9,10-Dihydro-8-hydroxy-3-methoxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid

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  • Identifiers

    CAS number
    176327-86-9

    Molecular formula
    C17H12O6

    SMILES
    CC1=C2C(=CC(=C1C(=O)O)OC)C(=O)C3=C(C2=O)C(=CC=C3)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 49.27%
    Phenolic 43.23%
    Sweet 41.39%
    Powdery 29.32%
    Balsamic 28.51%
    Dry 28.5%
    Vanilla 25.57%
    Bitter 24.41%
    Burnt 23.92%
    Spicy 23.08%

     

    Flavor
    Bitter 87.47%
    Odorless 34.73%
    Bland 23.09%
    Lovage 20.15%
    Sweet-like 19.91%
    Cedarleaf 19.91%
    Nitrile 19.89%
    Parsley 19.6%
    Very strong 19.11%
    Ripe apricot 19.05%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    6.45 (neutral)

    Molecular weight
    312.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    812°C

    Flash point

    • 277.29 ˚C est.

  • Synonyms

    • 9,10-Dihydro-8-hydroxy-3-methoxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid
    • 176327-86-9
    • RefChem:312544
    • 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid
    • SCHEMBL28549227
    • CHEBI:174248
    • DTXSID201135129
    • 8-hydroxy-3-methoxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
    • 1-methyl-3-methoxy-8-hydroxyanthraquinone-2-carboxylic acid
    • 8-hydroxy-3-methoxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid
    • 176327-86-9

  • Applications

    9,10-Dihydro-8-hydroxy-3-methoxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid (CAS 176327-86-9) is commonly regarded as a building block and intermediate for the synthesis of colored compounds and pigments based on the anthracene core, enabled by the carboxyl group and functionalizable substituents. In practice, it may be used as an intermediate in the production of colorants for textiles, plastics, and coatings, and as a precursor to derivatives for printing inks and specialty materials. Its carboxyl functionality and rigid aromatic framework also make it a potential component in polymer formulations where crosslinking or surface modification is desired. Additionally, it may be evaluated as a UV-absorber or photochemical stabilizer in coatings, plastics, or composites, and there is potential for exploration in organic-electronics contexts in research settings. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.61
    methanol 0.53
    isopropanol 0.6
    water 0.0
    ethyl acetate 1.88
    n-propanol 0.73
    acetone 2.67
    n-butanol 0.78
    acetonitrile 0.98
    DMF 23.81
    toluene 0.82
    isobutanol 0.55
    1,4-dioxane 6.35
    methyl acetate 2.09
    THF 22.16
    2-butanone 3.07
    n-pentanol 1.06
    sec-butanol 0.55
    n-hexane 0.05
    ethylene glycol 0.95
    NMP 28.46
    cyclohexane 0.03
    DMSO 38.07
    n-butyl acetate 3.42
    n-octanol 1.26
    chloroform 1.95
    n-propyl acetate 2.67
    acetic acid 1.6
    dichloromethane 2.32
    cyclohexanone 8.44
    propylene glycol 0.64
    isopropyl acetate 2.03
    DMAc 28.05
    2-ethoxyethanol 4.98
    isopentanol 1.12
    n-heptane 0.04
    ethyl formate 1.38
    1,2-dichloroethane 2.95
    n-hexanol 1.42
    2-methoxyethanol 9.35
    isobutyl acetate 1.72
    tetrachloromethane 0.25
    n-pentyl acetate 3.15
    transcutol 7.15
    n-heptanol 1.79
    ethylbenzene 0.76
    MIBK 3.15
    2-propoxyethanol 11.09
    tert-butanol 1.7
    MTBE 0.76
    2-butoxyethanol 6.5
    propionic acid 1.24
    o-xylene 0.82
    formic acid 1.92
    diethyl ether 0.75
    m-xylene 0.85
    p-xylene 1.12
    chlorobenzene 1.03
    dimethyl carbonate 4.52
    n-octane 0.04
    formamide 4.36
    cyclopentanone 14.66
    2-pentanone 3.13
    anisole 2.49
    cyclopentyl methyl ether 3.61
    gamma-butyrolactone 13.71
    1-methoxy-2-propanol 6.9
    pyridine 4.8
    3-pentanone 2.53
    furfural 10.7
    n-dodecane 0.07
    diethylene glycol 12.28
    diisopropyl ether 0.32
    tert-amyl alcohol 1.22
    acetylacetone 6.15
    n-hexadecane 0.09
    acetophenone 4.45
    methyl propionate 3.33
    isopentyl acetate 3.65
    trichloroethylene 5.97
    n-nonanol 1.61
    cyclohexanol 1.22
    benzyl alcohol 2.74
    2-ethylhexanol 1.36
    isooctanol 1.66
    dipropyl ether 1.62
    1,2-dichlorobenzene 1.59
    ethyl lactate 3.14
    propylene carbonate 4.52
    n-methylformamide 5.21
    2-pentanol 0.53
    n-pentane 0.02
    1-propoxy-2-propanol 6.77
    1-methoxy-2-propyl acetate 7.04
    2-(2-methoxypropoxy) propanol 7.55
    mesitylene 0.64
    ε-caprolactone 6.79
    p-cymene 0.92
    epichlorohydrin 16.42
    1,1,1-trichloroethane 1.43
    2-aminoethanol 1.24
    morpholine-4-carbaldehyde 22.39
    sulfolane 35.04
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 4.71
    n-hexyl acetate 3.25
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 7.06
    sec-butyl acetate 1.83
    tert-butyl acetate 3.41
    decalin 0.1
    glycerin 3.99
    diglyme 13.62
    acrylic acid 1.93
    isopropyl myristate 1.99
    n-butyric acid 1.67
    acetyl acetate 1.71
    di(2-ethylhexyl) phthalate 3.31
    ethyl propionate 2.99
    nitromethane 6.08
    1,2-diethoxyethane 3.14
    benzonitrile 2.69
    trioctyl phosphate 2.67
    1-bromopropane 1.0
    gamma-valerolactone 19.9
    n-decanol 1.31
    triethyl phosphate 3.31
    4-methyl-2-pentanol 0.73
    propionitrile 1.72
    vinylene carbonate 4.31
    1,1,2-trichlorotrifluoroethane 13.46
    DMS 5.0
    cumene 0.65
    2-octanol 1.17
    2-hexanone 3.95
    octyl acetate 2.64
    limonene 1.01
    1,2-dimethoxyethane 12.82
    ethyl orthosilicate 2.82
    tributyl phosphate 2.59
    diacetone alcohol 7.68
    N,N-dimethylaniline 2.64
    acrylonitrile 3.46
    aniline 1.81
    1,3-propanediol 2.31
    bromobenzene 0.95
    dibromomethane 1.38
    1,1,2,2-tetrachloroethane 5.37
    2-methyl-cyclohexyl acetate 3.89
    tetrabutyl urea 4.96
    diisobutyl methanol 1.17
    2-phenylethanol 4.21
    styrene 0.72
    dioctyl adipate 3.43
    dimethyl sulfate 13.7
    ethyl butyrate 2.86
    methyl lactate 4.81
    butyl lactate 3.33
    diethyl carbonate 2.36
    propanediol butyl ether 3.48
    triethyl orthoformate 3.08
    p-tert-butyltoluene 0.89
    methyl 4-tert-butylbenzoate 6.91
    morpholine 7.86
    tert-butylamine 0.55
    n-dodecanol 1.01
    dimethoxymethane 12.88
    ethylene carbonate 3.5
    cyrene 10.97
    2-ethoxyethyl acetate 4.67
    2-ethylhexyl acetate 3.02
    1,2,4-trichlorobenzene 2.42
    4-methylpyridine 4.21
    dibutyl ether 1.31
    2,6-dimethyl-4-heptanol 1.17
    DEF 6.59
    dimethyl isosorbide 15.95
    tetrachloroethylene 3.16
    eugenol 8.0
    triacetin 4.25
    span 80 5.11
    1,4-butanediol 1.13
    1,1-dichloroethane 1.11
    2-methyl-1-pentanol 1.36
    methyl formate 4.03
    2-methyl-1-butanol 0.86
    n-decane 0.1
    butyronitrile 1.37
    3,7-dimethyl-1-octanol 1.29
    1-chlorooctane 0.66
    1-chlorotetradecane 0.38
    n-nonane 0.07
    undecane 0.09
    tert-butylcyclohexane 0.08
    cyclooctane 0.03
    cyclopentanol 1.7
    tetrahydropyran 2.5
    tert-amyl methyl ether 1.14
    2,5,8-trioxanonane 12.92
    1-hexene 0.32
    2-isopropoxyethanol 3.75
    2,2,2-trifluoroethanol 1.7
    methyl butyrate 3.6

    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