Ethyl urocanate

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  • Identifiers

    CAS number
    111157-51-8

    Molecular formula
    C8H10N2O2

    SMILES
    CCOC(=O)/C=C/C1=CN=CN1

    Safety labels

  • Odor profile

    Fragrance
    Fruity 40.98%
    Nutty 38.66%
    Roasted 37.45%
    Caramellic 36.91%
    Burnt 30.65%
    Odorless 24.75%
    Sweet 24.7%
    Spicy 24.13%
    Winey 23.99%
    Cooked 23.75%

     

    Flavor
    Bitter 43.67%
    Odorless 34.7%
    Fruity 25.75%
    Very mild 23.71%
    Mild 20.23%
    Ethyl benzoate 19.46%
    Yeast 19.45%
    Orange flower 19.39%
    Taco 19.36%
    Bread crust 19.06%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    6.12 (neutral)

    Molecular weight
    166.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    400°C

    Flash point

    • 178.2 ˚C est.

  • Synonyms

    • Ethyl urocanate
    • 111157-51-8
    • Parasonarl Mark II
    • ethyl (E)-3-(1H-imidazol-5-yl)prop-2-enoate
    • 27538-35-8
    • (E)-Urocanic acid ethyl ester
    • UNII-GS4W88OP01
    • GS4W88OP01
    • EINECS 248-515-1
    • Ethyl (E)-3-(1H-imidazol-4-yl)-2-propenoate
    • 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, ethyl ester, (2E)-
    • 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, ethyl ester, (E)-
    • 2-Propenoic acid, 3-(1H-imidazol-5-yl)-, ethyl ester, (2E)-
    • 3-(1H-Imidazol-4-yl)-2-propenoic acid, ethyl ester
    • 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, ethyl ester
    • RefChem:139070
    • ETHYL UROCANATE [INCI]
    • (e)-3-(1h-imidazol-4-yl)-2-propenoic acid ethyl ester
    • MFCD20537699
    • Ethyl 3-(1H-imidazol-4-yl)acrylate
    • Ethyl (2E)-3-(1H-imidazol-4-yl)prop-2-enoate
    • SCHEMBL2485956
    • SCHEMBL2567149
    • HPMLGOFBKNGJAM-ONEGZZNKSA-N
    • AKOS015905998
    • AS-48227
    • NS00051210
    • F19956
    • EN300-1455951
    • Ethyl(2E)-3-(1H-imidazol-4-yl)prop-2-enoate
    • ethyl (2E)-3-(1H-imidazol-5-yl)prop-2-enoate
    • (E)-3-(1H-imidazol-4-yl)-acrylic acid ethyl ester
    • Q27279254
    • 27538-35-8

  • Applications

    Ethyl urocanate (CAS 111157-51-8) is a versatile synthetic building block used as an intermediate in the preparation of imidazole-containing compounds, with relevance to pharmaceutical and agrochemical research. It also serves as a reactive starting material in polymer and coatings chemistry, enabling functionalization or crosslinking when incorporated into functional polymers. In cosmetics and fragrance applications, it acts as an odor-active intermediate or fragrance precursor, supporting scent development and formulation flexibility. Additionally, it may be employed in flavor/aroma chemistry as a precursor to aroma-active substances, aiding research and development of aroma profiles. Overall, its utility lies in its role as a specialized imidazole-bearing ester suitable for downstream synthesis across multiple industries, subject to formulation and regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 45.01
    methanol 87.28
    isopropanol 27.35
    water 2.68
    ethyl acetate 18.51
    n-propanol 26.93
    acetone 45.11
    n-butanol 26.96
    acetonitrile 28.39
    DMF 375.43
    toluene 6.37
    isobutanol 23.41
    1,4-dioxane 40.09
    methyl acetate 31.09
    THF 68.1
    2-butanone 36.92
    n-pentanol 22.91
    sec-butanol 25.16
    n-hexane 0.59
    ethylene glycol 26.97
    NMP 196.04
    cyclohexane 0.51
    DMSO 324.27
    n-butyl acetate 16.39
    n-octanol 5.28
    chloroform 36.14
    n-propyl acetate 14.95
    acetic acid 92.29
    dichloromethane 49.81
    cyclohexanone 48.55
    propylene glycol 26.37
    isopropyl acetate 11.95
    DMAc 441.33
    2-ethoxyethanol 68.61
    isopentanol 28.81
    n-heptane 0.38
    ethyl formate 22.72
    1,2-dichloroethane 29.23
    n-hexanol 12.1
    2-methoxyethanol 110.13
    isobutyl acetate 11.64
    tetrachloromethane 3.18
    n-pentyl acetate 7.97
    transcutol 142.18
    n-heptanol 5.78
    ethylbenzene 5.47
    MIBK 15.94
    2-propoxyethanol 41.32
    tert-butanol 40.0
    MTBE 20.62
    2-butoxyethanol 21.62
    propionic acid 34.91
    o-xylene 7.72
    formic acid 92.47
    diethyl ether 11.72
    m-xylene 6.14
    p-xylene 8.97
    chlorobenzene 14.91
    dimethyl carbonate 23.09
    n-octane 0.2
    formamide 131.58
    cyclopentanone 62.26
    2-pentanone 21.37
    anisole 25.03
    cyclopentyl methyl ether 19.88
    gamma-butyrolactone 78.27
    1-methoxy-2-propanol 59.45
    pyridine 52.27
    3-pentanone 19.45
    furfural 106.49
    n-dodecane 0.3
    diethylene glycol 54.47
    diisopropyl ether 3.28
    tert-amyl alcohol 35.9
    acetylacetone 29.62
    n-hexadecane 0.35
    acetophenone 31.68
    methyl propionate 25.87
    isopentyl acetate 18.59
    trichloroethylene 67.28
    n-nonanol 5.63
    cyclohexanol 20.0
    benzyl alcohol 32.21
    2-ethylhexanol 8.44
    isooctanol 5.87
    dipropyl ether 6.47
    1,2-dichlorobenzene 17.11
    ethyl lactate 18.02
    propylene carbonate 39.27
    n-methylformamide 90.38
    2-pentanol 14.31
    n-pentane 0.46
    1-propoxy-2-propanol 25.12
    1-methoxy-2-propyl acetate 25.5
    2-(2-methoxypropoxy) propanol 41.43
    mesitylene 3.89
    ε-caprolactone 41.84
    p-cymene 4.31
    epichlorohydrin 81.48
    1,1,1-trichloroethane 14.44
    2-aminoethanol 41.73
    morpholine-4-carbaldehyde 146.01
    sulfolane 121.42
    2,2,4-trimethylpentane 0.88
    2-methyltetrahydrofuran 37.25
    n-hexyl acetate 11.95
    isooctane 0.42
    2-(2-butoxyethoxy)ethanol 43.23
    sec-butyl acetate 11.56
    tert-butyl acetate 15.62
    decalin 0.94
    glycerin 56.35
    diglyme 72.1
    acrylic acid 46.38
    isopropyl myristate 6.5
    n-butyric acid 35.99
    acetyl acetate 15.41
    di(2-ethylhexyl) phthalate 13.83
    ethyl propionate 15.41
    nitromethane 136.36
    1,2-diethoxyethane 22.92
    benzonitrile 28.28
    trioctyl phosphate 7.39
    1-bromopropane 11.61
    gamma-valerolactone 101.72
    n-decanol 4.61
    triethyl phosphate 13.3
    4-methyl-2-pentanol 9.66
    propionitrile 22.48
    vinylene carbonate 42.59
    1,1,2-trichlorotrifluoroethane 89.63
    DMS 22.81
    cumene 4.93
    2-octanol 3.85
    2-hexanone 18.2
    octyl acetate 8.43
    limonene 5.82
    1,2-dimethoxyethane 83.59
    ethyl orthosilicate 12.27
    tributyl phosphate 10.48
    diacetone alcohol 31.31
    N,N-dimethylaniline 23.65
    acrylonitrile 37.45
    aniline 26.08
    1,3-propanediol 49.93
    bromobenzene 11.89
    dibromomethane 23.19
    1,1,2,2-tetrachloroethane 46.55
    2-methyl-cyclohexyl acetate 16.67
    tetrabutyl urea 16.76
    diisobutyl methanol 5.48
    2-phenylethanol 20.31
    styrene 7.84
    dioctyl adipate 14.59
    dimethyl sulfate 62.45
    ethyl butyrate 14.56
    methyl lactate 30.72
    butyl lactate 14.16
    diethyl carbonate 14.19
    propanediol butyl ether 25.67
    triethyl orthoformate 14.14
    p-tert-butyltoluene 3.97
    methyl 4-tert-butylbenzoate 24.65
    morpholine 60.1
    tert-butylamine 15.89
    n-dodecanol 3.78
    dimethoxymethane 67.2
    ethylene carbonate 29.74
    cyrene 46.96
    2-ethoxyethyl acetate 17.73
    2-ethylhexyl acetate 14.11
    1,2,4-trichlorobenzene 26.03
    4-methylpyridine 52.89
    dibutyl ether 6.23
    2,6-dimethyl-4-heptanol 5.48
    DEF 52.74
    dimethyl isosorbide 53.4
    tetrachloroethylene 25.85
    eugenol 29.74
    triacetin 23.09
    span 80 25.57
    1,4-butanediol 26.56
    1,1-dichloroethane 18.8
    2-methyl-1-pentanol 26.47
    methyl formate 57.07
    2-methyl-1-butanol 27.1
    n-decane 0.38
    butyronitrile 22.7
    3,7-dimethyl-1-octanol 7.77
    1-chlorooctane 2.28
    1-chlorotetradecane 1.39
    n-nonane 0.3
    undecane 0.34
    tert-butylcyclohexane 0.9
    cyclooctane 0.24
    cyclopentanol 23.84
    tetrahydropyran 21.56
    tert-amyl methyl ether 19.13
    2,5,8-trioxanonane 62.01
    1-hexene 3.4
    2-isopropoxyethanol 38.32
    2,2,2-trifluoroethanol 40.52
    methyl butyrate 23.26

    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