Dimethyl mesaconate

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  • Identifiers

    CAS number
    617-53-8

    Molecular formula
    C7H10O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 84.67%
    Caramellic 58.6%
    Sweet 54.25%
    Apple 52.76%
    Ethereal 52.14%
    Winey 48.47%
    Rummy 47.34%
    Chamomile 44.62%
    Pungent 38.54%
    Herbal 38.09%

     

    Flavor
    Fruity 70.16%
    Sweet 32.05%
    Caramel 31.78%
    Berry 28.01%
    Floral 27.48%
    Creamy 25.82%
    Toffee 22.35%
    Tropical 22.3%
    Molasses 22.26%
    Buttery 22.14%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    5.12 (weak acid)

    Molecular weight
    158.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    228°C

    Flash point

    • 75.54 ˚C est.

  • Synonyms

    • Dimethyl mesaconate
    • 617-53-8
    • dimethyl (E)-2-methylbut-2-enedioate
    • 2-Methylfumaric acid dimethyl ester
    • 2-Methyl-but-2-enedioic acid dimethyl ester
    • dimethyl 2-methylfumarate
    • 1,4-dimethyl (2E)-2-methylbut-2-enedioate
    • 2-Methyl-but-2-enedioic acid dimethyl ester, E
    • MFCD00059306
    • 2-Butenedioic acid, 2-methyl-, dimethyl ester, (Z)-
    • Dimethyl methylmaleate
    • Methylfumaric acid, dimethyl ester
    • Mesaconic acid, dimethyl ester
    • 1,4-dimethyl (2Z)-2-methylbut-2-enedioate
    • Citraconate de dimethyle
    • DIMETHYL-CITRACONATE
    • CHEBI:4607
    • SCHEMBL7771274
    • (2E)-Dimethyl 2-methylfumarate
    • WQEXBUQDXKPVHR-SNAWJCMRSA-
    • DTXSID201031523
    • LMFA07010836
    • NSC226153
    • NSC-226153
    • Dimethyl (2E)-2-methyl-2-butenedioate
    • C05126
    • D89238
    • trans-2-methyl-but-2-enoic acid dimethyl ester
    • EN300-1387339
    • (E)-2-Methyl-2-butenedioic acid, dimethyl ester
    • Q27106419
    • InChI=1/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h4H,1-3H3/b5-4+
    • 84569-14-2
    • 617-53-8

  • Applications

    Dimethyl mesaconate is a diester used primarily as an organic synthesis intermediate. In polymers and plastics, it serves as a precursor for polyester and related resins; in coatings and inks, it can act as a monomer or reactive diluent in UV-curable systems; in fragrance and cosmetics, it is used as a fragrance ingredient or synthesis precursor for ester-based aroma compounds; in industrial formulations and cleaning applications, it may be used as a solvent or co-solvent for specialty formulations; it can also function as a synthetic intermediate to prepare other mesaconate derivatives. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 268.86
    methanol 412.8
    isopropanol 254.46
    water 20.82
    ethyl acetate 434.51
    n-propanol 217.85
    acetone 630.49
    n-butanol 182.26
    acetonitrile 691.16
    DMF 898.73
    toluene 235.97
    isobutanol 180.65
    1,4-dioxane 752.24
    methyl acetate 564.07
    THF 780.55
    2-butanone 449.17
    n-pentanol 141.67
    sec-butanol 236.57
    n-hexane 24.19
    ethylene glycol 94.16
    NMP 1011.37
    cyclohexane 40.22
    DMSO 771.96
    n-butyl acetate 134.37
    n-octanol 53.63
    chloroform 870.14
    n-propyl acetate 212.41
    acetic acid 646.86
    dichloromethane 915.6
    cyclohexanone 448.28
    propylene glycol 60.71
    isopropyl acetate 245.9
    DMAc 1016.18
    2-ethoxyethanol 421.59
    isopentanol 198.54
    n-heptane 12.12
    ethyl formate 311.76
    1,2-dichloroethane 590.45
    n-hexanol 92.47
    2-methoxyethanol 671.97
    isobutyl acetate 116.23
    tetrachloromethane 199.87
    n-pentyl acetate 89.66
    transcutol 383.74
    n-heptanol 56.13
    ethylbenzene 141.29
    MIBK 187.88
    2-propoxyethanol 231.87
    tert-butanol 513.63
    MTBE 449.03
    2-butoxyethanol 142.06
    propionic acid 297.93
    o-xylene 185.25
    formic acid 477.86
    diethyl ether 362.06
    m-xylene 143.66
    p-xylene 186.0
    chlorobenzene 257.72
    dimethyl carbonate 259.07
    n-octane 7.27
    formamide 913.06
    cyclopentanone 608.43
    2-pentanone 290.07
    anisole 364.11
    cyclopentyl methyl ether 361.69
    gamma-butyrolactone 844.02
    1-methoxy-2-propanol 365.27
    pyridine 651.96
    3-pentanone 289.0
    furfural 766.86
    n-dodecane 5.97
    diethylene glycol 217.43
    diisopropyl ether 102.3
    tert-amyl alcohol 424.76
    acetylacetone 413.01
    n-hexadecane 6.87
    acetophenone 333.83
    methyl propionate 379.29
    isopentyl acetate 137.15
    trichloroethylene 1238.73
    n-nonanol 50.46
    cyclohexanol 228.28
    benzyl alcohol 242.56
    2-ethylhexanol 66.6
    isooctanol 49.71
    dipropyl ether 89.75
    1,2-dichlorobenzene 259.69
    ethyl lactate 103.5
    propylene carbonate 358.66
    n-methylformamide 592.76
    2-pentanol 142.14
    n-pentane 26.35
    1-propoxy-2-propanol 123.45
    1-methoxy-2-propyl acetate 163.78
    2-(2-methoxypropoxy) propanol 134.18
    mesitylene 84.62
    ε-caprolactone 429.33
    p-cymene 56.57
    epichlorohydrin 924.74
    1,1,1-trichloroethane 612.46
    2-aminoethanol 166.03
    morpholine-4-carbaldehyde 847.92
    sulfolane 780.71
    2,2,4-trimethylpentane 23.45
    2-methyltetrahydrofuran 655.44
    n-hexyl acetate 123.4
    isooctane 10.96
    2-(2-butoxyethoxy)ethanol 152.47
    sec-butyl acetate 158.89
    tert-butyl acetate 284.75
    decalin 28.91
    glycerin 142.08
    diglyme 389.25
    acrylic acid 323.54
    isopropyl myristate 51.53
    n-butyric acid 307.79
    acetyl acetate 328.09
    di(2-ethylhexyl) phthalate 57.35
    ethyl propionate 217.09
    nitromethane 1484.95
    1,2-diethoxyethane 155.65
    benzonitrile 274.23
    trioctyl phosphate 36.98
    1-bromopropane 242.37
    gamma-valerolactone 830.12
    n-decanol 36.66
    triethyl phosphate 95.96
    4-methyl-2-pentanol 90.09
    propionitrile 340.55
    vinylene carbonate 364.1
    1,1,2-trichlorotrifluoroethane 656.8
    DMS 166.81
    cumene 90.91
    2-octanol 42.54
    2-hexanone 195.71
    octyl acetate 65.2
    limonene 74.9
    1,2-dimethoxyethane 665.11
    ethyl orthosilicate 92.46
    tributyl phosphate 50.75
    diacetone alcohol 288.7
    N,N-dimethylaniline 249.42
    acrylonitrile 498.21
    aniline 320.63
    1,3-propanediol 244.22
    bromobenzene 247.9
    dibromomethane 481.71
    1,1,2,2-tetrachloroethane 853.05
    2-methyl-cyclohexyl acetate 122.35
    tetrabutyl urea 71.66
    diisobutyl methanol 46.96
    2-phenylethanol 150.0
    styrene 172.01
    dioctyl adipate 78.8
    dimethyl sulfate 430.58
    ethyl butyrate 133.45
    methyl lactate 156.92
    butyl lactate 62.78
    diethyl carbonate 111.62
    propanediol butyl ether 83.89
    triethyl orthoformate 99.44
    p-tert-butyltoluene 53.02
    methyl 4-tert-butylbenzoate 171.0
    morpholine 804.93
    tert-butylamine 282.95
    n-dodecanol 28.4
    dimethoxymethane 577.96
    ethylene carbonate 286.94
    cyrene 210.91
    2-ethoxyethyl acetate 139.26
    2-ethylhexyl acetate 109.69
    1,2,4-trichlorobenzene 350.31
    4-methylpyridine 640.93
    dibutyl ether 72.06
    2,6-dimethyl-4-heptanol 46.96
    DEF 510.73
    dimethyl isosorbide 286.33
    tetrachloroethylene 661.84
    eugenol 155.13
    triacetin 143.9
    span 80 84.68
    1,4-butanediol 94.37
    1,1-dichloroethane 536.59
    2-methyl-1-pentanol 165.43
    methyl formate 484.76
    2-methyl-1-butanol 193.83
    n-decane 9.88
    butyronitrile 258.94
    3,7-dimethyl-1-octanol 61.34
    1-chlorooctane 40.75
    1-chlorotetradecane 18.18
    n-nonane 9.08
    undecane 7.42
    tert-butylcyclohexane 25.06
    cyclooctane 14.26
    cyclopentanol 250.99
    tetrahydropyran 472.17
    tert-amyl methyl ether 344.04
    2,5,8-trioxanonane 244.07
    1-hexene 82.81
    2-isopropoxyethanol 248.11
    2,2,2-trifluoroethanol 407.24
    methyl butyrate 281.79

    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