Amidinoproline

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  • Identifiers

    CAS number
    35404-57-0

    Molecular formula
    C6H11N3O2

    SMILES
    C1C[C@H](N(C1)C(=N)N)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 79.6%
    Savory 23.01%
    Cooling 20.45%
    Popcorn 20.04%
    Fishy 18.31%
    Roasted 18.2%
    Meaty 17.84%
    Cooked 17.28%
    Nutty 16.53%
    Bitter 15.52%

     

    Flavor
    Bitter 55.98%
    Odorless 47.37%
    Mild 23.99%
    Bland 21.71%
    Very mild 21.35%
    Roasted 21.23%
    Yeast 20.64%
    Nitrile 20.4%
    Taco 20.18%
    Sweet-like 19.96%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -0.4

    pKa est.
    8.33 (weak base)

    Molecular weight
    157.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    407°C

    Flash point

    • 167.53 ˚C est.

  • Synonyms

    • AMIDINOPROLINE
    • 35404-57-0
    • N-Amidino-L-proline
    • 1-Guanylproline
    • L-N-Amidinoproline
    • Proline, 1-amidino-
    • (S)-N-Amidinoproline
    • L-Proline, 1-(aminoiminomethyl)-
    • 4EIW83811H
    • DTXSID00188892
    • RefChem:1076642
    • DTXCID60111383
    • N-Guanylproline
    • (2S)-1-carbamimidoylpyrrolidine-2-carboxylic acid
    • (S)-1-Carbamimidoylpyrrolidine-2-carboxylic acid
    • Amidinoproline [INCI]
    • 1-carbamimidoyl-l-proline
    • UNII-4EIW83811H
    • Guanidino-L-proline
    • N-carbamimidoyl-l-proline
    • SCHEMBL212486
    • H40408
    • Q27259490
    • 35404-57-0

  • Applications

    Amidinoproline (CAS 35404-57-0) is chiefly employed as a chiral organocatalyst and ligand in asymmetric synthesis, enabling enantioselective transformations such as aldol and Mannich-type reactions in pharmaceutical and fine chemical research. It also serves as a building block or intermediate in the preparation of peptidomimetics and other bioactive compounds, and can function as a chiral auxiliary or scaffold in medicinal chemistry process development. In addition, it is often evaluated as a versatile source for designing chiral ligands and catalysts for varied catalytic applications, with potential use in polymer science or materials contexts where a proline-derived amidine framework is advantageous. Its utilization is typically confined to research and development settings and subject to local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.29
    methanol 13.76
    isopropanol 1.18
    water 143.55
    ethyl acetate 0.97
    n-propanol 1.81
    acetone 1.26
    n-butanol 1.32
    acetonitrile 1.36
    DMF 23.06
    toluene 0.36
    isobutanol 1.28
    1,4-dioxane 2.56
    methyl acetate 0.78
    THF 7.57
    2-butanone 0.84
    n-pentanol 1.12
    sec-butanol 1.04
    n-hexane 0.07
    ethylene glycol 36.74
    NMP 39.09
    cyclohexane 0.04
    DMSO 109.8
    n-butyl acetate 1.37
    n-octanol 1.04
    chloroform 2.21
    n-propyl acetate 0.57
    acetic acid 18.84
    dichloromethane 3.77
    cyclohexanone 3.89
    propylene glycol 14.05
    isopropyl acetate 0.76
    DMAc 23.71
    2-ethoxyethanol 13.11
    isopentanol 1.67
    n-heptane 0.09
    ethyl formate 3.86
    1,2-dichloroethane 1.98
    n-hexanol 2.32
    2-methoxyethanol 31.39
    isobutyl acetate 0.41
    tetrachloromethane 1.27
    n-pentyl acetate 1.22
    transcutol 7.69
    n-heptanol 2.2
    ethylbenzene 0.29
    MIBK 1.27
    2-propoxyethanol 14.62
    tert-butanol 1.93
    MTBE 0.35
    2-butoxyethanol 8.51
    propionic acid 4.58
    o-xylene 0.6
    formic acid 183.3
    diethyl ether 0.33
    m-xylene 0.71
    p-xylene 0.42
    chlorobenzene 0.75
    dimethyl carbonate 1.72
    n-octane 0.07
    formamide 83.32
    cyclopentanone 7.47
    2-pentanone 1.16
    anisole 0.78
    cyclopentyl methyl ether 1.75
    gamma-butyrolactone 14.14
    1-methoxy-2-propanol 11.85
    pyridine 2.7
    3-pentanone 0.75
    furfural 28.42
    n-dodecane 0.06
    diethylene glycol 35.99
    diisopropyl ether 0.19
    tert-amyl alcohol 1.81
    acetylacetone 2.65
    n-hexadecane 0.06
    acetophenone 2.03
    methyl propionate 1.41
    isopentyl acetate 1.57
    trichloroethylene 3.9
    n-nonanol 1.11
    cyclohexanol 1.27
    benzyl alcohol 2.41
    2-ethylhexanol 1.34
    isooctanol 1.79
    dipropyl ether 0.61
    1,2-dichlorobenzene 1.32
    ethyl lactate 2.98
    propylene carbonate 6.34
    n-methylformamide 19.96
    2-pentanol 0.75
    n-pentane 0.05
    1-propoxy-2-propanol 6.43
    1-methoxy-2-propyl acetate 3.41
    2-(2-methoxypropoxy) propanol 6.28
    mesitylene 0.55
    ε-caprolactone 4.94
    p-cymene 0.63
    epichlorohydrin 10.35
    1,1,1-trichloroethane 1.17
    2-aminoethanol 26.8
    morpholine-4-carbaldehyde 28.76
    sulfolane 40.91
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 2.15
    n-hexyl acetate 1.27
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 7.28
    sec-butyl acetate 0.41
    tert-butyl acetate 1.1
    decalin 0.07
    glycerin 56.0
    diglyme 11.63
    acrylic acid 9.04
    isopropyl myristate 0.62
    n-butyric acid 5.1
    acetyl acetate 1.08
    di(2-ethylhexyl) phthalate 2.5
    ethyl propionate 0.71
    nitromethane 15.49
    1,2-diethoxyethane 1.02
    benzonitrile 2.42
    trioctyl phosphate 1.78
    1-bromopropane 0.53
    gamma-valerolactone 20.77
    n-decanol 0.85
    triethyl phosphate 1.79
    4-methyl-2-pentanol 0.9
    propionitrile 0.92
    vinylene carbonate 6.61
    1,1,2-trichlorotrifluoroethane 30.33
    DMS 1.6
    cumene 0.38
    2-octanol 0.99
    2-hexanone 0.64
    octyl acetate 1.0
    limonene 0.64
    1,2-dimethoxyethane 7.74
    ethyl orthosilicate 1.43
    tributyl phosphate 1.65
    diacetone alcohol 5.24
    N,N-dimethylaniline 1.22
    acrylonitrile 2.77
    aniline 1.38
    1,3-propanediol 17.06
    bromobenzene 0.63
    dibromomethane 1.62
    1,1,2,2-tetrachloroethane 3.73
    2-methyl-cyclohexyl acetate 1.68
    tetrabutyl urea 2.57
    diisobutyl methanol 0.89
    2-phenylethanol 3.41
    styrene 0.24
    dioctyl adipate 1.26
    dimethyl sulfate 9.48
    ethyl butyrate 1.12
    methyl lactate 7.6
    butyl lactate 3.56
    diethyl carbonate 0.97
    propanediol butyl ether 6.95
    triethyl orthoformate 1.25
    p-tert-butyltoluene 0.57
    methyl 4-tert-butylbenzoate 4.76
    morpholine 3.91
    tert-butylamine 0.62
    n-dodecanol 0.63
    dimethoxymethane 7.07
    ethylene carbonate 4.34
    cyrene 14.41
    2-ethoxyethyl acetate 2.04
    2-ethylhexyl acetate 1.11
    1,2,4-trichlorobenzene 1.56
    4-methylpyridine 2.32
    dibutyl ether 0.37
    2,6-dimethyl-4-heptanol 0.89
    DEF 3.28
    dimethyl isosorbide 11.99
    tetrachloroethylene 3.8
    eugenol 7.18
    triacetin 2.29
    span 80 5.79
    1,4-butanediol 9.11
    1,1-dichloroethane 0.83
    2-methyl-1-pentanol 1.4
    methyl formate 14.94
    2-methyl-1-butanol 1.52
    n-decane 0.08
    butyronitrile 1.09
    3,7-dimethyl-1-octanol 1.0
    1-chlorooctane 0.33
    1-chlorotetradecane 0.16
    n-nonane 0.07
    undecane 0.07
    tert-butylcyclohexane 0.07
    cyclooctane 0.04
    cyclopentanol 3.12
    tetrahydropyran 0.68
    tert-amyl methyl ether 0.55
    2,5,8-trioxanonane 10.11
    1-hexene 0.17
    2-isopropoxyethanol 4.85
    2,2,2-trifluoroethanol 22.5
    methyl butyrate 1.14

    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