methyl (2E)-4-hydroxybut-2-enoate

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  • Identifiers

    CAS number
    29576-13-4

    Molecular formula
    C5H8O3

    SMILES
    COC(=O)/C=C/CO

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 70.25%
    Ethereal 55.14%
    Caramellic 51.7%
    Green 45.51%
    Winey 45.45%
    Sharp 44.61%
    Pungent 44.46%
    Rummy 42.87%
    Sweet 41.23%
    Apple 38.24%

     

    Flavor
    Fruity 45.99%
    Pungent 30.97%
    Caramel 27.11%
    Sweet 26.08%
    Butter 23.9%
    Buttery 23.61%
    Sour 22.95%
    Sharp 22.75%
    Strawberry 22.23%
    Creamy 21.61%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.3

    pKa est.
    7.31 (neutral)

    Molecular weight
    116.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    232°C

    Flash point

    • 90.52 ˚C est.

  • Synonyms

    • 29576-13-4
    • METHYL (2E)-4-HYDROXYBUT-2-ENOATE
    • RefChem:811992
    • 899-814-4
    • methyl (E)-4-hydroxybut-2-enoate
    • (E)-Methyl 4-hydroxybut-2-enoate
    • 2-Butenoic acid, 4-hydroxy-, methyl ester, (2E)-
    • methyl-4-oxybutenoate
    • SCHEMBL3144795
    • SCHEMBL3278433
    • QBFTZEUCFMABJD-NSCUHMNNSA-N
    • AKOS006279503
    • AT12483
    • Methyl (2E)-4-hydroxy-2-butenoate #
    • 2-Butenoic acid, 4-hydroxy-, methyl ester
    • EN300-724809
    • 29576-13-4

  • Applications

    methyl (2E)-4-hydroxybut-2-enoate is a reactive vinyl ester monomer bearing a terminal hydroxyl group. In industry, it is used as a building block for hydroxy-functional acrylates and polyacrylates to enable post-polymerization crosslinking in coatings, inks, and adhesives; it serves as an intermediate for synthesizing crosslinkable polyesters and polyurethanes; it may function as a reactive diluent or comonomer in UV-curable coatings; it supports formulation of waterborne polymers to improve adhesion and hydrophilicity; and it is commonly evaluated as a precursor for specialty monomers used in polymerization.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 270.44
    methanol 488.96
    isopropanol 197.48
    water 71.76
    ethyl acetate 74.31
    n-propanol 185.59
    acetone 175.16
    n-butanol 146.05
    acetonitrile 242.37
    DMF 553.0
    toluene 23.53
    isobutanol 130.17
    1,4-dioxane 277.94
    methyl acetate 150.96
    THF 201.13
    2-butanone 121.63
    n-pentanol 96.75
    sec-butanol 163.67
    n-hexane 5.05
    ethylene glycol 211.8
    NMP 400.19
    cyclohexane 12.22
    DMSO 688.36
    n-butyl acetate 36.75
    n-octanol 53.7
    chloroform 145.08
    n-propyl acetate 47.62
    acetic acid 336.49
    dichloromethane 283.62
    cyclohexanone 137.56
    propylene glycol 132.84
    isopropyl acetate 34.85
    DMAc 502.44
    2-ethoxyethanol 234.75
    isopentanol 103.44
    n-heptane 7.47
    ethyl formate 140.1
    1,2-dichloroethane 155.03
    n-hexanol 61.11
    2-methoxyethanol 406.82
    isobutyl acetate 25.14
    tetrachloromethane 25.59
    n-pentyl acetate 32.06
    transcutol 226.57
    n-heptanol 44.62
    ethylbenzene 20.97
    MIBK 39.48
    2-propoxyethanol 123.22
    tert-butanol 248.93
    MTBE 97.81
    2-butoxyethanol 87.15
    propionic acid 183.36
    o-xylene 34.33
    formic acid 337.61
    diethyl ether 66.8
    m-xylene 22.95
    p-xylene 30.19
    chlorobenzene 45.85
    dimethyl carbonate 51.1
    n-octane 4.38
    formamide 428.86
    cyclopentanone 180.69
    2-pentanone 67.24
    anisole 75.19
    cyclopentyl methyl ether 72.43
    gamma-butyrolactone 248.51
    1-methoxy-2-propanol 196.47
    pyridine 146.33
    3-pentanone 55.05
    furfural 260.02
    n-dodecane 4.7
    diethylene glycol 154.56
    diisopropyl ether 17.09
    tert-amyl alcohol 195.63
    acetylacetone 71.45
    n-hexadecane 4.98
    acetophenone 75.96
    methyl propionate 84.8
    isopentyl acetate 35.71
    trichloroethylene 220.94
    n-nonanol 44.76
    cyclohexanol 105.64
    benzyl alcohol 84.93
    2-ethylhexanol 42.48
    isooctanol 37.99
    dipropyl ether 35.22
    1,2-dichlorobenzene 53.89
    ethyl lactate 52.34
    propylene carbonate 115.44
    n-methylformamide 338.69
    2-pentanol 78.9
    n-pentane 7.89
    1-propoxy-2-propanol 74.34
    1-methoxy-2-propyl acetate 41.63
    2-(2-methoxypropoxy) propanol 93.6
    mesitylene 17.41
    ε-caprolactone 126.57
    p-cymene 19.35
    epichlorohydrin 263.27
    1,1,1-trichloroethane 78.49
    2-aminoethanol 255.13
    morpholine-4-carbaldehyde 346.02
    sulfolane 352.66
    2,2,4-trimethylpentane 6.8
    2-methyltetrahydrofuran 153.57
    n-hexyl acetate 49.8
    isooctane 3.92
    2-(2-butoxyethoxy)ethanol 110.56
    sec-butyl acetate 27.32
    tert-butyl acetate 40.28
    decalin 7.36
    glycerin 222.87
    diglyme 212.86
    acrylic acid 198.11
    isopropyl myristate 25.26
    n-butyric acid 146.82
    acetyl acetate 47.32
    di(2-ethylhexyl) phthalate 34.78
    ethyl propionate 45.35
    nitromethane 469.5
    1,2-diethoxyethane 60.1
    benzonitrile 88.18
    trioctyl phosphate 27.92
    1-bromopropane 67.35
    gamma-valerolactone 237.89
    n-decanol 35.2
    triethyl phosphate 34.29
    4-methyl-2-pentanol 41.16
    propionitrile 146.47
    vinylene carbonate 130.33
    1,1,2-trichlorotrifluoroethane 223.39
    DMS 43.51
    cumene 20.27
    2-octanol 31.87
    2-hexanone 51.52
    octyl acetate 35.66
    limonene 28.51
    1,2-dimethoxyethane 282.62
    ethyl orthosilicate 31.61
    tributyl phosphate 28.96
    diacetone alcohol 89.85
    N,N-dimethylaniline 69.94
    acrylonitrile 214.41
    aniline 72.99
    1,3-propanediol 250.19
    bromobenzene 36.52
    dibromomethane 139.6
    1,1,2,2-tetrachloroethane 159.27
    2-methyl-cyclohexyl acetate 42.98
    tetrabutyl urea 47.5
    diisobutyl methanol 27.75
    2-phenylethanol 57.07
    styrene 26.24
    dioctyl adipate 45.8
    dimethyl sulfate 105.82
    ethyl butyrate 43.01
    methyl lactate 86.78
    butyl lactate 40.6
    diethyl carbonate 37.15
    propanediol butyl ether 84.72
    triethyl orthoformate 37.81
    p-tert-butyltoluene 18.02
    methyl 4-tert-butylbenzoate 72.59
    morpholine 308.64
    tert-butylamine 127.91
    n-dodecanol 28.49
    dimethoxymethane 178.41
    ethylene carbonate 98.89
    cyrene 107.82
    2-ethoxyethyl acetate 46.93
    2-ethylhexyl acetate 26.99
    1,2,4-trichlorobenzene 67.03
    4-methylpyridine 122.81
    dibutyl ether 34.92
    2,6-dimethyl-4-heptanol 27.75
    DEF 166.34
    dimethyl isosorbide 127.7
    tetrachloroethylene 110.07
    eugenol 82.36
    triacetin 64.11
    span 80 72.39
    1,4-butanediol 127.49
    1,1-dichloroethane 110.19
    2-methyl-1-pentanol 82.79
    methyl formate 234.23
    2-methyl-1-butanol 112.24
    n-decane 6.43
    butyronitrile 135.37
    3,7-dimethyl-1-octanol 45.43
    1-chlorooctane 24.44
    1-chlorotetradecane 11.55
    n-nonane 6.15
    undecane 5.31
    tert-butylcyclohexane 6.92
    cyclooctane 4.68
    cyclopentanol 149.96
    tetrahydropyran 140.54
    tert-amyl methyl ether 75.47
    2,5,8-trioxanonane 165.94
    1-hexene 18.77
    2-isopropoxyethanol 122.55
    2,2,2-trifluoroethanol 160.79
    methyl butyrate 77.03

    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