2-Hydroxy-1,4-naphthoquinone

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  • Identifiers

    CAS number
    83-72-7

    Molecular formula
    C10H6O3

    SMILES
    C1=CC=C2C(=C1)C(=CC(=O)C2=O)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 50.54%
    Caramellic 49.14%
    Burnt 46.5%
    Phenolic 38.2%
    Nutty 34.2%
    Odorless 33.0%
    Spicy 30.86%
    Bitter 27.87%
    Coumarinic 27.09%
    Almond 25.1%

     

    Flavor
    Bitter 61.05%
    Odorless 23.2%
    Fenugreek 21.24%
    Lovage 21.08%
    Nitrile 20.85%
    Maple syrup 20.67%
    Urine 20.64%
    Balsam 20.34%
    Seedy 20.28%
    Extremely sweet 19.95%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    7.67 (neutral)

    Molecular weight
    174.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    344°C

    Flash point

    • 156.88 ˚C est.

  • Synonyms

    • Lawsone
    • 83-72-7
    • 2-Hydroxy-1,4-naphthoquinone
    • 2-hydroxynaphthalene-1,4-dione
    • 2-Hydroxy-1,4-naphoquinone
    • 2-Hydroxynaphthoquinone
    • Henna
    • Mehendi
    • HANA
    • Natural Orange 6
    • Lawson
    • Mendi
    • 2-Hydroxy-1,4-naphthalenedione
    • C.I. Natural Orange 6
    • 1,4-Naphthalenedione, 2-hydroxy-
    • 4-hydroxynaphthalene-1,2-dione
    • 1,4-Naphthoquinone, 2-hydroxy-
    • C.I. 75480
    • NSC 8625
    • 2-HYDROXY-1,4-NAPTHOQUINONE
    • MFCD00001678
    • NSC 27285
    • 2-hydroxy-1,4-dihydronaphthalene-1,4-dione
    • NSC-8625
    • TLH4A6LV1W
    • CHEBI:44401
    • 2-hydroxy-naphthalene-1,4-dione
    • NSC8625
    • NSC-27285
    • 1, 2-hydroxy-
    • Lawsonia alba
    • Henna leaves
    • 2-Hydroxy-p-naphthoquinone
    • 27699-93-0
    • CCRIS 6248
    • NSC-52500
    • EINECS 201-496-3
    • UNII-TLH4A6LV1W
    • BRN 1565260
    • AI3-12099
    • Henna;
    • IMEXINE OG
    • Spectrum_001200
    • SpecPlus_000482
    • LAWSONE [MI]
    • LAWSONE [MART.]
    • Spectrum2_001506
    • Spectrum3_001538
    • Spectrum4_001697
    • Spectrum5_000374
    • HENNA (DYE)
    • SCHEMBL16541
    • BSPBio_002956
    • KBioGR_001994
    • KBioSS_001680
    • 4-08-00-02360 (Beilstein Handbook Reference)
    • DivK1c_006578
    • SCHEMBL342409
    • SPECTRUM1502250
    • 2-hydroxy-1,4-naphthaquinone
    • SPBio_001551
    • 2-hydroxyl-1,4-naphthoquinone
    • CHEMBL240963
    • NQ-6
    • orb1304790
    • DTXSID2025428
    • SCHEMBL11804609
    • SCHEMBL29350263
    • KBio1_001522
    • KBio2_001680
    • KBio2_004248
    • KBio2_006816
    • KBio3_002456
    • WVCHIGAIXREVNS-UHFFFAOYSA-N
    • HMS5082C19
    • BB_NC-00481
    • HY-N2493
    • NSC27285
    • BBL027350
    • BDBM50049066
    • CCG-38882
    • EBC-44217
    • s3858
    • SBB069496
    • STK801825
    • 2-Hydroxy-1,4-naphthoquinone, 97%
    • AKOS000120111
    • DB04744
    • FL02351
    • GS-3117
    • SDCCGMLS-0066674.P001
    • UPCMLD0ENAT5883810:001
    • Lawsone (2-Hydroxy-1,4-naphthoquinone)
    • NCGC00095834-01
    • NCGC00095834-02
    • NCGC00095834-03
    • AC-34621
    • PD006431
    • ST097865
    • SY012958
    • DB-005248
    • CS-0022764
    • H0285
    • NS00015309
    • EN300-20637
    • F17705
    • F209636
    • SR-05000002407
    • Q1075492
    • SR-05000002407-1
    • Z104479394
    • Q 0
    • 83-72-7

  • Applications

    2-Hydroxy-1,4-naphthoquinone (CAS 83-72-7) is used as a natural colorant and dye for hair, skin, and textiles (henna); in cosmetics and personal care it is used as a colorant for products and for temporary body art; in industrial manufacturing it acts as an intermediate and precursor for the production of dyes and pigments used in paints, coatings, and inks; it is also considered a chemical intermediate in organic synthesis and may function as a redox-active component in analytical chemistry and related research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.22
    methanol 22.17
    isopropanol 8.95
    water 0.4
    ethyl acetate 31.81
    n-propanol 10.06
    acetone 84.72
    n-butanol 9.54
    acetonitrile 40.43
    DMF 255.52
    toluene 12.73
    isobutanol 6.81
    1,4-dioxane 112.47
    methyl acetate 53.83
    THF 194.21
    2-butanone 55.01
    n-pentanol 11.58
    sec-butanol 8.03
    n-hexane 1.09
    ethylene glycol 17.51
    NMP 143.5
    cyclohexane 0.82
    DMSO 279.67
    n-butyl acetate 29.75
    n-octanol 19.26
    chloroform 34.58
    n-propyl acetate 26.69
    acetic acid 22.06
    dichloromethane 50.66
    cyclohexanone 65.32
    propylene glycol 6.76
    isopropyl acetate 24.8
    DMAc 162.07
    2-ethoxyethanol 43.26
    isopentanol 11.55
    n-heptane 2.35
    ethyl formate 23.45
    1,2-dichloroethane 62.97
    n-hexanol 19.86
    2-methoxyethanol 74.75
    isobutyl acetate 15.65
    tetrachloromethane 6.38
    n-pentyl acetate 26.48
    transcutol 104.3
    n-heptanol 17.15
    ethylbenzene 11.65
    MIBK 31.29
    2-propoxyethanol 59.19
    tert-butanol 19.56
    MTBE 18.73
    2-butoxyethanol 42.08
    propionic acid 16.13
    o-xylene 13.32
    formic acid 15.87
    diethyl ether 22.51
    m-xylene 13.56
    p-xylene 15.13
    chlorobenzene 21.15
    dimethyl carbonate 46.1
    n-octane 1.89
    formamide 51.47
    cyclopentanone 135.94
    2-pentanone 42.17
    anisole 31.84
    cyclopentyl methyl ether 41.98
    gamma-butyrolactone 135.81
    1-methoxy-2-propanol 48.31
    pyridine 58.03
    3-pentanone 35.0
    furfural 96.29
    n-dodecane 2.41
    diethylene glycol 68.8
    diisopropyl ether 9.16
    tert-amyl alcohol 15.15
    acetylacetone 78.82
    n-hexadecane 2.78
    acetophenone 36.16
    methyl propionate 41.17
    isopentyl acetate 27.46
    trichloroethylene 90.44
    n-nonanol 18.55
    cyclohexanol 12.03
    benzyl alcohol 23.73
    2-ethylhexanol 15.74
    isooctanol 14.35
    dipropyl ether 19.5
    1,2-dichlorobenzene 23.63
    ethyl lactate 21.7
    propylene carbonate 46.01
    n-methylformamide 72.28
    2-pentanol 8.24
    n-pentane 0.65
    1-propoxy-2-propanol 38.56
    1-methoxy-2-propyl acetate 44.37
    2-(2-methoxypropoxy) propanol 41.96
    mesitylene 10.41
    ε-caprolactone 52.55
    p-cymene 12.2
    epichlorohydrin 163.64
    1,1,1-trichloroethane 32.7
    2-aminoethanol 16.03
    morpholine-4-carbaldehyde 136.49
    sulfolane 174.93
    2,2,4-trimethylpentane 1.11
    2-methyltetrahydrofuran 56.69
    n-hexyl acetate 36.15
    isooctane 1.19
    2-(2-butoxyethoxy)ethanol 54.72
    sec-butyl acetate 18.35
    tert-butyl acetate 34.28
    decalin 2.34
    glycerin 24.48
    diglyme 114.27
    acrylic acid 20.32
    isopropyl myristate 18.65
    n-butyric acid 18.43
    acetyl acetate 26.74
    di(2-ethylhexyl) phthalate 16.35
    ethyl propionate 26.87
    nitromethane 104.53
    1,2-diethoxyethane 37.01
    benzonitrile 30.99
    trioctyl phosphate 14.68
    1-bromopropane 17.06
    gamma-valerolactone 131.48
    n-decanol 15.05
    triethyl phosphate 20.37
    4-methyl-2-pentanol 8.98
    propionitrile 26.5
    vinylene carbonate 42.16
    1,1,2-trichlorotrifluoroethane 66.19
    DMS 43.7
    cumene 9.68
    2-octanol 13.36
    2-hexanone 33.1
    octyl acetate 22.89
    limonene 14.39
    1,2-dimethoxyethane 88.23
    ethyl orthosilicate 17.91
    tributyl phosphate 15.2
    diacetone alcohol 51.45
    N,N-dimethylaniline 26.31
    acrylonitrile 48.66
    aniline 18.79
    1,3-propanediol 23.57
    bromobenzene 19.82
    dibromomethane 26.42
    1,1,2,2-tetrachloroethane 59.18
    2-methyl-cyclohexyl acetate 23.64
    tetrabutyl urea 24.97
    diisobutyl methanol 12.69
    2-phenylethanol 31.0
    styrene 12.63
    dioctyl adipate 23.69
    dimethyl sulfate 94.74
    ethyl butyrate 23.81
    methyl lactate 33.86
    butyl lactate 22.38
    diethyl carbonate 19.28
    propanediol butyl ether 30.59
    triethyl orthoformate 20.2
    p-tert-butyltoluene 12.14
    methyl 4-tert-butylbenzoate 40.55
    morpholine 83.39
    tert-butylamine 9.38
    n-dodecanol 11.98
    dimethoxymethane 116.76
    ethylene carbonate 33.12
    cyrene 45.54
    2-ethoxyethyl acetate 39.99
    2-ethylhexyl acetate 22.24
    1,2,4-trichlorobenzene 30.43
    4-methylpyridine 47.5
    dibutyl ether 19.2
    2,6-dimethyl-4-heptanol 12.69
    DEF 54.51
    dimethyl isosorbide 75.23
    tetrachloroethylene 39.24
    eugenol 41.47
    triacetin 37.54
    span 80 28.27
    1,4-butanediol 12.72
    1,1-dichloroethane 30.46
    2-methyl-1-pentanol 12.4
    methyl formate 65.51
    2-methyl-1-butanol 9.05
    n-decane 3.33
    butyronitrile 20.05
    3,7-dimethyl-1-octanol 16.47
    1-chlorooctane 14.17
    1-chlorotetradecane 7.06
    n-nonane 2.87
    undecane 2.81
    tert-butylcyclohexane 2.32
    cyclooctane 0.72
    cyclopentanol 19.19
    tetrahydropyran 43.95
    tert-amyl methyl ether 18.67
    2,5,8-trioxanonane 77.87
    1-hexene 5.5
    2-isopropoxyethanol 31.49
    2,2,2-trifluoroethanol 20.72
    methyl butyrate 33.84

    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