1,3,8-Trihydroxy-6-methyl-9(10H)-anthracenone

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  • Identifiers

    CAS number
    491-60-1

    Molecular formula
    C15H12O4

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

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 56.37%
    Odorless 45.27%
    Woody 31.95%
    Spicy 29.37%
    Burnt 26.73%
    Dry 25.84%
    Medicinal 25.31%
    Animal 23.67%
    Smoky 21.68%
    Fruity 20.65%

     

    Flavor
    Bitter 93.08%
    Odorless 23.87%
    Cedarleaf 20.66%
    Sweet-like 20.23%
    Very strong 20.09%
    Indole 20.02%
    Nitrile 19.9%
    Parsley 19.68%
    Lovage 19.66%
    Bland 19.6%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    10.52 (weak base)

    Molecular weight
    256.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    622°C

    Melting point expt.

    • 250 - 258 °C

    Flash point

    • 261.58 ˚C est.

  • Synonyms

    • Emodin anthrone
    • 491-60-1
    • 1,3,8-Trihydroxy-6-methylanthrone
    • 77C500W1A2
    • 9(10H)-Anthracenone, 1,3,8-trihydroxy-6-methyl-
    • CHEBI:150013
    • DTXSID80197684
    • 1,3,8-Trihydroxy-6-methyl-9(10H)-Anthracenone
    • RefChem:906847
    • DTXCID40120175
    • Emodinanthrone
    • 1,3,8-Trihydroxy-6-methyl-10H-anthracen-9-one
    • emodin-9-anthrone
    • Frangula emodin anthrone
    • CHEMBL122192
    • 1,3,8-TRIHYDROXY-6-METHYL-9,10-DIHYDROANTHRACEN-9-ONE
    • 1,3,8-trihydroxy-6-methylanthracen-9(10H)-one
    • 1,6,8-trihydroxy-3-methyl-10-hydroanthracen-9-one
    • Emodinanthranol
    • Emodinol
    • Protophyscihydrone
    • UNII-77C500W1A2
    • Frangulaemodinanthrone
    • Frangulaemodinanthranol
    • orb1297007
    • SCHEMBL6046328
    • SCHEMBL29811105
    • SCHEMBL29811113
    • SCHEMBL31003276
    • HY-N9362
    • BDBM50060878
    • AKOS025401350
    • AC-1208
    • EBC-616432
    • FE151701
    • TS-10156
    • CS-0159524
    • NS00094804
    • ANTHRONE, 1,3,8-TRIHYDROXY-6-METHYL-
    • G13662
    • 1,3,8,9-TETRAHYDROXY-6-METHYLANTHRACENE
    • 491E601
    • Q27266578
    • 491-60-1

  • Applications

    1,3,8-Trihydroxy-6-methyl-9(10H)-anthracenone, CAS 491-60-1, is primarily used as a synthetic building block in the preparation of organic pigments and dyes based on the anthracene core, leveraging its multiple phenolic OH groups and the anthracene framework for functionalization. It is commonly evaluated as an intermediate for pharmaceutical and other fine-chemical syntheses. The polyphenolic structure also supports its use as an antioxidant or photostabilizer additive in polymers, coatings, and adhesives to improve oxidative and light stability. In cosmetic applications, it may be explored as a colorant or antioxidant ingredient in formulations, subject to regulatory and formulation limits. Overall, the applications are centered on its role as an intermediate, with potential utility in materials and specialty formulations depending on local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.31
    methanol 7.32
    isopropanol 6.3
    water 0.01
    ethyl acetate 17.37
    n-propanol 6.63
    acetone 16.04
    n-butanol 6.86
    acetonitrile 10.49
    DMF 136.2
    toluene 1.26
    isobutanol 4.88
    1,4-dioxane 35.15
    methyl acetate 16.93
    THF 141.09
    2-butanone 13.6
    n-pentanol 7.29
    sec-butanol 3.93
    n-hexane 0.06
    ethylene glycol 13.09
    NMP 110.43
    cyclohexane 0.03
    DMSO 264.44
    n-butyl acetate 19.79
    n-octanol 9.6
    chloroform 1.1
    n-propyl acetate 19.64
    acetic acid 30.58
    dichloromethane 1.32
    cyclohexanone 24.17
    propylene glycol 23.98
    isopropyl acetate 16.31
    DMAc 75.07
    2-ethoxyethanol 51.01
    isopentanol 8.23
    n-heptane 0.18
    ethyl formate 14.9
    1,2-dichloroethane 2.37
    n-hexanol 9.51
    2-methoxyethanol 135.72
    isobutyl acetate 14.82
    tetrachloromethane 0.19
    n-pentyl acetate 18.49
    transcutol 240.58
    n-heptanol 8.94
    ethylbenzene 0.91
    MIBK 17.23
    2-propoxyethanol 95.85
    tert-butanol 13.77
    MTBE 4.54
    2-butoxyethanol 43.27
    propionic acid 17.07
    o-xylene 1.02
    formic acid 20.03
    diethyl ether 3.82
    m-xylene 2.08
    p-xylene 1.22
    chlorobenzene 1.81
    dimethyl carbonate 31.62
    n-octane 0.12
    formamide 40.71
    cyclopentanone 67.36
    2-pentanone 17.46
    anisole 8.09
    cyclopentyl methyl ether 19.83
    gamma-butyrolactone 122.51
    1-methoxy-2-propanol 131.45
    pyridine 10.57
    3-pentanone 7.54
    furfural 68.26
    n-dodecane 0.27
    diethylene glycol 119.31
    diisopropyl ether 1.93
    tert-amyl alcohol 6.72
    acetylacetone 51.32
    n-hexadecane 0.32
    acetophenone 13.16
    methyl propionate 25.63
    isopentyl acetate 19.43
    trichloroethylene 5.91
    n-nonanol 10.24
    cyclohexanol 5.26
    benzyl alcohol 10.53
    2-ethylhexanol 6.86
    isooctanol 8.36
    dipropyl ether 8.64
    1,2-dichlorobenzene 2.41
    ethyl lactate 30.86
    propylene carbonate 51.31
    n-methylformamide 49.22
    2-pentanol 4.72
    n-pentane 0.04
    1-propoxy-2-propanol 73.78
    1-methoxy-2-propyl acetate 62.68
    2-(2-methoxypropoxy) propanol 55.09
    mesitylene 1.33
    ε-caprolactone 36.66
    p-cymene 2.28
    epichlorohydrin 86.3
    1,1,1-trichloroethane 1.62
    2-aminoethanol 20.98
    morpholine-4-carbaldehyde 137.04
    sulfolane 200.22
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 26.12
    n-hexyl acetate 24.74
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 85.97
    sec-butyl acetate 12.48
    tert-butyl acetate 25.12
    decalin 0.14
    glycerin 82.35
    diglyme 125.32
    acrylic acid 24.04
    isopropyl myristate 11.33
    n-butyric acid 25.43
    acetyl acetate 16.38
    di(2-ethylhexyl) phthalate 13.37
    ethyl propionate 17.59
    nitromethane 99.53
    1,2-diethoxyethane 34.4
    benzonitrile 10.31
    trioctyl phosphate 11.37
    1-bromopropane 0.82
    gamma-valerolactone 149.21
    n-decanol 7.8
    triethyl phosphate 13.1
    4-methyl-2-pentanol 6.31
    propionitrile 7.69
    vinylene carbonate 35.23
    1,1,2-trichlorotrifluoroethane 67.02
    DMS 31.58
    cumene 1.03
    2-octanol 6.46
    2-hexanone 15.12
    octyl acetate 15.06
    limonene 2.91
    1,2-dimethoxyethane 74.14
    ethyl orthosilicate 11.2
    tributyl phosphate 13.11
    diacetone alcohol 63.04
    N,N-dimethylaniline 6.49
    acrylonitrile 17.33
    aniline 5.38
    1,3-propanediol 36.02
    bromobenzene 1.29
    dibromomethane 0.61
    1,1,2,2-tetrachloroethane 5.33
    2-methyl-cyclohexyl acetate 16.18
    tetrabutyl urea 18.7
    diisobutyl methanol 6.84
    2-phenylethanol 15.16
    styrene 0.87
    dioctyl adipate 19.84
    dimethyl sulfate 60.99
    ethyl butyrate 18.41
    methyl lactate 58.18
    butyl lactate 32.64
    diethyl carbonate 13.34
    propanediol butyl ether 56.72
    triethyl orthoformate 18.74
    p-tert-butyltoluene 2.8
    methyl 4-tert-butylbenzoate 28.31
    morpholine 56.76
    tert-butylamine 3.38
    n-dodecanol 5.6
    dimethoxymethane 97.86
    ethylene carbonate 28.04
    cyrene 59.96
    2-ethoxyethyl acetate 39.66
    2-ethylhexyl acetate 12.97
    1,2,4-trichlorobenzene 4.12
    4-methylpyridine 11.29
    dibutyl ether 9.31
    2,6-dimethyl-4-heptanol 6.84
    DEF 26.63
    dimethyl isosorbide 115.19
    tetrachloroethylene 2.0
    eugenol 36.05
    triacetin 39.96
    span 80 42.26
    1,4-butanediol 13.14
    1,1-dichloroethane 1.35
    2-methyl-1-pentanol 6.67
    methyl formate 43.72
    2-methyl-1-butanol 5.58
    n-decane 0.37
    butyronitrile 8.01
    3,7-dimethyl-1-octanol 9.68
    1-chlorooctane 2.46
    1-chlorotetradecane 1.25
    n-nonane 0.26
    undecane 0.32
    tert-butylcyclohexane 0.22
    cyclooctane 0.03
    cyclopentanol 11.91
    tetrahydropyran 10.07
    tert-amyl methyl ether 5.24
    2,5,8-trioxanonane 94.43
    1-hexene 0.48
    2-isopropoxyethanol 34.24
    2,2,2-trifluoroethanol 14.64
    methyl butyrate 20.96

    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