4-Oxohex-2-enedioate

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  • Identifiers

    CAS number
    24740-88-3

    Molecular formula
    C6H6O5

    SMILES
    C(C(=O)/C=C\C(=O)O)C(=O)O

  • Odor profile

    Fragrance
    Sour 54.76%
    Caramellic 48.59%
    Winey 46.94%
    Sweet 40.35%
    Burnt 39.95%
    Odorless 38.87%
    Sharp 34.19%
    Buttery 30.91%
    Nutty 28.95%
    Creamy 25.77%

     

    Flavor
    Odorless 64.07%
    Sour 43.74%
    Nutty 42.51%
    Very mild 35.55%
    Caramellic 29.04%
    Musty 28.64%
    Mild 25.0%
    Yeast 23.43%
    Acidic 22.8%
    Mousy 21.05%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    5.57 (weak acid)

    Molecular weight
    158.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    349°C

    Flash point

    • 196.31 ˚C est.

  • Synonyms

    • maleylacetate
    • maleylacetic acid
    • Maleoylacetic acid
    • 2-maleylacetate
    • 24740-88-3
    • 4-oxohex-2-enedioate
    • (Z)-4-oxohex-2-enedioic acid
    • (Z)-4-oxo-2-hexenedioic acid
    • (2Z)-4-oxohex-2-enedioic acid
    • (2Z)-4-Oxo-2-hexenedioic acid
    • JAD9FA3JG6
    • z-4-oxo-2-hexenedioic acid
    • CHEBI:1184
    • SCHEMBL1225122
    • DTXSID001029401
    • 4-Oxidanylidenehex-2-enedioic acid
    • 2-Hexenedioic acid, 4-oxo-, (Z)-
    • 2-Hexenedioic acid, 4-oxo-, (2Z)-
    • C02222

  • Applications

    4-Oxohex-2-enedioate, CAS 24740-88-3, is used as an organic synthesis intermediate with relevance to industrial manufacturing and fine chemicals; it commonly serves as a building block for pharmaceutical intermediates and other specialty chemicals; it may act as a monomer or co-monomer precursor for polymers and copolymers after functionalization; it can function as a chelating agent or ligand in metal-catalyzed processes; and it finds use in coatings and inks as a functional additive or linking component.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 72.01
    methanol 180.97
    isopropanol 36.98
    water 63.9
    ethyl acetate 5.29
    n-propanol 40.26
    acetone 34.86
    n-butanol 27.11
    acetonitrile 13.32
    DMF 309.14
    toluene 0.49
    isobutanol 19.64
    1,4-dioxane 13.83
    methyl acetate 14.97
    THF 55.0
    2-butanone 26.19
    n-pentanol 14.45
    sec-butanol 26.27
    n-hexane 1.04
    ethylene glycol 76.18
    NMP 137.28
    cyclohexane 0.34
    DMSO 550.4
    n-butyl acetate 4.88
    n-octanol 5.03
    chloroform 1.94
    n-propyl acetate 5.83
    acetic acid 13.88
    dichloromethane 3.85
    cyclohexanone 11.49
    propylene glycol 51.26
    isopropyl acetate 2.93
    DMAc 229.69
    2-ethoxyethanol 62.92
    isopentanol 16.2
    n-heptane 0.63
    ethyl formate 22.3
    1,2-dichloroethane 4.88
    n-hexanol 8.37
    2-methoxyethanol 142.14
    isobutyl acetate 1.68
    tetrachloromethane 1.31
    n-pentyl acetate 2.63
    transcutol 29.63
    n-heptanol 4.33
    ethylbenzene 0.93
    MIBK 5.88
    2-propoxyethanol 33.92
    tert-butanol 38.07
    MTBE 10.3
    2-butoxyethanol 16.22
    propionic acid 18.87
    o-xylene 1.15
    formic acid 74.39
    diethyl ether 9.42
    m-xylene 0.55
    p-xylene 1.07
    chlorobenzene 0.47
    dimethyl carbonate 12.03
    n-octane 0.23
    formamide 121.63
    cyclopentanone 27.31
    2-pentanone 12.39
    anisole 5.86
    cyclopentyl methyl ether 9.06
    gamma-butyrolactone 30.23
    1-methoxy-2-propanol 63.57
    pyridine 6.81
    3-pentanone 9.92
    furfural 31.38
    n-dodecane 0.19
    diethylene glycol 50.02
    diisopropyl ether 1.5
    tert-amyl alcohol 27.27
    acetylacetone 7.83
    n-hexadecane 0.19
    acetophenone 6.96
    methyl propionate 12.2
    isopentyl acetate 3.47
    trichloroethylene 3.52
    n-nonanol 4.41
    cyclohexanol 7.52
    benzyl alcohol 6.21
    2-ethylhexanol 3.73
    isooctanol 2.77
    dipropyl ether 5.45
    1,2-dichlorobenzene 0.86
    ethyl lactate 10.32
    propylene carbonate 9.89
    n-methylformamide 140.42
    2-pentanol 10.84
    n-pentane 0.88
    1-propoxy-2-propanol 18.98
    1-methoxy-2-propyl acetate 6.75
    2-(2-methoxypropoxy) propanol 19.96
    mesitylene 0.52
    ε-caprolactone 11.06
    p-cymene 1.03
    epichlorohydrin 27.19
    1,1,1-trichloroethane 1.7
    2-aminoethanol 88.46
    morpholine-4-carbaldehyde 72.84
    sulfolane 72.21
    2,2,4-trimethylpentane 0.38
    2-methyltetrahydrofuran 18.71
    n-hexyl acetate 3.85
    isooctane 0.19
    2-(2-butoxyethoxy)ethanol 19.12
    sec-butyl acetate 2.44
    tert-butyl acetate 4.03
    decalin 0.31
    glycerin 87.45
    diglyme 36.07
    acrylic acid 18.99
    isopropyl myristate 1.68
    n-butyric acid 10.71
    acetyl acetate 1.92
    di(2-ethylhexyl) phthalate 3.31
    ethyl propionate 6.89
    nitromethane 39.96
    1,2-diethoxyethane 5.0
    benzonitrile 2.83
    trioctyl phosphate 2.71
    1-bromopropane 3.16
    gamma-valerolactone 38.83
    n-decanol 3.24
    triethyl phosphate 4.71
    4-methyl-2-pentanol 4.79
    propionitrile 12.73
    vinylene carbonate 8.13
    1,1,2-trichlorotrifluoroethane 28.17
    DMS 3.78
    cumene 1.0
    2-octanol 2.7
    2-hexanone 9.25
    octyl acetate 2.69
    limonene 1.52
    1,2-dimethoxyethane 86.35
    ethyl orthosilicate 3.85
    tributyl phosphate 3.14
    diacetone alcohol 15.55
    N,N-dimethylaniline 7.63
    acrylonitrile 16.34
    aniline 2.84
    1,3-propanediol 64.14
    bromobenzene 0.28
    dibromomethane 2.32
    1,1,2,2-tetrachloroethane 4.27
    2-methyl-cyclohexyl acetate 3.57
    tetrabutyl urea 7.64
    diisobutyl methanol 2.2
    2-phenylethanol 4.46
    styrene 0.74
    dioctyl adipate 3.39
    dimethyl sulfate 31.65
    ethyl butyrate 5.06
    methyl lactate 22.83
    butyl lactate 5.92
    diethyl carbonate 4.1
    propanediol butyl ether 16.97
    triethyl orthoformate 4.45
    p-tert-butyltoluene 0.95
    methyl 4-tert-butylbenzoate 7.94
    morpholine 32.96
    tert-butylamine 15.6
    n-dodecanol 2.24
    dimethoxymethane 72.89
    ethylene carbonate 6.43
    cyrene 22.61
    2-ethoxyethyl acetate 3.69
    2-ethylhexyl acetate 2.65
    1,2,4-trichlorobenzene 1.15
    4-methylpyridine 6.56
    dibutyl ether 3.12
    2,6-dimethyl-4-heptanol 2.2
    DEF 32.24
    dimethyl isosorbide 24.09
    tetrachloroethylene 3.47
    eugenol 10.36
    triacetin 4.29
    span 80 8.77
    1,4-butanediol 28.6
    1,1-dichloroethane 2.27
    2-methyl-1-pentanol 9.27
    methyl formate 78.8
    2-methyl-1-butanol 17.78
    n-decane 0.32
    butyronitrile 9.87
    3,7-dimethyl-1-octanol 3.43
    1-chlorooctane 1.04
    1-chlorotetradecane 0.44
    n-nonane 0.33
    undecane 0.24
    tert-butylcyclohexane 0.32
    cyclooctane 0.15
    cyclopentanol 15.42
    tetrahydropyran 8.53
    tert-amyl methyl ether 10.43
    2,5,8-trioxanonane 26.5
    1-hexene 2.57
    2-isopropoxyethanol 20.66
    2,2,2-trifluoroethanol 15.81
    methyl butyrate 11.38

    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