Ethyl 4-hydroxycrotonate

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  • Identifiers

    CAS number
    10080-68-9

    Molecular formula
    C6H10O3

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

    Safety labels

  • Odor profile

    Fragrance
    Fruity 77.1%
    Caramellic 51.23%
    Winey 50.71%
    Apple 48.61%
    Green 48.5%
    Ethereal 48.04%
    Sweet 45.83%
    Rummy 38.72%
    Herbal 37.98%
    Fresh 35.3%

     

    Flavor
    Fruity 46.14%
    Buttery 23.29%
    Pungent 22.87%
    Sharp 22.57%
    Sour 22.52%
    Caramel 22.25%
    Odorless 21.31%
    Sweet 21.28%
    Butter 21.19%
    Plastic 21.06%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.1

    pKa est.
    8.3 (weak base)

    Molecular weight
    130.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    227°C

    Flash point

    • 89.95 ˚C est.

  • Synonyms

    • 10080-68-9
    • Ethyl 4-hydroxycrotonate
    • Ethyl (E)-4-hydroxybut-2-enoate
    • (E)-4-Hydroxycrotonoic Acid Ethyl Ester
    • (E)-ethyl 4-hydroxybut-2-enoate
    • 2-Butenoic acid, 4-hydroxy-, ethyl ester, (2E)-
    • MFCD10566331
    • (E)-4-Hydroxycrotonoic Acid Ethyl Ester (~85%)
    • Ethyl trans-4-Hydroxy-2-butenoate; (2E)-4-Hydroxy-2-butenoic Acid Ethyl Ester
    • Ethyl trans-4-Hydroxy-2-butenoate
    • ethyl 4-oxybutenoate
    • ETHYL (2E)-4-HYDROXYBUT-2-ENOATE
    • SCHEMBL1405925
    • SCHEMBL17434696
    • ethyl (2E)-4-hydroxy-2-butenoate
    • AKOS006303360
    • AT14907
    • DB-220434
    • (E)-4-hydroxy-but-2-enoic acid ethyl ester
    • ETHYL (2E)-4-HYDROXY-BUT-2-ENOATE
    • A1-00552
    • 10080-68-9

  • Applications

    Ethyl 4-hydroxycrotonate (CAS 10080-68-9) is commonly used as an intermediate in fragrance and flavor synthesis, serving as a gateway to aroma compounds and hydroxyl-functional esters used in perfumery and flavor formulations. In cosmetics and personal care, it may act as a precursor to fragrance-related derivatives and other hydroxylated compounds that can be further functionalized for formulation. In the polymer and plastics sector, it can participate in the preparation of hydroxy-functional monomers for polyesters and polyurethanes, enabling adjustment of mechanical properties and crosslinking potential. In coatings, inks, and adhesives, it can serve as a reactive monomer or ester-linked intermediate to enhance surface functionality and adhesion. Additionally, it may be used as a building block or fragrance ingredient in cleaning formulations and other industrial applications, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 649.49
    methanol 1248.54
    isopropanol 436.82
    water 14.09
    ethyl acetate 278.7
    n-propanol 408.82
    acetone 763.12
    n-butanol 345.11
    acetonitrile 781.23
    DMF 1553.68
    toluene 62.6
    isobutanol 272.38
    1,4-dioxane 561.47
    methyl acetate 414.2
    THF 586.69
    2-butanone 426.23
    n-pentanol 240.26
    sec-butanol 344.13
    n-hexane 21.63
    ethylene glycol 293.69
    NMP 987.99
    cyclohexane 29.5
    DMSO 2261.41
    n-butyl acetate 213.13
    n-octanol 96.49
    chloroform 387.18
    n-propyl acetate 198.48
    acetic acid 973.59
    dichloromethane 672.23
    cyclohexanone 434.19
    propylene glycol 213.97
    isopropyl acetate 123.65
    DMAc 1028.37
    2-ethoxyethanol 462.59
    isopentanol 244.19
    n-heptane 13.82
    ethyl formate 334.33
    1,2-dichloroethane 459.44
    n-hexanol 160.22
    2-methoxyethanol 799.13
    isobutyl acetate 91.52
    tetrachloromethane 49.56
    n-pentyl acetate 109.75
    transcutol 797.4
    n-heptanol 70.13
    ethylbenzene 61.84
    MIBK 128.73
    2-propoxyethanol 300.64
    tert-butanol 490.8
    MTBE 260.43
    2-butoxyethanol 154.94
    propionic acid 477.6
    o-xylene 71.94
    formic acid 578.75
    diethyl ether 240.78
    m-xylene 56.46
    p-xylene 89.37
    chlorobenzene 161.0
    dimethyl carbonate 131.2
    n-octane 7.55
    formamide 802.47
    cyclopentanone 549.61
    2-pentanone 269.32
    anisole 195.26
    cyclopentyl methyl ether 208.46
    gamma-butyrolactone 735.38
    1-methoxy-2-propanol 436.45
    pyridine 417.01
    3-pentanone 200.63
    furfural 652.94
    n-dodecane 8.57
    diethylene glycol 308.64
    diisopropyl ether 47.04
    tert-amyl alcohol 393.41
    acetylacetone 274.39
    n-hexadecane 9.32
    acetophenone 204.93
    methyl propionate 260.54
    isopentyl acetate 156.35
    trichloroethylene 652.33
    n-nonanol 77.98
    cyclohexanol 239.51
    benzyl alcohol 196.48
    2-ethylhexanol 99.7
    isooctanol 61.8
    dipropyl ether 93.94
    1,2-dichlorobenzene 171.16
    ethyl lactate 122.43
    propylene carbonate 334.1
    n-methylformamide 834.53
    2-pentanol 187.5
    n-pentane 21.2
    1-propoxy-2-propanol 190.7
    1-methoxy-2-propyl acetate 149.98
    2-(2-methoxypropoxy) propanol 188.89
    mesitylene 43.03
    ε-caprolactone 373.83
    p-cymene 47.88
    epichlorohydrin 652.37
    1,1,1-trichloroethane 215.74
    2-aminoethanol 396.93
    morpholine-4-carbaldehyde 706.81
    sulfolane 1004.5
    2,2,4-trimethylpentane 14.77
    2-methyltetrahydrofuran 411.2
    n-hexyl acetate 173.44
    isooctane 8.98
    2-(2-butoxyethoxy)ethanol 256.83
    sec-butyl acetate 101.32
    tert-butyl acetate 136.64
    decalin 20.72
    glycerin 330.73
    diglyme 448.68
    acrylic acid 493.73
    isopropyl myristate 62.51
    n-butyric acid 403.42
    acetyl acetate 166.42
    di(2-ethylhexyl) phthalate 75.88
    ethyl propionate 168.53
    nitromethane 1380.18
    1,2-diethoxyethane 209.99
    benzonitrile 282.68
    trioctyl phosphate 56.16
    1-bromopropane 205.14
    gamma-valerolactone 633.84
    n-decanol 59.92
    triethyl phosphate 82.33
    4-methyl-2-pentanol 88.01
    propionitrile 425.09
    vinylene carbonate 353.8
    1,1,2-trichlorotrifluoroethane 485.41
    DMS 148.82
    cumene 50.33
    2-octanol 58.46
    2-hexanone 198.43
    octyl acetate 85.91
    limonene 71.05
    1,2-dimethoxyethane 680.5
    ethyl orthosilicate 74.78
    tributyl phosphate 78.14
    diacetone alcohol 206.6
    N,N-dimethylaniline 149.32
    acrylonitrile 603.79
    aniline 166.42
    1,3-propanediol 438.44
    bromobenzene 144.74
    dibromomethane 373.22
    1,1,2,2-tetrachloroethane 497.59
    2-methyl-cyclohexyl acetate 117.5
    tetrabutyl urea 110.74
    diisobutyl methanol 58.07
    2-phenylethanol 132.55
    styrene 89.6
    dioctyl adipate 111.63
    dimethyl sulfate 304.01
    ethyl butyrate 149.28
    methyl lactate 182.11
    butyl lactate 115.46
    diethyl carbonate 118.6
    propanediol butyl ether 189.47
    triethyl orthoformate 100.03
    p-tert-butyltoluene 41.81
    methyl 4-tert-butylbenzoate 142.74
    morpholine 656.88
    tert-butylamine 267.08
    n-dodecanol 48.26
    dimethoxymethane 447.76
    ethylene carbonate 266.42
    cyrene 202.8
    2-ethoxyethyl acetate 157.92
    2-ethylhexyl acetate 120.93
    1,2,4-trichlorobenzene 208.72
    4-methylpyridine 388.46
    dibutyl ether 101.12
    2,6-dimethyl-4-heptanol 58.07
    DEF 460.05
    dimethyl isosorbide 270.44
    tetrachloroethylene 313.25
    eugenol 159.08
    triacetin 171.44
    span 80 157.36
    1,4-butanediol 213.1
    1,1-dichloroethane 321.13
    2-methyl-1-pentanol 206.92
    methyl formate 566.39
    2-methyl-1-butanol 246.96
    n-decane 12.53
    butyronitrile 389.26
    3,7-dimethyl-1-octanol 96.52
    1-chlorooctane 54.76
    1-chlorotetradecane 25.2
    n-nonane 12.21
    undecane 9.94
    tert-butylcyclohexane 18.22
    cyclooctane 9.03
    cyclopentanol 315.2
    tetrahydropyran 393.71
    tert-amyl methyl ether 192.46
    2,5,8-trioxanonane 335.22
    1-hexene 89.82
    2-isopropoxyethanol 247.93
    2,2,2-trifluoroethanol 293.23
    methyl butyrate 272.76

    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