Indoleacetyl phenylalanine

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  • Identifiers

    CAS number
    57105-50-7

    Molecular formula
    C19H18N2O3

    SMILES
    C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)CC2=CNC3=CC=CC=C32

    Safety labels

  • Odor profile

    Fragrance
    Fruity 43.02%
    Odorless 41.38%
    Savory 31.43%
    Cooked 28.75%
    Grape 27.19%
    Bitter 23.0%
    Meaty 22.83%
    Cheesy 21.52%
    Milky 21.04%
    Fatty 20.63%

     

    Flavor
    Bitter 66.8%
    Odorless 55.76%
    Mild 31.5%
    Bland 25.91%
    Sweet-like 20.86%
    Nitrile 20.37%
    Yeast 20.12%
    Very mild 19.36%
    Orange flower 19.15%
    Heather 18.93%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    6.19 (neutral)

    Molecular weight
    322.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    719°C

    Flash point

    • 289.62 ˚C est.

  • Synonyms

    • 57105-50-7
    • N-(3-Indolylacetyl)-L-phenylalanine
    • Indoleacetyl phenylalanine
    • Indole-3-acetylphenylalanine
    • Indol acetyl phenylalanine
    • Indol-3 acetyl phenylalanine
    • L-phenylalanine, N-(1H-indol-3-ylacetyl)-
    • 7DQ9F5L55Y
    • L-Phenylalanine, N-(2-(1H-indol-3-yl)acetyl)-
    • DTXSID30205728
    • RefChem:1087369
    • DTXCID60128219
    • (S)-2-(2-(1H-indol-3-yl)acetamido)-3-phenylpropanoic acid
    • Indole-3-acetyl-L-phenylalanine
    • MFCD00075336
    • (2S)-2-[[2-(1H-indol-3-yl)acetyl]amino]-3-phenylpropanoic acid
    • (2-(1H-indol-3-yl)acetyl)-L-phenylalanine
    • IAA-L-Phe
    • UNII-7DQ9F5L55Y
    • N-[(1H-Indol-3-yl)acetyl]-L-phenylalanine
    • SCHEMBL503091
    • orb1705603
    • CHEMBL4788202
    • SCHEMBL29557188
    • CHEBI:177048
    • (S)-2-(2-(1H-Indol-3-yl)acetamido)-3-phenylpropanoicacid
    • (2S)-2-[[2-(1H-indol-3-yl)acetyl]amino]-3-phenyl-propanoic acid
    • AKOS015889635
    • CS-W011996
    • FI30447
    • HY-W011280
    • s12337
    • AS-15813
    • NS00120533
    • A13327
    • I-1600
    • 105I507
    • F219932
    • L-Phenylalanine, N-(1H-indol-3-ylacetyl)- (9CI)
    • Q27268117
    • 57105-50-7

  • Applications

    Indoleacetyl phenylalanine (CAS 57105-50-7) is typically used as a synthetic amino-acid-derived intermediate and is mainly applied in research as a building block for peptide-like and indole-containing compounds; it also serves as a biochemical probe and substrate for studies of auxin metabolism, supporting investigations into how indole-3-acetic acid conjugates are formed, hydrolyzed, and regulated in plant physiology. In medicinal and pharmaceutical chemistry contexts, the compound may be explored as a chiral building block for the design of dipeptide-like architectures and other small-molecule regulators. In agrochemical and plant-science research, it can be evaluated as a model substrate to study auxin-pathway regulation and plant growth regulator dynamics.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 15.69
    methanol 22.43
    isopropanol 6.17
    water 0.33
    ethyl acetate 5.82
    n-propanol 9.36
    acetone 27.1
    n-butanol 6.07
    acetonitrile 4.19
    DMF 188.68
    toluene 0.05
    isobutanol 3.58
    1,4-dioxane 6.45
    methyl acetate 13.25
    THF 36.89
    2-butanone 27.39
    n-pentanol 6.37
    sec-butanol 6.64
    n-hexane 0.01
    ethylene glycol 15.62
    NMP 28.32
    cyclohexane 0.0
    DMSO 93.14
    n-butyl acetate 2.5
    n-octanol 0.45
    chloroform 0.34
    n-propyl acetate 4.33
    acetic acid 31.12
    dichloromethane 0.43
    cyclohexanone 5.64
    propylene glycol 18.05
    isopropyl acetate 2.53
    DMAc 304.19
    2-ethoxyethanol 106.98
    isopentanol 4.36
    n-heptane 0.01
    ethyl formate 7.12
    1,2-dichloroethane 0.61
    n-hexanol 1.93
    2-methoxyethanol 174.49
    isobutyl acetate 1.4
    tetrachloromethane 0.06
    n-pentyl acetate 1.61
    transcutol 46.5
    n-heptanol 1.18
    ethylbenzene 0.12
    MIBK 2.75
    2-propoxyethanol 36.83
    tert-butanol 3.68
    MTBE 1.23
    2-butoxyethanol 14.65
    propionic acid 10.55
    o-xylene 0.07
    formic acid 48.42
    diethyl ether 1.28
    m-xylene 0.05
    p-xylene 0.21
    chlorobenzene 0.13
    dimethyl carbonate 7.31
    n-octane 0.01
    formamide 121.07
    cyclopentanone 20.84
    2-pentanone 9.01
    anisole 1.72
    cyclopentyl methyl ether 1.47
    gamma-butyrolactone 24.37
    1-methoxy-2-propanol 68.75
    pyridine 3.71
    3-pentanone 4.16
    furfural 19.66
    n-dodecane 0.01
    diethylene glycol 48.65
    diisopropyl ether 0.18
    tert-amyl alcohol 4.35
    acetylacetone 14.55
    n-hexadecane 0.02
    acetophenone 3.68
    methyl propionate 9.78
    isopentyl acetate 2.36
    trichloroethylene 1.64
    n-nonanol 0.64
    cyclohexanol 0.98
    benzyl alcohol 3.9
    2-ethylhexanol 0.74
    isooctanol 0.94
    dipropyl ether 1.02
    1,2-dichlorobenzene 0.2
    ethyl lactate 6.36
    propylene carbonate 5.46
    n-methylformamide 69.93
    2-pentanol 2.04
    n-pentane 0.01
    1-propoxy-2-propanol 13.89
    1-methoxy-2-propyl acetate 7.0
    2-(2-methoxypropoxy) propanol 13.28
    mesitylene 0.04
    ε-caprolactone 8.45
    p-cymene 0.12
    epichlorohydrin 24.16
    1,1,1-trichloroethane 0.24
    2-aminoethanol 28.13
    morpholine-4-carbaldehyde 53.59
    sulfolane 23.69
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 6.23
    n-hexyl acetate 1.45
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 19.69
    sec-butyl acetate 2.18
    tert-butyl acetate 2.41
    decalin 0.01
    glycerin 50.0
    diglyme 40.45
    acrylic acid 10.96
    isopropyl myristate 0.68
    n-butyric acid 10.6
    acetyl acetate 2.08
    di(2-ethylhexyl) phthalate 1.45
    ethyl propionate 4.18
    nitromethane 93.18
    1,2-diethoxyethane 5.68
    benzonitrile 1.15
    trioctyl phosphate 0.8
    1-bromopropane 0.18
    gamma-valerolactone 53.51
    n-decanol 0.55
    triethyl phosphate 1.7
    4-methyl-2-pentanol 0.97
    propionitrile 2.01
    vinylene carbonate 4.17
    1,1,2-trichlorotrifluoroethane 25.84
    DMS 3.03
    cumene 0.11
    2-octanol 0.55
    2-hexanone 6.74
    octyl acetate 1.09
    limonene 0.11
    1,2-dimethoxyethane 68.51
    ethyl orthosilicate 1.57
    tributyl phosphate 1.13
    diacetone alcohol 14.29
    N,N-dimethylaniline 1.13
    acrylonitrile 4.44
    aniline 0.57
    1,3-propanediol 50.35
    bromobenzene 0.08
    dibromomethane 0.14
    1,1,2,2-tetrachloroethane 1.5
    2-methyl-cyclohexyl acetate 1.69
    tetrabutyl urea 2.68
    diisobutyl methanol 0.42
    2-phenylethanol 2.43
    styrene 0.15
    dioctyl adipate 1.78
    dimethyl sulfate 12.81
    ethyl butyrate 2.49
    methyl lactate 16.35
    butyl lactate 3.99
    diethyl carbonate 1.75
    propanediol butyl ether 9.59
    triethyl orthoformate 2.38
    p-tert-butyltoluene 0.1
    methyl 4-tert-butylbenzoate 3.64
    morpholine 16.92
    tert-butylamine 0.49
    n-dodecanol 0.43
    dimethoxymethane 45.27
    ethylene carbonate 3.03
    cyrene 15.9
    2-ethoxyethyl acetate 6.01
    2-ethylhexyl acetate 1.38
    1,2,4-trichlorobenzene 0.39
    4-methylpyridine 1.92
    dibutyl ether 0.69
    2,6-dimethyl-4-heptanol 0.42
    DEF 17.59
    dimethyl isosorbide 14.61
    tetrachloroethylene 0.85
    eugenol 6.77
    triacetin 4.2
    span 80 5.83
    1,4-butanediol 20.66
    1,1-dichloroethane 0.3
    2-methyl-1-pentanol 4.37
    methyl formate 35.11
    2-methyl-1-butanol 4.58
    n-decane 0.02
    butyronitrile 1.98
    3,7-dimethyl-1-octanol 0.59
    1-chlorooctane 0.09
    1-chlorotetradecane 0.06
    n-nonane 0.01
    undecane 0.02
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 3.29
    tetrahydropyran 1.99
    tert-amyl methyl ether 1.5
    2,5,8-trioxanonane 26.89
    1-hexene 0.13
    2-isopropoxyethanol 31.26
    2,2,2-trifluoroethanol 10.09
    methyl butyrate 7.88

    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
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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