4-(beta-D-Glucopyranosyloxy)-1H-indole-3-acetonitrile

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  • Identifiers

    CAS number
    229483-41-4

    Molecular formula
    C16H18N2O6

    SMILES
    C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=CN2)CC#N

    Safety labels

  • Odor profile

    Fragrance
    Odorless 65.42%
    Sweet 30.79%
    Vanilla 25.71%
    Savory 21.66%
    Bitter 20.52%
    Milky 19.29%
    Animal 16.93%
    Smoky 15.53%
    Powdery 15.44%
    Spicy 15.32%

     

    Flavor
    Bitter 87.34%
    Odorless 38.59%
    Bland 31.43%
    Sweet-like 25.06%
    Cedarleaf 19.43%
    Nitrile 18.59%
    Parsley 18.06%
    Lovage 17.88%
    Alkaline 17.85%
    Bread crust 17.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    5.54 (weak acid)

    Molecular weight
    334.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2710°C

    Flash point

    • 301.55 ˚C est.

  • Synonyms

    • 229483-41-4
    • DTXSID201228138
    • RefChem:1070044
    • 4-(beta-D-Glucopyranosyloxy)-1H-indole-3-acetonitrile
    • DTXCID701659380
    • Cappariloside A
    • orb2893380
    • SCHEMBL30001028
    • CHEBI:142256
    • 4-(|A-D-Glucopyranosyloxy)-1H-indole-3-acetonitrile
    • 4-(I(2)-D-Glucopyranosyloxy)-1H-indole-3-acetonitrile
    • [4-(beta-D-Glucopyranosyloxy)-1H-indol-3-yl]acetonitrile
    • 2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-indol-3-yl]acetonitrile
    • 229483-41-4

  • Applications

    4-(beta-D-Glucopyranosyloxy)-1H-indole-3-acetonitrile (CAS 229483-41-4) is principally regarded as a glycosyl indole building block for chemical synthesis, enabling the preparation of glycosyl indole derivatives with potential biological activity in medicinal chemistry. It is also used as an intermediate for lead diversification in agrochemical research and other pharmaceutical-related synthesis. Additionally, it may be evaluated for cosmetic/personal care or fragrance applications as a masked glycoside precursor, where the glycosidic moiety can influence solubility or release properties under formulation conditions; any use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.74
    methanol 23.2
    isopropanol 2.43
    water 6.48
    ethyl acetate 0.8
    n-propanol 3.64
    acetone 4.6
    n-butanol 2.2
    acetonitrile 1.76
    DMF 85.22
    toluene 0.09
    isobutanol 1.38
    1,4-dioxane 2.49
    methyl acetate 1.67
    THF 7.88
    2-butanone 2.82
    n-pentanol 1.34
    sec-butanol 1.76
    n-hexane 0.03
    ethylene glycol 36.79
    NMP 49.7
    cyclohexane 0.06
    DMSO 110.97
    n-butyl acetate 0.55
    n-octanol 1.14
    chloroform 0.23
    n-propyl acetate 0.71
    acetic acid 40.22
    dichloromethane 0.27
    cyclohexanone 3.57
    propylene glycol 23.87
    isopropyl acetate 0.52
    DMAc 71.81
    2-ethoxyethanol 17.98
    isopentanol 1.21
    n-heptane 0.09
    ethyl formate 1.95
    1,2-dichloroethane 0.3
    n-hexanol 1.09
    2-methoxyethanol 44.87
    isobutyl acetate 0.36
    tetrachloromethane 0.08
    n-pentyl acetate 1.04
    transcutol 26.08
    n-heptanol 1.61
    ethylbenzene 0.07
    MIBK 0.86
    2-propoxyethanol 10.57
    tert-butanol 1.25
    MTBE 0.34
    2-butoxyethanol 8.57
    propionic acid 6.61
    o-xylene 0.09
    formic acid 153.92
    diethyl ether 0.6
    m-xylene 0.07
    p-xylene 0.1
    chlorobenzene 0.1
    dimethyl carbonate 3.53
    n-octane 0.07
    formamide 125.05
    cyclopentanone 7.78
    2-pentanone 1.59
    anisole 0.44
    cyclopentyl methyl ether 1.31
    gamma-butyrolactone 10.98
    1-methoxy-2-propanol 21.58
    pyridine 2.14
    3-pentanone 1.31
    furfural 11.46
    n-dodecane 0.05
    diethylene glycol 28.88
    diisopropyl ether 0.15
    tert-amyl alcohol 1.15
    acetylacetone 3.07
    n-hexadecane 0.05
    acetophenone 1.16
    methyl propionate 2.1
    isopentyl acetate 0.53
    trichloroethylene 0.6
    n-nonanol 1.21
    cyclohexanol 1.28
    benzyl alcohol 1.44
    2-ethylhexanol 0.47
    isooctanol 1.03
    dipropyl ether 0.76
    1,2-dichlorobenzene 0.12
    ethyl lactate 3.87
    propylene carbonate 3.28
    n-methylformamide 35.77
    2-pentanol 0.96
    n-pentane 0.04
    1-propoxy-2-propanol 5.27
    1-methoxy-2-propyl acetate 2.09
    2-(2-methoxypropoxy) propanol 8.6
    mesitylene 0.06
    ε-caprolactone 3.59
    p-cymene 0.11
    epichlorohydrin 4.44
    1,1,1-trichloroethane 0.1
    2-aminoethanol 26.87
    morpholine-4-carbaldehyde 32.74
    sulfolane 28.03
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 1.81
    n-hexyl acetate 1.2
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 11.66
    sec-butyl acetate 0.36
    tert-butyl acetate 0.59
    decalin 0.02
    glycerin 71.02
    diglyme 17.16
    acrylic acid 14.43
    isopropyl myristate 0.52
    n-butyric acid 4.01
    acetyl acetate 0.68
    di(2-ethylhexyl) phthalate 1.26
    ethyl propionate 0.71
    nitromethane 42.86
    1,2-diethoxyethane 1.81
    benzonitrile 0.68
    trioctyl phosphate 1.0
    1-bromopropane 0.15
    gamma-valerolactone 19.82
    n-decanol 0.86
    triethyl phosphate 0.81
    4-methyl-2-pentanol 0.47
    propionitrile 1.0
    vinylene carbonate 3.24
    1,1,2-trichlorotrifluoroethane 18.14
    DMS 1.58
    cumene 0.06
    2-octanol 0.81
    2-hexanone 0.9
    octyl acetate 0.95
    limonene 0.18
    1,2-dimethoxyethane 8.92
    ethyl orthosilicate 0.65
    tributyl phosphate 0.88
    diacetone alcohol 3.96
    N,N-dimethylaniline 0.49
    acrylonitrile 2.43
    aniline 0.51
    1,3-propanediol 19.13
    bromobenzene 0.06
    dibromomethane 0.15
    1,1,2,2-tetrachloroethane 0.63
    2-methyl-cyclohexyl acetate 0.78
    tetrabutyl urea 1.95
    diisobutyl methanol 0.27
    2-phenylethanol 1.16
    styrene 0.08
    dioctyl adipate 1.35
    dimethyl sulfate 9.7
    ethyl butyrate 0.76
    methyl lactate 12.46
    butyl lactate 3.16
    diethyl carbonate 0.65
    propanediol butyl ether 11.24
    triethyl orthoformate 0.96
    p-tert-butyltoluene 0.1
    methyl 4-tert-butylbenzoate 2.76
    morpholine 6.4
    tert-butylamine 0.36
    n-dodecanol 0.6
    dimethoxymethane 13.63
    ethylene carbonate 2.05
    cyrene 12.54
    2-ethoxyethyl acetate 2.36
    2-ethylhexyl acetate 0.37
    1,2,4-trichlorobenzene 0.21
    4-methylpyridine 0.88
    dibutyl ether 0.57
    2,6-dimethyl-4-heptanol 0.27
    DEF 4.98
    dimethyl isosorbide 8.3
    tetrachloroethylene 0.55
    eugenol 4.96
    triacetin 3.32
    span 80 6.61
    1,4-butanediol 8.77
    1,1-dichloroethane 0.13
    2-methyl-1-pentanol 0.81
    methyl formate 18.08
    2-methyl-1-butanol 1.25
    n-decane 0.08
    butyronitrile 0.75
    3,7-dimethyl-1-octanol 0.59
    1-chlorooctane 0.21
    1-chlorotetradecane 0.1
    n-nonane 0.08
    undecane 0.06
    tert-butylcyclohexane 0.01
    cyclooctane 0.03
    cyclopentanol 2.47
    tetrahydropyran 1.35
    tert-amyl methyl ether 0.45
    2,5,8-trioxanonane 13.99
    1-hexene 0.1
    2-isopropoxyethanol 6.07
    2,2,2-trifluoroethanol 16.92
    methyl butyrate 1.16

    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