N-Feruloyl Serotonin

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  • Identifiers

    CAS number
    68573-23-9

    Molecular formula
    C20H20N2O4

    SMILES
    COC1=C(C=CC(=C1)/C=C/C(=O)NCCC2=CNC3=C2C=C(C=C3)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 55.96%
    Savory 45.16%
    Meaty 42.49%
    Cooked 27.81%
    Burnt 26.53%
    Roasted 25.48%
    Milky 21.94%
    Cooling 20.13%
    Spicy 19.02%
    Dairy 18.35%

     

    Flavor
    Bitter 88.98%
    Odorless 43.14%
    Bland 28.02%
    Mild 21.93%
    Sweet-like 21.08%
    Nitrile 19.95%
    Cedarleaf 19.32%
    Lovage 18.99%
    Parsley 18.75%
    Very strong 18.75%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    9.99 (weak base)

    Molecular weight
    352.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1001°C

    Melting point expt.

    • 115 - 117 °C

    Flash point

    • 289.62 ˚C est.

  • Synonyms

    • Moschamine
    • N-Feruloylserotonin
    • N-Feruloyl Serotonin
    • 68573-23-9
    • feruloylserotonin
    • Feruloylserotonin 98
    • UNII-2PP8322487
    • ferulic acid serotonin amide
    • CHEBI:85158
    • DTXSID70172925
    • 2-Propenamide, N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)-, (2E)-
    • 2-Propenamide, N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)-, (E)-
    • RefChem:163374
    • DTXCID5095416
    • N-FERULOYL SEROTONIN [INCI]
    • 849-485-8
    • 193224-22-5
    • (E)-N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
    • (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
    • TRYPTAMINE, N-FERULOYL
    • (E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
    • CHEMBL564482
    • 2PP8322487
    • N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
    • N-[2-(5-HYDROXY-1H-INDOL-3-YL)ETHYL]-3-(4-HYDROXY-3-METHOXY-PHENYL)PROP-2-ENAMIDE
    • N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide; N-Feruloylserotonin; NSC 369502;
    • MFCD28125425
    • SEROTONIN (I), N-(FERULOYL)-
    • Nb-(E)-Feruloylserotonin
    • N-(Feruloyl)-Serotonin (I)
    • orb1685029
    • orb1739424
    • SCHEMBL12063415
    • SCHEMBL30037765
    • GLXC-10976
    • BDBM50296246
    • EBC-518564
    • HY-118824A
    • NSC-369502
    • N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide
    • DA-75683
    • MS-25464
    • CS-0068597
    • CS-0131111
    • G14381
    • Q25099720
    • (e)-N-(3-methoxy-4-hydroxycinnamoyl)-5-hydroxytryptamine
    • (E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enamide
    • 193224-22-5

  • Applications

    N-Feruloyl Serotonin (CAS 68573-23-9) is typically regarded as a chemical intermediate and a bioactive-inspired compound with antioxidant potential. It is evaluated for cosmetic/personal care applications as an antioxidant and stabilizer to improve formulation stability. In pharmaceutical research it serves as a scaffold for the development of serotonin-related bioactive derivatives. It is also used as a precursor for feruloyl-serotonin derivatives in synthetic chemistry. In the polymers, plastics, coatings, and inks sectors, it can function as an antioxidant and stabilizing additive for resins and coatings. Any use should be limited by local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 17.18
    methanol 15.72
    isopropanol 16.01
    water 0.04
    ethyl acetate 4.29
    n-propanol 18.37
    acetone 32.89
    n-butanol 12.93
    acetonitrile 2.57
    DMF 63.22
    toluene 0.21
    isobutanol 7.55
    1,4-dioxane 16.67
    methyl acetate 7.82
    THF 142.21
    2-butanone 32.12
    n-pentanol 9.77
    sec-butanol 13.9
    n-hexane 0.04
    ethylene glycol 6.73
    NMP 7.74
    cyclohexane 0.03
    DMSO 243.0
    n-butyl acetate 1.35
    n-octanol 2.5
    chloroform 1.43
    n-propyl acetate 2.58
    acetic acid 18.09
    dichloromethane 1.22
    cyclohexanone 14.71
    propylene glycol 13.36
    isopropyl acetate 2.27
    DMAc 89.74
    2-ethoxyethanol 55.03
    isopentanol 7.2
    n-heptane 0.04
    ethyl formate 5.06
    1,2-dichloroethane 1.33
    n-hexanol 2.82
    2-methoxyethanol 99.69
    isobutyl acetate 1.22
    tetrachloromethane 0.14
    n-pentyl acetate 2.76
    transcutol 37.96
    n-heptanol 2.92
    ethylbenzene 0.21
    MIBK 3.57
    2-propoxyethanol 23.61
    tert-butanol 9.49
    MTBE 2.96
    2-butoxyethanol 14.31
    propionic acid 7.26
    o-xylene 0.17
    formic acid 14.23
    diethyl ether 2.44
    m-xylene 0.13
    p-xylene 0.34
    chlorobenzene 0.29
    dimethyl carbonate 3.76
    n-octane 0.05
    formamide 31.09
    cyclopentanone 32.75
    2-pentanone 12.49
    anisole 1.81
    cyclopentyl methyl ether 3.56
    gamma-butyrolactone 18.49
    1-methoxy-2-propanol 48.43
    pyridine 7.37
    3-pentanone 6.07
    furfural 11.51
    n-dodecane 0.06
    diethylene glycol 21.76
    diisopropyl ether 0.28
    tert-amyl alcohol 8.87
    acetylacetone 10.92
    n-hexadecane 0.07
    acetophenone 2.54
    methyl propionate 5.91
    isopentyl acetate 1.47
    trichloroethylene 3.09
    n-nonanol 2.97
    cyclohexanol 4.13
    benzyl alcohol 4.22
    2-ethylhexanol 0.96
    isooctanol 1.98
    dipropyl ether 1.4
    1,2-dichlorobenzene 0.26
    ethyl lactate 3.27
    propylene carbonate 3.1
    n-methylformamide 23.44
    2-pentanol 4.19
    n-pentane 0.02
    1-propoxy-2-propanol 9.83
    1-methoxy-2-propyl acetate 3.41
    2-(2-methoxypropoxy) propanol 10.59
    mesitylene 0.08
    ε-caprolactone 8.67
    p-cymene 0.15
    epichlorohydrin 28.28
    1,1,1-trichloroethane 0.55
    2-aminoethanol 15.72
    morpholine-4-carbaldehyde 21.77
    sulfolane 27.92
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 13.46
    n-hexyl acetate 3.44
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 18.42
    sec-butyl acetate 1.45
    tert-butyl acetate 2.34
    decalin 0.03
    glycerin 26.67
    diglyme 29.6
    acrylic acid 6.49
    isopropyl myristate 1.38
    n-butyric acid 9.9
    acetyl acetate 1.47
    di(2-ethylhexyl) phthalate 1.79
    ethyl propionate 2.36
    nitromethane 34.7
    1,2-diethoxyethane 7.2
    benzonitrile 1.34
    trioctyl phosphate 1.41
    1-bromopropane 0.61
    gamma-valerolactone 47.23
    n-decanol 2.07
    triethyl phosphate 1.03
    4-methyl-2-pentanol 1.58
    propionitrile 2.85
    vinylene carbonate 2.63
    1,1,2-trichlorotrifluoroethane 18.46
    DMS 2.15
    cumene 0.15
    2-octanol 1.93
    2-hexanone 7.02
    octyl acetate 2.2
    limonene 0.21
    1,2-dimethoxyethane 53.11
    ethyl orthosilicate 1.1
    tributyl phosphate 1.56
    diacetone alcohol 10.47
    N,N-dimethylaniline 1.04
    acrylonitrile 4.48
    aniline 1.49
    1,3-propanediol 40.42
    bromobenzene 0.17
    dibromomethane 0.58
    1,1,2,2-tetrachloroethane 3.35
    2-methyl-cyclohexyl acetate 1.24
    tetrabutyl urea 3.65
    diisobutyl methanol 0.56
    2-phenylethanol 2.17
    styrene 0.24
    dioctyl adipate 2.72
    dimethyl sulfate 6.51
    ethyl butyrate 1.38
    methyl lactate 7.71
    butyl lactate 3.88
    diethyl carbonate 0.88
    propanediol butyl ether 11.67
    triethyl orthoformate 1.72
    p-tert-butyltoluene 0.14
    methyl 4-tert-butylbenzoate 3.33
    morpholine 32.8
    tert-butylamine 1.54
    n-dodecanol 1.38
    dimethoxymethane 37.75
    ethylene carbonate 2.36
    cyrene 9.54
    2-ethoxyethyl acetate 6.0
    2-ethylhexyl acetate 0.88
    1,2,4-trichlorobenzene 0.5
    4-methylpyridine 3.43
    dibutyl ether 2.47
    2,6-dimethyl-4-heptanol 0.56
    DEF 9.72
    dimethyl isosorbide 8.76
    tetrachloroethylene 1.7
    eugenol 5.23
    triacetin 3.91
    span 80 6.75
    1,4-butanediol 12.91
    1,1-dichloroethane 0.95
    2-methyl-1-pentanol 5.59
    methyl formate 13.71
    2-methyl-1-butanol 7.61
    n-decane 0.1
    butyronitrile 3.33
    3,7-dimethyl-1-octanol 1.47
    1-chlorooctane 0.5
    1-chlorotetradecane 0.22
    n-nonane 0.07
    undecane 0.07
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 9.33
    tetrahydropyran 10.51
    tert-amyl methyl ether 2.5
    2,5,8-trioxanonane 20.94
    1-hexene 0.3
    2-isopropoxyethanol 21.38
    2,2,2-trifluoroethanol 5.07
    methyl butyrate 4.1

    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