Oxindole-3-acetic acid

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  • Identifiers

    CAS number
    2971-31-5

    Molecular formula
    C10H9NO3

    SMILES
    C1=CC=C2C(=C1)C(C(=O)N2)CC(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 62.07%
    Nutty 24.19%
    Burnt 23.87%
    Bitter 23.7%
    Cooked 23.45%
    Fruity 22.19%
    Savory 22.09%
    Sweet 21.03%
    Roasted 19.61%
    Caramellic 19.23%

     

    Flavor
    Odorless 52.41%
    Bitter 49.72%
    Mild 31.64%
    Very mild 27.42%
    Faint 23.28%
    Sour 22.19%
    Yeast 21.75%
    Bland 21.43%
    Urine 21.16%
    Nitrile 20.83%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    6.99 (neutral)

    Molecular weight
    191.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    414°C

    Melting point expt.

    • 146 °C

    Flash point

    • 229.47 ˚C est.

  • Synonyms

    • 2971-31-5
    • oxindole-3-acetic acid
    • 2-Oxindole-3-acetic acid
    • CHEBI:133221
    • RefChem:928368
    • 2-(2-oxoindolin-3-yl)acetic acid
    • (2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid
    • 1H-Indole-3-acetic acid, 2,3-dihydro-2-oxo-
    • 2-(2-oxo-1,3-dihydroindol-3-yl)acetic acid
    • MFCD09035909
    • 2-(2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid
    • (2-Oxo-2,3-dihydro-1H-indol-3-yl)-acetic acid
    • 2-(2-Oxo-3-indolinyl)acetic acid
    • 2-oxindole-3-acetate
    • 2-oxoindole-3-acetate
    • 2-indolinone-3-acetate
    • 2-oxoindole-3-acetic acid
    • 2-Oxo-3-Indolineacetic Acid; (+/-)-2,3-Dihydro-2-oxoindole-3-acetic Acid; (+/-)-2-Oxindoline-3-acetic Acid; (+/-)-2-Oxo-3-indolineacetic Acid; 2-(2-Oxoindolin-3-yl)acetic Acid;
    • 2-oxindole-3-aceticacid
    • 2-oxindol-3-yl-acetic acid
    • CHEMBL443641
    • SCHEMBL1302976
    • SCHEMBL29437202
    • DTXSID30952164
    • 2-(2-oxoindolin-3-yl)aceticacid
    • ALBB-012260
    • (2-Hydroxy-3H-indol-3-yl)acetato
    • 2-Hydroxy-1H-indole-3-acetic acid
    • MSK157473
    • SBB018853
    • STK523902
    • (+/-)-2-Oxo-3-indolineacetic acid
    • AKOS000506116
    • AKOS016345720
    • AB49450
    • FD30496
    • (2-Hydroxy-3H-indol-3-yl)acetic acid
    • LS-03835
    • 2-(2-oxo-1,3-dihydroindol-3-yl)acetate
    • DB-068151
    • ST4145755
    • 2,3-Dihydro-2-oxo-1H-indole-3-aceticacid
    • CS-0131902
    • 1H-Indole-3-aceticacid,2,3-dihydro-2-oxo-
    • EN300-59490
    • C22202
    • F10191
    • xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid
    • F369241
    • Z336080924
    • (2-Oxo-2,3-dihydro-1H-indol-3-yl)acetic acid, AldrichCPR
    • 2971-31-5

  • Applications

    Oxindole-3-acetic acid (CAS 2971-31-5) is primarily used as a synthetic intermediate in medicinal chemistry, serving as a starting point for the preparation of oxindole-based pharmacophores and related heterocycles to access diverse oxindole-3-acetic acid derivatives. In organic synthesis, it functions as a versatile building block for functionalization to access a range of oxindole derivatives with an acetic acid side chain. In pharmaceutical research, it provides a scaffold for exploring isoxindole-containing compounds. In plant science, it is a known metabolite in auxin-related pathways and is used as a physiological marker in hormone studies. In analytical chemistry, it is used as a reference standard for LC-MS/HPLC methods targeting plant hormones and oxindole derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.6
    methanol 3.31
    isopropanol 1.09
    water 1.83
    ethyl acetate 1.68
    n-propanol 1.0
    acetone 3.08
    n-butanol 0.85
    acetonitrile 2.2
    DMF 19.79
    toluene 0.14
    isobutanol 0.74
    1,4-dioxane 4.82
    methyl acetate 3.32
    THF 10.46
    2-butanone 3.01
    n-pentanol 1.2
    sec-butanol 1.3
    n-hexane 0.01
    ethylene glycol 10.64
    NMP 56.38
    cyclohexane 0.01
    DMSO 23.82
    n-butyl acetate 4.75
    n-octanol 1.99
    chloroform 0.29
    n-propyl acetate 2.57
    acetic acid 5.99
    dichloromethane 0.51
    cyclohexanone 3.6
    propylene glycol 4.51
    isopropyl acetate 1.91
    DMAc 73.44
    2-ethoxyethanol 24.03
    isopentanol 2.04
    n-heptane 0.04
    ethyl formate 2.76
    1,2-dichloroethane 0.54
    n-hexanol 2.62
    2-methoxyethanol 33.17
    isobutyl acetate 1.59
    tetrachloromethane 0.24
    n-pentyl acetate 2.52
    transcutol 38.48
    n-heptanol 2.56
    ethylbenzene 0.39
    MIBK 2.72
    2-propoxyethanol 25.76
    tert-butanol 3.29
    MTBE 0.86
    2-butoxyethanol 13.95
    propionic acid 2.92
    o-xylene 0.4
    formic acid 20.43
    diethyl ether 0.43
    m-xylene 0.29
    p-xylene 0.65
    chlorobenzene 0.29
    dimethyl carbonate 5.04
    n-octane 0.03
    formamide 37.43
    cyclopentanone 8.48
    2-pentanone 1.69
    anisole 3.51
    cyclopentyl methyl ether 1.62
    gamma-butyrolactone 18.2
    1-methoxy-2-propanol 18.73
    pyridine 2.08
    3-pentanone 1.26
    furfural 22.21
    n-dodecane 0.05
    diethylene glycol 43.93
    diisopropyl ether 0.34
    tert-amyl alcohol 3.27
    acetylacetone 6.71
    n-hexadecane 0.06
    acetophenone 6.05
    methyl propionate 2.79
    isopentyl acetate 5.81
    trichloroethylene 1.13
    n-nonanol 2.17
    cyclohexanol 0.85
    benzyl alcohol 3.89
    2-ethylhexanol 2.13
    isooctanol 2.34
    dipropyl ether 1.37
    1,2-dichlorobenzene 0.82
    ethyl lactate 7.2
    propylene carbonate 9.04
    n-methylformamide 11.26
    2-pentanol 0.66
    n-pentane 0.01
    1-propoxy-2-propanol 13.94
    1-methoxy-2-propyl acetate 10.35
    2-(2-methoxypropoxy) propanol 19.46
    mesitylene 0.33
    ε-caprolactone 7.18
    p-cymene 0.82
    epichlorohydrin 12.62
    1,1,1-trichloroethane 0.49
    2-aminoethanol 8.38
    morpholine-4-carbaldehyde 45.13
    sulfolane 33.53
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 3.99
    n-hexyl acetate 3.66
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 22.25
    sec-butyl acetate 2.1
    tert-butyl acetate 3.64
    decalin 0.05
    glycerin 23.44
    diglyme 39.93
    acrylic acid 4.4
    isopropyl myristate 2.05
    n-butyric acid 2.65
    acetyl acetate 2.27
    di(2-ethylhexyl) phthalate 4.76
    ethyl propionate 2.89
    nitromethane 18.1
    1,2-diethoxyethane 4.78
    benzonitrile 2.69
    trioctyl phosphate 3.15
    1-bromopropane 0.13
    gamma-valerolactone 23.71
    n-decanol 1.74
    triethyl phosphate 5.3
    4-methyl-2-pentanol 1.13
    propionitrile 1.39
    vinylene carbonate 6.57
    1,1,2-trichlorotrifluoroethane 19.99
    DMS 5.86
    cumene 0.56
    2-octanol 1.38
    2-hexanone 2.91
    octyl acetate 2.93
    limonene 0.76
    1,2-dimethoxyethane 28.16
    ethyl orthosilicate 4.19
    tributyl phosphate 3.66
    diacetone alcohol 11.94
    N,N-dimethylaniline 3.46
    acrylonitrile 3.06
    aniline 0.8
    1,3-propanediol 9.13
    bromobenzene 0.21
    dibromomethane 0.18
    1,1,2,2-tetrachloroethane 1.2
    2-methyl-cyclohexyl acetate 5.3
    tetrabutyl urea 6.82
    diisobutyl methanol 1.64
    2-phenylethanol 5.65
    styrene 0.32
    dioctyl adipate 4.21
    dimethyl sulfate 16.33
    ethyl butyrate 4.18
    methyl lactate 10.59
    butyl lactate 6.66
    diethyl carbonate 4.34
    propanediol butyl ether 13.26
    triethyl orthoformate 4.51
    p-tert-butyltoluene 0.72
    methyl 4-tert-butylbenzoate 10.14
    morpholine 6.65
    tert-butylamine 0.7
    n-dodecanol 1.3
    dimethoxymethane 9.74
    ethylene carbonate 4.91
    cyrene 24.98
    2-ethoxyethyl acetate 5.64
    2-ethylhexyl acetate 4.19
    1,2,4-trichlorobenzene 1.26
    4-methylpyridine 1.89
    dibutyl ether 1.32
    2,6-dimethyl-4-heptanol 1.64
    DEF 5.45
    dimethyl isosorbide 32.56
    tetrachloroethylene 1.03
    eugenol 14.27
    triacetin 7.62
    span 80 10.21
    1,4-butanediol 5.94
    1,1-dichloroethane 0.21
    2-methyl-1-pentanol 2.15
    methyl formate 8.06
    2-methyl-1-butanol 1.54
    n-decane 0.07
    butyronitrile 0.97
    3,7-dimethyl-1-octanol 2.4
    1-chlorooctane 0.4
    1-chlorotetradecane 0.24
    n-nonane 0.05
    undecane 0.06
    tert-butylcyclohexane 0.06
    cyclooctane 0.01
    cyclopentanol 1.88
    tetrahydropyran 0.81
    tert-amyl methyl ether 1.19
    2,5,8-trioxanonane 32.44
    1-hexene 0.08
    2-isopropoxyethanol 13.38
    2,2,2-trifluoroethanol 9.26
    methyl butyrate 3.94

    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