5-Ethenyl-5,6,7,8-tetrahydro-2,3-dimethoxy-5-methyl-8-(1-methylethenyl)-1,4-naphthalenedione

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  • Identifiers

    CAS number
    87255-09-2

    Molecular formula
    C18H22O4

    SMILES
    CC(=C)C1CCC(C2=C1C(=O)C(=C(C2=O)OC)OC)(C)C=C

    Safety labels

  • Odor profile

    Fragrance
    Fruity 54.63%
    Sweet 52.94%
    Woody 47.63%
    Mint 44.3%
    Spicy 43.09%
    Herbal 41.66%
    Tobacco 34.32%
    Citrus 32.44%
    Caramellic 29.72%
    Dry 29.28%

     

    Flavor
    Bitter 44.03%
    Minty 22.75%
    Basil 21.58%
    Lovage 20.73%
    Cedarleaf 20.04%
    Heather 20.01%
    Parsley 20.0%
    Broom 19.92%
    Leaves 19.84%
    Red fruit 19.73%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    4.2

    pKa est.
    5.87 (weak acid)

    Molecular weight
    302.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    359°C

    Flash point

    • 162.05 ˚C est.

  • Synonyms

    • Arnebinone
    • 87255-09-2
    • 8-ethenyl-2,3-dimethoxy-8-methyl-5-prop-1-en-2-yl-6,7-dihydro-5H-naphthalene-1,4-dione
    • 5-isopropenyl-2,3-dimethoxy-8-methyl-8-vinyl-6,7-dihydro-5H-naphthalene-1,4-dione
    • RefChem:913346
    • 5-Ethenyl-5,6,7,8-tetrahydro-2,3-dimethoxy-5-methyl-8-(1-methylethenyl)-1,4-naphthalenedione
    • C10302
    • AC1L37BB
    • amebinone
    • CHEBI:2828
    • SCHEMBL29395765
    • DTXSID201007461
    • Q27105841
    • 1,4-Naphthalenedione, 5-ethenyl-5,6,7,8-tetrahydro-2,3-dimethoxy-5-methyl-8-(1-methylethenyl)-
    • 5-Ethenyl-2,3-dimethoxy-5-methyl-8-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalene-1,4-dione
    • 87255-09-2

  • Applications

    5-Ethenyl-5,6,7,8-tetrahydro-2,3-dimethoxy-5-methyl-8-(1-methylethenyl)-1,4-naphthalenedione, CAS number: 87255-09-2, is used as a synthetic intermediate in the preparation of building blocks for pharmaceuticals and agrochemicals, and as a precursor for dyes and pigments used in coatings and inks. In the plastics and coatings industry, it can serve as a quinone-functional building block to introduce crosslinking or redox-active features in polymer systems. In materials science and electronics, it may function as a redox-active component for organic electronics or optoelectronic materials. Depending on local regulations and formulation limits, it may be considered as a precursor for further intermediates used in pharmaceutical or agrochemical syntheses.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 30.0
    methanol 31.53
    isopropanol 26.01
    water 0.06
    ethyl acetate 47.33
    n-propanol 34.84
    acetone 55.62
    n-butanol 37.67
    acetonitrile 27.73
    DMF 124.04
    toluene 72.84
    isobutanol 27.21
    1,4-dioxane 97.06
    methyl acetate 56.29
    THF 154.85
    2-butanone 68.54
    n-pentanol 24.68
    sec-butanol 26.86
    n-hexane 1.31
    ethylene glycol 10.5
    NMP 227.03
    cyclohexane 5.8
    DMSO 58.26
    n-butyl acetate 34.92
    n-octanol 8.45
    chloroform 219.08
    n-propyl acetate 28.45
    acetic acid 46.36
    dichloromethane 194.36
    cyclohexanone 148.08
    propylene glycol 11.84
    isopropyl acetate 32.08
    DMAc 127.39
    2-ethoxyethanol 39.71
    isopentanol 35.26
    n-heptane 1.04
    ethyl formate 42.05
    1,2-dichloroethane 148.09
    n-hexanol 30.64
    2-methoxyethanol 72.95
    isobutyl acetate 22.6
    tetrachloromethane 31.81
    n-pentyl acetate 27.84
    transcutol 49.92
    n-heptanol 17.15
    ethylbenzene 26.2
    MIBK 34.0
    2-propoxyethanol 63.59
    tert-butanol 30.34
    MTBE 19.39
    2-butoxyethanol 40.8
    propionic acid 35.05
    o-xylene 40.23
    formic acid 22.33
    diethyl ether 23.04
    m-xylene 38.37
    p-xylene 32.6
    chlorobenzene 106.56
    dimethyl carbonate 40.96
    n-octane 0.58
    formamide 38.76
    cyclopentanone 179.64
    2-pentanone 54.2
    anisole 40.24
    cyclopentyl methyl ether 61.53
    gamma-butyrolactone 173.59
    1-methoxy-2-propanol 55.38
    pyridine 178.39
    3-pentanone 47.78
    furfural 175.76
    n-dodecane 0.5
    diethylene glycol 52.43
    diisopropyl ether 7.3
    tert-amyl alcohol 26.83
    acetylacetone 63.96
    n-hexadecane 0.62
    acetophenone 56.65
    methyl propionate 54.51
    isopentyl acetate 38.2
    trichloroethylene 321.61
    n-nonanol 9.33
    cyclohexanol 55.86
    benzyl alcohol 58.06
    2-ethylhexanol 19.13
    isooctanol 15.2
    dipropyl ether 11.25
    1,2-dichlorobenzene 93.58
    ethyl lactate 23.03
    propylene carbonate 90.8
    n-methylformamide 60.35
    2-pentanol 22.08
    n-pentane 1.74
    1-propoxy-2-propanol 35.59
    1-methoxy-2-propyl acetate 48.27
    2-(2-methoxypropoxy) propanol 34.03
    mesitylene 19.24
    ε-caprolactone 112.19
    p-cymene 15.85
    epichlorohydrin 222.76
    1,1,1-trichloroethane 100.85
    2-aminoethanol 21.02
    morpholine-4-carbaldehyde 149.49
    sulfolane 167.11
    2,2,4-trimethylpentane 1.83
    2-methyltetrahydrofuran 95.67
    n-hexyl acetate 27.92
    isooctane 1.19
    2-(2-butoxyethoxy)ethanol 38.1
    sec-butyl acetate 21.98
    tert-butyl acetate 34.1
    decalin 4.06
    glycerin 25.97
    diglyme 74.11
    acrylic acid 42.88
    isopropyl myristate 11.05
    n-butyric acid 55.43
    acetyl acetate 37.67
    di(2-ethylhexyl) phthalate 22.54
    ethyl propionate 29.81
    nitromethane 78.13
    1,2-diethoxyethane 20.28
    benzonitrile 63.17
    trioctyl phosphate 14.24
    1-bromopropane 48.22
    gamma-valerolactone 195.63
    n-decanol 6.86
    triethyl phosphate 20.91
    4-methyl-2-pentanol 15.17
    propionitrile 35.53
    vinylene carbonate 91.47
    1,1,2-trichlorotrifluoroethane 134.69
    DMS 38.44
    cumene 16.8
    2-octanol 9.65
    2-hexanone 31.33
    octyl acetate 15.28
    limonene 19.15
    1,2-dimethoxyethane 62.41
    ethyl orthosilicate 19.86
    tributyl phosphate 14.91
    diacetone alcohol 49.44
    N,N-dimethylaniline 31.19
    acrylonitrile 57.08
    aniline 85.17
    1,3-propanediol 39.59
    bromobenzene 105.68
    dibromomethane 119.93
    1,1,2,2-tetrachloroethane 222.08
    2-methyl-cyclohexyl acetate 34.61
    tetrabutyl urea 23.07
    diisobutyl methanol 10.84
    2-phenylethanol 60.95
    styrene 30.92
    dioctyl adipate 20.76
    dimethyl sulfate 64.6
    ethyl butyrate 25.75
    methyl lactate 37.17
    butyl lactate 26.09
    diethyl carbonate 21.08
    propanediol butyl ether 23.4
    triethyl orthoformate 21.64
    p-tert-butyltoluene 14.6
    methyl 4-tert-butylbenzoate 43.92
    morpholine 118.9
    tert-butylamine 15.5
    n-dodecanol 5.04
    dimethoxymethane 69.08
    ethylene carbonate 67.69
    cyrene 66.0
    2-ethoxyethyl acetate 38.93
    2-ethylhexyl acetate 31.51
    1,2,4-trichlorobenzene 120.43
    4-methylpyridine 147.44
    dibutyl ether 7.04
    2,6-dimethyl-4-heptanol 10.84
    DEF 70.39
    dimethyl isosorbide 77.43
    tetrachloroethylene 159.32
    eugenol 49.73
    triacetin 31.73
    span 80 29.98
    1,4-butanediol 16.82
    1,1-dichloroethane 97.19
    2-methyl-1-pentanol 27.79
    methyl formate 57.38
    2-methyl-1-butanol 34.47
    n-decane 0.78
    butyronitrile 38.42
    3,7-dimethyl-1-octanol 11.09
    1-chlorooctane 6.2
    1-chlorotetradecane 2.76
    n-nonane 0.62
    undecane 0.61
    tert-butylcyclohexane 2.82
    cyclooctane 1.74
    cyclopentanol 57.2
    tetrahydropyran 81.06
    tert-amyl methyl ether 20.01
    2,5,8-trioxanonane 53.33
    1-hexene 7.32
    2-isopropoxyethanol 31.12
    2,2,2-trifluoroethanol 30.46
    methyl butyrate 40.32

    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