Diethyl Maleate

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  • Identifiers

    CAS number
    141-05-9

    Molecular formula
    C8H12O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 88.23%
    Apple 71.9%
    Green 66.92%
    Winey 66.73%
    Sweet 48.64%
    Herbal 47.54%
    Ethereal 44.12%
    Caramellic 41.73%
    Rummy 40.22%
    Tropical 37.46%

     

    Flavor
    Fruity 56.41%
    Mild 26.16%
    Buttery 23.46%
    Creamy 23.11%
    Odorless 22.96%
    Yeast 22.46%
    Grape 22.14%
    Dried berry 20.35%
    Marshmallow 20.3%
    Very mild 20.27%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    6.2 (neutral)

    Molecular weight
    172.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 1 - 2 °C

    Boiling point

    • 218.00 °C. @ 760.00 mm Hg

    Flash point

    • 92.64 ˚C est.

    Solubility expt.

    • 1.40E+04 mg/L @ 30 °C (exp)

  • Synonyms

    • DIETHYL MALEATE
    • 141-05-9
    • Diethylmaleate
    • Maleic acid, diethyl ester
    • Maleic acid diethyl ester
    • diethyl (Z)-but-2-enedioate
    • 2-Butenedioic acid (Z)-, diethyl ester
    • diethyl (2Z)-but-2-enedioate
    • 2-Butenedioic acid (2Z)-, diethyl ester
    • Diethyl (Z)-2-butenedioate
    • CCRIS 941
    • Diethylester kyseliny maleinove
    • 2-Butenedioic acid (2Z)-, 1,4-diethyl ester
    • UNII-G81WQB56OL
    • NSC 8394
    • EINECS 205-451-9
    • G81WQB56OL
    • Diethylester kyseliny maleinove [Czech]
    • BRN 1100825
    • DTXSID8020464
    • CHEBI:68508
    • STAFLEX DEM
    • AI3-00678
    • NSC-8394
    • 1,4-diethyl (2Z)-but-2-enedioate
    • DIETHYL MALEATE [MI]
    • DTXCID80464
    • 2-Butenedioic acid, diethyl ester, (Z)-
    • 2-Butenedioic acid, diethyl ester, (2Z)-
    • (2Z)-2-Butenedioic acid, 1,4-diethyl ester
    • EC 205-451-9
    • 4-02-00-02207 (Beilstein Handbook Reference)
    • Diethyl (2E)-2-butenedioate
    • CAS-141-05-9
    • WLN: 2OV1U1VO2
    • MFCD00009191
    • diethyl maleic acid diester
    • Fumaric acid, diethyl ester (8CI)
    • Diethyl ester of (E)-2-Butenedioic acid
    • Diethyl-2-butenedioate
    • 2-Butenedioic acid (E)-, diethyl ester (9CI)
    • Diethyl maleate, 97%
    • SCHEMBL60423
    • CHEMBL2037000
    • Diethyl maleate, >=96%, FG
    • Diethyl (2Z)-2-butenedioate #
    • NSC8394
    • HY-Y1147
    • Diethyl maleate, analytical standard
    • Tox21_201512
    • Tox21_303020
    • Diethyl ester(E)-2-Butenedioic acid
    • s4712
    • 2-Butenedioic acid(E)-,diethyl ester
    • 2Butenedioic acid (Z), diethyl ester
    • AKOS015960830
    • Diethyl ester(2E)-2-butenedioic acid
    • CCG-266368
    • NCGC00249057-01
    • NCGC00256390-01
    • NCGC00259062-01
    • BS-15532
    • DA-52528
    • CS-0017148
    • M0010
    • NS00007455
    • D70233
    • Diethyl maleate 100 microg/mL in Acetonitrile
    • EN300-344747
    • 2-Butenedioic acid (Z)-, diethyl ester (9CI)
    • Q1646591
    • F1908-0131
    • Z3234965665
    • 205-451-9

  • Applications

    Diethyl maleate (DEM, CAS 141-05-9) is a typical ester of maleic acid with widespread industrial and research uses: owing to its strong dienophilic character, DEM serves as a key intermediate in organic synthesis, participating in Diels-Alder reactions to build bicyclic frameworks and malate derivatives; in the manufacture of polymers, alkyd resins, paints, adhesives and plastics, it functions as a cross-linking agent and plasticizer that enhances durability, flexibility and chemical resistance; in pharmaceutical and flavor industries, it acts as a precursor for antioxidants, fruity aroma compounds and other specialized esters; in biological research, DEM is routinely employed to deplete intracellular glutathione, creating oxidative stress models for studying cytoprotection, detoxification and drug screening; moreover, the compound is incorporated into lubricants, fuel additives and crop-protection formulations as a synergist, stabilizer or viscosity modifier, underscoring its versatility across many applied chemistry domains.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 22.92
    methanol 35.78
    isopropanol 15.54
    water 0.29
    ethyl acetate 164.75
    n-propanol 15.8
    acetone 279.72
    n-butanol 13.94
    acetonitrile 240.35
    DMF 801.49
    toluene 78.72
    isobutanol 13.14
    1,4-dioxane 155.84
    methyl acetate 230.92
    THF 283.69
    2-butanone 191.89
    n-pentanol 14.31
    sec-butanol 18.16
    n-hexane 7.6
    ethylene glycol 8.55
    NMP 1545.92
    cyclohexane 7.96
    DMSO 1207.9
    n-butyl acetate 122.51
    n-octanol 9.77
    chloroform 413.86
    n-propyl acetate 102.68
    acetic acid 152.7
    dichloromethane 676.12
    cyclohexanone 262.04
    propylene glycol 7.42
    isopropyl acetate 86.92
    DMAc 1006.26
    2-ethoxyethanol 68.63
    isopentanol 16.77
    n-heptane 3.38
    ethyl formate 105.37
    1,2-dichloroethane 415.38
    n-hexanol 13.9
    2-methoxyethanol 99.3
    isobutyl acetate 43.33
    tetrachloromethane 42.32
    n-pentyl acetate 44.16
    transcutol 288.96
    n-heptanol 6.74
    ethylbenzene 63.89
    MIBK 56.46
    2-propoxyethanol 63.35
    tert-butanol 28.74
    MTBE 72.75
    2-butoxyethanol 29.84
    propionic acid 77.82
    o-xylene 79.33
    formic acid 73.74
    diethyl ether 56.32
    m-xylene 49.17
    p-xylene 92.25
    chlorobenzene 225.09
    dimethyl carbonate 136.42
    n-octane 1.38
    formamide 218.12
    cyclopentanone 454.76
    2-pentanone 108.3
    anisole 215.06
    cyclopentyl methyl ether 116.13
    gamma-butyrolactone 702.14
    1-methoxy-2-propanol 60.53
    pyridine 348.44
    3-pentanone 142.62
    furfural 847.24
    n-dodecane 1.23
    diethylene glycol 51.34
    diisopropyl ether 19.34
    tert-amyl alcohol 37.43
    acetylacetone 301.19
    n-hexadecane 1.49
    acetophenone 300.55
    methyl propionate 170.74
    isopentyl acetate 100.49
    trichloroethylene 1015.42
    n-nonanol 9.95
    cyclohexanol 25.3
    benzyl alcohol 86.5
    2-ethylhexanol 16.26
    isooctanol 6.83
    dipropyl ether 33.6
    1,2-dichlorobenzene 303.78
    ethyl lactate 51.54
    propylene carbonate 327.39
    n-methylformamide 237.94
    2-pentanol 12.01
    n-pentane 3.64
    1-propoxy-2-propanol 47.56
    1-methoxy-2-propyl acetate 150.2
    2-(2-methoxypropoxy) propanol 90.04
    mesitylene 30.08
    ε-caprolactone 279.13
    p-cymene 32.51
    epichlorohydrin 628.13
    1,1,1-trichloroethane 277.74
    2-aminoethanol 15.05
    morpholine-4-carbaldehyde 707.81
    sulfolane 1350.85
    2,2,4-trimethylpentane 5.13
    2-methyltetrahydrofuran 195.77
    n-hexyl acetate 65.05
    isooctane 1.96
    2-(2-butoxyethoxy)ethanol 69.32
    sec-butyl acetate 68.68
    tert-butyl acetate 106.31
    decalin 11.14
    glycerin 21.69
    diglyme 227.04
    acrylic acid 115.77
    isopropyl myristate 27.78
    n-butyric acid 72.66
    acetyl acetate 192.98
    di(2-ethylhexyl) phthalate 37.73
    ethyl propionate 124.44
    nitromethane 875.19
    1,2-diethoxyethane 100.71
    benzonitrile 198.53
    trioctyl phosphate 17.99
    1-bromopropane 104.19
    gamma-valerolactone 626.82
    n-decanol 7.26
    triethyl phosphate 84.74
    4-methyl-2-pentanol 9.24
    propionitrile 88.9
    vinylene carbonate 311.09
    1,1,2-trichlorotrifluoroethane 401.31
    DMS 197.19
    cumene 42.02
    2-octanol 5.89
    2-hexanone 91.55
    octyl acetate 33.94
    limonene 42.12
    1,2-dimethoxyethane 244.42
    ethyl orthosilicate 62.18
    tributyl phosphate 37.8
    diacetone alcohol 88.58
    N,N-dimethylaniline 166.24
    acrylonitrile 207.52
    aniline 101.94
    1,3-propanediol 21.11
    bromobenzene 275.65
    dibromomethane 332.31
    1,1,2,2-tetrachloroethane 606.16
    2-methyl-cyclohexyl acetate 92.87
    tetrabutyl urea 60.15
    diisobutyl methanol 12.29
    2-phenylethanol 60.99
    styrene 98.27
    dioctyl adipate 67.76
    dimethyl sulfate 516.32
    ethyl butyrate 105.51
    methyl lactate 74.78
    butyl lactate 42.06
    diethyl carbonate 99.82
    propanediol butyl ether 27.31
    triethyl orthoformate 72.46
    p-tert-butyltoluene 28.94
    methyl 4-tert-butylbenzoate 119.09
    morpholine 168.14
    tert-butylamine 18.55
    n-dodecanol 5.68
    dimethoxymethane 192.21
    ethylene carbonate 191.86
    cyrene 143.23
    2-ethoxyethyl acetate 100.43
    2-ethylhexyl acetate 91.7
    1,2,4-trichlorobenzene 409.12
    4-methylpyridine 388.07
    dibutyl ether 30.46
    2,6-dimethyl-4-heptanol 12.29
    DEF 297.17
    dimethyl isosorbide 289.8
    tetrachloroethylene 322.94
    eugenol 97.45
    triacetin 146.27
    span 80 49.36
    1,4-butanediol 11.39
    1,1-dichloroethane 239.04
    2-methyl-1-pentanol 21.02
    methyl formate 210.94
    2-methyl-1-butanol 17.84
    n-decane 2.07
    butyronitrile 62.6
    3,7-dimethyl-1-octanol 16.34
    1-chlorooctane 13.47
    1-chlorotetradecane 6.05
    n-nonane 1.89
    undecane 1.52
    tert-butylcyclohexane 8.4
    cyclooctane 3.15
    cyclopentanol 36.32
    tetrahydropyran 83.99
    tert-amyl methyl ether 79.77
    2,5,8-trioxanonane 169.13
    1-hexene 24.45
    2-isopropoxyethanol 44.94
    2,2,2-trifluoroethanol 92.93
    methyl butyrate 163.33

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0 %
Category 2
Products applied to the axillae
 0 % Category 7B
Leave-on products applied to the hair with some hand contact
 0 %
Category 3
Products applied to the face/body using fingertips
 0 % Category 8
Products with significant anogenital exposure
 0 %
Category 4
Products related to fine fragrance
 0 % Category 9
Products with body and hand exposure, primarily rinse off
 0 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0 % Category 10A
Household care products with mostly hand contact
 0 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0 %
Category 5D
Baby Creams, baby Oils and baby talc
 0 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0 %
Category 6
Products with oral and lip exposure
 0 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 0 %

Prohibition
Diethyl maleate should not be used as a fragrance ingredient.