Coumaperine

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  • Identifiers

    CAS number
    76733-91-0

    Molecular formula
    C16H19NO2

    SMILES
    C1CCN(CC1)C(=O)/C=C/C=C/C2=CC=C(C=C2)O

    Safety labels

  • Odor profile

    Fragrance
    Spicy 57.04%
    Meaty 30.0%
    Herbal 28.03%
    Savory 26.78%
    Roasted 25.54%
    Warm 23.79%
    Fruity 21.77%
    Cooked 20.6%
    Sweet 19.73%
    Odorless 19.46%

     

    Flavor
    Bitter 44.21%
    Odorless 22.59%
    Nitrile 21.99%
    Cinnamon 20.84%
    Lovage 20.42%
    Oriental 20.33%
    Basil 20.11%
    Balsam 19.51%
    Animal 19.36%
    Ethyl benzoate 19.35%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    9.04 (weak base)

    Molecular weight
    257.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    510°C

    Flash point

    • 215.96 ˚C est.

  • Synonyms

    • Coumaperine
    • 76733-91-0
    • 6M586HW0PD
    • 2,4-Pentadien-1-one, 5-(4-hydroxyphenyl)-1-(1-piperidinyl)-, (2E,4E)-
    • n-5-(4-hydroxyphenyl)-2e,4e-pentadienoyl piperidine
    • Piperidine, 1-(5-(4-hydroxyphenyl)-1-oxo-2,4-pentadienyl)-, (E,E)-
    • (2E,4E)-5-(4-hydroxyphenyl)-1-piperidin-1-ylpenta-2,4-dien-1-one
    • DTXSID101319112
    • N-5-(4-hydroxyphenyl)-2E,4E-pentadienoylpiperidine
    • RefChem:33497
    • DTXCID101748068
    • Coumaperine (constituent of Black pepper)
    • UNII-6M586HW0PD
    • Coumaperine (constituent of Black pepper) [DSC]
    • orb1740751
    • SCHEMBL4919407
    • CHEMBL4061010
    • CHEBI:169029
    • (2E,4E)-5-(4-hydroxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
    • Q27265139
    • 76733-91-0

  • Applications

    Coumaperine (CAS 76733-91-0) is typically handled as a building block in organic synthesis and may serve as an intermediate for the production of pharmaceuticals, agrochemicals, or fine chemicals. In manufacturing contexts, it can be used as a solvent or processing aid where compatible with formulations. It is also evaluated as an odorant or fixative in perfumery and cosmetics, subject to regulatory compliance. Additionally, Coumaperine may function as a raw material or intermediate in polymer, coating, and ink applications, contributing to synthesis or acting as a specialty additive. As with other specialty chemicals, usage is governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 44.32
    methanol 55.6
    isopropanol 25.52
    water 0.05
    ethyl acetate 54.88
    n-propanol 34.89
    acetone 59.44
    n-butanol 31.52
    acetonitrile 40.69
    DMF 83.5
    toluene 37.02
    isobutanol 20.12
    1,4-dioxane 80.04
    methyl acetate 61.16
    THF 142.03
    2-butanone 86.87
    n-pentanol 30.92
    sec-butanol 29.2
    n-hexane 0.75
    ethylene glycol 8.0
    NMP 39.02
    cyclohexane 1.05
    DMSO 236.51
    n-butyl acetate 40.14
    n-octanol 7.18
    chloroform 209.55
    n-propyl acetate 41.31
    acetic acid 54.97
    dichloromethane 212.36
    cyclohexanone 79.96
    propylene glycol 25.45
    isopropyl acetate 30.24
    DMAc 188.13
    2-ethoxyethanol 74.88
    isopentanol 29.13
    n-heptane 0.7
    ethyl formate 35.2
    1,2-dichloroethane 144.84
    n-hexanol 22.64
    2-methoxyethanol 94.09
    isobutyl acetate 25.49
    tetrachloromethane 7.88
    n-pentyl acetate 17.79
    transcutol 358.36
    n-heptanol 10.79
    ethylbenzene 15.91
    MIBK 33.59
    2-propoxyethanol 63.82
    tert-butanol 31.11
    MTBE 23.69
    2-butoxyethanol 39.17
    propionic acid 37.57
    o-xylene 18.81
    formic acid 24.53
    diethyl ether 26.75
    m-xylene 18.3
    p-xylene 18.8
    chlorobenzene 41.18
    dimethyl carbonate 24.29
    n-octane 0.47
    formamide 53.81
    cyclopentanone 95.65
    2-pentanone 53.64
    anisole 39.21
    cyclopentyl methyl ether 37.39
    gamma-butyrolactone 106.82
    1-methoxy-2-propanol 72.64
    pyridine 107.15
    3-pentanone 42.42
    furfural 109.35
    n-dodecane 0.57
    diethylene glycol 56.31
    diisopropyl ether 6.32
    tert-amyl alcohol 29.9
    acetylacetone 61.27
    n-hexadecane 0.66
    acetophenone 44.87
    methyl propionate 46.57
    isopentyl acetate 34.73
    trichloroethylene 255.78
    n-nonanol 8.45
    cyclohexanol 24.27
    benzyl alcohol 42.7
    2-ethylhexanol 14.45
    isooctanol 10.62
    dipropyl ether 14.61
    1,2-dichlorobenzene 37.51
    ethyl lactate 28.34
    propylene carbonate 53.8
    n-methylformamide 41.6
    2-pentanol 20.17
    n-pentane 0.48
    1-propoxy-2-propanol 45.66
    1-methoxy-2-propyl acetate 51.75
    2-(2-methoxypropoxy) propanol 50.75
    mesitylene 9.57
    ε-caprolactone 63.42
    p-cymene 9.64
    epichlorohydrin 182.15
    1,1,1-trichloroethane 53.11
    2-aminoethanol 25.65
    morpholine-4-carbaldehyde 77.43
    sulfolane 112.33
    2,2,4-trimethylpentane 1.22
    2-methyltetrahydrofuran 59.2
    n-hexyl acetate 22.28
    isooctane 0.83
    2-(2-butoxyethoxy)ethanol 73.37
    sec-butyl acetate 27.96
    tert-butyl acetate 31.57
    decalin 1.75
    glycerin 35.94
    diglyme 131.2
    acrylic acid 36.04
    isopropyl myristate 10.76
    n-butyric acid 52.44
    acetyl acetate 29.91
    di(2-ethylhexyl) phthalate 17.16
    ethyl propionate 32.71
    nitromethane 104.47
    1,2-diethoxyethane 64.66
    benzonitrile 44.1
    trioctyl phosphate 9.88
    1-bromopropane 42.86
    gamma-valerolactone 112.0
    n-decanol 7.06
    triethyl phosphate 19.81
    4-methyl-2-pentanol 14.58
    propionitrile 38.82
    vinylene carbonate 51.55
    1,1,2-trichlorotrifluoroethane 104.62
    DMS 30.03
    cumene 11.08
    2-octanol 6.11
    2-hexanone 41.49
    octyl acetate 13.68
    limonene 11.27
    1,2-dimethoxyethane 99.48
    ethyl orthosilicate 18.59
    tributyl phosphate 13.81
    diacetone alcohol 47.89
    N,N-dimethylaniline 26.08
    acrylonitrile 52.02
    aniline 48.14
    1,3-propanediol 37.33
    bromobenzene 39.75
    dibromomethane 108.54
    1,1,2,2-tetrachloroethane 183.89
    2-methyl-cyclohexyl acetate 27.42
    tetrabutyl urea 18.46
    diisobutyl methanol 10.24
    2-phenylethanol 33.09
    styrene 20.86
    dioctyl adipate 22.28
    dimethyl sulfate 45.08
    ethyl butyrate 31.59
    methyl lactate 33.12
    butyl lactate 25.77
    diethyl carbonate 24.81
    propanediol butyl ether 34.79
    triethyl orthoformate 25.0
    p-tert-butyltoluene 8.48
    methyl 4-tert-butylbenzoate 33.25
    morpholine 101.22
    tert-butylamine 14.6
    n-dodecanol 5.79
    dimethoxymethane 75.63
    ethylene carbonate 39.54
    cyrene 44.92
    2-ethoxyethyl acetate 40.11
    2-ethylhexyl acetate 26.23
    1,2,4-trichlorobenzene 48.53
    4-methylpyridine 75.8
    dibutyl ether 13.45
    2,6-dimethyl-4-heptanol 10.24
    DEF 49.03
    dimethyl isosorbide 77.12
    tetrachloroethylene 88.53
    eugenol 39.07
    triacetin 37.87
    span 80 33.5
    1,4-butanediol 19.15
    1,1-dichloroethane 89.19
    2-methyl-1-pentanol 30.01
    methyl formate 32.51
    2-methyl-1-butanol 25.95
    n-decane 0.8
    butyronitrile 37.29
    3,7-dimethyl-1-octanol 11.22
    1-chlorooctane 4.6
    1-chlorotetradecane 2.5
    n-nonane 0.61
    undecane 0.66
    tert-butylcyclohexane 1.57
    cyclooctane 0.48
    cyclopentanol 21.81
    tetrahydropyran 61.56
    tert-amyl methyl ether 21.9
    2,5,8-trioxanonane 92.45
    1-hexene 7.1
    2-isopropoxyethanol 48.31
    2,2,2-trifluoroethanol 19.61
    methyl butyrate 46.02

    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