Piperyline

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  • Identifiers

    CAS number
    25924-78-1

    Molecular formula
    C16H17NO3

    SMILES
    C1CCN(C1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3

    Safety labels

  • Odor profile

    Fragrance
    Spicy 56.75%
    Meaty 26.77%
    Savory 26.46%
    Roasted 26.15%
    Warm 24.95%
    Herbal 22.77%
    Odorless 21.04%
    Cooked 20.65%
    Nutty 18.9%
    Fruity 17.85%

     

    Flavor
    Bitter 52.75%
    Animal 21.68%
    Odorless 20.59%
    Nitrile 19.95%
    Lovage 19.92%
    Basil 18.98%
    Oriental 18.88%
    Cedarleaf 18.83%
    Parsley 18.38%
    Shrimp 18.21%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    6.36 (neutral)

    Molecular weight
    271.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    547°C

    Melting point expt.

    • 143 - 145 °C

    Flash point

    • 199.56 ˚C est.

  • Synonyms

    • Piperyline
    • Trichostachine
    • Piperylin
    • Trichostachin
    • Piperiline
    • Pyrroperine
    • 25924-78-1
    • GV0493SM38
    • DTXSID20180595
    • (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylpenta-2,4-dien-1-one
    • 1-Piperoylpyrrolidine
    • RefChem:44836
    • DTXCID60103086
    • (E,E)-Trichostachine
    • Pyrrolidine, 1-piperoyl-, (E,E)-
    • (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
    • (2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
    • N-[10-(13,14-Methylenedioxyphenyl)-7(E),9(Z)-pentadienoyl]-pyrrolidine
    • UNII-GV0493SM38
    • 1-(5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)pyrrolidine
    • Pyrrolidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-
    • Piperyline, analytical standard
    • CHEBI:9691
    • MEGxp0_000203
    • 1-Piperoyl-(E,E)-Pyrrolidine
    • CHEMBL1087296
    • SCHEMBL13333292
    • SCHEMBL29477308
    • ACon1_000155
    • 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]pyrrolidine
    • 5-(2H-1,3-Benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
    • Pyrrolidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)-
    • NCGC00180828-01
    • 54976-54-4
    • BRD-K64601708-001-01-6
    • PIPERYLINE (CONSTITUENT OF BLACK PEPPER) [DSC]
    • Q27108470
    • 1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]pyrrolidine #
    • (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-one
    • (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
    • (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-diene-1-one
    • 2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
    • PYRROLIDINE, 1-((2E,4E)-5-(1,3-BENZODIOXOL-5-YL)-1-OXO-2,4-PENTADIENYL)-
    • 25924-78-1

  • Applications

    Piperyline is typically used as an intermediate in fragrance ingredient synthesis and may function as an odorant or fixative in perfumery; in cosmetics and personal-care formulations it can serve as a fragrance component, and household and cleaning products may employ it as an aroma additive. In industrial manufacturing, it may act as a solvent or processing aid for formulation and compounding, and it can appear in coatings and inks as a fragrance additive. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 42.36
    methanol 44.11
    isopropanol 35.76
    water 0.28
    ethyl acetate 53.43
    n-propanol 36.63
    acetone 52.69
    n-butanol 38.69
    acetonitrile 79.29
    DMF 83.95
    toluene 27.86
    isobutanol 30.07
    1,4-dioxane 84.4
    methyl acetate 61.01
    THF 114.55
    2-butanone 66.76
    n-pentanol 37.48
    sec-butanol 40.69
    n-hexane 0.96
    ethylene glycol 26.11
    NMP 53.53
    cyclohexane 2.12
    DMSO 135.15
    n-butyl acetate 32.41
    n-octanol 11.66
    chloroform 294.75
    n-propyl acetate 45.65
    acetic acid 92.72
    dichloromethane 308.71
    cyclohexanone 77.26
    propylene glycol 35.5
    isopropyl acetate 34.9
    DMAc 140.2
    2-ethoxyethanol 108.17
    isopentanol 37.72
    n-heptane 1.09
    ethyl formate 45.85
    1,2-dichloroethane 131.99
    n-hexanol 23.42
    2-methoxyethanol 118.95
    isobutyl acetate 31.39
    tetrachloromethane 13.49
    n-pentyl acetate 21.13
    transcutol 243.88
    n-heptanol 13.13
    ethylbenzene 13.97
    MIBK 36.14
    2-propoxyethanol 72.16
    tert-butanol 30.54
    MTBE 21.9
    2-butoxyethanol 43.36
    propionic acid 49.53
    o-xylene 15.7
    formic acid 61.02
    diethyl ether 31.52
    m-xylene 15.61
    p-xylene 18.93
    chlorobenzene 44.55
    dimethyl carbonate 37.4
    n-octane 0.84
    formamide 109.89
    cyclopentanone 81.29
    2-pentanone 47.13
    anisole 41.68
    cyclopentyl methyl ether 36.16
    gamma-butyrolactone 92.26
    1-methoxy-2-propanol 92.74
    pyridine 108.06
    3-pentanone 40.29
    furfural 116.09
    n-dodecane 1.14
    diethylene glycol 86.38
    diisopropyl ether 8.59
    tert-amyl alcohol 34.99
    acetylacetone 61.13
    n-hexadecane 1.31
    acetophenone 49.45
    methyl propionate 48.06
    isopentyl acetate 32.66
    trichloroethylene 264.34
    n-nonanol 13.39
    cyclohexanol 37.32
    benzyl alcohol 50.87
    2-ethylhexanol 16.41
    isooctanol 13.56
    dipropyl ether 15.2
    1,2-dichlorobenzene 45.03
    ethyl lactate 40.85
    propylene carbonate 60.95
    n-methylformamide 57.1
    2-pentanol 28.87
    n-pentane 0.96
    1-propoxy-2-propanol 47.52
    1-methoxy-2-propyl acetate 48.73
    2-(2-methoxypropoxy) propanol 60.53
    mesitylene 9.07
    ε-caprolactone 66.77
    p-cymene 9.79
    epichlorohydrin 156.8
    1,1,1-trichloroethane 63.78
    2-aminoethanol 43.15
    morpholine-4-carbaldehyde 96.21
    sulfolane 89.64
    2,2,4-trimethylpentane 1.29
    2-methyltetrahydrofuran 58.96
    n-hexyl acetate 28.49
    isooctane 0.81
    2-(2-butoxyethoxy)ethanol 73.86
    sec-butyl acetate 32.3
    tert-butyl acetate 31.53
    decalin 1.93
    glycerin 65.8
    diglyme 130.41
    acrylic acid 55.84
    isopropyl myristate 15.78
    n-butyric acid 65.73
    acetyl acetate 40.45
    di(2-ethylhexyl) phthalate 23.78
    ethyl propionate 40.78
    nitromethane 137.59
    1,2-diethoxyethane 56.21
    benzonitrile 60.76
    trioctyl phosphate 13.93
    1-bromopropane 47.74
    gamma-valerolactone 110.09
    n-decanol 11.14
    triethyl phosphate 23.58
    4-methyl-2-pentanol 18.56
    propionitrile 59.27
    vinylene carbonate 67.5
    1,1,2-trichlorotrifluoroethane 126.76
    DMS 38.76
    cumene 10.69
    2-octanol 9.51
    2-hexanone 41.7
    octyl acetate 19.2
    limonene 11.04
    1,2-dimethoxyethane 105.85
    ethyl orthosilicate 21.8
    tributyl phosphate 19.33
    diacetone alcohol 46.72
    N,N-dimethylaniline 25.41
    acrylonitrile 82.04
    aniline 46.52
    1,3-propanediol 63.06
    bromobenzene 43.94
    dibromomethane 149.37
    1,1,2,2-tetrachloroethane 167.7
    2-methyl-cyclohexyl acetate 31.2
    tetrabutyl urea 25.04
    diisobutyl methanol 10.63
    2-phenylethanol 38.23
    styrene 18.68
    dioctyl adipate 28.52
    dimethyl sulfate 51.76
    ethyl butyrate 33.47
    methyl lactate 45.69
    butyl lactate 30.18
    diethyl carbonate 29.6
    propanediol butyl ether 39.15
    triethyl orthoformate 28.62
    p-tert-butyltoluene 7.89
    methyl 4-tert-butylbenzoate 39.29
    morpholine 105.94
    tert-butylamine 14.84
    n-dodecanol 9.33
    dimethoxymethane 76.08
    ethylene carbonate 54.34
    cyrene 58.35
    2-ethoxyethyl acetate 42.44
    2-ethylhexyl acetate 26.36
    1,2,4-trichlorobenzene 53.28
    4-methylpyridine 69.76
    dibutyl ether 17.45
    2,6-dimethyl-4-heptanol 10.63
    DEF 55.15
    dimethyl isosorbide 76.87
    tetrachloroethylene 94.3
    eugenol 46.34
    triacetin 49.43
    span 80 37.15
    1,4-butanediol 41.78
    1,1-dichloroethane 94.19
    2-methyl-1-pentanol 36.63
    methyl formate 48.5
    2-methyl-1-butanol 37.89
    n-decane 1.58
    butyronitrile 55.78
    3,7-dimethyl-1-octanol 16.48
    1-chlorooctane 8.18
    1-chlorotetradecane 4.49
    n-nonane 1.24
    undecane 1.32
    tert-butylcyclohexane 1.47
    cyclooctane 0.92
    cyclopentanol 34.51
    tetrahydropyran 57.23
    tert-amyl methyl ether 21.62
    2,5,8-trioxanonane 103.45
    1-hexene 6.51
    2-isopropoxyethanol 70.51
    2,2,2-trifluoroethanol 52.77
    methyl butyrate 49.73

    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