4-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)-1H-indole-3-acetonitrile

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  • Identifiers

    CAS number
    229483-42-5

    Molecular formula
    C22H28N2O11

    SMILES
    C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)C(=CN2)CC#N

    Safety labels

  • Odor profile

    Fragrance
    Odorless 71.42%
    Sweet 34.0%
    Vanilla 24.74%
    Savory 21.39%
    Bitter 18.95%
    Milky 18.78%
    Smoky 15.79%
    Cooling 15.02%
    Spicy 14.55%
    Burnt 14.26%

     

    Flavor
    Bitter 76.76%
    Odorless 40.43%
    Bland 32.01%
    Sweet-like 28.56%
    Cedarleaf 19.46%
    Very mild 19.21%
    Very slight 18.92%
    Alkaline 18.84%
    Nitrile 18.54%
    Cauliflower 18.33%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -2.6

    pKa est.
    4.76 (weak acid)

    Molecular weight
    496.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    5108°C

    Flash point

    • 317.12 ˚C est.

  • Synonyms

    • DTXSID601143269
    • 229483-42-5
    • RefChem:1069670
    • DTXCID801574874
    • 4-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)-1H-indole-3-acetonitrile
    • Cappariloside B
    • CHEBI:186372
    • {4-[(6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]-1H-indol-3-yl}acetonitrile
    • 4-[(6-O-I(2)-D-Glucopyranosyl-I(2)-D-glucopyranosyl)oxy]-1H-indole-3-acetonitrile
    • 2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1H-indol-3-yl]acetonitrile
    • 229483-42-5

  • Applications

    4-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)-1H-indole-3-acetonitrile (CAS 229483-42-5) is primarily used as an advanced synthetic intermediate and building block in pharmaceutical chemistry, enabling access to glycosylated indole derivatives for drug discovery; it is also evaluated as a chemical probe and research reagent in chemical biology to explore structure–activity relationships of indole-related targets; in agrochemical research it may serve as a scaffold for the development of plant-active indole glycoside analogs; and in general organic synthesis it can function as a specialized substrate for glycoside coupling and further functionalization to expand glycosylated indole libraries.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.96
    methanol 12.07
    isopropanol 0.77
    water 2.93
    ethyl acetate 0.37
    n-propanol 1.4
    acetone 1.71
    n-butanol 0.79
    acetonitrile 0.63
    DMF 25.14
    toluene 0.06
    isobutanol 0.44
    1,4-dioxane 1.95
    methyl acetate 0.8
    THF 3.26
    2-butanone 1.22
    n-pentanol 0.4
    sec-butanol 0.58
    n-hexane 0.01
    ethylene glycol 11.76
    NMP 21.2
    cyclohexane 0.02
    DMSO 39.61
    n-butyl acetate 0.14
    n-octanol 0.42
    chloroform 0.16
    n-propyl acetate 0.18
    acetic acid 13.04
    dichloromethane 0.22
    cyclohexanone 1.41
    propylene glycol 7.79
    isopropyl acetate 0.17
    DMAc 19.57
    2-ethoxyethanol 5.5
    isopentanol 0.29
    n-heptane 0.03
    ethyl formate 0.91
    1,2-dichloroethane 0.17
    n-hexanol 0.25
    2-methoxyethanol 17.91
    isobutyl acetate 0.08
    tetrachloromethane 0.04
    n-pentyl acetate 0.43
    transcutol 8.9
    n-heptanol 0.55
    ethylbenzene 0.03
    MIBK 0.21
    2-propoxyethanol 3.14
    tert-butanol 0.28
    MTBE 0.12
    2-butoxyethanol 3.42
    propionic acid 2.4
    o-xylene 0.05
    formic acid 51.37
    diethyl ether 0.3
    m-xylene 0.03
    p-xylene 0.03
    chlorobenzene 0.04
    dimethyl carbonate 1.41
    n-octane 0.02
    formamide 36.28
    cyclopentanone 3.13
    2-pentanone 0.71
    anisole 0.14
    cyclopentyl methyl ether 0.56
    gamma-butyrolactone 4.0
    1-methoxy-2-propanol 6.97
    pyridine 1.17
    3-pentanone 0.56
    furfural 5.13
    n-dodecane 0.01
    diethylene glycol 7.75
    diisopropyl ether 0.04
    tert-amyl alcohol 0.3
    acetylacetone 1.07
    n-hexadecane 0.02
    acetophenone 0.32
    methyl propionate 0.92
    isopentyl acetate 0.11
    trichloroethylene 0.34
    n-nonanol 0.42
    cyclohexanol 0.44
    benzyl alcohol 0.44
    2-ethylhexanol 0.1
    isooctanol 0.28
    dipropyl ether 0.23
    1,2-dichlorobenzene 0.04
    ethyl lactate 0.84
    propylene carbonate 1.01
    n-methylformamide 11.95
    2-pentanol 0.29
    n-pentane 0.02
    1-propoxy-2-propanol 1.55
    1-methoxy-2-propyl acetate 0.56
    2-(2-methoxypropoxy) propanol 2.29
    mesitylene 0.02
    ε-caprolactone 1.4
    p-cymene 0.03
    epichlorohydrin 2.05
    1,1,1-trichloroethane 0.04
    2-aminoethanol 8.47
    morpholine-4-carbaldehyde 16.97
    sulfolane 11.35
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.79
    n-hexyl acetate 0.43
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.93
    sec-butyl acetate 0.09
    tert-butyl acetate 0.14
    decalin 0.01
    glycerin 24.95
    diglyme 6.22
    acrylic acid 5.32
    isopropyl myristate 0.12
    n-butyric acid 1.38
    acetyl acetate 0.28
    di(2-ethylhexyl) phthalate 0.29
    ethyl propionate 0.2
    nitromethane 14.33
    1,2-diethoxyethane 0.7
    benzonitrile 0.2
    trioctyl phosphate 0.25
    1-bromopropane 0.07
    gamma-valerolactone 10.24
    n-decanol 0.27
    triethyl phosphate 0.17
    4-methyl-2-pentanol 0.1
    propionitrile 0.34
    vinylene carbonate 1.22
    1,1,2-trichlorotrifluoroethane 7.07
    DMS 0.47
    cumene 0.02
    2-octanol 0.27
    2-hexanone 0.27
    octyl acetate 0.27
    limonene 0.05
    1,2-dimethoxyethane 2.88
    ethyl orthosilicate 0.14
    tributyl phosphate 0.18
    diacetone alcohol 0.92
    N,N-dimethylaniline 0.14
    acrylonitrile 0.87
    aniline 0.28
    1,3-propanediol 6.66
    bromobenzene 0.02
    dibromomethane 0.1
    1,1,2,2-tetrachloroethane 0.3
    2-methyl-cyclohexyl acetate 0.14
    tetrabutyl urea 0.47
    diisobutyl methanol 0.06
    2-phenylethanol 0.29
    styrene 0.03
    dioctyl adipate 0.33
    dimethyl sulfate 3.98
    ethyl butyrate 0.18
    methyl lactate 4.15
    butyl lactate 1.11
    diethyl carbonate 0.13
    propanediol butyl ether 4.73
    triethyl orthoformate 0.23
    p-tert-butyltoluene 0.03
    methyl 4-tert-butylbenzoate 0.8
    morpholine 3.65
    tert-butylamine 0.08
    n-dodecanol 0.17
    dimethoxymethane 5.71
    ethylene carbonate 0.7
    cyrene 3.98
    2-ethoxyethyl acetate 1.14
    2-ethylhexyl acetate 0.08
    1,2,4-trichlorobenzene 0.07
    4-methylpyridine 0.47
    dibutyl ether 0.18
    2,6-dimethyl-4-heptanol 0.06
    DEF 1.89
    dimethyl isosorbide 2.2
    tetrachloroethylene 0.26
    eugenol 1.41
    triacetin 1.11
    span 80 2.22
    1,4-butanediol 2.36
    1,1-dichloroethane 0.07
    2-methyl-1-pentanol 0.18
    methyl formate 7.57
    2-methyl-1-butanol 0.37
    n-decane 0.03
    butyronitrile 0.27
    3,7-dimethyl-1-octanol 0.15
    1-chlorooctane 0.08
    1-chlorotetradecane 0.03
    n-nonane 0.03
    undecane 0.02
    tert-butylcyclohexane 0.0
    cyclooctane 0.01
    cyclopentanol 0.84
    tetrahydropyran 0.71
    tert-amyl methyl ether 0.16
    2,5,8-trioxanonane 4.64
    1-hexene 0.03
    2-isopropoxyethanol 1.59
    2,2,2-trifluoroethanol 6.21
    methyl butyrate 0.32

    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
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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