2,5-Dihydroxy-3,6-diphenyl-2,5-cyclohexadiene-1,4-dione

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  • Identifiers

    CAS number
    548-59-4

    Molecular formula
    C18H12O4

    SMILES
    C1=CC=C(C=C1)C2=C(C(=O)C(=C(C2=O)O)C3=CC=CC=C3)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 54.23%
    Caramellic 42.29%
    Spicy 37.95%
    Fruity 37.64%
    Burnt 33.88%
    Balsamic 33.7%
    Phenolic 31.99%
    Honey 31.53%
    Green 27.37%
    Bitter 27.1%

     

    Flavor
    Bitter 70.44%
    Odorless 21.13%
    Nitrile 21.11%
    Lovage 21.05%
    Fenugreek 19.48%
    Honey 19.44%
    Urine 19.42%
    Basil 19.41%
    Balsam 19.24%
    Very strong 19.2%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    5.98 (weak acid)

    Molecular weight
    292.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    443°C

    Flash point

    • 217.38 ˚C est.

  • Synonyms

    • 548-59-4
    • 2,5-dihydroxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione
    • 2,5-Dihydroxy-3,6-diphenyl-2,5-cyclohexadiene-1,4-dione
    • VM7U3VEH5G
    • 2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3,6-diphenyl-
    • NSC-44175
    • DTXSID50203281
    • RefChem:908817
    • DTXCID50125772
    • Orygameic acid
    • 2,5-Dihydroxy-3,6-diphenyl-p-benzoquinone
    • NSC 44175
    • 2,5-Dihydroxy-3,6-diphenyl-1,4-benzoquinone
    • S 1148
    • NSC44175
    • 3',6'-dihydroxy-[1,1':4',1''-terphenyl]-2',5'-dione
    • p-BENZOQUINONE, 2,5-DIHYDROXY-3,6-DIPHENYL-
    • 2,5-Dihydroxy-3,6-diphenylbenzo-1,4-quinone
    • 2~3~,2~6~-Dihydroxy[1~1~,2~1~:2~4~,3~1~-terphenyl]-2~2~,2~5~-dione
    • BRN 2057889
    • UNII-VM7U3VEH5G
    • 2,5-diphenyl-3,6-dihydroxy-1,4-benzoquinone
    • 4-08-00-03298 (Beilstein Handbook Reference)
    • SCHEMBL2445444
    • CHEBI:144197
    • HZKFHDXTSAYOSN-UHFFFAOYSA-N
    • AKOS030239814
    • 2,5-Diphenyl-3,6-dihydroxybenzochinon
    • Quinone, 2,5-dihydroxy-3,6-diphenyl-
    • p-Benzoquinone,5-dihydroxy-3,6-diphenyl-
    • 2,4-dione, 2,5-dihydroxy-3,6-diphenyl-
    • NS00075454
    • C23049
    • doi:10.14272/HZKFHDXTSAYOSN-UHFFFAOYSA-N.1
    • Q21402073
    • 548-59-4

  • Applications

    2,5-Dihydroxy-3,6-diphenyl-2,5-cyclohexadiene-1,4-dione (CAS 548-59-4) is primarily used as an intermediate in organic synthesis, notably as a precursor for dyes and pigments and as a building block for fine chemicals in pharmaceutical and agrochemical research. The compound can function as a redox-active component or mediator in electrochemical and polymerization processes, and may serve as an antioxidant or stabilizer in polymers, coatings, and plastics formulations. It is also considered as a precursor for quinone-based materials in electronics and energy-storage applications, and may be evaluated for specialty dyeing systems and coating formulations. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.66
    methanol 2.62
    isopropanol 1.8
    water 0.01
    ethyl acetate 7.12
    n-propanol 2.92
    acetone 13.59
    n-butanol 2.2
    acetonitrile 4.7
    DMF 93.47
    toluene 11.34
    isobutanol 1.83
    1,4-dioxane 14.74
    methyl acetate 11.63
    THF 64.51
    2-butanone 17.14
    n-pentanol 2.11
    sec-butanol 2.09
    n-hexane 0.25
    ethylene glycol 1.89
    NMP 102.12
    cyclohexane 0.47
    DMSO 41.96
    n-butyl acetate 6.56
    n-octanol 2.23
    chloroform 11.14
    n-propyl acetate 4.05
    acetic acid 4.1
    dichloromethane 14.73
    cyclohexanone 30.05
    propylene glycol 1.66
    isopropyl acetate 6.0
    DMAc 99.1
    2-ethoxyethanol 5.39
    isopentanol 2.32
    n-heptane 0.44
    ethyl formate 4.42
    1,2-dichloroethane 18.29
    n-hexanol 3.84
    2-methoxyethanol 12.9
    isobutyl acetate 2.51
    tetrachloromethane 1.38
    n-pentyl acetate 5.56
    transcutol 6.5
    n-heptanol 3.16
    ethylbenzene 4.76
    MIBK 7.5
    2-propoxyethanol 10.91
    tert-butanol 3.02
    MTBE 4.12
    2-butoxyethanol 6.7
    propionic acid 4.44
    o-xylene 7.51
    formic acid 2.41
    diethyl ether 4.42
    m-xylene 6.28
    p-xylene 5.3
    chlorobenzene 9.22
    dimethyl carbonate 15.67
    n-octane 0.34
    formamide 8.36
    cyclopentanone 61.12
    2-pentanone 12.23
    anisole 7.86
    cyclopentyl methyl ether 17.83
    gamma-butyrolactone 48.9
    1-methoxy-2-propanol 9.27
    pyridine 35.46
    3-pentanone 13.45
    furfural 31.9
    n-dodecane 0.33
    diethylene glycol 8.18
    diisopropyl ether 1.64
    tert-amyl alcohol 3.17
    acetylacetone 16.23
    n-hexadecane 0.41
    acetophenone 11.58
    methyl propionate 14.86
    isopentyl acetate 6.66
    trichloroethylene 40.81
    n-nonanol 2.6
    cyclohexanol 4.25
    benzyl alcohol 6.89
    2-ethylhexanol 3.36
    isooctanol 2.73
    dipropyl ether 4.35
    1,2-dichlorobenzene 9.25
    ethyl lactate 4.2
    propylene carbonate 13.19
    n-methylformamide 18.62
    2-pentanol 1.77
    n-pentane 0.22
    1-propoxy-2-propanol 7.19
    1-methoxy-2-propyl acetate 12.1
    2-(2-methoxypropoxy) propanol 6.34
    mesitylene 3.55
    ε-caprolactone 19.32
    p-cymene 3.96
    epichlorohydrin 54.97
    1,1,1-trichloroethane 8.22
    2-aminoethanol 3.01
    morpholine-4-carbaldehyde 39.34
    sulfolane 72.77
    2,2,4-trimethylpentane 0.3
    2-methyltetrahydrofuran 21.34
    n-hexyl acetate 5.48
    isooctane 0.21
    2-(2-butoxyethoxy)ethanol 6.43
    sec-butyl acetate 3.64
    tert-butyl acetate 7.68
    decalin 0.63
    glycerin 4.38
    diglyme 16.15
    acrylic acid 6.35
    isopropyl myristate 3.06
    n-butyric acid 4.79
    acetyl acetate 5.4
    di(2-ethylhexyl) phthalate 3.49
    ethyl propionate 5.52
    nitromethane 16.25
    1,2-diethoxyethane 4.57
    benzonitrile 9.25
    trioctyl phosphate 2.89
    1-bromopropane 5.55
    gamma-valerolactone 47.27
    n-decanol 2.06
    triethyl phosphate 4.83
    4-methyl-2-pentanol 1.75
    propionitrile 6.78
    vinylene carbonate 12.89
    1,1,2-trichlorotrifluoroethane 23.74
    DMS 10.37
    cumene 3.09
    2-octanol 2.19
    2-hexanone 6.57
    octyl acetate 3.72
    limonene 4.92
    1,2-dimethoxyethane 13.73
    ethyl orthosilicate 4.19
    tributyl phosphate 2.85
    diacetone alcohol 11.47
    N,N-dimethylaniline 7.46
    acrylonitrile 14.08
    aniline 10.17
    1,3-propanediol 3.66
    bromobenzene 9.57
    dibromomethane 7.84
    1,1,2,2-tetrachloroethane 26.75
    2-methyl-cyclohexyl acetate 6.15
    tetrabutyl urea 5.9
    diisobutyl methanol 2.64
    2-phenylethanol 8.49
    styrene 5.25
    dioctyl adipate 4.46
    dimethyl sulfate 32.45
    ethyl butyrate 4.95
    methyl lactate 10.49
    butyl lactate 4.69
    diethyl carbonate 3.79
    propanediol butyl ether 3.47
    triethyl orthoformate 4.55
    p-tert-butyltoluene 3.7
    methyl 4-tert-butylbenzoate 10.6
    morpholine 21.91
    tert-butylamine 1.73
    n-dodecanol 1.64
    dimethoxymethane 27.43
    ethylene carbonate 8.84
    cyrene 12.43
    2-ethoxyethyl acetate 7.54
    2-ethylhexyl acetate 5.78
    1,2,4-trichlorobenzene 12.37
    4-methylpyridine 25.05
    dibutyl ether 2.62
    2,6-dimethyl-4-heptanol 2.64
    DEF 22.38
    dimethyl isosorbide 18.18
    tetrachloroethylene 16.98
    eugenol 9.15
    triacetin 6.38
    span 80 5.11
    1,4-butanediol 1.52
    1,1-dichloroethane 7.53
    2-methyl-1-pentanol 2.69
    methyl formate 13.58
    2-methyl-1-butanol 2.47
    n-decane 0.53
    butyronitrile 4.65
    3,7-dimethyl-1-octanol 2.51
    1-chlorooctane 2.22
    1-chlorotetradecane 1.1
    n-nonane 0.41
    undecane 0.41
    tert-butylcyclohexane 0.52
    cyclooctane 0.3
    cyclopentanol 7.02
    tetrahydropyran 13.17
    tert-amyl methyl ether 5.25
    2,5,8-trioxanonane 12.18
    1-hexene 1.31
    2-isopropoxyethanol 3.87
    2,2,2-trifluoroethanol 3.02
    methyl butyrate 6.77

    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