(E)-hex-2-enedioic acid

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  • Identifiers

    CAS number
    4440-68-0

    Molecular formula
    C6H8O4

    SMILES
    C(CC(=O)O)/C=C/C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Sour 63.49%
    Odorless 41.16%
    Caramellic 41.02%
    Sharp 35.38%
    Winey 31.62%
    Buttery 31.53%
    Burnt 31.47%
    Cheesy 31.18%
    Pungent 28.1%
    Roasted 26.16%

     

    Flavor
    Odorless 65.2%
    Sour 46.46%
    Acidic 29.6%
    Very mild 27.37%
    Yeast 23.11%
    Nutty 22.66%
    Mild 22.31%
    Caramellic 22.29%
    Vinegar 21.58%
    Formyl 21.29%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    6.3 (neutral)

    Molecular weight
    144.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    333°C

    Flash point

    • 186.77 ˚C est.

  • Synonyms

    • (E)-hex-2-enedioic acid
    • trans-2-hexenedioic acid
    • (2E)-hex-2-enedioic acid
    • 2E-hexenedioic acid
    • CHEBI:49296
    • RefChem:70042
    • beta-Dihydromuconic acid
    • 4440-68-0
    • 2583-24-6
    • trans-2,3-dehydroadipic acid
    • trans-2,3-didehydroadipic acid
    • MFCD19228126
    • hexenedioic acid
    • 2-Hexenedioic acid, (2E)-
    • alpha-hydromuconic acid
    • (E)-2-Hexenedioic acid
    • (2E)-2-Hexenedioic acid
    • hex-2-enedioicacid
    • (E)-hex-2-enedioate
    • (2E)-hex-2-enedioate
    • NHW7BL749N
    • SCHEMBL128035
    • orb1301960
    • 1-Butene-1,4-dicarboxylic Acid
    • DTXSID801333155
    • STR05054
    • LMFA01170070
    • AKOS006380129
    • EBC-616003
    • s11920
    • AS-82996
    • EN300-114536
    • EN300-7441317
    • Q27121603
    • 4440-68-0

  • Applications

    (E)-hex-2-enedioic acid (CAS 4440-68-0) is an unsaturated dicarboxylic acid primarily used as a chemical building block in polymers and coatings. In industry, it serves as a diacid monomer or co-monomer for the synthesis of unsaturated polyesters and related resins, enabling crosslinking and improved adhesion in coatings and inks. It can be esterified with diols to form diesters that act as reactive intermediates for polyurethane and acrylic resin formulations, or used directly in radical polymerizations to produce specialty polymers with tailored properties. It also functions as an intermediate for producing other derivatives (esters, anhydrides, or amide/amine adducts) in industrial manufacturing. Additionally, due to its C=C unsaturation, it may be used in resin systems as a crosslinking component to modify cure behavior and performance in adhesives and high-performance coatings, subject to formulation limits and local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 81.18
    methanol 169.78
    isopropanol 36.43
    water 38.6
    ethyl acetate 5.56
    n-propanol 42.38
    acetone 34.88
    n-butanol 25.77
    acetonitrile 5.52
    DMF 287.37
    toluene 0.58
    isobutanol 20.88
    1,4-dioxane 13.73
    methyl acetate 12.69
    THF 29.36
    2-butanone 22.97
    n-pentanol 15.21
    sec-butanol 28.75
    n-hexane 1.24
    ethylene glycol 101.76
    NMP 180.72
    cyclohexane 0.4
    DMSO 431.95
    n-butyl acetate 6.03
    n-octanol 6.39
    chloroform 1.59
    n-propyl acetate 3.88
    acetic acid 26.5
    dichloromethane 2.58
    cyclohexanone 12.11
    propylene glycol 79.55
    isopropyl acetate 3.28
    DMAc 205.1
    2-ethoxyethanol 54.41
    isopentanol 17.37
    n-heptane 0.76
    ethyl formate 14.92
    1,2-dichloroethane 3.88
    n-hexanol 12.51
    2-methoxyethanol 131.25
    isobutyl acetate 1.04
    tetrachloromethane 1.4
    n-pentyl acetate 4.13
    transcutol 58.68
    n-heptanol 6.7
    ethylbenzene 1.03
    MIBK 6.46
    2-propoxyethanol 37.08
    tert-butanol 42.71
    MTBE 10.82
    2-butoxyethanol 20.92
    propionic acid 36.73
    o-xylene 1.66
    formic acid 103.52
    diethyl ether 6.89
    m-xylene 0.85
    p-xylene 1.2
    chlorobenzene 0.74
    dimethyl carbonate 9.79
    n-octane 0.31
    formamide 132.23
    cyclopentanone 24.67
    2-pentanone 12.0
    anisole 5.04
    cyclopentyl methyl ether 7.68
    gamma-butyrolactone 31.44
    1-methoxy-2-propanol 64.19
    pyridine 6.12
    3-pentanone 9.98
    furfural 35.18
    n-dodecane 0.2
    diethylene glycol 60.47
    diisopropyl ether 1.8
    tert-amyl alcohol 37.35
    acetylacetone 10.43
    n-hexadecane 0.22
    acetophenone 7.73
    methyl propionate 12.16
    isopentyl acetate 4.61
    trichloroethylene 4.34
    n-nonanol 5.66
    cyclohexanol 9.21
    benzyl alcohol 7.66
    2-ethylhexanol 5.17
    isooctanol 4.33
    dipropyl ether 3.78
    1,2-dichlorobenzene 1.48
    ethyl lactate 9.67
    propylene carbonate 11.28
    n-methylformamide 131.8
    2-pentanol 12.04
    n-pentane 0.92
    1-propoxy-2-propanol 21.92
    1-methoxy-2-propyl acetate 9.24
    2-(2-methoxypropoxy) propanol 27.92
    mesitylene 0.93
    ε-caprolactone 13.22
    p-cymene 1.57
    epichlorohydrin 20.58
    1,1,1-trichloroethane 1.78
    2-aminoethanol 108.83
    morpholine-4-carbaldehyde 84.12
    sulfolane 96.27
    2,2,4-trimethylpentane 0.73
    2-methyltetrahydrofuran 14.63
    n-hexyl acetate 6.54
    isooctane 0.35
    2-(2-butoxyethoxy)ethanol 29.76
    sec-butyl acetate 2.1
    tert-butyl acetate 5.64
    decalin 0.43
    glycerin 125.89
    diglyme 41.67
    acrylic acid 39.98
    isopropyl myristate 2.25
    n-butyric acid 15.95
    acetyl acetate 2.59
    di(2-ethylhexyl) phthalate 6.04
    ethyl propionate 4.98
    nitromethane 46.39
    1,2-diethoxyethane 6.19
    benzonitrile 3.06
    trioctyl phosphate 4.08
    1-bromopropane 2.18
    gamma-valerolactone 41.38
    n-decanol 3.97
    triethyl phosphate 4.87
    4-methyl-2-pentanol 6.24
    propionitrile 6.17
    vinylene carbonate 9.31
    1,1,2-trichlorotrifluoroethane 43.26
    DMS 6.25
    cumene 1.22
    2-octanol 3.93
    2-hexanone 7.47
    octyl acetate 3.56
    limonene 2.4
    1,2-dimethoxyethane 50.19
    ethyl orthosilicate 4.1
    tributyl phosphate 4.49
    diacetone alcohol 22.51
    N,N-dimethylaniline 7.22
    acrylonitrile 10.14
    aniline 3.59
    1,3-propanediol 72.76
    bromobenzene 0.44
    dibromomethane 1.76
    1,1,2,2-tetrachloroethane 5.17
    2-methyl-cyclohexyl acetate 4.4
    tetrabutyl urea 9.1
    diisobutyl methanol 3.19
    2-phenylethanol 7.37
    styrene 0.91
    dioctyl adipate 4.31
    dimethyl sulfate 34.55
    ethyl butyrate 4.47
    methyl lactate 25.92
    butyl lactate 10.4
    diethyl carbonate 3.44
    propanediol butyl ether 30.27
    triethyl orthoformate 4.34
    p-tert-butyltoluene 1.57
    methyl 4-tert-butylbenzoate 12.69
    morpholine 27.87
    tert-butylamine 16.52
    n-dodecanol 2.61
    dimethoxymethane 52.76
    ethylene carbonate 6.08
    cyrene 28.49
    2-ethoxyethyl acetate 6.91
    2-ethylhexyl acetate 3.44
    1,2,4-trichlorobenzene 2.34
    4-methylpyridine 5.75
    dibutyl ether 2.71
    2,6-dimethyl-4-heptanol 3.19
    DEF 32.15
    dimethyl isosorbide 30.77
    tetrachloroethylene 5.19
    eugenol 16.03
    triacetin 7.57
    span 80 17.35
    1,4-butanediol 32.35
    1,1-dichloroethane 1.81
    2-methyl-1-pentanol 11.86
    methyl formate 64.64
    2-methyl-1-butanol 19.48
    n-decane 0.37
    butyronitrile 5.03
    3,7-dimethyl-1-octanol 4.74
    1-chlorooctane 1.3
    1-chlorotetradecane 0.51
    n-nonane 0.38
    undecane 0.27
    tert-butylcyclohexane 0.48
    cyclooctane 0.24
    cyclopentanol 17.35
    tetrahydropyran 6.3
    tert-amyl methyl ether 11.54
    2,5,8-trioxanonane 33.06
    1-hexene 2.49
    2-isopropoxyethanol 21.1
    2,2,2-trifluoroethanol 21.64
    methyl butyrate 7.66

    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