N-(4-Aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enamide

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  • Identifiers

    CAS number
    29554-26-5

    Molecular formula
    C13H18N2O3

    SMILES
    C1=CC(=C(C=C1C=CC(=O)NCCCCN)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 56.73%
    Meaty 45.25%
    Savory 45.19%
    Fishy 32.54%
    Cooked 22.89%
    Cooling 22.64%
    Burnt 21.72%
    Cheesy 20.75%
    Pungent 19.66%
    Roasted 18.9%

     

    Flavor
    Bitter 57.86%
    Odorless 48.85%
    Mild 33.17%
    Bland 26.54%
    Sweet-like 21.22%
    Nitrile 21.08%
    Orange flower 19.7%
    Cedarleaf 19.58%
    Lovage 19.38%
    Taco 19.02%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    9.76 (weak base)

    Molecular weight
    250.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    529°C

    Flash point

    • 234.44 ˚C est.

  • Synonyms

    • N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enamide
    • DTXSID60331448
    • RefChem:361726
    • DTXCID60282542
    • 29554-26-5
    • caffeoylputrescine
    • 2-Propenamide, N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)-
    • orb1684387
    • SCHEMBL1675934
    • SCHEMBL29941354
    • CHEBI:182693
    • BBA14806
    • EBA55426
    • DB-230949
    • N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)propenamide
    • (E)-N-(4-Aminobutyl)-3-(3,4-dihydroxyphenyl)propenamide
    • 29554-26-5

  • Applications

    N-(4-Aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enamide, CAS 29554-26-5, is primarily encountered as an organic intermediate and functional building block in chemical synthesis, with real-world applications including use as a dye/pigment precursor for coatings and inks, as a polymer/plastic building block where the catechol moiety can contribute antioxidant and stabilizing properties, as a curing or crosslinking component in adhesive and epoxy resin formulations via its amine functionality, and as a potential pharmaceutical synthesis intermediate in medicinal chemistry explorations; its versatility is subject to regulatory controls and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 29.2
    methanol 108.58
    isopropanol 10.88
    water 4.54
    ethyl acetate 16.59
    n-propanol 16.53
    acetone 35.9
    n-butanol 10.13
    acetonitrile 7.93
    DMF 136.12
    toluene 1.89
    isobutanol 6.97
    1,4-dioxane 18.39
    methyl acetate 13.23
    THF 65.43
    2-butanone 17.72
    n-pentanol 8.47
    sec-butanol 8.75
    n-hexane 0.18
    ethylene glycol 55.68
    NMP 57.25
    cyclohexane 0.26
    DMSO 516.84
    n-butyl acetate 3.8
    n-octanol 1.77
    chloroform 2.85
    n-propyl acetate 5.46
    acetic acid 166.79
    dichloromethane 2.46
    cyclohexanone 25.31
    propylene glycol 60.28
    isopropyl acetate 6.73
    DMAc 233.14
    2-ethoxyethanol 82.51
    isopentanol 8.19
    n-heptane 0.22
    ethyl formate 20.59
    1,2-dichloroethane 3.57
    n-hexanol 6.01
    2-methoxyethanol 173.41
    isobutyl acetate 2.62
    tetrachloromethane 1.08
    n-pentyl acetate 2.66
    transcutol 64.96
    n-heptanol 3.94
    ethylbenzene 1.07
    MIBK 6.46
    2-propoxyethanol 34.66
    tert-butanol 18.34
    MTBE 4.05
    2-butoxyethanol 18.45
    propionic acid 36.34
    o-xylene 2.15
    formic acid 236.32
    diethyl ether 2.63
    m-xylene 1.74
    p-xylene 1.54
    chlorobenzene 1.72
    dimethyl carbonate 13.49
    n-octane 0.15
    formamide 318.06
    cyclopentanone 46.81
    2-pentanone 12.33
    anisole 4.38
    cyclopentyl methyl ether 7.82
    gamma-butyrolactone 58.27
    1-methoxy-2-propanol 70.11
    pyridine 14.27
    3-pentanone 7.71
    furfural 59.53
    n-dodecane 0.11
    diethylene glycol 71.09
    diisopropyl ether 0.95
    tert-amyl alcohol 13.43
    acetylacetone 29.74
    n-hexadecane 0.12
    acetophenone 8.62
    methyl propionate 16.83
    isopentyl acetate 4.53
    trichloroethylene 8.6
    n-nonanol 2.15
    cyclohexanol 8.79
    benzyl alcohol 11.85
    2-ethylhexanol 2.82
    isooctanol 3.18
    dipropyl ether 2.12
    1,2-dichlorobenzene 2.03
    ethyl lactate 12.7
    propylene carbonate 21.25
    n-methylformamide 94.34
    2-pentanol 4.34
    n-pentane 0.14
    1-propoxy-2-propanol 16.97
    1-methoxy-2-propyl acetate 11.84
    2-(2-methoxypropoxy) propanol 18.94
    mesitylene 1.13
    ε-caprolactone 21.78
    p-cymene 1.15
    epichlorohydrin 33.32
    1,1,1-trichloroethane 2.6
    2-aminoethanol 77.09
    morpholine-4-carbaldehyde 65.56
    sulfolane 100.36
    2,2,4-trimethylpentane 0.18
    2-methyltetrahydrofuran 12.75
    n-hexyl acetate 3.23
    isooctane 0.1
    2-(2-butoxyethoxy)ethanol 26.75
    sec-butyl acetate 3.29
    tert-butyl acetate 7.78
    decalin 0.21
    glycerin 130.33
    diglyme 41.65
    acrylic acid 46.86
    isopropyl myristate 1.8
    n-butyric acid 40.08
    acetyl acetate 11.75
    di(2-ethylhexyl) phthalate 4.5
    ethyl propionate 5.49
    nitromethane 193.01
    1,2-diethoxyethane 6.42
    benzonitrile 5.57
    trioctyl phosphate 3.31
    1-bromopropane 1.1
    gamma-valerolactone 76.41
    n-decanol 1.83
    triethyl phosphate 4.6
    4-methyl-2-pentanol 3.21
    propionitrile 4.98
    vinylene carbonate 17.59
    1,1,2-trichlorotrifluoroethane 76.75
    DMS 6.33
    cumene 0.92
    2-octanol 1.63
    2-hexanone 5.74
    octyl acetate 2.61
    limonene 1.42
    1,2-dimethoxyethane 48.91
    ethyl orthosilicate 4.27
    tributyl phosphate 3.59
    diacetone alcohol 25.66
    N,N-dimethylaniline 4.38
    acrylonitrile 12.25
    aniline 8.7
    1,3-propanediol 86.82
    bromobenzene 1.08
    dibromomethane 1.39
    1,1,2,2-tetrachloroethane 8.85
    2-methyl-cyclohexyl acetate 4.87
    tetrabutyl urea 5.79
    diisobutyl methanol 2.07
    2-phenylethanol 8.27
    styrene 1.19
    dioctyl adipate 4.5
    dimethyl sulfate 32.05
    ethyl butyrate 4.17
    methyl lactate 34.62
    butyl lactate 7.68
    diethyl carbonate 3.86
    propanediol butyl ether 17.73
    triethyl orthoformate 4.66
    p-tert-butyltoluene 1.13
    methyl 4-tert-butylbenzoate 10.37
    morpholine 35.4
    tert-butylamine 3.91
    n-dodecanol 1.49
    dimethoxymethane 48.2
    ethylene carbonate 13.72
    cyrene 27.89
    2-ethoxyethyl acetate 7.06
    2-ethylhexyl acetate 2.72
    1,2,4-trichlorobenzene 3.28
    4-methylpyridine 9.6
    dibutyl ether 1.27
    2,6-dimethyl-4-heptanol 2.07
    DEF 23.74
    dimethyl isosorbide 25.77
    tetrachloroethylene 7.63
    eugenol 13.84
    triacetin 8.74
    span 80 13.9
    1,4-butanediol 35.73
    1,1-dichloroethane 1.91
    2-methyl-1-pentanol 7.44
    methyl formate 67.25
    2-methyl-1-butanol 7.58
    n-decane 0.16
    butyronitrile 5.12
    3,7-dimethyl-1-octanol 2.37
    1-chlorooctane 0.51
    1-chlorotetradecane 0.33
    n-nonane 0.14
    undecane 0.13
    tert-butylcyclohexane 0.17
    cyclooctane 0.15
    cyclopentanol 13.42
    tetrahydropyran 7.33
    tert-amyl methyl ether 3.88
    2,5,8-trioxanonane 34.36
    1-hexene 0.69
    2-isopropoxyethanol 29.14
    2,2,2-trifluoroethanol 58.92
    methyl butyrate 9.38

    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