Monoethyl maleate

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  • Identifiers

    CAS number
    3990-03-2

    Molecular formula
    C6H8O4

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

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 75.06%
    Winey 62.21%
    Caramellic 58.02%
    Sweet 45.61%
    Apple 43.95%
    Sour 43.15%
    Green 37.75%
    Sharp 37.33%
    Burnt 36.78%
    Ethereal 36.6%

     

    Flavor
    Odorless 38.74%
    Sour 33.31%
    Fruity 27.64%
    Very mild 27.55%
    Caramellic 24.37%
    Caramel 23.02%
    Buttery 21.25%
    Nutty 21.09%
    Yeast 20.94%
    Acidic 20.78%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    6.39 (neutral)

    Molecular weight
    144.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    242°C

    Melting point expt.

    • 66 - 68 °C

    Flash point

    • 116.36 ˚C est.

  • Synonyms

    • Monoethyl maleate
    • 3990-03-2
    • (Z)-4-ethoxy-4-oxobut-2-enoic acid
    • AK5N1DQX7U
    • maleic acid, ethyl ester
    • NSC-11206
    • NSC-525207
    • DTXSID60892145
    • RefChem:138984
    • DTXCID80991907
    • 223-635-7
    • Ethyl maleate
    • Maleic Acid Monoethyl Ester
    • Ethyl hydrogen maleate
    • Maleic acid, monoethyl ester
    • 2-Butenedioic acid (Z)-, monoethyl ester
    • MFCD00063175
    • (2Z)-4-ethoxy-4-oxobut-2-enoic acid
    • 2-Butenedioic acid (Z), monoethyl ester
    • 2-Butenedioic acid (2Z)-, 1-ethyl ester
    • (2Z)-2-Butenedioic Acid 1-Ethyl Ester, ~ 90%
    • 2-Butenedioic acid (2Z)-, monoethyl ester
    • propenoic acid, 3-ethoxycarbonyl-
    • MALEICACIDMONOETHYLESTER
    • Sipomer MEM
    • MONOETHYL (2Z)-2-BUTENEDIOATE
    • Maleinsaureathylester
    • EINECS 223-635-7
    • NSC 11206
    • NSC 525207
    • (Z)-4-ethoxy-4-oxo-but-2-enoic acid
    • (~{Z})-4-ethoxy-4-oxidanylidene-but-2-enoic acid
    • maleic acidmonoethyl ester
    • UNII-AK5N1DQX7U
    • maleic acid-monoethyl ester
    • SCHEMBL60568
    • SCHEMBL8190843
    • CHEBI:165633
    • NSC11206
    • LMFA07010876
    • NSC524101
    • NSC525207
    • AKOS025311447
    • (Z)-4-Ethoxy-4-oxo-2-butenoic Acid
    • (2E)-4-Ethoxy-4-oxo-2-butenoic acid
    • BS-23648
    • SY107666
    • (2Z)-4-Ethoxy-4-oxo-2-butenoic acid #
    • CS-0151926
    • M0614
    • NS00013661
    • E75735
    • Q27273964
    • 3990-03-2

  • Applications

    Monoethyl maleate (CAS 3990-03-2) is primarily used as an intermediate for the synthesis of functional monomers and specialty polymers. In polymers and plastics applications, MEM can act as a reactive monomer or comonomer to build resin systems with unsaturation and ester functionality, supporting coatings resins and adhesive formulations. It serves as a precursor to functional maleate-containing polymers and oligomers and can participate in polymerization reactions such as free-radical polymerization or Diels–Alder-type cycloadditions to form crosslinked networks. In electronics and specialty materials, MEM-derived monomers may be evaluated for specialty resins and photoresist formulations, subject to formulation limits. Overall, its role as an unsaturated ester intermediate enables further functionalization in chemical synthesis and materials development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 73.51
    methanol 128.94
    isopropanol 40.25
    water 8.11
    ethyl acetate 27.06
    n-propanol 36.73
    acetone 95.4
    n-butanol 30.28
    acetonitrile 50.38
    DMF 475.41
    toluene 5.3
    isobutanol 24.49
    1,4-dioxane 64.7
    methyl acetate 59.02
    THF 98.43
    2-butanone 56.33
    n-pentanol 23.26
    sec-butanol 35.37
    n-hexane 1.81
    ethylene glycol 35.55
    NMP 441.3
    cyclohexane 1.03
    DMSO 796.54
    n-butyl acetate 24.3
    n-octanol 9.13
    chloroform 12.32
    n-propyl acetate 21.79
    acetic acid 80.14
    dichloromethane 35.1
    cyclohexanone 48.39
    propylene glycol 25.66
    isopropyl acetate 15.49
    DMAc 479.88
    2-ethoxyethanol 95.89
    isopentanol 29.05
    n-heptane 0.9
    ethyl formate 46.58
    1,2-dichloroethane 34.23
    n-hexanol 13.72
    2-methoxyethanol 162.53
    isobutyl acetate 8.99
    tetrachloromethane 2.85
    n-pentyl acetate 11.35
    transcutol 176.14
    n-heptanol 6.64
    ethylbenzene 8.57
    MIBK 17.18
    2-propoxyethanol 45.96
    tert-butanol 58.3
    MTBE 40.76
    2-butoxyethanol 23.29
    propionic acid 42.55
    o-xylene 10.38
    formic acid 117.8
    diethyl ether 24.01
    m-xylene 5.56
    p-xylene 10.3
    chlorobenzene 11.41
    dimethyl carbonate 33.14
    n-octane 0.46
    formamide 238.04
    cyclopentanone 89.04
    2-pentanone 29.46
    anisole 45.05
    cyclopentyl methyl ether 28.28
    gamma-butyrolactone 141.71
    1-methoxy-2-propanol 74.96
    pyridine 52.37
    3-pentanone 24.5
    furfural 187.6
    n-dodecane 0.49
    diethylene glycol 61.61
    diisopropyl ether 5.53
    tert-amyl alcohol 62.97
    acetylacetone 46.11
    n-hexadecane 0.55
    acetophenone 50.23
    methyl propionate 36.79
    isopentyl acetate 22.42
    trichloroethylene 45.83
    n-nonanol 8.55
    cyclohexanol 16.98
    benzyl alcohol 38.14
    2-ethylhexanol 9.12
    isooctanol 6.39
    dipropyl ether 9.11
    1,2-dichlorobenzene 17.04
    ethyl lactate 20.25
    propylene carbonate 60.67
    n-methylformamide 166.89
    2-pentanol 16.77
    n-pentane 1.3
    1-propoxy-2-propanol 28.27
    1-methoxy-2-propyl acetate 30.72
    2-(2-methoxypropoxy) propanol 54.06
    mesitylene 4.48
    ε-caprolactone 59.43
    p-cymene 6.42
    epichlorohydrin 122.44
    1,1,1-trichloroethane 11.84
    2-aminoethanol 51.88
    morpholine-4-carbaldehyde 262.54
    sulfolane 286.38
    2,2,4-trimethylpentane 1.48
    2-methyltetrahydrofuran 65.73
    n-hexyl acetate 18.71
    isooctane 0.61
    2-(2-butoxyethoxy)ethanol 53.73
    sec-butyl acetate 13.55
    tert-butyl acetate 23.97
    decalin 1.71
    glycerin 58.2
    diglyme 112.1
    acrylic acid 53.01
    isopropyl myristate 7.46
    n-butyric acid 32.93
    acetyl acetate 21.01
    di(2-ethylhexyl) phthalate 16.24
    ethyl propionate 22.02
    nitromethane 250.52
    1,2-diethoxyethane 32.87
    benzonitrile 31.87
    trioctyl phosphate 8.57
    1-bromopropane 12.58
    gamma-valerolactone 152.72
    n-decanol 6.28
    triethyl phosphate 20.38
    4-methyl-2-pentanol 10.08
    propionitrile 27.1
    vinylene carbonate 56.03
    1,1,2-trichlorotrifluoroethane 93.97
    DMS 30.61
    cumene 7.6
    2-octanol 5.19
    2-hexanone 25.74
    octyl acetate 10.37
    limonene 8.25
    1,2-dimethoxyethane 148.74
    ethyl orthosilicate 16.21
    tributyl phosphate 13.52
    diacetone alcohol 43.95
    N,N-dimethylaniline 44.04
    acrylonitrile 49.3
    aniline 23.33
    1,3-propanediol 62.5
    bromobenzene 8.35
    dibromomethane 17.46
    1,1,2,2-tetrachloroethane 34.77
    2-methyl-cyclohexyl acetate 20.89
    tetrabutyl urea 23.44
    diisobutyl methanol 6.32
    2-phenylethanol 22.74
    styrene 11.19
    dioctyl adipate 17.97
    dimethyl sulfate 117.97
    ethyl butyrate 19.71
    methyl lactate 36.26
    butyl lactate 16.29
    diethyl carbonate 20.12
    propanediol butyl ether 30.28
    triethyl orthoformate 16.99
    p-tert-butyltoluene 5.85
    methyl 4-tert-butylbenzoate 36.17
    morpholine 87.95
    tert-butylamine 28.21
    n-dodecanol 4.62
    dimethoxymethane 99.06
    ethylene carbonate 37.26
    cyrene 70.36
    2-ethoxyethyl acetate 24.73
    2-ethylhexyl acetate 17.35
    1,2,4-trichlorobenzene 25.61
    4-methylpyridine 62.13
    dibutyl ether 10.01
    2,6-dimethyl-4-heptanol 6.32
    DEF 83.78
    dimethyl isosorbide 92.7
    tetrachloroethylene 23.21
    eugenol 39.2
    triacetin 33.71
    span 80 29.14
    1,4-butanediol 27.95
    1,1-dichloroethane 14.47
    2-methyl-1-pentanol 26.38
    methyl formate 118.55
    2-methyl-1-butanol 30.79
    n-decane 0.77
    butyronitrile 22.03
    3,7-dimethyl-1-octanol 11.07
    1-chlorooctane 3.99
    1-chlorotetradecane 1.79
    n-nonane 0.69
    undecane 0.61
    tert-butylcyclohexane 1.61
    cyclooctane 0.53
    cyclopentanol 26.42
    tetrahydropyran 25.94
    tert-amyl methyl ether 39.66
    2,5,8-trioxanonane 89.69
    1-hexene 6.25
    2-isopropoxyethanol 46.53
    2,2,2-trifluoroethanol 43.53
    methyl butyrate 35.31

    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