Indole-3-pyruvic acid

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  • Identifiers

    CAS number
    392-12-1

    Molecular formula
    C11H9NO3

    SMILES
    C1=CC=C2C(=C1)C(=CN2)CC(=O)C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 37.03%
    Odorless 35.19%
    Honey 31.63%
    Caramellic 30.56%
    Burnt 30.2%
    Fatty 29.26%
    Sweet 26.84%
    Green 26.62%
    Cooked 25.77%
    Nutty 24.79%

     

    Flavor
    Odorless 52.39%
    Bitter 47.91%
    Mild 30.24%
    Very mild 29.38%
    Faint 24.82%
    Sour 23.04%
    Bland 21.81%
    Yeast 21.3%
    Orange flower 20.89%
    Nitrile 20.82%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    5.54 (weak acid)

    Molecular weight
    203.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    441°C

    Flash point

    • 227.86 ˚C est.

  • Synonyms

    • Indole-3-pyruvic acid
    • 392-12-1
    • indolepyruvate
    • indol-3-yl pyruvic acid
    • alpha-Oxo-1H-indole-3-propanoic acid
    • DTXSID3042053
    • 1H-Indole-3-propanoic acid, alpha-oxo-
    • 4QM0LT13A8
    • NSC-88874
    • DTXCID1022053
    • 3-(1H-indol-3-yl)-2-oxidanylidene-propanoic acid
    • RefChem:790954
    • 206-874-1
    • 3-(1H-Indol-3-yl)-2-oxopropanoic acid
    • Indole-3-pyruvate
    • 3-Indolylpyruvic acid
    • Indolepyruvic acid
    • 3-(indol-3-yl)pyruvic acid
    • Indolyl-3-pyruvate
    • 3-(3-Indolyl)-2-oxopropanoic acid
    • 3-Indolepyruvic acid
    • 3-Indolylpyroracemic acid
    • MFCD00005640
    • NSC 88874
    • (Indol-3-yl)pyruvate
    • (indol-3-yl)pyruvic acid
    • 1H-Indole-3-propanoic acid, .alpha.-oxo-
    • 3-indol-3-yl-2-oxopropanoic acid
    • 3IO
    • beta-Indolepyruvic acid
    • beta-Indolylpyruvic acid
    • Indole-3-pyruvic acid monohydrate
    • Indole pyruvic acid
    • EINECS 206-874-1
    • BRN 0172966
    • UNII-4QM0LT13A8
    • 3-Indolpyruvic acid
    • indol-3-pyruvic acid
    • KETO TRYPTOPHAN
    • 3-indole-pyruvic acid
    • 3-(1H-indol-3-yl)-2-oxo-propanoic acid
    • .beta.-Indolepyruvic acid
    • .beta.-Indolylpyruvic acid
    • bmse000646
    • bmse000685
    • 1H-Indole-3-pyruvic acid
    • 5-22-06-00324 (Beilstein Handbook Reference)
    • MLS000515792
    • SCHEMBL125249
    • CHEMBL485012
    • orb1302435
    • SCHEMBL29362070
    • CHEBI:29750
    • HMS2270A21
    • NSC88874
    • Tox21_301365
    • SBB003515
    • STL286879
    • AKOS005267243
    • EBC-616982
    • FI30479
    • HY-W028393
    • NCGC00247042-01
    • NCGC00255790-01
    • AC-10208
    • AS-63461
    • CAS-392-12-1
    • SMR000112266
    • ST056381
    • SY041936
    • 3-(1H-indol-3-yl)-2-keto-propionic acid
    • Indole-3-pyruvic acid, >=98.0% (TLC)
    • CS-0072417
    • NS00014851
    • C00331
    • EN300-218335
    • 1H-INDOLE-3-PROPANOIC ACID, .ALPHA.-OXO
    • 392I121
    • F210523
    • AC17FD8D-94BC-4C87-B5E6-D2B60F03B45D
    • BRD-K09109825-001-07-3
    • Q23905803
    • F9995-2651
    • 392-12-1

  • Applications

    Indole-3-pyruvic acid (CAS 392-12-1) is primarily encountered as an intermediate in the tryptophan-to-auxin (IAA) biosynthetic pathway in plants and in research contexts. In practical terms, it is commonly used as a chemical intermediate for the synthesis of indole-containing derivatives, including plant growth regulator precursors and related agrochemical research tools. It is also used as a substrate or starting material in organic synthesis and in enzyme/biochemical studies focused on auxin biosynthesis, transport, and signaling. In addition, it serves as a chiral building block in the preparation of more complex molecules for pharmaceutical and agricultural chemistry. Within industry and R&D, it may be evaluated for roles as a precursor to plant hormones, as a reagent in synthetic routes for indole-based compounds, and for use in biochemical assay development and metabolic studies.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.56
    methanol 2.55
    isopropanol 0.73
    water 0.39
    ethyl acetate 1.34
    n-propanol 1.05
    acetone 0.61
    n-butanol 0.95
    acetonitrile 0.18
    DMF 6.22
    toluene 0.06
    isobutanol 0.83
    1,4-dioxane 0.44
    methyl acetate 1.5
    THF 3.26
    2-butanone 2.16
    n-pentanol 0.97
    sec-butanol 1.93
    n-hexane 0.01
    ethylene glycol 7.72
    NMP 41.34
    cyclohexane 0.0
    DMSO 4.81
    n-butyl acetate 1.6
    n-octanol 0.21
    chloroform 0.02
    n-propyl acetate 1.02
    acetic acid 3.5
    dichloromethane 0.04
    cyclohexanone 1.05
    propylene glycol 6.68
    isopropyl acetate 1.18
    DMAc 58.51
    2-ethoxyethanol 20.79
    isopentanol 1.9
    n-heptane 0.02
    ethyl formate 0.63
    1,2-dichloroethane 0.07
    n-hexanol 1.3
    2-methoxyethanol 33.01
    isobutyl acetate 0.45
    tetrachloromethane 0.02
    n-pentyl acetate 0.83
    transcutol 42.11
    n-heptanol 0.78
    ethylbenzene 0.13
    MIBK 1.51
    2-propoxyethanol 16.99
    tert-butanol 2.04
    MTBE 0.83
    2-butoxyethanol 7.9
    propionic acid 3.3
    o-xylene 0.18
    formic acid 17.85
    diethyl ether 0.32
    m-xylene 0.13
    p-xylene 0.15
    chlorobenzene 0.05
    dimethyl carbonate 2.44
    n-octane 0.01
    formamide 37.72
    cyclopentanone 2.97
    2-pentanone 1.28
    anisole 0.99
    cyclopentyl methyl ether 1.01
    gamma-butyrolactone 6.41
    1-methoxy-2-propanol 22.14
    pyridine 0.59
    3-pentanone 1.09
    furfural 6.99
    n-dodecane 0.01
    diethylene glycol 30.94
    diisopropyl ether 0.27
    tert-amyl alcohol 5.03
    acetylacetone 3.23
    n-hexadecane 0.01
    acetophenone 2.24
    methyl propionate 2.52
    isopentyl acetate 2.35
    trichloroethylene 0.16
    n-nonanol 0.3
    cyclohexanol 0.57
    benzyl alcohol 1.67
    2-ethylhexanol 0.94
    isooctanol 0.91
    dipropyl ether 0.6
    1,2-dichlorobenzene 0.12
    ethyl lactate 4.88
    propylene carbonate 3.02
    n-methylformamide 4.15
    2-pentanol 1.03
    n-pentane 0.01
    1-propoxy-2-propanol 9.72
    1-methoxy-2-propyl acetate 7.21
    2-(2-methoxypropoxy) propanol 15.88
    mesitylene 0.12
    ε-caprolactone 3.19
    p-cymene 0.29
    epichlorohydrin 3.02
    1,1,1-trichloroethane 0.05
    2-aminoethanol 10.44
    morpholine-4-carbaldehyde 19.36
    sulfolane 14.89
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 2.13
    n-hexyl acetate 0.77
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 15.93
    sec-butyl acetate 1.25
    tert-butyl acetate 2.92
    decalin 0.02
    glycerin 32.56
    diglyme 21.98
    acrylic acid 4.41
    isopropyl myristate 0.52
    n-butyric acid 2.56
    acetyl acetate 0.76
    di(2-ethylhexyl) phthalate 1.7
    ethyl propionate 1.64
    nitromethane 5.09
    1,2-diethoxyethane 2.03
    benzonitrile 0.33
    trioctyl phosphate 0.83
    1-bromopropane 0.03
    gamma-valerolactone 7.9
    n-decanol 0.27
    triethyl phosphate 2.32
    4-methyl-2-pentanol 1.14
    propionitrile 0.24
    vinylene carbonate 1.34
    1,1,2-trichlorotrifluoroethane 9.71
    DMS 2.88
    cumene 0.17
    2-octanol 0.35
    2-hexanone 1.12
    octyl acetate 0.67
    limonene 0.31
    1,2-dimethoxyethane 7.76
    ethyl orthosilicate 2.04
    tributyl phosphate 1.05
    diacetone alcohol 13.98
    N,N-dimethylaniline 1.24
    acrylonitrile 0.47
    aniline 0.42
    1,3-propanediol 10.97
    bromobenzene 0.03
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.17
    2-methyl-cyclohexyl acetate 2.05
    tetrabutyl urea 2.17
    diisobutyl methanol 0.82
    2-phenylethanol 1.93
    styrene 0.1
    dioctyl adipate 1.31
    dimethyl sulfate 7.77
    ethyl butyrate 1.78
    methyl lactate 10.98
    butyl lactate 3.61
    diethyl carbonate 1.55
    propanediol butyl ether 7.38
    triethyl orthoformate 2.08
    p-tert-butyltoluene 0.28
    methyl 4-tert-butylbenzoate 5.06
    morpholine 1.31
    tert-butylamine 0.48
    n-dodecanol 0.23
    dimethoxymethane 4.98
    ethylene carbonate 0.85
    cyrene 16.89
    2-ethoxyethyl acetate 3.39
    2-ethylhexyl acetate 1.52
    1,2,4-trichlorobenzene 0.29
    4-methylpyridine 0.45
    dibutyl ether 0.24
    2,6-dimethyl-4-heptanol 0.82
    DEF 4.51
    dimethyl isosorbide 20.22
    tetrachloroethylene 0.2
    eugenol 7.55
    triacetin 4.04
    span 80 6.49
    1,4-butanediol 5.11
    1,1-dichloroethane 0.03
    2-methyl-1-pentanol 2.16
    methyl formate 1.89
    2-methyl-1-butanol 2.42
    n-decane 0.01
    butyronitrile 0.18
    3,7-dimethyl-1-octanol 0.55
    1-chlorooctane 0.04
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.02
    cyclooctane 0.0
    cyclopentanol 1.09
    tetrahydropyran 0.18
    tert-amyl methyl ether 1.99
    2,5,8-trioxanonane 21.42
    1-hexene 0.04
    2-isopropoxyethanol 11.25
    2,2,2-trifluoroethanol 3.84
    methyl butyrate 1.88

    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