5-Hydroxy-2,3-Dimethyl-1,4-naphthoquinone

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  • Identifiers

    CAS number
    80596-51-6

    Molecular formula
    C12H10O3

    SMILES
    CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 59.14%
    Caramellic 52.11%
    Burnt 47.49%
    Phenolic 42.32%
    Spicy 32.76%
    Tobacco 26.8%
    Coumarinic 26.55%
    Vanilla 26.13%
    Hay 24.97%
    Bitter 24.94%

     

    Flavor
    Bitter 68.24%
    Lovage 21.43%
    Basil 20.95%
    Nitrile 20.32%
    Fenugreek 20.29%
    Seedy 20.0%
    Leaves 19.95%
    Ripe apricot 19.92%
    Red fruit 19.79%
    Maple syrup 19.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    7.94 (neutral)

    Molecular weight
    202.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    390°C

    Melting point expt.

    • 120 - 121 °C

    Flash point

    • 163.04 ˚C est.

  • Synonyms

    • 5-Hydroxy-2,3-dimethyl-1,4-naphthoquinone
    • 80596-51-6
    • 5-hydroxy-2,3-dimethyl-1,4-dihydronaphthalene-1,4-dione
    • RefChem:102738
    • 5-HYDROXY-2,3-DIMETHYLNAPHTHALENE-1,4-DIONE
    • 3-Methylplumbagin
    • SCHEMBL5793791
    • SCHEMBL30003218
    • CHEBI:173556
    • DTXSID001272658
    • 5-hydroxy-2,3-dimethyl-[1,4]naphthoquinone
    • 80596-51-6

  • Applications

    5-Hydroxy-2,3-Dimethyl-1,4-naphthoquinone is primarily used as an organic synthesis intermediate, providing a versatile building block for the preparation of other naphthoquinone derivatives in pharmaceutical and specialty chemical research. It can serve as a dye precursor or pigment component for specialty coatings and inks. The quinone core also enables redox-active applications, so the compound may function as a redox mediator or electron-transfer material in electrochemical sensing and energy-storage research. In polymer and materials science, it is occasionally evaluated as a functional additive or crosslinking precursor to impart chromophoric or redox properties. These uses are typical in research and development settings and are subject to local regulations and formulation limits. CAS 80596-51-6.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 10.3
    methanol 10.73
    isopropanol 11.04
    water 0.26
    ethyl acetate 30.83
    n-propanol 9.63
    acetone 62.01
    n-butanol 9.11
    acetonitrile 29.47
    DMF 209.08
    toluene 27.08
    isobutanol 8.44
    1,4-dioxane 85.61
    methyl acetate 50.25
    THF 78.41
    2-butanone 49.74
    n-pentanol 12.5
    sec-butanol 9.35
    n-hexane 1.26
    ethylene glycol 7.0
    NMP 104.0
    cyclohexane 1.9
    DMSO 98.55
    n-butyl acetate 34.4
    n-octanol 19.1
    chloroform 80.33
    n-propyl acetate 28.8
    acetic acid 16.02
    dichloromethane 104.48
    cyclohexanone 76.51
    propylene glycol 3.76
    isopropyl acetate 22.31
    DMAc 140.36
    2-ethoxyethanol 29.49
    isopentanol 10.97
    n-heptane 2.14
    ethyl formate 37.65
    1,2-dichloroethane 78.05
    n-hexanol 20.71
    2-methoxyethanol 39.5
    isobutyl acetate 16.08
    tetrachloromethane 16.91
    n-pentyl acetate 32.84
    transcutol 32.65
    n-heptanol 19.68
    ethylbenzene 21.65
    MIBK 24.29
    2-propoxyethanol 45.5
    tert-butanol 20.26
    MTBE 15.99
    2-butoxyethanol 34.58
    propionic acid 14.67
    o-xylene 26.58
    formic acid 9.42
    diethyl ether 16.47
    m-xylene 24.81
    p-xylene 31.95
    chlorobenzene 38.05
    dimethyl carbonate 33.75
    n-octane 2.46
    formamide 32.32
    cyclopentanone 100.5
    2-pentanone 34.97
    anisole 37.77
    cyclopentyl methyl ether 28.42
    gamma-butyrolactone 100.15
    1-methoxy-2-propanol 27.29
    pyridine 78.07
    3-pentanone 34.69
    furfural 101.5
    n-dodecane 2.68
    diethylene glycol 38.78
    diisopropyl ether 7.25
    tert-amyl alcohol 15.51
    acetylacetone 54.64
    n-hexadecane 3.22
    acetophenone 48.19
    methyl propionate 37.07
    isopentyl acetate 30.3
    trichloroethylene 143.22
    n-nonanol 19.12
    cyclohexanol 14.37
    benzyl alcohol 31.52
    2-ethylhexanol 16.22
    isooctanol 16.86
    dipropyl ether 14.23
    1,2-dichlorobenzene 41.9
    ethyl lactate 19.01
    propylene carbonate 47.69
    n-methylformamide 59.83
    2-pentanol 7.62
    n-pentane 0.96
    1-propoxy-2-propanol 27.24
    1-methoxy-2-propyl acetate 38.86
    2-(2-methoxypropoxy) propanol 29.17
    mesitylene 16.9
    ε-caprolactone 58.18
    p-cymene 17.88
    epichlorohydrin 111.86
    1,1,1-trichloroethane 55.88
    2-aminoethanol 8.53
    morpholine-4-carbaldehyde 117.59
    sulfolane 107.16
    2,2,4-trimethylpentane 1.19
    2-methyltetrahydrofuran 41.95
    n-hexyl acetate 37.91
    isooctane 1.14
    2-(2-butoxyethoxy)ethanol 32.43
    sec-butyl acetate 17.03
    tert-butyl acetate 26.24
    decalin 3.04
    glycerin 11.05
    diglyme 69.37
    acrylic acid 16.43
    isopropyl myristate 18.95
    n-butyric acid 17.49
    acetyl acetate 25.9
    di(2-ethylhexyl) phthalate 19.94
    ethyl propionate 26.22
    nitromethane 67.36
    1,2-diethoxyethane 26.75
    benzonitrile 48.46
    trioctyl phosphate 16.78
    1-bromopropane 23.23
    gamma-valerolactone 125.26
    n-decanol 15.64
    triethyl phosphate 20.16
    4-methyl-2-pentanol 7.58
    propionitrile 27.03
    vinylene carbonate 58.55
    1,1,2-trichlorotrifluoroethane 57.58
    DMS 39.63
    cumene 16.7
    2-octanol 17.01
    2-hexanone 34.32
    octyl acetate 24.87
    limonene 18.15
    1,2-dimethoxyethane 80.0
    ethyl orthosilicate 17.73
    tributyl phosphate 17.12
    diacetone alcohol 34.86
    N,N-dimethylaniline 32.64
    acrylonitrile 47.62
    aniline 26.45
    1,3-propanediol 14.67
    bromobenzene 39.75
    dibromomethane 56.02
    1,1,2,2-tetrachloroethane 86.81
    2-methyl-cyclohexyl acetate 26.72
    tetrabutyl urea 30.13
    diisobutyl methanol 12.61
    2-phenylethanol 39.87
    styrene 21.27
    dioctyl adipate 24.18
    dimethyl sulfate 60.15
    ethyl butyrate 25.45
    methyl lactate 21.17
    butyl lactate 21.8
    diethyl carbonate 22.37
    propanediol butyl ether 22.2
    triethyl orthoformate 20.29
    p-tert-butyltoluene 15.91
    methyl 4-tert-butylbenzoate 44.99
    morpholine 62.5
    tert-butylamine 11.25
    n-dodecanol 12.58
    dimethoxymethane 78.25
    ethylene carbonate 46.28
    cyrene 41.06
    2-ethoxyethyl acetate 37.91
    2-ethylhexyl acetate 26.43
    1,2,4-trichlorobenzene 45.03
    4-methylpyridine 69.0
    dibutyl ether 17.3
    2,6-dimethyl-4-heptanol 12.61
    DEF 56.82
    dimethyl isosorbide 62.95
    tetrachloroethylene 72.36
    eugenol 44.54
    triacetin 33.56
    span 80 23.96
    1,4-butanediol 9.46
    1,1-dichloroethane 48.66
    2-methyl-1-pentanol 13.22
    methyl formate 62.66
    2-methyl-1-butanol 9.67
    n-decane 4.1
    butyronitrile 22.47
    3,7-dimethyl-1-octanol 15.62
    1-chlorooctane 16.23
    1-chlorotetradecane 7.61
    n-nonane 3.42
    undecane 3.3
    tert-butylcyclohexane 2.91
    cyclooctane 1.15
    cyclopentanol 18.3
    tetrahydropyran 35.74
    tert-amyl methyl ether 14.82
    2,5,8-trioxanonane 50.45
    1-hexene 5.88
    2-isopropoxyethanol 24.4
    2,2,2-trifluoroethanol 18.32
    methyl butyrate 37.66

    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