(E)-Herclavine

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  • Identifiers

    CAS number
    539-18-4

    Molecular formula
    C19H21NO2

    SMILES
    CN(CCC1=CC=C(C=C1)OC)C(=O)/C=C/C2=CC=CC=C2

    Safety labels

  • Odor profile

    Fragrance
    Fruity 42.26%
    Floral 41.76%
    Spicy 38.19%
    Sweet 35.36%
    Citrus 32.06%
    Grape 31.8%
    Herbal 31.79%
    Balsamic 30.22%
    Grapefruit 29.05%
    Fresh 28.65%

     

    Flavor
    Fruity 41.35%
    Bitter 32.51%
    Floral 22.65%
    Herbal 21.65%
    Balsam 21.41%
    Sweet 20.79%
    Genet 19.79%
    Heather 19.77%
    Mild 19.59%
    Broom 19.58%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.7

    pKa est.
    6.89 (neutral)

    Molecular weight
    295.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    546°C

    Melting point expt.

    • 76 °C

    Flash point

    • 198.54 ˚C est.

  • Synonyms

    • (E)-Herclavine
    • (E)-N-[2-(4-methoxyphenyl)ethyl]-N-methyl-3-phenylprop-2-enamide
    • (2E)-N-[2-(4-methoxyphenyl)ethyl]-N-methyl-3-phenylprop-2-enamide
    • 539-18-4
    • NSC52653
    • CHEBI:174123
    • DTXSID001167146
    • NSC-52653
    • (2E)-N-[2-(4-Methoxyphenyl)ethyl]-N-methyl-3-phenyl-2-propenamide
    • 539-18-4

  • Applications

    (E)-Herclavine, CAS 539-18-4, is primarily utilized as an alkaloid scaffold and intermediate in the synthesis of ergot alkaloid derivatives. In medicinal and synthetic chemistry contexts, it serves as a chiral building block for constructing complex heterocycles and for structure-activity relationship exploration of ergoline-type compounds. In academic research, it supports studies of alkaloid biosynthesis, enzyme interactions, and receptor affinities related to ergot alkaloids. It may also be used as a reference material or analytical standard in laboratories developing and validating methods for these compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 56.38
    methanol 79.22
    isopropanol 28.4
    water 0.16
    ethyl acetate 114.33
    n-propanol 49.12
    acetone 22.97
    n-butanol 38.35
    acetonitrile 55.28
    DMF 34.38
    toluene 70.09
    isobutanol 22.85
    1,4-dioxane 185.99
    methyl acetate 87.72
    THF 137.31
    2-butanone 70.77
    n-pentanol 33.26
    sec-butanol 34.46
    n-hexane 1.05
    ethylene glycol 11.5
    NMP 19.28
    cyclohexane 3.6
    DMSO 100.44
    n-butyl acetate 26.2
    n-octanol 4.09
    chloroform 658.27
    n-propyl acetate 36.24
    acetic acid 81.02
    dichloromethane 693.71
    cyclohexanone 62.28
    propylene glycol 27.05
    isopropyl acetate 40.05
    DMAc 144.76
    2-ethoxyethanol 107.03
    isopentanol 24.92
    n-heptane 1.01
    ethyl formate 41.46
    1,2-dichloroethane 352.57
    n-hexanol 16.6
    2-methoxyethanol 114.67
    isobutyl acetate 20.39
    tetrachloromethane 22.68
    n-pentyl acetate 11.52
    transcutol 268.29
    n-heptanol 7.11
    ethylbenzene 22.94
    MIBK 25.77
    2-propoxyethanol 57.45
    tert-butanol 32.45
    MTBE 30.85
    2-butoxyethanol 27.47
    propionic acid 46.98
    o-xylene 28.22
    formic acid 42.89
    diethyl ether 68.82
    m-xylene 21.32
    p-xylene 22.16
    chlorobenzene 71.39
    dimethyl carbonate 35.51
    n-octane 0.5
    formamide 93.95
    cyclopentanone 44.05
    2-pentanone 39.37
    anisole 63.12
    cyclopentyl methyl ether 37.99
    gamma-butyrolactone 74.72
    1-methoxy-2-propanol 69.77
    pyridine 197.45
    3-pentanone 51.33
    furfural 109.58
    n-dodecane 0.47
    diethylene glycol 47.26
    diisopropyl ether 8.23
    tert-amyl alcohol 29.98
    acetylacetone 62.2
    n-hexadecane 0.54
    acetophenone 50.71
    methyl propionate 72.82
    isopentyl acetate 25.69
    trichloroethylene 555.62
    n-nonanol 5.13
    cyclohexanol 27.22
    benzyl alcohol 52.12
    2-ethylhexanol 9.64
    isooctanol 6.8
    dipropyl ether 19.0
    1,2-dichlorobenzene 66.81
    ethyl lactate 20.82
    propylene carbonate 44.66
    n-methylformamide 38.78
    2-pentanol 19.61
    n-pentane 0.91
    1-propoxy-2-propanol 30.67
    1-methoxy-2-propyl acetate 48.77
    2-(2-methoxypropoxy) propanol 41.21
    mesitylene 9.83
    ε-caprolactone 57.0
    p-cymene 9.15
    epichlorohydrin 219.71
    1,1,1-trichloroethane 127.05
    2-aminoethanol 33.4
    morpholine-4-carbaldehyde 75.72
    sulfolane 65.21
    2,2,4-trimethylpentane 1.32
    2-methyltetrahydrofuran 60.42
    n-hexyl acetate 12.81
    isooctane 0.66
    2-(2-butoxyethoxy)ethanol 53.73
    sec-butyl acetate 27.58
    tert-butyl acetate 35.33
    decalin 2.39
    glycerin 39.31
    diglyme 139.04
    acrylic acid 45.07
    isopropyl myristate 7.61
    n-butyric acid 58.28
    acetyl acetate 59.99
    di(2-ethylhexyl) phthalate 11.75
    ethyl propionate 38.99
    nitromethane 145.26
    1,2-diethoxyethane 65.26
    benzonitrile 43.34
    trioctyl phosphate 5.68
    1-bromopropane 98.89
    gamma-valerolactone 96.94
    n-decanol 4.03
    triethyl phosphate 21.88
    4-methyl-2-pentanol 9.84
    propionitrile 51.28
    vinylene carbonate 54.57
    1,1,2-trichlorotrifluoroethane 134.48
    DMS 28.9
    cumene 11.93
    2-octanol 3.5
    2-hexanone 30.25
    octyl acetate 8.52
    limonene 10.4
    1,2-dimethoxyethane 136.62
    ethyl orthosilicate 21.57
    tributyl phosphate 8.92
    diacetone alcohol 37.37
    N,N-dimethylaniline 32.68
    acrylonitrile 69.41
    aniline 69.76
    1,3-propanediol 50.48
    bromobenzene 79.34
    dibromomethane 330.79
    1,1,2,2-tetrachloroethane 406.08
    2-methyl-cyclohexyl acetate 26.34
    tetrabutyl urea 11.92
    diisobutyl methanol 7.27
    2-phenylethanol 33.86
    styrene 33.31
    dioctyl adipate 17.78
    dimethyl sulfate 50.02
    ethyl butyrate 29.86
    methyl lactate 28.75
    butyl lactate 13.65
    diethyl carbonate 27.14
    propanediol butyl ether 17.32
    triethyl orthoformate 26.91
    p-tert-butyltoluene 8.18
    methyl 4-tert-butylbenzoate 29.52
    morpholine 176.17
    tert-butylamine 14.59
    n-dodecanol 3.33
    dimethoxymethane 78.37
    ethylene carbonate 42.14
    cyrene 39.04
    2-ethoxyethyl acetate 36.09
    2-ethylhexyl acetate 20.08
    1,2,4-trichlorobenzene 79.76
    4-methylpyridine 94.54
    dibutyl ether 10.64
    2,6-dimethyl-4-heptanol 7.27
    DEF 49.54
    dimethyl isosorbide 73.32
    tetrachloroethylene 213.83
    eugenol 34.08
    triacetin 32.14
    span 80 22.83
    1,4-butanediol 21.85
    1,1-dichloroethane 177.31
    2-methyl-1-pentanol 28.5
    methyl formate 30.34
    2-methyl-1-butanol 25.68
    n-decane 0.73
    butyronitrile 38.23
    3,7-dimethyl-1-octanol 6.51
    1-chlorooctane 3.91
    1-chlorotetradecane 1.95
    n-nonane 0.59
    undecane 0.56
    tert-butylcyclohexane 1.87
    cyclooctane 0.99
    cyclopentanol 18.78
    tetrahydropyran 109.68
    tert-amyl methyl ether 24.07
    2,5,8-trioxanonane 92.47
    1-hexene 8.11
    2-isopropoxyethanol 53.32
    2,2,2-trifluoroethanol 30.63
    methyl butyrate 42.41

    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