(2E)-N-(2-(1-beta-D-Glucopyranosyl-1H-imidazol-4-yl)ethyl)-N-methyl-3-phenyl-2-propenamide

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  • Identifiers

    CAS number
    5853-02-1

    Molecular formula
    C21H27N3O6

    SMILES
    CN(CCC1=CN(C=N1)[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)/C=C/C3=CC=CC=C3

    Safety labels

  • Odor profile

    Fragrance
    Odorless 61.85%
    Savory 34.7%
    Meaty 25.35%
    Cooling 23.97%
    Milky 21.4%
    Cooked 21.17%
    Bitter 20.42%
    Sweet 20.11%
    Roasted 19.7%
    Spicy 17.62%

     

    Flavor
    Bitter 84.79%
    Odorless 35.38%
    Bland 27.49%
    Sweet-like 22.54%
    Cedarleaf 20.1%
    Nitrile 19.46%
    Lovage 18.63%
    Heather 18.58%
    Broom 18.56%
    Parsley 18.5%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.3

    pKa est.
    5.86 (weak acid)

    Molecular weight
    417.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2934°C

    Melting point expt.

    • 226.5 - 228 °C

    Flash point

    • 284.22 ˚C est.

  • Synonyms

    • Casimiroedine
    • 5853-02-1
    • 577E0U1P0H
    • NSC-140860
    • 4-(2-(N-Methyl-N-trans-cinnamoylamino)ethyl)-1-beta-D-glucopyranosylimidazole
    • Cinnamamide, N-(2-(1-beta-D-glucopyranosylimidazol-4-yl)ethyl)-N-methyl-
    • (E)-N-methyl-3-phenyl-N-[2-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]imidazol-4-yl]ethyl]prop-2-enamide
    • (E)-N-methyl-3-phenyl-N-(2-(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)imidazol-4-yl)ethyl)prop-2-enamide
    • RefChem:905802
    • (2E)-N-(2-(1-beta-D-Glucopyranosyl-1H-imidazol-4-yl)ethyl)-N-methyl-3-phenyl-2-propenamide
    • (E)-Casimiroedine
    • Casimiroedin
    • Cassimiroedine
    • NSC 140860
    • CASIMIROEDINE [MI]
    • UNII-577E0U1P0H
    • CHEBI:3451
    • SCHEMBL28802563
    • CINNAMAMIDE, N-(2-(1-.BETA.-D-GLUCOPYRANOSYLIMIDAZOL-4-YL)ETHYL)-N-METHYL-
    • (2E)-N-methyl-3-phenyl-N-(2-{1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-imidazol-4-yl}ethyl)prop-2-enamide
    • 2-Propenamide, N-(2-(1-beta-D-glucopyranosyl-1H-imidazol-4-yl)ethyl)-N-methyl-3-phenyl-, (E)-
    • Nalpha-Cinnamoyl-Nalpha-methylhistamine N-glucoside
    • Q27106085
    • N-[2-(1-b-D-Glucopyranosyl-1H-imidazol-4-yl)ethyl]-N-methyl-3-phenyl-2-propenamide, 9CI
    • 2-PROPENAMIDE, N-(2-(1-.BETA.-D-GLUCOPYRANOSYL-1H-IMIDAZOL-4-YL)ETHYL)-N-METHYL-3-PHENYL-, (2E)-
    • 5853-02-1

  • Applications

    Chemical name: (2E)-N-(2-(1-beta-D-Glucopyranosyl-1H-imidazol-4-yl)ethyl)-N-methyl-3-phenyl-2-propenamide, CAS 5853-02-1, may be used as an intermediate in pharmaceutical synthesis and as a building block for glycosylated imidazole compounds, supporting medicinal chemistry work and library development; it serves as a platform for preparing analogs to explore targets and enzyme inhibition; the glucose moiety offers potential for prodrug design or conjugation to other molecules to yield glycosylated derivatives; in organic and biochemical research, it can be used as a reference material or precursor for transformations and to explore glycosylated imidazole motifs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 12.32
    methanol 45.95
    isopropanol 6.7
    water 10.4
    ethyl acetate 4.34
    n-propanol 10.65
    acetone 19.71
    n-butanol 10.71
    acetonitrile 6.71
    DMF 131.75
    toluene 3.02
    isobutanol 4.71
    1,4-dioxane 18.95
    methyl acetate 5.79
    THF 52.29
    2-butanone 12.17
    n-pentanol 4.58
    sec-butanol 6.94
    n-hexane 0.14
    ethylene glycol 29.31
    NMP 79.15
    cyclohexane 0.59
    DMSO 295.71
    n-butyl acetate 0.62
    n-octanol 2.58
    chloroform 4.54
    n-propyl acetate 1.11
    acetic acid 84.31
    dichloromethane 4.83
    cyclohexanone 23.7
    propylene glycol 30.66
    isopropyl acetate 2.36
    DMAc 183.95
    2-ethoxyethanol 34.5
    isopentanol 5.22
    n-heptane 0.32
    ethyl formate 6.14
    1,2-dichloroethane 3.86
    n-hexanol 2.14
    2-methoxyethanol 93.28
    isobutyl acetate 0.59
    tetrachloromethane 0.97
    n-pentyl acetate 1.87
    transcutol 38.76
    n-heptanol 3.4
    ethylbenzene 0.79
    MIBK 3.61
    2-propoxyethanol 13.57
    tert-butanol 4.74
    MTBE 2.03
    2-butoxyethanol 12.07
    propionic acid 14.84
    o-xylene 2.0
    formic acid 162.02
    diethyl ether 3.6
    m-xylene 1.57
    p-xylene 0.96
    chlorobenzene 1.52
    dimethyl carbonate 11.27
    n-octane 0.23
    formamide 144.95
    cyclopentanone 36.64
    2-pentanone 10.01
    anisole 2.5
    cyclopentyl methyl ether 10.48
    gamma-butyrolactone 29.12
    1-methoxy-2-propanol 46.74
    pyridine 15.54
    3-pentanone 7.91
    furfural 29.67
    n-dodecane 0.14
    diethylene glycol 25.59
    diisopropyl ether 0.63
    tert-amyl alcohol 5.25
    acetylacetone 14.63
    n-hexadecane 0.16
    acetophenone 4.15
    methyl propionate 9.29
    isopentyl acetate 0.71
    trichloroethylene 9.08
    n-nonanol 2.72
    cyclohexanol 10.1
    benzyl alcohol 6.95
    2-ethylhexanol 1.08
    isooctanol 2.23
    dipropyl ether 1.74
    1,2-dichlorobenzene 1.4
    ethyl lactate 4.42
    propylene carbonate 7.4
    n-methylformamide 52.1
    2-pentanol 4.41
    n-pentane 0.26
    1-propoxy-2-propanol 6.3
    1-methoxy-2-propyl acetate 3.11
    2-(2-methoxypropoxy) propanol 9.73
    mesitylene 0.8
    ε-caprolactone 15.04
    p-cymene 0.57
    epichlorohydrin 25.23
    1,1,1-trichloroethane 1.69
    2-aminoethanol 34.83
    morpholine-4-carbaldehyde 64.35
    sulfolane 68.29
    2,2,4-trimethylpentane 0.14
    2-methyltetrahydrofuran 11.91
    n-hexyl acetate 2.41
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 15.14
    sec-butyl acetate 0.82
    tert-butyl acetate 2.1
    decalin 0.16
    glycerin 77.25
    diglyme 27.06
    acrylic acid 27.12
    isopropyl myristate 0.93
    n-butyric acid 14.77
    acetyl acetate 3.71
    di(2-ethylhexyl) phthalate 1.98
    ethyl propionate 1.7
    nitromethane 78.15
    1,2-diethoxyethane 4.04
    benzonitrile 3.03
    trioctyl phosphate 1.46
    1-bromopropane 1.6
    gamma-valerolactone 59.22
    n-decanol 1.9
    triethyl phosphate 1.29
    4-methyl-2-pentanol 1.78
    propionitrile 4.21
    vinylene carbonate 8.71
    1,1,2-trichlorotrifluoroethane 51.74
    DMS 3.08
    cumene 0.5
    2-octanol 1.81
    2-hexanone 2.43
    octyl acetate 1.67
    limonene 0.95
    1,2-dimethoxyethane 21.61
    ethyl orthosilicate 1.3
    tributyl phosphate 1.31
    diacetone alcohol 11.18
    N,N-dimethylaniline 2.64
    acrylonitrile 8.34
    aniline 8.4
    1,3-propanediol 42.77
    bromobenzene 1.11
    dibromomethane 2.38
    1,1,2,2-tetrachloroethane 8.41
    2-methyl-cyclohexyl acetate 1.32
    tetrabutyl urea 2.94
    diisobutyl methanol 0.69
    2-phenylethanol 3.24
    styrene 0.88
    dioctyl adipate 2.19
    dimethyl sulfate 23.66
    ethyl butyrate 1.03
    methyl lactate 21.26
    butyl lactate 3.65
    diethyl carbonate 0.8
    propanediol butyl ether 13.22
    triethyl orthoformate 1.55
    p-tert-butyltoluene 0.53
    methyl 4-tert-butylbenzoate 5.67
    morpholine 32.3
    tert-butylamine 1.35
    n-dodecanol 1.32
    dimethoxymethane 47.89
    ethylene carbonate 6.45
    cyrene 20.95
    2-ethoxyethyl acetate 4.04
    2-ethylhexyl acetate 0.55
    1,2,4-trichlorobenzene 2.47
    4-methylpyridine 9.28
    dibutyl ether 1.4
    2,6-dimethyl-4-heptanol 0.69
    DEF 21.01
    dimethyl isosorbide 11.33
    tetrachloroethylene 6.46
    eugenol 7.02
    triacetin 5.14
    span 80 8.8
    1,4-butanediol 14.17
    1,1-dichloroethane 2.0
    2-methyl-1-pentanol 3.17
    methyl formate 33.16
    2-methyl-1-butanol 5.74
    n-decane 0.28
    butyronitrile 3.99
    3,7-dimethyl-1-octanol 1.51
    1-chlorooctane 0.77
    1-chlorotetradecane 0.32
    n-nonane 0.25
    undecane 0.19
    tert-butylcyclohexane 0.09
    cyclooctane 0.27
    cyclopentanol 13.9
    tetrahydropyran 11.46
    tert-amyl methyl ether 2.81
    2,5,8-trioxanonane 20.32
    1-hexene 0.44
    2-isopropoxyethanol 11.63
    2,2,2-trifluoroethanol 33.79
    methyl butyrate 2.44

    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