4-Cyclopentene-1,3-dione, 4-hydroxy-2,5-bis(4-hydroxyphenyl)-

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  • Identifiers

    CAS number
    52591-12-5

    Molecular formula
    C17H12O5

    SMILES
    C1=CC(=CC=C1C2C(=O)C(=C(C2=O)O)C3=CC=C(C=C3)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 53.83%
    Sweet 40.24%
    Odorless 38.73%
    Spicy 34.76%
    Burnt 32.8%
    Bitter 31.65%
    Vanilla 31.06%
    Balsamic 27.72%
    Medicinal 26.17%
    Caramellic 25.87%

     

    Flavor
    Bitter 91.19%
    Odorless 25.89%
    Lovage 20.42%
    Nitrile 20.32%
    Sweet-like 19.79%
    Cedarleaf 19.7%
    Very strong 19.11%
    Indole 18.85%
    Basil 18.57%
    Parsley 18.56%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    8.59 (weak base)

    Molecular weight
    296.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    588°C

    Melting point expt.

    • 240 °C

    Flash point

    • 251.33 ˚C est.

  • Synonyms

    • DTXSID201180617
    • 52591-12-5
    • 4-Cyclopentene-1,3-dione, 4-hydroxy-2,5-bis(4-hydroxyphenyl)-
    • RefChem:1070562
    • DTXCID801611959
    • Gyrocyanin
    • 4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione
    • CHEBI:174127
    • 4-HYDROXY-2,5-BIS(4-HYDROXYPHENYL)-4-CYCLOPENTENE-1,3-DIONE
    • DB-325030
    • 3,5-Bis(4-hydroxyphenyl)-1,2,4-cyclopentanetrione
    • 4-Hydroxy-2,5-bis(4-hydroxyphenyl)-4-cyclopentene-1,3-dione, 9CI
    • 52591-12-5

  • Applications

    For 4-Cyclopentene-1,3-dione, 4-hydroxy-2,5-bis(4-hydroxyphenyl)- (CAS 52591-12-5), applications are focused in specialty polymer and coating chemistries as a reactive building block. It can function as a crosslinking agent or monomer in high-performance resins such as phenolic and epoxy systems to improve thermal and mechanical properties. The two para-hydroxyphenyl groups allow derivatization to tailor solubility, adhesion, and color, making it a precursor for specialty dyes or pigments and for resin modifiers in coatings and inks. In electronics- and aerospace-oriented formulations, it may be evaluated as a rigid aromatic linker to enhance thermal stability. The compound can also act as a stabilizer or antioxidant in polymer formulations and as a component in adhesive formulations where robust crosslinking is required. Use is formulation-specific and subject to local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.08
    methanol 32.15
    isopropanol 17.4
    water 0.03
    ethyl acetate 11.7
    n-propanol 18.5
    acetone 112.03
    n-butanol 14.58
    acetonitrile 15.15
    DMF 186.8
    toluene 1.66
    isobutanol 7.73
    1,4-dioxane 42.38
    methyl acetate 19.12
    THF 346.99
    2-butanone 67.64
    n-pentanol 9.49
    sec-butanol 12.51
    n-hexane 0.02
    ethylene glycol 13.47
    NMP 52.68
    cyclohexane 0.05
    DMSO 546.82
    n-butyl acetate 8.58
    n-octanol 6.9
    chloroform 0.49
    n-propyl acetate 9.62
    acetic acid 15.58
    dichloromethane 0.38
    cyclohexanone 57.3
    propylene glycol 14.41
    isopropyl acetate 10.03
    DMAc 218.23
    2-ethoxyethanol 48.87
    isopentanol 12.18
    n-heptane 0.04
    ethyl formate 11.29
    1,2-dichloroethane 1.58
    n-hexanol 8.82
    2-methoxyethanol 140.01
    isobutyl acetate 3.86
    tetrachloromethane 0.14
    n-pentyl acetate 6.57
    transcutol 39.51
    n-heptanol 6.89
    ethylbenzene 1.25
    MIBK 19.45
    2-propoxyethanol 46.31
    tert-butanol 29.85
    MTBE 7.77
    2-butoxyethanol 21.69
    propionic acid 8.53
    o-xylene 1.43
    formic acid 13.71
    diethyl ether 4.9
    m-xylene 1.27
    p-xylene 1.61
    chlorobenzene 0.9
    dimethyl carbonate 14.03
    n-octane 0.05
    formamide 41.68
    cyclopentanone 125.76
    2-pentanone 41.77
    anisole 8.48
    cyclopentyl methyl ether 15.4
    gamma-butyrolactone 61.62
    1-methoxy-2-propanol 70.98
    pyridine 20.04
    3-pentanone 16.63
    furfural 26.49
    n-dodecane 0.16
    diethylene glycol 44.88
    diisopropyl ether 1.09
    tert-amyl alcohol 16.66
    acetylacetone 49.24
    n-hexadecane 0.18
    acetophenone 12.68
    methyl propionate 17.78
    isopentyl acetate 8.1
    trichloroethylene 3.47
    n-nonanol 7.34
    cyclohexanol 9.9
    benzyl alcohol 11.16
    2-ethylhexanol 4.44
    isooctanol 5.42
    dipropyl ether 3.84
    1,2-dichlorobenzene 1.06
    ethyl lactate 10.35
    propylene carbonate 12.65
    n-methylformamide 62.51
    2-pentanol 6.57
    n-pentane 0.02
    1-propoxy-2-propanol 25.19
    1-methoxy-2-propyl acetate 17.71
    2-(2-methoxypropoxy) propanol 22.27
    mesitylene 0.8
    ε-caprolactone 27.81
    p-cymene 1.34
    epichlorohydrin 61.91
    1,1,1-trichloroethane 1.06
    2-aminoethanol 22.13
    morpholine-4-carbaldehyde 55.21
    sulfolane 97.77
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 39.5
    n-hexyl acetate 9.16
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 28.89
    sec-butyl acetate 5.59
    tert-butyl acetate 15.02
    decalin 0.08
    glycerin 39.12
    diglyme 45.5
    acrylic acid 8.86
    isopropyl myristate 5.63
    n-butyric acid 13.42
    acetyl acetate 6.15
    di(2-ethylhexyl) phthalate 5.46
    ethyl propionate 8.65
    nitromethane 60.71
    1,2-diethoxyethane 11.81
    benzonitrile 7.37
    trioctyl phosphate 5.13
    1-bromopropane 0.62
    gamma-valerolactone 106.73
    n-decanol 5.78
    triethyl phosphate 5.14
    4-methyl-2-pentanol 4.96
    propionitrile 14.03
    vinylene carbonate 9.94
    1,1,2-trichlorotrifluoroethane 27.75
    DMS 8.85
    cumene 0.98
    2-octanol 4.73
    2-hexanone 23.09
    octyl acetate 7.19
    limonene 1.64
    1,2-dimethoxyethane 80.0
    ethyl orthosilicate 4.49
    tributyl phosphate 5.38
    diacetone alcohol 39.82
    N,N-dimethylaniline 5.97
    acrylonitrile 21.9
    aniline 5.84
    1,3-propanediol 42.03
    bromobenzene 0.54
    dibromomethane 0.24
    1,1,2,2-tetrachloroethane 3.81
    2-methyl-cyclohexyl acetate 6.96
    tetrabutyl urea 11.3
    diisobutyl methanol 3.57
    2-phenylethanol 12.21
    styrene 1.23
    dioctyl adipate 7.97
    dimethyl sulfate 25.11
    ethyl butyrate 6.75
    methyl lactate 22.52
    butyl lactate 9.07
    diethyl carbonate 4.31
    propanediol butyl ether 17.28
    triethyl orthoformate 6.11
    p-tert-butyltoluene 1.35
    methyl 4-tert-butylbenzoate 12.9
    morpholine 68.88
    tert-butylamine 5.08
    n-dodecanol 4.36
    dimethoxymethane 99.5
    ethylene carbonate 9.12
    cyrene 22.33
    2-ethoxyethyl acetate 9.91
    2-ethylhexyl acetate 5.19
    1,2,4-trichlorobenzene 1.86
    4-methylpyridine 15.49
    dibutyl ether 4.98
    2,6-dimethyl-4-heptanol 3.57
    DEF 35.38
    dimethyl isosorbide 31.73
    tetrachloroethylene 1.92
    eugenol 14.17
    triacetin 9.89
    span 80 14.09
    1,4-butanediol 11.61
    1,1-dichloroethane 0.82
    2-methyl-1-pentanol 7.5
    methyl formate 35.87
    2-methyl-1-butanol 9.17
    n-decane 0.2
    butyronitrile 13.6
    3,7-dimethyl-1-octanol 5.67
    1-chlorooctane 1.5
    1-chlorotetradecane 0.85
    n-nonane 0.13
    undecane 0.17
    tert-butylcyclohexane 0.08
    cyclooctane 0.03
    cyclopentanol 15.94
    tetrahydropyran 20.97
    tert-amyl methyl ether 7.15
    2,5,8-trioxanonane 40.37
    1-hexene 0.29
    2-isopropoxyethanol 21.54
    2,2,2-trifluoroethanol 6.06
    methyl butyrate 15.06

    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