    • Green cross warble
    • CUBE
    • (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-(2alpha,6aalpha,12aalpha))-
    • (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
    • (2R-(6aalpha,12aalpha)-1,2-Dihydro-2-isopropenyl-8,9-dimethoxychromano(3,4-b)furo(2,3-h)chroman-6-on
    • [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
    • NCGC00017358-05
    • Rotacide
    • Nekoe
    • ROTENONE (MART.)
    • (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
    • [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)-
    • Rotenona [Spanish]
    • Foliafume
    • Nusyn
    • Protax
    • MFCD09025614
    • 5'.beta.-Rotenone
    • CAS-83-79-4
    • (2R,6AS,12AS)-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)-1,2,12,12a-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
    • (2R,6aS,12aS)-2-isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
    • (2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrofuro[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-6(6aH)-one
    • SR-01000076110
    • Cuberol
    • Rotenoid
    • Roteonone
    • Derri
    • Sinid
    • ChemFish
    • ChemMite
    • Derris powder
    • FishTox
    • DriKil
    • Cibe Extract
    • WLN: T G5 D6 B666 CV HO MO POT&TT&J IY1&U1 SO1 TO1
    • ProNox fish
    • Fish Tox
    • PBNox
    • 5''beta-rotenone
    • 5'b-Rotenone
    • Rotenone commercial
    • Rotocide E.C.
    • (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(6aalphaH)-one, 1,2,12,12aalpha-tetrahydro-2alpha-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-(2ALPHA,6AALPHA,12A.ALPHA)).-

  • Applications

    Rotenone (CAS 83-79-4) is used in agriculture as an insecticide to protect crops from certain pests; in addition, it serves as a piscicide for managing fish populations in freshwater ecosystems. It is also employed as a biochemical research tool, inhibiting mitochondrial complex I to study respiration, apoptosis, and cellular metabolism. In some jurisdictions, rotenone-containing formulations are used in specialty pest-control products under strict regulatory controls, reflecting the need for careful handling and environmental considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.53
    methanol 2.56
    isopropanol 2.66
    water 0.04
    ethyl acetate 30.1
    n-propanol 2.53
    acetone 32.77
    n-butanol 3.48
    acetonitrile 26.64
    DMF 36.39
    toluene 8.57
    isobutanol 3.06
    1,4-dioxane 32.3
    methyl acetate 29.75
    THF 48.17
    2-butanone 26.7
    n-pentanol 3.79
    sec-butanol 2.37
    n-hexane 0.11
    ethylene glycol 2.57
    NMP 48.32
    cyclohexane 0.47
    DMSO 53.21
    n-butyl acetate 17.7
    n-octanol 3.64
    chloroform 107.92
    n-propyl acetate 21.55
    acetic acid 60.03
    dichloromethane 99.34
    cyclohexanone 50.3
    propylene glycol 1.35
    isopropyl acetate 22.35
    DMAc 80.81
    2-ethoxyethanol 18.05
    isopentanol 5.97
    n-heptane 0.23
    ethyl formate 21.24
    1,2-dichloroethane 44.96
    n-hexanol 4.0
    2-methoxyethanol 19.31
    isobutyl acetate 17.11
    tetrachloromethane 8.79
    n-pentyl acetate 16.59
    transcutol 53.65
    n-heptanol 4.78
    ethylbenzene 3.88
    MIBK 17.29
    2-propoxyethanol 24.85
    tert-butanol 5.07
    MTBE 5.11
    2-butoxyethanol 19.74
    propionic acid 15.46
    o-xylene 5.54
    formic acid 18.54
    diethyl ether 6.72
    m-xylene 5.57
    p-xylene 6.72
    chlorobenzene 19.72
    dimethyl carbonate 32.42
    n-octane 0.18
    formamide 25.47
    cyclopentanone 55.96
    2-pentanone 20.86
    anisole 12.65
    cyclopentyl methyl ether 13.67
    gamma-butyrolactone 73.28
    1-methoxy-2-propanol 15.04
    pyridine 35.17
    3-pentanone 20.93
    furfural 72.93
    n-dodecane 0.31
    diethylene glycol 25.66
    diisopropyl ether 2.7
    tert-amyl alcohol 4.17
    acetylacetone 53.82
    n-hexadecane 0.38
    acetophenone 24.61
    methyl propionate 25.28
    isopentyl acetate 19.78
    trichloroethylene 130.07
    n-nonanol 4.72
    cyclohexanol 6.82
    benzyl alcohol 14.93
    2-ethylhexanol 4.74
    isooctanol 5.53
    dipropyl ether 5.68
    1,2-dichlorobenzene 24.48
    ethyl lactate 16.65
    propylene carbonate 44.05
    n-methylformamide 17.15
    2-pentanol 2.63
    n-pentane 0.13
    1-propoxy-2-propanol 16.31
    1-methoxy-2-propyl acetate 34.51
    2-(2-methoxypropoxy) propanol 27.08
    mesitylene 3.22
    ε-caprolactone 43.16
    p-cymene 4.37
    epichlorohydrin 79.58
    1,1,1-trichloroethane 38.52
    2-aminoethanol 2.72
    morpholine-4-carbaldehyde 66.34
    sulfolane 76.8
    2,2,4-trimethylpentane 0.23
    2-methyltetrahydrofuran 16.63
    n-hexyl acetate 16.34
    isooctane 0.18
    2-(2-butoxyethoxy)ethanol 27.53
    sec-butyl acetate 15.55
    tert-butyl acetate 20.84
    decalin 0.49
    glycerin 7.73
    diglyme 60.9
    acrylic acid 24.23
    isopropyl myristate 9.08
    n-butyric acid 25.01
    acetyl acetate 50.55
    di(2-ethylhexyl) phthalate 14.11
    ethyl propionate 20.35
    nitromethane 120.8
    1,2-diethoxyethane 18.53
    benzonitrile 26.49
    trioctyl phosphate 8.94
    1-bromopropane 9.89
    gamma-valerolactone 88.24
    n-decanol 3.64
    triethyl phosphate 16.95
    4-methyl-2-pentanol 3.61
    propionitrile 18.19
    vinylene carbonate 53.14
    1,1,2-trichlorotrifluoroethane 71.2
    DMS 27.12
    cumene 3.19
    2-octanol 2.95
    2-hexanone 18.01
    octyl acetate 11.05
    limonene 4.74
    1,2-dimethoxyethane 36.29
    ethyl orthosilicate 14.07
    tributyl phosphate 11.54
    diacetone alcohol 24.48
    N,N-dimethylaniline 9.15
    acrylonitrile 34.13
    aniline 13.57
    1,3-propanediol 7.22
    bromobenzene 21.19
    dibromomethane 41.48
    1,1,2,2-tetrachloroethane 73.46
    2-methyl-cyclohexyl acetate 19.89
    tetrabutyl urea 15.86
    diisobutyl methanol 3.95
    2-phenylethanol 16.79
    styrene 5.06
    dioctyl adipate 17.55
    dimethyl sulfate 51.23
    ethyl butyrate 18.61
    methyl lactate 18.99
    butyl lactate 15.59
    diethyl carbonate 18.47
    propanediol butyl ether 11.12
    triethyl orthoformate 16.87
    p-tert-butyltoluene 3.61
    methyl 4-tert-butylbenzoate 26.69
    morpholine 25.43
    tert-butylamine 2.23
    n-dodecanol 2.92
    dimethoxymethane 34.65
    ethylene carbonate 45.6
    cyrene 35.25
    2-ethoxyethyl acetate 30.53
    2-ethylhexyl acetate 16.17
    1,2,4-trichlorobenzene 30.34
    4-methylpyridine 28.38
    dibutyl ether 5.66
    2,6-dimethyl-4-heptanol 3.95
    DEF 27.57
    dimethyl isosorbide 53.29
    tetrachloroethylene 50.36
    eugenol 26.02
    triacetin 33.49
    span 80 16.73
    1,4-butanediol 4.14
    1,1-dichloroethane 29.84
    2-methyl-1-pentanol 5.71
    methyl formate 22.79
    2-methyl-1-butanol 4.28
    n-decane 0.47
    butyronitrile 13.05
    3,7-dimethyl-1-octanol 5.43
    1-chlorooctane 2.73
    1-chlorotetradecane 1.45
    n-nonane 0.33
    undecane 0.37
    tert-butylcyclohexane 0.37
    cyclooctane 0.2
    cyclopentanol 6.54
    tetrahydropyran 15.08
    tert-amyl methyl ether 4.97
    2,5,8-trioxanonane 48.42
    1-hexene 0.75
    2-isopropoxyethanol 16.34
    2,2,2-trifluoroethanol 35.85
    methyl butyrate 24.89

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction