Mesaconic acid

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  • Identifiers

    CAS number
    498-24-8

    Molecular formula
    C5H6O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 62.59%
    Sour 56.41%
    Sweet 47.38%
    Burnt 46.97%
    Sharp 40.55%
    Winey 40.12%
    Buttery 36.38%
    Creamy 34.57%
    Nutty 33.09%
    Pungent 33.06%

     

    Flavor
    Odorless 47.04%
    Nutty 44.63%
    Sour 36.23%
    Phenolic 31.91%
    Musty 30.6%
    Very mild 28.88%
    Caramellic 27.89%
    Acidic 23.68%
    Acetoin 21.45%
    Mousy 20.69%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    5.5 (weak acid)

    Molecular weight
    130.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    308°C

    Melting point expt.

    • 200 - 202 °C

    Flash point

    • 158.58 ˚C est.

    Solubility expt.

    • 26.3 mg/mL at 18 °C

  • Synonyms

    • mesaconic acid
    • 498-24-8
    • 2-Methylfumaric acid
    • 2-Butenedioic acid, 2-methyl-, (2E)-
    • Fumaric acid, methyl-
    • (2E)-2-METHYLBUT-2-ENEDIOIC ACID
    • trans-2-Methyl-2-butenedioic acid
    • trans-1-Propene-1,2-dicarboxylic acid
    • Kyselina mesakonova
    • (E)-2-methylbut-2-enedioic acid
    • Citronic acid
    • Butenedioic acid, methyl-, (E)-
    • 2-Butenedioic acid, 2-methyl-, (E)-
    • Kyselina mesakonova [Czech]
    • (E)-Citraconic acid
    • NSC 65438
    • (2E)-2-Methyl-2-butenedioic acid
    • EINECS 207-859-2
    • 2-methyl-2E-butenedioic acid
    • BRN 1722680
    • NSC-65438
    • MESACONIC ACID [MI]
    • CHEBI:16600
    • DTXSID10883407
    • 4-02-00-02231 (Beilstein Handbook Reference)
    • RefChem:811137
    • DTXCID101022939
    • 2-Butenedioic acid, 2-methyl-, (E)-(9CI)
    • 207-859-2
    • Methylfumaric acid
    • mesaconate
    • 2-methylfumarate
    • (E)-2-Methyl-2-butenedioic acid
    • MFCD00002653
    • NSC32949
    • 90UTM639KK
    • methylfumarate
    • UNII-90UTM639KK
    • Citronate
    • (E)-Citraconate
    • Mesaconic acid, 99%
    • bmse000746
    • WLN: QVY1&U1VQ
    • SCHEMBL28517
    • trans-2-Methyl-2-butenedioate
    • WLN: QVY1&U1VQ -T
    • orb1306509
    • (2E)-2-Methyl-2-butenedioate
    • MESACONIC ACID; MESACONATE
    • NSC65438
    • trans-1-Propene-1,2-dicarboxylate
    • (E)-2-methyl-but-2-enedioic acid
    • BBL023435
    • LMFA01170116
    • STL299679
    • AKOS000119631
    • (2E)-2-Methyl-2-butenedioic acid #
    • EBC-617279
    • EBC-618170
    • FM168005
    • HY-78036
    • SY051520
    • CS-0007669
    • CS-0368860
    • M0066
    • NS00015255
    • EN300-19991
    • C01732
    • G77236
    • 2-Butenedioic acid, 2-methyl-, (E)- (9CI)
    • EN300-1387340
    • Q3544981
    • Z104476308
    • FB1827E3-2A34-43A5-BDDC-481FC6606513
    • 498-24-8

  • Applications

    Mesaconic acid (CAS 498-24-8) is primarily used as an intermediate and building block in organic synthesis, enabling the preparation of specialty chemicals and derivatives. It is employed as a monomer or comonomer in unsaturated polymer systems, notably in the production of polyesters and other resins for coatings and adhesives, where its dicarboxylic functionality participates in crosslinking reactions. Esterification of mesaconic acid affords ester derivatives that can function as plasticizers or specialty intermediates in formulation. It may also serve as a precursor to more complex intermediates for pharmaceutical or agrochemical research, and its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 163.4
    methanol 252.32
    isopropanol 116.38
    water 283.22
    ethyl acetate 11.19
    n-propanol 102.38
    acetone 60.61
    n-butanol 85.18
    acetonitrile 18.94
    DMF 458.36
    toluene 4.63
    isobutanol 61.14
    1,4-dioxane 102.11
    methyl acetate 22.11
    THF 175.94
    2-butanone 37.69
    n-pentanol 55.95
    sec-butanol 85.1
    n-hexane 4.32
    ethylene glycol 180.66
    NMP 122.67
    cyclohexane 1.43
    DMSO 371.99
    n-butyl acetate 9.54
    n-octanol 25.38
    chloroform 10.27
    n-propyl acetate 9.49
    acetic acid 33.02
    dichloromethane 18.47
    cyclohexanone 25.3
    propylene glycol 90.84
    isopropyl acetate 9.14
    DMAc 223.93
    2-ethoxyethanol 185.03
    isopentanol 65.72
    n-heptane 2.75
    ethyl formate 37.74
    1,2-dichloroethane 20.75
    n-hexanol 40.32
    2-methoxyethanol 305.84
    isobutyl acetate 3.54
    tetrachloromethane 6.82
    n-pentyl acetate 11.13
    transcutol 64.25
    n-heptanol 30.09
    ethylbenzene 6.21
    MIBK 20.32
    2-propoxyethanol 101.28
    tert-butanol 163.41
    MTBE 46.26
    2-butoxyethanol 63.18
    propionic acid 24.01
    o-xylene 7.92
    formic acid 141.38
    diethyl ether 32.32
    m-xylene 6.17
    p-xylene 6.07
    chlorobenzene 3.31
    dimethyl carbonate 20.93
    n-octane 1.97
    formamide 178.19
    cyclopentanone 54.33
    2-pentanone 29.55
    anisole 23.82
    cyclopentyl methyl ether 36.07
    gamma-butyrolactone 54.77
    1-methoxy-2-propanol 156.39
    pyridine 19.92
    3-pentanone 17.53
    furfural 59.68
    n-dodecane 1.57
    diethylene glycol 138.34
    diisopropyl ether 8.06
    tert-amyl alcohol 114.46
    acetylacetone 23.36
    n-hexadecane 1.61
    acetophenone 17.54
    methyl propionate 20.3
    isopentyl acetate 9.36
    trichloroethylene 17.79
    n-nonanol 22.91
    cyclohexanol 31.91
    benzyl alcohol 29.12
    2-ethylhexanol 17.23
    isooctanol 21.23
    dipropyl ether 14.32
    1,2-dichlorobenzene 4.77
    ethyl lactate 16.65
    propylene carbonate 17.82
    n-methylformamide 172.35
    2-pentanol 47.96
    n-pentane 3.81
    1-propoxy-2-propanol 48.2
    1-methoxy-2-propyl acetate 15.32
    2-(2-methoxypropoxy) propanol 44.0
    mesitylene 5.16
    ε-caprolactone 23.49
    p-cymene 4.5
    epichlorohydrin 84.5
    1,1,1-trichloroethane 8.43
    2-aminoethanol 187.68
    morpholine-4-carbaldehyde 150.16
    sulfolane 88.24
    2,2,4-trimethylpentane 2.26
    2-methyltetrahydrofuran 67.42
    n-hexyl acetate 15.94
    isooctane 1.59
    2-(2-butoxyethoxy)ethanol 58.61
    sec-butyl acetate 5.7
    tert-butyl acetate 17.09
    decalin 1.72
    glycerin 138.51
    diglyme 98.74
    acrylic acid 22.82
    isopropyl myristate 7.86
    n-butyric acid 24.08
    acetyl acetate 4.86
    di(2-ethylhexyl) phthalate 10.48
    ethyl propionate 10.8
    nitromethane 56.55
    1,2-diethoxyethane 21.55
    benzonitrile 9.28
    trioctyl phosphate 10.48
    1-bromopropane 11.16
    gamma-valerolactone 78.46
    n-decanol 18.1
    triethyl phosphate 8.92
    4-methyl-2-pentanol 25.91
    propionitrile 17.42
    vinylene carbonate 15.68
    1,1,2-trichlorotrifluoroethane 62.97
    DMS 8.58
    cumene 5.49
    2-octanol 19.23
    2-hexanone 17.87
    octyl acetate 11.64
    limonene 5.8
    1,2-dimethoxyethane 220.37
    ethyl orthosilicate 9.13
    tributyl phosphate 8.41
    diacetone alcohol 51.45
    N,N-dimethylaniline 27.17
    acrylonitrile 23.49
    aniline 14.88
    1,3-propanediol 169.24
    bromobenzene 2.43
    dibromomethane 10.77
    1,1,2,2-tetrachloroethane 20.23
    2-methyl-cyclohexyl acetate 8.47
    tetrabutyl urea 16.57
    diisobutyl methanol 11.35
    2-phenylethanol 22.07
    styrene 5.38
    dioctyl adipate 10.29
    dimethyl sulfate 48.66
    ethyl butyrate 8.53
    methyl lactate 33.04
    butyl lactate 14.01
    diethyl carbonate 6.24
    propanediol butyl ether 45.42
    triethyl orthoformate 8.81
    p-tert-butyltoluene 4.92
    methyl 4-tert-butylbenzoate 26.84
    morpholine 131.88
    tert-butylamine 68.69
    n-dodecanol 13.59
    dimethoxymethane 185.1
    ethylene carbonate 13.3
    cyrene 44.69
    2-ethoxyethyl acetate 14.58
    2-ethylhexyl acetate 6.33
    1,2,4-trichlorobenzene 5.69
    4-methylpyridine 23.56
    dibutyl ether 11.65
    2,6-dimethyl-4-heptanol 11.35
    DEF 58.85
    dimethyl isosorbide 54.25
    tetrachloroethylene 17.85
    eugenol 35.59
    triacetin 11.11
    span 80 29.35
    1,4-butanediol 95.46
    1,1-dichloroethane 10.47
    2-methyl-1-pentanol 43.88
    methyl formate 118.73
    2-methyl-1-butanol 59.42
    n-decane 2.43
    butyronitrile 20.32
    3,7-dimethyl-1-octanol 18.27
    1-chlorooctane 7.6
    1-chlorotetradecane 3.35
    n-nonane 2.35
    undecane 1.93
    tert-butylcyclohexane 1.97
    cyclooctane 1.11
    cyclopentanol 53.19
    tetrahydropyran 39.56
    tert-amyl methyl ether 40.28
    2,5,8-trioxanonane 76.32
    1-hexene 10.15
    2-isopropoxyethanol 81.45
    2,2,2-trifluoroethanol 34.97
    methyl butyrate 17.76

    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