8-Hydroxy-1-methoxy-3-methyl-9,10-anthracenedione

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  • Identifiers

    CAS number
    67116-22-7

    Molecular formula
    C16H12O4

    SMILES
    CC1=CC2=C(C(=C1)OC)C(=O)C3=C(C2=O)C=CC=C3O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 51.95%
    Phenolic 49.61%
    Spicy 34.6%
    Odorless 32.69%
    Powdery 32.51%
    Woody 31.19%
    Vanilla 30.41%
    Dry 28.89%
    Balsamic 26.49%
    Bitter 26.45%

     

    Flavor
    Bitter 94.42%
    Odorless 20.53%
    Lovage 19.66%
    Cedarleaf 19.23%
    Parsley 18.99%
    Nitrile 18.67%
    Very strong 18.34%
    Sweet-like 18.27%
    Ripe apricot 18.25%
    Red fruit 18.19%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    7.98 (neutral)

    Molecular weight
    268.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    500°C

    Melting point expt.

    • 199 - 200 °C

    Flash point

    • 223.33 ˚C est.

  • Synonyms

    • 67116-22-7
    • RefChem:1074707
    • 8-Hydroxy-1-methoxy-3-methyl-9,10-anthracenedione
    • 8-Hydroxy-1-methoxy-3-methylanthraquinone
    • 8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione
    • CHEMBL454477
    • SCHEMBL8930315
    • DTXSID20540019
    • CHEBI:174530
    • 8-HYDROXY-1-METHOXY-3-METHYL-9,10-DIHYDROANTHRACENE-9,10-DIONE
    • 1-methoxy-3-methyl-8-hydroxy-anthraquinone
    • 67116-22-7

  • Applications

    8-Hydroxy-1-methoxy-3-methyl-9,10-anthracenedione (CAS 67116-22-7) is used as a dye/pigment intermediate for coatings and inks, often serving as a precursor in pigment synthesis; it can function as a photosensitizer in UV-curable resins and adhesives; it may act as a UV absorber or optical stabilizer in polymer formulations; and it is employed in research and development as an analytical reference or colorant for materials science applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.84
    methanol 0.74
    isopropanol 0.65
    water 0.0
    ethyl acetate 4.82
    n-propanol 0.93
    acetone 5.64
    n-butanol 1.07
    acetonitrile 3.36
    DMF 32.1
    toluene 4.4
    isobutanol 0.84
    1,4-dioxane 12.18
    methyl acetate 7.26
    THF 28.5
    2-butanone 7.26
    n-pentanol 1.18
    sec-butanol 0.6
    n-hexane 0.04
    ethylene glycol 1.17
    NMP 51.1
    cyclohexane 0.1
    DMSO 21.75
    n-butyl acetate 10.53
    n-octanol 2.6
    chloroform 14.13
    n-propyl acetate 7.62
    acetic acid 5.22
    dichloromethane 12.57
    cyclohexanone 22.06
    propylene glycol 0.79
    isopropyl acetate 6.05
    DMAc 52.61
    2-ethoxyethanol 5.34
    isopentanol 1.97
    n-heptane 0.07
    ethyl formate 3.86
    1,2-dichloroethane 11.88
    n-hexanol 2.96
    2-methoxyethanol 10.01
    isobutyl acetate 7.71
    tetrachloromethane 1.2
    n-pentyl acetate 8.16
    transcutol 13.11
    n-heptanol 3.49
    ethylbenzene 3.49
    MIBK 7.09
    2-propoxyethanol 13.9
    tert-butanol 2.27
    MTBE 1.96
    2-butoxyethanol 10.63
    propionic acid 3.31
    o-xylene 3.89
    formic acid 2.4
    diethyl ether 1.23
    m-xylene 3.78
    p-xylene 4.81
    chlorobenzene 6.36
    dimethyl carbonate 12.19
    n-octane 0.08
    formamide 5.84
    cyclopentanone 31.96
    2-pentanone 5.48
    anisole 9.67
    cyclopentyl methyl ether 8.37
    gamma-butyrolactone 32.35
    1-methoxy-2-propanol 7.27
    pyridine 18.54
    3-pentanone 5.15
    furfural 33.49
    n-dodecane 0.18
    diethylene glycol 13.83
    diisopropyl ether 0.82
    tert-amyl alcohol 1.78
    acetylacetone 14.69
    n-hexadecane 0.23
    acetophenone 15.4
    methyl propionate 7.42
    isopentyl acetate 13.09
    trichloroethylene 34.09
    n-nonanol 3.17
    cyclohexanol 2.38
    benzyl alcohol 8.17
    2-ethylhexanol 3.79
    isooctanol 3.57
    dipropyl ether 3.05
    1,2-dichlorobenzene 8.97
    ethyl lactate 7.2
    propylene carbonate 16.59
    n-methylformamide 7.38
    2-pentanol 0.71
    n-pentane 0.02
    1-propoxy-2-propanol 9.41
    1-methoxy-2-propyl acetate 18.5
    2-(2-methoxypropoxy) propanol 12.78
    mesitylene 2.55
    ε-caprolactone 19.52
    p-cymene 4.08
    epichlorohydrin 35.76
    1,1,1-trichloroethane 8.23
    2-aminoethanol 1.47
    morpholine-4-carbaldehyde 40.61
    sulfolane 50.11
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 10.3
    n-hexyl acetate 9.13
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 11.54
    sec-butyl acetate 6.74
    tert-butyl acetate 10.48
    decalin 0.35
    glycerin 4.47
    diglyme 26.81
    acrylic acid 5.66
    isopropyl myristate 5.18
    n-butyric acid 4.84
    acetyl acetate 7.03
    di(2-ethylhexyl) phthalate 7.78
    ethyl propionate 7.77
    nitromethane 16.63
    1,2-diethoxyethane 6.31
    benzonitrile 11.4
    trioctyl phosphate 5.56
    1-bromopropane 2.52
    gamma-valerolactone 38.84
    n-decanol 2.58
    triethyl phosphate 9.51
    4-methyl-2-pentanol 1.45
    propionitrile 4.05
    vinylene carbonate 16.83
    1,1,2-trichlorotrifluoroethane 32.0
    DMS 16.23
    cumene 3.01
    2-octanol 2.22
    2-hexanone 7.3
    octyl acetate 6.08
    limonene 4.2
    1,2-dimethoxyethane 16.4
    ethyl orthosilicate 8.2
    tributyl phosphate 5.93
    diacetone alcohol 15.14
    N,N-dimethylaniline 8.91
    acrylonitrile 9.52
    aniline 7.01
    1,3-propanediol 3.0
    bromobenzene 6.66
    dibromomethane 5.85
    1,1,2,2-tetrachloroethane 23.48
    2-methyl-cyclohexyl acetate 12.42
    tetrabutyl urea 9.63
    diisobutyl methanol 3.13
    2-phenylethanol 13.05
    styrene 3.59
    dioctyl adipate 8.38
    dimethyl sulfate 28.86
    ethyl butyrate 8.89
    methyl lactate 9.14
    butyl lactate 7.67
    diethyl carbonate 8.25
    propanediol butyl ether 5.76
    triethyl orthoformate 8.82
    p-tert-butyltoluene 3.65
    methyl 4-tert-butylbenzoate 16.27
    morpholine 13.65
    tert-butylamine 1.02
    n-dodecanol 2.05
    dimethoxymethane 16.02
    ethylene carbonate 12.23
    cyrene 20.96
    2-ethoxyethyl acetate 12.0
    2-ethylhexyl acetate 11.1
    1,2,4-trichlorobenzene 13.77
    4-methylpyridine 16.72
    dibutyl ether 2.99
    2,6-dimethyl-4-heptanol 3.13
    DEF 12.86
    dimethyl isosorbide 29.62
    tetrachloroethylene 14.33
    eugenol 16.51
    triacetin 12.09
    span 80 8.98
    1,4-butanediol 1.18
    1,1-dichloroethane 5.07
    2-methyl-1-pentanol 2.32
    methyl formate 7.45
    2-methyl-1-butanol 1.38
    n-decane 0.24
    butyronitrile 3.33
    3,7-dimethyl-1-octanol 3.44
    1-chlorooctane 1.98
    1-chlorotetradecane 1.11
    n-nonane 0.15
    undecane 0.21
    tert-butylcyclohexane 0.3
    cyclooctane 0.05
    cyclopentanol 3.04
    tetrahydropyran 6.3
    tert-amyl methyl ether 2.43
    2,5,8-trioxanonane 20.82
    1-hexene 0.39
    2-isopropoxyethanol 5.06
    2,2,2-trifluoroethanol 4.68
    methyl butyrate 9.58

    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