Plumbagin

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  • Identifiers

    CAS number
    481-42-5

    Molecular formula
    C11H8O3

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

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Sweet 62.0%
    Caramellic 49.25%
    Burnt 44.23%
    Phenolic 42.94%
    Spicy 34.73%
    Coumarinic 32.0%
    Bitter 30.46%
    Nutty 30.32%
    Vanilla 28.64%
    Hay 27.54%

     

    Flavor
    Bitter 75.25%
    Lovage 21.21%
    Basil 20.4%
    Nitrile 20.3%
    Odorless 20.3%
    Fenugreek 20.06%
    Seedy 19.56%
    Maple syrup 19.48%
    Leaves 19.42%
    Very strong 19.4%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    8.14 (weak base)

    Molecular weight
    188.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    378°C

    Flash point

    • 162.69 ˚C est.

  • Synonyms

    • Plumbagin
    • 481-42-5
    • 5-hydroxy-2-methylnaphthalene-1,4-dione
    • Plumbagine
    • 5-Hydroxy-2-methyl-1,4-naphthoquinone
    • 2-Methyljuglone
    • Plumbaein
    • Plumbagone
    • 5-Hydroxy-2-methyl-1,4-naphthalenedione
    • 2-Methyl-5-hydroxy-1,4-naphthoquinone
    • 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
    • YAS4TBQ4OQ
    • NSC-236613
    • NSC-688284
    • PCUR-101
    • CHEBI:8273
    • RefChem:863847
    • PCUR101
    • PCUR 101
    • Synthetic Plumbagin PCUR-101
    • 207-569-6
    • 1,4-Naphthalenedione, 5-hydroxy-2-methyl-
    • 5-Hydroxy-2-methyl-[1,4]naphthoquinone
    • MFCD00001682
    • NSC 236613
    • NSC 688284
    • 5-Hydroxy-2-methyl-naphthalene-1,4-dione
    • CHEMBL295316
    • 1,4-NAPHTHOQUINONE, 5-HYDROXY-2-METHYL-
    • NSC236613
    • NSC688284
    • ST069355
    • Ophioxylin
    • CCRIS 6671
    • SR-05000002263
    • UNII-YAS4TBQ4OQ
    • EINECS 207-569-6
    • BRN 1870475
    • Pumbagin
    • AI3-38055
    • DTXSID8075413
    • 5-Hydroxy-2-methylnaphthoquinone
    • Plumbagin (Standard)
    • Plumbagin [WHO-DD]
    • PLUMBAGIN [MI]
    • RTK1
    • 1, 5-hydroxy-2-methyl-
    • SCHEMBL34186
    • BSPBio_002546
    • 4-08-00-02376 (Beilstein Handbook Reference)
    • Plumbagin from Plumbago indica
    • SPECTRUM1505129
    • GTPL7003
    • orb1304950
    • SCHEMBL29386213
    • ACon1_001611
    • HY-N1497R
    • GLXC-07459
    • HMS3870L13
    • WLN: L66 BV EVJ C1 GQ
    • HY-N1497
    • BDBM50012070
    • MSK177647
    • s4777
    • SBB012388
    • STL564479
    • AKOS015969699
    • CCG-208032
    • CCG-208410
    • EBC-421050
    • FP13778
    • NCGC00094567-01
    • NCGC00094567-02
    • NCGC00094567-03
    • NCGC00094567-04
    • NCGC00094567-05
    • NCGC00094567-06
    • NCGC00094567-10
    • BP-25404
    • NCI60_001904
    • PS-11338
    • SY050738
    • DB-051524
    • CS-0017042
    • NS00031768
    • P1139
    • 5- HYDROXY,2-METHYL-1,4-NAPHTOQUINONE
    • AP-782/41885488
    • A1-00788
    • Q2550553
    • SR-05000002263-2
    • SR-05000002263-3
    • BRD-K36137799-001-02-4
    • BRD-K36137799-001-03-2
    • InChI=1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H
    • Plumbagin2-Methyljuglone; 5-hydroxy-2-methylnaphthalene-1,4-dione; 5-Hydroxy-2-methyl-1,4-naphthoquinone
    • 481-42-5

  • Applications

    Plumbagin (CAS 481-42-5) is a natural naphthoquinone that is primarily used as an intermediate in organic synthesis and is actively studied as a lead compound in pharmaceutical and biochemical research. It has also been explored as a natural pigment for coatings, inks, and textiles, and is considered for applications in polymers and materials science because of its redox-active and photoresponsive properties.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.86
    methanol 24.31
    isopropanol 15.66
    water 0.29
    ethyl acetate 57.64
    n-propanol 16.08
    acetone 105.43
    n-butanol 14.97
    acetonitrile 57.99
    DMF 279.81
    toluene 36.51
    isobutanol 11.66
    1,4-dioxane 114.98
    methyl acetate 79.46
    THF 129.81
    2-butanone 73.03
    n-pentanol 18.85
    sec-butanol 13.08
    n-hexane 1.73
    ethylene glycol 12.98
    NMP 170.71
    cyclohexane 2.13
    DMSO 178.1
    n-butyl acetate 46.61
    n-octanol 24.93
    chloroform 80.61
    n-propyl acetate 48.68
    acetic acid 30.01
    dichloromethane 131.11
    cyclohexanone 99.65
    propylene glycol 6.58
    isopropyl acetate 35.24
    DMAc 164.98
    2-ethoxyethanol 50.11
    isopentanol 16.09
    n-heptane 3.75
    ethyl formate 59.96
    1,2-dichloroethane 97.64
    n-hexanol 27.21
    2-methoxyethanol 70.83
    isobutyl acetate 24.9
    tetrachloromethane 11.08
    n-pentyl acetate 36.98
    transcutol 69.18
    n-heptanol 22.05
    ethylbenzene 26.97
    MIBK 39.0
    2-propoxyethanol 66.18
    tert-butanol 26.92
    MTBE 20.63
    2-butoxyethanol 40.75
    propionic acid 24.48
    o-xylene 29.9
    formic acid 16.82
    diethyl ether 27.66
    m-xylene 34.23
    p-xylene 34.57
    chlorobenzene 49.78
    dimethyl carbonate 57.22
    n-octane 3.03
    formamide 54.43
    cyclopentanone 143.57
    2-pentanone 58.99
    anisole 57.26
    cyclopentyl methyl ether 46.96
    gamma-butyrolactone 158.4
    1-methoxy-2-propanol 47.84
    pyridine 90.26
    3-pentanone 49.25
    furfural 140.38
    n-dodecane 3.96
    diethylene glycol 61.28
    diisopropyl ether 11.27
    tert-amyl alcohol 19.77
    acetylacetone 89.76
    n-hexadecane 4.6
    acetophenone 63.83
    methyl propionate 64.74
    isopentyl acetate 38.75
    trichloroethylene 151.54
    n-nonanol 23.4
    cyclohexanol 18.47
    benzyl alcohol 44.08
    2-ethylhexanol 21.78
    isooctanol 19.78
    dipropyl ether 26.15
    1,2-dichlorobenzene 49.26
    ethyl lactate 30.17
    propylene carbonate 74.37
    n-methylformamide 98.84
    2-pentanol 11.65
    n-pentane 1.44
    1-propoxy-2-propanol 40.52
    1-methoxy-2-propyl acetate 55.94
    2-(2-methoxypropoxy) propanol 43.47
    mesitylene 21.2
    ε-caprolactone 81.35
    p-cymene 20.81
    epichlorohydrin 165.97
    1,1,1-trichloroethane 53.53
    2-aminoethanol 15.36
    morpholine-4-carbaldehyde 160.25
    sulfolane 163.02
    2,2,4-trimethylpentane 1.61
    2-methyltetrahydrofuran 65.85
    n-hexyl acetate 47.89
    isooctane 1.8
    2-(2-butoxyethoxy)ethanol 49.46
    sec-butyl acetate 28.53
    tert-butyl acetate 38.95
    decalin 4.18
    glycerin 18.42
    diglyme 101.4
    acrylic acid 29.35
    isopropyl myristate 24.83
    n-butyric acid 30.26
    acetyl acetate 45.82
    di(2-ethylhexyl) phthalate 24.54
    ethyl propionate 46.26
    nitromethane 122.42
    1,2-diethoxyethane 41.74
    benzonitrile 65.76
    trioctyl phosphate 20.41
    1-bromopropane 30.76
    gamma-valerolactone 164.84
    n-decanol 20.18
    triethyl phosphate 27.73
    4-methyl-2-pentanol 11.3
    propionitrile 44.61
    vinylene carbonate 82.53
    1,1,2-trichlorotrifluoroethane 71.57
    DMS 55.21
    cumene 20.42
    2-octanol 18.26
    2-hexanone 52.34
    octyl acetate 31.4
    limonene 23.19
    1,2-dimethoxyethane 120.49
    ethyl orthosilicate 23.99
    tributyl phosphate 22.03
    diacetone alcohol 51.18
    N,N-dimethylaniline 43.94
    acrylonitrile 76.19
    aniline 38.65
    1,3-propanediol 23.92
    bromobenzene 48.92
    dibromomethane 67.85
    1,1,2,2-tetrachloroethane 92.18
    2-methyl-cyclohexyl acetate 36.81
    tetrabutyl urea 36.52
    diisobutyl methanol 16.47
    2-phenylethanol 47.86
    styrene 29.96
    dioctyl adipate 34.07
    dimethyl sulfate 88.12
    ethyl butyrate 43.12
    methyl lactate 36.14
    butyl lactate 26.6
    diethyl carbonate 33.4
    propanediol butyl ether 31.32
    triethyl orthoformate 30.03
    p-tert-butyltoluene 18.88
    methyl 4-tert-butylbenzoate 52.92
    morpholine 85.55
    tert-butylamine 14.02
    n-dodecanol 17.42
    dimethoxymethane 129.35
    ethylene carbonate 66.33
    cyrene 60.49
    2-ethoxyethyl acetate 49.71
    2-ethylhexyl acetate 32.26
    1,2,4-trichlorobenzene 55.97
    4-methylpyridine 87.52
    dibutyl ether 25.96
    2,6-dimethyl-4-heptanol 16.47
    DEF 82.29
    dimethyl isosorbide 92.43
    tetrachloroethylene 60.32
    eugenol 54.26
    triacetin 46.55
    span 80 33.86
    1,4-butanediol 14.65
    1,1-dichloroethane 59.81
    2-methyl-1-pentanol 18.75
    methyl formate 107.7
    2-methyl-1-butanol 13.91
    n-decane 5.45
    butyronitrile 37.4
    3,7-dimethyl-1-octanol 21.98
    1-chlorooctane 20.69
    1-chlorotetradecane 11.02
    n-nonane 4.66
    undecane 4.61
    tert-butylcyclohexane 3.97
    cyclooctane 1.52
    cyclopentanol 24.19
    tetrahydropyran 49.65
    tert-amyl methyl ether 20.88
    2,5,8-trioxanonane 76.53
    1-hexene 8.92
    2-isopropoxyethanol 38.36
    2,2,2-trifluoroethanol 25.62
    methyl butyrate 61.56

    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