(+-)-Aegeline

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  • Identifiers

    CAS number
    456-12-2

    Molecular formula
    C18H19NO3

    SMILES
    COC1=CC=C(C=C1)C(CNC(=O)/C=C/C2=CC=CC=C2)O

    Safety labels

  • Odor profile

    Fragrance
    Savory 39.07%
    Spicy 36.51%
    Meaty 32.1%
    Sweet 31.55%
    Fruity 29.59%
    Odorless 27.44%
    Cooked 25.82%
    Bitter 24.71%
    Roasted 23.82%
    Balsamic 23.66%

     

    Flavor
    Bitter 51.65%
    Odorless 33.92%
    Fruity 31.21%
    Mild 25.02%
    Sweet 24.91%
    Balsam 21.72%
    Orange flower 20.21%
    Orange blossom 19.97%
    Sweet-like 19.83%
    Nitrile 19.75%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    7.08 (neutral)

    Molecular weight
    297.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    651°C

    Melting point expt.

    • 176 °C

    Flash point

    • 223.82 ˚C est.

  • Synonyms

    • (+-)-Aegeline
    • DTXSID101318019
    • RefChem:390686
    • DTXCID801747811
    • AEGELINE
    • Aegelin
    • 456-12-2
    • N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide
    • MFCD00048045
    • (+/-)-Aegeline
    • (E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
    • (2E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
    • 60T59LN3SG
    • N-[2-hydroxy-2(4-methoxyphenyl) ethyl]-3-phenyl-2-propenamide
    • (+-)-Egeline
    • N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]cinnamamide
    • UNII-60T59LN3SG
    • Aegeline (Standard)
    • EGELINE
    • (A+/-)-Aegeline
    • EGELINE [USP-RS]
    • MEGxp0_001339
    • orb1299452
    • CHEMBL5402588
    • SCHEMBL15697607
    • ACon1_000768
    • CHEBI:196319
    • GLXC-20027
    • HY-W042156R
    • N-(2-hydroxy-2(4-methoxyphenyl)ethyl)-3-phenyl-2-propenamide
    • N-(2-Hydroxy-2(4-methoxyphenyl)ethyl)-3-phenyl-2-propenamide, (E)-
    • AKOS022174795
    • CS-W022896
    • EBC-616470
    • HY-W042156
    • NCGC00169378-01
    • DA-50251
    • SY029914
    • A3170
    • BRD-A95848471-001-01-3
    • Q27263252
    • (E)-N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]cinnamamide
    • (E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenyl-prop-2-enamide
    • 2-Propenamide, N-(2-hydroxy-2-(4-methoxyphenyl)ethyl)-3-phenyl-, (E)-
    • 2-PROPENAMIDE, N-(2-HYDROXY-2-(4-METHOXYPHENYL)ETHYL)-3-PHENYL-, (E)-(+/-)-
    • 37791-13-2
    • 456-12-2

  • Applications

    (+-)-Aegeline (CAS 456-12-2) is a chiral alkaloid that is primarily considered as an intermediate and, in some contexts, as a fragrance-related ingredient. In perfumery and cosmetics, it may be used as an odorant or fragrance intermediate, subject to formulation limits; in pharmaceutical and industrial chemistry, it is often evaluated as a chiral building block or synthetic intermediate for the preparation of related alkaloids and bioactive compounds. It may also be regarded as an intermediate in broader chemical manufacturing workflows, with use governed by local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 15.06
    methanol 31.38
    isopropanol 8.8
    water 0.17
    ethyl acetate 22.96
    n-propanol 16.0
    acetone 16.04
    n-butanol 11.17
    acetonitrile 12.19
    DMF 56.28
    toluene 5.1
    isobutanol 6.43
    1,4-dioxane 49.23
    methyl acetate 25.46
    THF 118.9
    2-butanone 26.54
    n-pentanol 8.8
    sec-butanol 10.14
    n-hexane 0.15
    ethylene glycol 11.02
    NMP 22.86
    cyclohexane 0.28
    DMSO 217.7
    n-butyl acetate 4.98
    n-octanol 2.11
    chloroform 41.64
    n-propyl acetate 7.39
    acetic acid 43.43
    dichloromethane 45.28
    cyclohexanone 22.95
    propylene glycol 19.2
    isopropyl acetate 10.46
    DMAc 170.63
    2-ethoxyethanol 50.7
    isopentanol 7.79
    n-heptane 0.29
    ethyl formate 11.09
    1,2-dichloroethane 33.67
    n-hexanol 5.11
    2-methoxyethanol 70.51
    isobutyl acetate 4.23
    tetrachloromethane 2.04
    n-pentyl acetate 3.46
    transcutol 140.27
    n-heptanol 3.13
    ethylbenzene 2.62
    MIBK 8.91
    2-propoxyethanol 27.13
    tert-butanol 11.86
    MTBE 9.41
    2-butoxyethanol 13.74
    propionic acid 19.83
    o-xylene 3.74
    formic acid 35.66
    diethyl ether 12.75
    m-xylene 2.37
    p-xylene 2.71
    chlorobenzene 7.37
    dimethyl carbonate 21.45
    n-octane 0.15
    formamide 78.27
    cyclopentanone 34.22
    2-pentanone 14.78
    anisole 14.89
    cyclopentyl methyl ether 15.19
    gamma-butyrolactone 46.4
    1-methoxy-2-propanol 43.96
    pyridine 37.85
    3-pentanone 16.78
    furfural 43.74
    n-dodecane 0.15
    diethylene glycol 31.42
    diisopropyl ether 2.11
    tert-amyl alcohol 10.76
    acetylacetone 28.5
    n-hexadecane 0.17
    acetophenone 13.42
    methyl propionate 24.97
    isopentyl acetate 6.09
    trichloroethylene 69.55
    n-nonanol 2.66
    cyclohexanol 8.05
    benzyl alcohol 14.39
    2-ethylhexanol 3.25
    isooctanol 2.78
    dipropyl ether 6.81
    1,2-dichlorobenzene 8.51
    ethyl lactate 10.04
    propylene carbonate 15.38
    n-methylformamide 31.56
    2-pentanol 6.42
    n-pentane 0.13
    1-propoxy-2-propanol 16.37
    1-methoxy-2-propyl acetate 18.31
    2-(2-methoxypropoxy) propanol 23.51
    mesitylene 1.55
    ε-caprolactone 19.08
    p-cymene 1.96
    epichlorohydrin 78.08
    1,1,1-trichloroethane 10.51
    2-aminoethanol 22.1
    morpholine-4-carbaldehyde 53.21
    sulfolane 58.97
    2,2,4-trimethylpentane 0.27
    2-methyltetrahydrofuran 23.54
    n-hexyl acetate 4.81
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 28.86
    sec-butyl acetate 6.06
    tert-butyl acetate 11.9
    decalin 0.36
    glycerin 35.37
    diglyme 68.64
    acrylic acid 22.55
    isopropyl myristate 3.01
    n-butyric acid 19.27
    acetyl acetate 15.45
    di(2-ethylhexyl) phthalate 4.7
    ethyl propionate 10.14
    nitromethane 91.99
    1,2-diethoxyethane 21.06
    benzonitrile 8.64
    trioctyl phosphate 2.55
    1-bromopropane 7.1
    gamma-valerolactone 48.79
    n-decanol 2.08
    triethyl phosphate 8.05
    4-methyl-2-pentanol 3.61
    propionitrile 12.22
    vinylene carbonate 16.37
    1,1,2-trichlorotrifluoroethane 66.13
    DMS 12.44
    cumene 1.86
    2-octanol 1.6
    2-hexanone 8.34
    octyl acetate 3.49
    limonene 2.63
    1,2-dimethoxyethane 62.88
    ethyl orthosilicate 7.86
    tributyl phosphate 3.74
    diacetone alcohol 20.9
    N,N-dimethylaniline 9.49
    acrylonitrile 18.97
    aniline 14.34
    1,3-propanediol 26.86
    bromobenzene 6.46
    dibromomethane 17.02
    1,1,2,2-tetrachloroethane 53.87
    2-methyl-cyclohexyl acetate 8.1
    tetrabutyl urea 5.84
    diisobutyl methanol 2.8
    2-phenylethanol 9.44
    styrene 3.56
    dioctyl adipate 7.3
    dimethyl sulfate 40.74
    ethyl butyrate 7.7
    methyl lactate 20.88
    butyl lactate 6.49
    diethyl carbonate 7.49
    propanediol butyl ether 11.49
    triethyl orthoformate 9.32
    p-tert-butyltoluene 1.94
    methyl 4-tert-butylbenzoate 13.36
    morpholine 59.38
    tert-butylamine 3.89
    n-dodecanol 1.67
    dimethoxymethane 59.06
    ethylene carbonate 12.62
    cyrene 23.07
    2-ethoxyethyl acetate 11.61
    2-ethylhexyl acetate 4.46
    1,2,4-trichlorobenzene 12.8
    4-methylpyridine 16.2
    dibutyl ether 4.22
    2,6-dimethyl-4-heptanol 2.8
    DEF 24.08
    dimethyl isosorbide 36.28
    tetrachloroethylene 28.89
    eugenol 14.79
    triacetin 14.84
    span 80 12.81
    1,4-butanediol 10.53
    1,1-dichloroethane 12.71
    2-methyl-1-pentanol 7.69
    methyl formate 23.26
    2-methyl-1-butanol 8.04
    n-decane 0.25
    butyronitrile 7.88
    3,7-dimethyl-1-octanol 2.8
    1-chlorooctane 1.27
    1-chlorotetradecane 0.63
    n-nonane 0.19
    undecane 0.19
    tert-butylcyclohexane 0.29
    cyclooctane 0.14
    cyclopentanol 8.76
    tetrahydropyran 27.24
    tert-amyl methyl ether 8.88
    2,5,8-trioxanonane 49.41
    1-hexene 1.1
    2-isopropoxyethanol 24.03
    2,2,2-trifluoroethanol 17.14
    methyl butyrate 10.6

    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