Isoplumbagin

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  • Identifiers

    CAS number
    14777-17-4

    Molecular formula
    C11H8O3

    SMILES
    CC1=CC(=O)C2=C(C1=O)C(=CC=C2)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 64.62%
    Caramellic 49.62%
    Burnt 44.82%
    Phenolic 43.57%
    Spicy 34.98%
    Coumarinic 31.55%
    Bitter 30.3%
    Vanilla 29.7%
    Nutty 29.53%
    Hay 27.57%

     

    Flavor
    Bitter 75.97%
    Lovage 21.29%
    Odorless 20.41%
    Nitrile 20.38%
    Basil 20.29%
    Fenugreek 20.24%
    Seedy 19.73%
    Maple syrup 19.66%
    Very strong 19.49%
    Leaves 19.46%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    8.13 (weak base)

    Molecular weight
    188.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    406°C

    Melting point expt.

    • 67 - 68 °C

    Flash point

    • 157.13 ˚C est.

  • Synonyms

    • Isoplumbagin
    • 14777-17-4
    • SW8KH5YY53
    • 8-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
    • DTXSID701317990
    • RefChem:1087664
    • DTXCID201747782
    • 8-hydroxy-2-methylnaphthalene-1,4-dione
    • 1,4-Naphthalenedione, 8-hydroxy-2-methyl-
    • 2-Methyl-8-hydroxy-1,4-naphthoquinone
    • UNII-SW8KH5YY53
    • 8-Hydroxy-2-methyl-1,4-naphthalenedione
    • 2-Methyl-8-oxidanyl-naphthalene-1,4-dione
    • Naphthsaritone
    • 5-hydroxy-3-methyl-1,4-naphthoquinone
    • NSC654206
    • orb2813868
    • SCHEMBL4304001
    • CHEMBL1988478
    • SCHEMBL29440907
    • CHEBI:173524
    • PAA77717
    • AKOS006277326
    • HY-W452285
    • NSC-654206
    • NCI60_018820
    • CS-0530608
    • 8-Hydroxy-2-methyl-1,4-naphthalenedione, 9CI
    • EN300-4274971
    • 14777-17-4

  • Applications

    Isoplumbagin (CAS 14777-17-4) is a natural-product type naphthoquinone that is commonly used as a synthetic intermediate in organic synthesis and as a starting point for preparing related naphthoquinone derivatives. In industrial R&D, it may serve as an intermediate for the synthesis of other naphthoquinone compounds and, because of its redox-active core, as a component in formulations for coatings, inks, and electronics-related materials. The compound has been explored for biological activity, including antimicrobial properties, so it may be evaluated in R&D contexts related to agriculture or bioactive research, depending on local regulations. Its use is typically limited by supplier quality, availability, and regulatory constraints, and is usually confined to laboratory-scale or controlled applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 27.84
    methanol 34.04
    isopropanol 22.49
    water 0.56
    ethyl acetate 48.58
    n-propanol 20.78
    acetone 108.63
    n-butanol 20.44
    acetonitrile 54.23
    DMF 338.68
    toluene 29.92
    isobutanol 16.7
    1,4-dioxane 113.11
    methyl acetate 74.05
    THF 126.57
    2-butanone 77.33
    n-pentanol 23.2
    sec-butanol 19.1
    n-hexane 1.82
    ethylene glycol 25.35
    NMP 128.82
    cyclohexane 2.14
    DMSO 227.11
    n-butyl acetate 47.77
    n-octanol 33.91
    chloroform 87.82
    n-propyl acetate 44.17
    acetic acid 23.94
    dichloromethane 118.59
    cyclohexanone 93.87
    propylene glycol 11.03
    isopropyl acetate 34.04
    DMAc 207.45
    2-ethoxyethanol 59.32
    isopentanol 21.16
    n-heptane 3.22
    ethyl formate 62.2
    1,2-dichloroethane 99.19
    n-hexanol 35.96
    2-methoxyethanol 86.83
    isobutyl acetate 24.91
    tetrachloromethane 15.04
    n-pentyl acetate 40.36
    transcutol 53.54
    n-heptanol 30.68
    ethylbenzene 26.19
    MIBK 42.53
    2-propoxyethanol 76.44
    tert-butanol 33.13
    MTBE 22.47
    2-butoxyethanol 52.5
    propionic acid 23.86
    o-xylene 28.68
    formic acid 18.64
    diethyl ether 27.48
    m-xylene 31.32
    p-xylene 35.55
    chlorobenzene 43.76
    dimethyl carbonate 56.7
    n-octane 3.54
    formamide 54.47
    cyclopentanone 141.55
    2-pentanone 61.94
    anisole 55.55
    cyclopentyl methyl ether 42.58
    gamma-butyrolactone 128.1
    1-methoxy-2-propanol 55.21
    pyridine 81.83
    3-pentanone 49.13
    furfural 128.43
    n-dodecane 4.68
    diethylene glycol 77.5
    diisopropyl ether 10.7
    tert-amyl alcohol 27.01
    acetylacetone 94.18
    n-hexadecane 5.41
    acetophenone 65.63
    methyl propionate 59.71
    isopentyl acetate 39.75
    trichloroethylene 146.53
    n-nonanol 31.14
    cyclohexanol 22.75
    benzyl alcohol 46.97
    2-ethylhexanol 25.24
    isooctanol 25.57
    dipropyl ether 23.64
    1,2-dichlorobenzene 48.62
    ethyl lactate 36.03
    propylene carbonate 61.22
    n-methylformamide 111.91
    2-pentanol 16.18
    n-pentane 1.38
    1-propoxy-2-propanol 45.42
    1-methoxy-2-propyl acetate 55.38
    2-(2-methoxypropoxy) propanol 45.03
    mesitylene 21.96
    ε-caprolactone 73.09
    p-cymene 22.56
    epichlorohydrin 156.19
    1,1,1-trichloroethane 56.54
    2-aminoethanol 22.91
    morpholine-4-carbaldehyde 149.47
    sulfolane 148.93
    2,2,4-trimethylpentane 1.74
    2-methyltetrahydrofuran 57.39
    n-hexyl acetate 49.74
    isooctane 1.88
    2-(2-butoxyethoxy)ethanol 49.47
    sec-butyl acetate 26.28
    tert-butyl acetate 38.11
    decalin 4.17
    glycerin 27.89
    diglyme 94.9
    acrylic acid 26.28
    isopropyl myristate 27.5
    n-butyric acid 28.11
    acetyl acetate 37.1
    di(2-ethylhexyl) phthalate 26.98
    ethyl propionate 42.95
    nitromethane 99.25
    1,2-diethoxyethane 35.64
    benzonitrile 63.35
    trioctyl phosphate 24.93
    1-bromopropane 33.99
    gamma-valerolactone 151.91
    n-decanol 26.03
    triethyl phosphate 28.65
    4-methyl-2-pentanol 14.28
    propionitrile 46.95
    vinylene carbonate 70.77
    1,1,2-trichlorotrifluoroethane 86.55
    DMS 54.08
    cumene 21.62
    2-octanol 26.33
    2-hexanone 54.14
    octyl acetate 36.01
    limonene 24.07
    1,2-dimethoxyethane 135.51
    ethyl orthosilicate 23.82
    tributyl phosphate 23.96
    diacetone alcohol 56.04
    N,N-dimethylaniline 45.86
    acrylonitrile 79.12
    aniline 34.28
    1,3-propanediol 33.62
    bromobenzene 44.85
    dibromomethane 66.38
    1,1,2,2-tetrachloroethane 109.33
    2-methyl-cyclohexyl acetate 36.74
    tetrabutyl urea 42.89
    diisobutyl methanol 18.72
    2-phenylethanol 56.0
    styrene 28.45
    dioctyl adipate 33.94
    dimethyl sulfate 89.22
    ethyl butyrate 39.18
    methyl lactate 41.26
    butyl lactate 30.65
    diethyl carbonate 32.62
    propanediol butyl ether 37.86
    triethyl orthoformate 27.67
    p-tert-butyltoluene 20.49
    methyl 4-tert-butylbenzoate 56.94
    morpholine 88.25
    tert-butylamine 17.46
    n-dodecanol 22.16
    dimethoxymethane 138.1
    ethylene carbonate 58.44
    cyrene 57.4
    2-ethoxyethyl acetate 46.95
    2-ethylhexyl acetate 34.28
    1,2,4-trichlorobenzene 50.5
    4-methylpyridine 81.31
    dibutyl ether 23.81
    2,6-dimethyl-4-heptanol 18.72
    DEF 85.92
    dimethyl isosorbide 78.51
    tetrachloroethylene 74.9
    eugenol 62.57
    triacetin 44.13
    span 80 35.35
    1,4-butanediol 22.73
    1,1-dichloroethane 61.8
    2-methyl-1-pentanol 22.22
    methyl formate 117.2
    2-methyl-1-butanol 18.62
    n-decane 6.42
    butyronitrile 44.98
    3,7-dimethyl-1-octanol 25.83
    1-chlorooctane 25.58
    1-chlorotetradecane 13.3
    n-nonane 5.46
    undecane 5.48
    tert-butylcyclohexane 4.21
    cyclooctane 1.56
    cyclopentanol 28.37
    tetrahydropyran 47.49
    tert-amyl methyl ether 23.1
    2,5,8-trioxanonane 73.08
    1-hexene 9.42
    2-isopropoxyethanol 43.89
    2,2,2-trifluoroethanol 24.08
    methyl butyrate 61.57

    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