Feruloylputrescine

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  • Identifiers

    CAS number
    501-13-3

    Molecular formula
    C14H20N2O3

    SMILES
    COC1=C(C=CC(=C1)/C=C/C(=O)NCCCCN)O

    Safety labels

  • Odor profile

    Fragrance
    Meaty 50.29%
    Savory 47.74%
    Odorless 44.63%
    Fishy 32.79%
    Cooling 24.95%
    Cooked 24.73%
    Roasted 24.65%
    Cheesy 22.73%
    Burnt 21.95%
    Pungent 21.28%

     

    Flavor
    Odorless 45.03%
    Bitter 44.35%
    Mild 31.73%
    Bland 26.92%
    Sweet-like 20.47%
    Nitrile 20.33%
    Faint 20.1%
    Orange flower 19.95%
    Lovage 19.59%
    Ethyl benzoate 19.57%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    9.51 (weak base)

    Molecular weight
    264.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    541°C

    Flash point

    • 209.41 ˚C est.

  • Synonyms

    • Feruloylputrescine
    • 501-13-3
    • (E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
    • DTXSID90904144
    • RefChem:921587
    • DTXCID901332029
    • Subaphylline
    • N-Feruloylputrescine
    • 91000-11-2
    • N-(4-Aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
    • Subaphyllin
    • 4-Oxy-3-methoxycinnamylputrescine
    • N-trans-Feruloylputrescine
    • N-(4-Aminobutyl)-4-hydroxy-3-methoxycinnamamide
    • NSC-602818
    • J3HM10B75D
    • CINNAMAMIDE, N-(4-AMINOBUTYL)-4-HYDROXY-3-METHOXY-
    • 2-Propenamide, N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)-
    • (2E)-N-(4-AMINOBUTYL)-3-(4-HYDROXY-3-METHOXYPHENYL)PROP-2-ENAMIDE
    • (E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
    • N-(4-Aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide
    • (E)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enamide
    • 2-Propenamide, N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)-, (2E)-
    • trans-N-Feruloylputrescine
    • MFCD01736565
    • trans N-feruloylputrescine
    • UNII-J3HM10B75D
    • CHEBI:9299
    • orb1943129
    • SCHEMBL26486026
    • SCHEMBL30429479
    • SFUVCMKSYKHYLD-FNORWQNLSA-N
    • NSC602818
    • EBC-617598
    • Feruloyl putrescine (isomer of 1178)
    • HY-W327449
    • HY-W707850
    • AS-75663
    • DA-76327
    • CS-0367848
    • CS-0816179
    • Q27108351
    • (2E)-N-(4-Aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide #
    • 501-13-3

  • Applications

    Feruloylputrescine (CAS 501-13-3) is a hydroxycinnamoyl polyamine that is primarily investigated as a plant metabolite; in industry, it is considered as a potential cosmetic antioxidant and bioactive ingredient to stabilize formulations and confer antioxidant benefits; in agriculture, it is studied as a plant-defense-related metabolite and can serve as a biomarker of stress or a precursor for natural defense elicitors; in pharmaceutical research, it and related HCAs are evaluated as intermediates for the synthesis of bioactive compounds and may show antimicrobial or anti-inflammatory activity in vitro; in polymers and coatings, it can be used as a building block or functional intermediate for bio-based polyphenolic materials, potentially enabling cross-linking or UV-stabilization in coatings and inks.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 72.37
    methanol 191.71
    isopropanol 25.3
    water 2.84
    ethyl acetate 43.84
    n-propanol 36.46
    acetone 86.98
    n-butanol 25.3
    acetonitrile 30.84
    DMF 178.8
    toluene 4.5
    isobutanol 16.35
    1,4-dioxane 60.45
    methyl acetate 33.83
    THF 128.36
    2-butanone 35.79
    n-pentanol 19.69
    sec-butanol 17.23
    n-hexane 0.19
    ethylene glycol 75.85
    NMP 71.87
    cyclohexane 0.52
    DMSO 832.99
    n-butyl acetate 7.41
    n-octanol 4.23
    chloroform 25.91
    n-propyl acetate 13.29
    acetic acid 311.22
    dichloromethane 30.64
    cyclohexanone 54.57
    propylene glycol 91.45
    isopropyl acetate 13.55
    DMAc 240.38
    2-ethoxyethanol 131.64
    isopentanol 16.79
    n-heptane 0.26
    ethyl formate 47.04
    1,2-dichloroethane 24.93
    n-hexanol 10.98
    2-methoxyethanol 250.24
    isobutyl acetate 7.38
    tetrachloromethane 3.62
    n-pentyl acetate 5.25
    transcutol 118.94
    n-heptanol 6.55
    ethylbenzene 2.35
    MIBK 11.04
    2-propoxyethanol 55.33
    tert-butanol 34.36
    MTBE 7.36
    2-butoxyethanol 26.78
    propionic acid 68.41
    o-xylene 4.2
    formic acid 287.87
    diethyl ether 5.88
    m-xylene 3.39
    p-xylene 3.27
    chlorobenzene 7.89
    dimethyl carbonate 24.75
    n-octane 0.23
    formamide 341.11
    cyclopentanone 83.65
    2-pentanone 23.22
    anisole 10.54
    cyclopentyl methyl ether 13.76
    gamma-butyrolactone 105.31
    1-methoxy-2-propanol 107.05
    pyridine 36.62
    3-pentanone 14.31
    furfural 114.81
    n-dodecane 0.24
    diethylene glycol 106.37
    diisopropyl ether 1.45
    tert-amyl alcohol 22.21
    acetylacetone 51.59
    n-hexadecane 0.26
    acetophenone 18.14
    methyl propionate 35.16
    isopentyl acetate 8.76
    trichloroethylene 51.23
    n-nonanol 4.77
    cyclohexanol 19.5
    benzyl alcohol 25.7
    2-ethylhexanol 5.0
    isooctanol 5.63
    dipropyl ether 3.32
    1,2-dichlorobenzene 8.63
    ethyl lactate 22.36
    propylene carbonate 42.72
    n-methylformamide 125.78
    2-pentanol 8.79
    n-pentane 0.18
    1-propoxy-2-propanol 25.31
    1-methoxy-2-propyl acetate 19.7
    2-(2-methoxypropoxy) propanol 27.41
    mesitylene 2.04
    ε-caprolactone 44.79
    p-cymene 2.12
    epichlorohydrin 93.7
    1,1,1-trichloroethane 12.93
    2-aminoethanol 110.64
    morpholine-4-carbaldehyde 98.97
    sulfolane 158.44
    2,2,4-trimethylpentane 0.3
    2-methyltetrahydrofuran 27.48
    n-hexyl acetate 6.9
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 38.73
    sec-butyl acetate 6.86
    tert-butyl acetate 13.61
    decalin 0.41
    glycerin 168.11
    diglyme 68.99
    acrylic acid 77.91
    isopropyl myristate 3.52
    n-butyric acid 77.61
    acetyl acetate 29.72
    di(2-ethylhexyl) phthalate 8.66
    ethyl propionate 11.47
    nitromethane 364.96
    1,2-diethoxyethane 14.53
    benzonitrile 16.53
    trioctyl phosphate 5.76
    1-bromopropane 4.86
    gamma-valerolactone 132.58
    n-decanol 3.82
    triethyl phosphate 8.42
    4-methyl-2-pentanol 5.54
    propionitrile 16.35
    vinylene carbonate 40.53
    1,1,2-trichlorotrifluoroethane 139.81
    DMS 13.58
    cumene 2.02
    2-octanol 3.14
    2-hexanone 13.0
    octyl acetate 5.15
    limonene 2.76
    1,2-dimethoxyethane 85.11
    ethyl orthosilicate 7.59
    tributyl phosphate 6.78
    diacetone alcohol 38.07
    N,N-dimethylaniline 8.22
    acrylonitrile 32.91
    aniline 21.2
    1,3-propanediol 134.22
    bromobenzene 5.5
    dibromomethane 13.42
    1,1,2,2-tetrachloroethane 40.2
    2-methyl-cyclohexyl acetate 9.38
    tetrabutyl urea 9.71
    diisobutyl methanol 3.35
    2-phenylethanol 15.62
    styrene 3.06
    dioctyl adipate 9.0
    dimethyl sulfate 52.38
    ethyl butyrate 7.91
    methyl lactate 54.51
    butyl lactate 12.76
    diethyl carbonate 8.24
    propanediol butyl ether 28.44
    triethyl orthoformate 8.24
    p-tert-butyltoluene 1.97
    methyl 4-tert-butylbenzoate 16.88
    morpholine 83.02
    tert-butylamine 7.04
    n-dodecanol 2.98
    dimethoxymethane 79.32
    ethylene carbonate 31.56
    cyrene 40.34
    2-ethoxyethyl acetate 15.42
    2-ethylhexyl acetate 5.33
    1,2,4-trichlorobenzene 12.45
    4-methylpyridine 25.24
    dibutyl ether 2.98
    2,6-dimethyl-4-heptanol 3.35
    DEF 38.89
    dimethyl isosorbide 38.43
    tetrachloroethylene 27.33
    eugenol 22.9
    triacetin 17.46
    span 80 21.55
    1,4-butanediol 58.27
    1,1-dichloroethane 13.48
    2-methyl-1-pentanol 14.93
    methyl formate 100.34
    2-methyl-1-butanol 15.59
    n-decane 0.34
    butyronitrile 15.27
    3,7-dimethyl-1-octanol 4.54
    1-chlorooctane 1.59
    1-chlorotetradecane 0.88
    n-nonane 0.27
    undecane 0.27
    tert-butylcyclohexane 0.33
    cyclooctane 0.24
    cyclopentanol 25.8
    tetrahydropyran 23.19
    tert-amyl methyl ether 6.67
    2,5,8-trioxanonane 52.07
    1-hexene 1.04
    2-isopropoxyethanol 48.82
    2,2,2-trifluoroethanol 107.3
    methyl butyrate 19.04

    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