4-{2-[2-Carboxy-5-hydroxy-6-({6-O-[3-(4-hydroxyphenyl)prop-2-enoyl]hexopyranosyl}oxy)-2,3-dihydro-1H-indol-1-yl]ethenyl}-2,3-dihydropyridine-2,6-dicarboxylic acid

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  • Identifiers

    CAS number
    143022-02-0

    Molecular formula
    C33H32N2O15

    SMILES
    C1C(N=C(C=C1C=CN2C(CC3=CC(=C(C=C32)OC4C(C(C(C(O4)COC(=O)C=CC5=CC=C(C=C5)O)O)O)O)O)C(=O)O)C(=O)O)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 79.7%
    Savory 26.31%
    Milky 18.63%
    Cooked 18.39%
    Bitter 16.82%
    Meaty 16.05%
    Roasted 15.82%
    Burnt 15.1%
    Spicy 14.82%
    Cooling 14.52%

     

    Flavor
    Bitter 84.85%
    Odorless 44.9%
    Bland 29.94%
    Very mild 25.51%
    Sweet-like 22.19%
    Nitrile 19.21%
    Cedarleaf 18.91%
    Lovage 18.54%
    Yeast 18.48%
    Taco 18.33%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    4.14 (weak acid)

    Molecular weight
    696.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    4352°C

    Flash point

    • 358.16 ˚C est.

  • Synonyms

    • DTXSID501317782
    • 143022-02-0
    • 4-{2-[2-Carboxy-5-hydroxy-6-({6-O-[3-(4-hydroxyphenyl)prop-2-enoyl]hexopyranosyl}oxy)-2,3-dihydro-1H-indol-1-yl]ethenyl}-2,3-dihydropyridine-2,6-dicarboxylic acid
    • 143022-02-0

  • Applications

    Compound 4-{2-[2-Carboxy-5-hydroxy-6-({6-O-[3-(4-hydroxyphenyl)prop-2-enoyl]hexopyranosyl}oxy)-2,3-dihydro-1H-indol-1-yl]ethenyl}-2,3-dihydropyridine-2,6-dicarboxylic acid (CAS 143022-02-0) is a multifunctional heterocyclic glycosylated intermediate that is primarily used as a synthetic building block in pharmaceutical development. In medicinal chemistry, it provides a versatile scaffold for structure-activity relationship studies, enabling diversification at the indole/pyridine core and the attached sugar moiety to generate novel derivatives. It is commonly evaluated as a glycosylated intermediate for the synthesis of complex indole-based analogs and natural product-inspired constructs. In chemical biology and research settings, it can serve as a reagent or probe in SAR-driven investigations due to its polyfunctional framework. In polymer and materials science, the multiple carboxyl groups and aromatic rings offer potential as a functional monomer or crosslinking fragment for specialized polymers, subject to formulation constraints and regulatory considerations. It also may serve as a starting point for synthetic routes to more elaborate heterocycles, with compliance to regulatory and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 38.57
    methanol 52.23
    isopropanol 23.35
    water 0.42
    ethyl acetate 11.78
    n-propanol 27.68
    acetone 110.61
    n-butanol 14.81
    acetonitrile 14.12
    DMF 213.66
    toluene 0.98
    isobutanol 8.15
    1,4-dioxane 67.29
    methyl acetate 23.04
    THF 176.01
    2-butanone 49.01
    n-pentanol 6.78
    sec-butanol 13.7
    n-hexane 0.05
    ethylene glycol 40.47
    NMP 104.06
    cyclohexane 0.14
    DMSO 565.44
    n-butyl acetate 1.45
    n-octanol 3.23
    chloroform 3.28
    n-propyl acetate 3.23
    acetic acid 127.05
    dichloromethane 4.7
    cyclohexanone 32.92
    propylene glycol 54.34
    isopropyl acetate 4.48
    DMAc 198.95
    2-ethoxyethanol 77.27
    isopentanol 5.15
    n-heptane 0.07
    ethyl formate 19.03
    1,2-dichloroethane 4.88
    n-hexanol 1.73
    2-methoxyethanol 213.63
    isobutyl acetate 0.76
    tetrachloromethane 0.34
    n-pentyl acetate 3.41
    transcutol 54.16
    n-heptanol 2.57
    ethylbenzene 0.25
    MIBK 3.93
    2-propoxyethanol 26.26
    tert-butanol 10.04
    MTBE 3.44
    2-butoxyethanol 17.63
    propionic acid 27.81
    o-xylene 0.48
    formic acid 101.53
    diethyl ether 7.5
    m-xylene 0.35
    p-xylene 0.29
    chlorobenzene 0.71
    dimethyl carbonate 17.27
    n-octane 0.06
    formamide 122.57
    cyclopentanone 88.44
    2-pentanone 22.28
    anisole 2.48
    cyclopentyl methyl ether 8.13
    gamma-butyrolactone 72.49
    1-methoxy-2-propanol 94.63
    pyridine 24.94
    3-pentanone 11.44
    furfural 43.66
    n-dodecane 0.06
    diethylene glycol 36.89
    diisopropyl ether 0.47
    tert-amyl alcohol 6.66
    acetylacetone 34.53
    n-hexadecane 0.07
    acetophenone 3.35
    methyl propionate 18.26
    isopentyl acetate 0.81
    trichloroethylene 8.02
    n-nonanol 3.15
    cyclohexanol 6.21
    benzyl alcohol 5.43
    2-ethylhexanol 0.5
    isooctanol 1.3
    dipropyl ether 1.84
    1,2-dichlorobenzene 0.42
    ethyl lactate 5.28
    propylene carbonate 10.44
    n-methylformamide 101.12
    2-pentanol 4.59
    n-pentane 0.1
    1-propoxy-2-propanol 11.45
    1-methoxy-2-propyl acetate 4.7
    2-(2-methoxypropoxy) propanol 11.5
    mesitylene 0.15
    ε-caprolactone 22.58
    p-cymene 0.11
    epichlorohydrin 63.25
    1,1,1-trichloroethane 1.21
    2-aminoethanol 52.07
    morpholine-4-carbaldehyde 124.42
    sulfolane 116.73
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 24.65
    n-hexyl acetate 4.2
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 25.51
    sec-butyl acetate 1.3
    tert-butyl acetate 2.84
    decalin 0.02
    glycerin 111.01
    diglyme 44.18
    acrylic acid 36.29
    isopropyl myristate 1.19
    n-butyric acid 23.83
    acetyl acetate 6.31
    di(2-ethylhexyl) phthalate 1.25
    ethyl propionate 3.29
    nitromethane 188.44
    1,2-diethoxyethane 8.31
    benzonitrile 2.06
    trioctyl phosphate 1.33
    1-bromopropane 1.49
    gamma-valerolactone 180.59
    n-decanol 2.09
    triethyl phosphate 0.63
    4-methyl-2-pentanol 1.04
    propionitrile 6.99
    vinylene carbonate 9.52
    1,1,2-trichlorotrifluoroethane 52.94
    DMS 2.92
    cumene 0.12
    2-octanol 1.62
    2-hexanone 6.02
    octyl acetate 2.68
    limonene 0.2
    1,2-dimethoxyethane 69.39
    ethyl orthosilicate 0.63
    tributyl phosphate 1.03
    diacetone alcohol 15.32
    N,N-dimethylaniline 1.41
    acrylonitrile 13.67
    aniline 5.1
    1,3-propanediol 76.24
    bromobenzene 0.4
    dibromomethane 1.69
    1,1,2,2-tetrachloroethane 6.98
    2-methyl-cyclohexyl acetate 0.72
    tetrabutyl urea 3.03
    diisobutyl methanol 0.26
    2-phenylethanol 1.92
    styrene 0.37
    dioctyl adipate 2.51
    dimethyl sulfate 25.94
    ethyl butyrate 1.48
    methyl lactate 30.11
    butyl lactate 4.63
    diethyl carbonate 0.77
    propanediol butyl ether 21.29
    triethyl orthoformate 1.44
    p-tert-butyltoluene 0.1
    methyl 4-tert-butylbenzoate 3.31
    morpholine 93.57
    tert-butylamine 1.68
    n-dodecanol 1.34
    dimethoxymethane 86.7
    ethylene carbonate 7.77
    cyrene 16.68
    2-ethoxyethyl acetate 8.61
    2-ethylhexyl acetate 0.48
    1,2,4-trichlorobenzene 0.86
    4-methylpyridine 10.02
    dibutyl ether 2.18
    2,6-dimethyl-4-heptanol 0.26
    DEF 27.77
    dimethyl isosorbide 8.77
    tetrachloroethylene 3.47
    eugenol 4.54
    triacetin 5.68
    span 80 11.49
    1,4-butanediol 21.31
    1,1-dichloroethane 2.83
    2-methyl-1-pentanol 2.49
    methyl formate 72.03
    2-methyl-1-butanol 5.63
    n-decane 0.11
    butyronitrile 5.86
    3,7-dimethyl-1-octanol 1.08
    1-chlorooctane 0.57
    1-chlorotetradecane 0.21
    n-nonane 0.1
    undecane 0.08
    tert-butylcyclohexane 0.01
    cyclooctane 0.04
    cyclopentanol 17.51
    tetrahydropyran 23.95
    tert-amyl methyl ether 2.69
    2,5,8-trioxanonane 29.21
    1-hexene 0.28
    2-isopropoxyethanol 22.77
    2,2,2-trifluoroethanol 28.32
    methyl butyrate 5.55

    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