N-Hydroxy-L-proline

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  • Identifiers

    CAS number
    18610-59-8

    Molecular formula
    C5H9NO3

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 76.28%
    Sweet 39.39%
    Bitter 17.92%
    Caramellic 16.08%
    Nutty 16.03%
    Savory 15.89%
    Cooling 15.43%
    Fishy 14.36%
    Clean 14.23%
    Milky 13.27%

     

    Flavor
    Odorless 53.11%
    Bitter 48.23%
    Mild 24.91%
    Bland 24.14%
    Very mild 24.01%
    Sweet-like 23.58%
    Yeast 21.51%
    Formyl 20.1%
    Alkaline 19.85%
    Taco 19.82%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.8

    pKa est.
    7.09 (neutral)

    Molecular weight
    131.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    262°C

    Flash point

    • 154.55 ˚C est.

  • Synonyms

    • N-Hydroxy-L-proline
    • L-Proline, 1-hydroxy-
    • ZF3SDT86E7
    • 1-HYDROXYPROLINE, L-
    • (2S)-1-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
    • NSC-109549
    • DTXSID30296479
    • RefChem:163511
    • DTXCID20247617
    • 1-HYDROXY-L-PROLINE
    • 18610-59-8
    • NSC 109549
    • UNII-ZF3SDT86E7
    • 1-Hydroxyproline
    • L-Proline, 1-hydroxy
    • OXY-L-prolin
    • SCHEMBL8089
    • SCHEMBL8148300
    • DTXSID101372217
    • AKOS006377436
    • AKOS015856761
    • Q27295419
    • 18610-59-8

  • Applications

    N-Hydroxy-L-proline (CAS 18610-59-8) is primarily used as a chiral building block and synthetic intermediate in pharmaceutical and fine-chemical manufacturing. It serves as a versatile starting material for the preparation of proline-derived ligands and catalysts in asymmetric, metal-catalyzed transformations. It can be converted to hydroxamic acid-type derivatives as building blocks for medicinal chemistry and as chelating precursors in catalyst systems. In polymer and peptide chemistry, it can serve as a chiral monomer or building block for polypeptide synthesis and functional materials. Its amino-alcohol functionality also enables further derivatization for specialty applications, while usage is typically governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 36.24
    methanol 211.54
    isopropanol 12.13
    water 267.53
    ethyl acetate 7.42
    n-propanol 20.43
    acetone 13.33
    n-butanol 13.72
    acetonitrile 9.23
    DMF 171.61
    toluene 0.93
    isobutanol 14.42
    1,4-dioxane 17.85
    methyl acetate 5.95
    THF 50.05
    2-butanone 7.42
    n-pentanol 11.3
    sec-butanol 9.5
    n-hexane 0.25
    ethylene glycol 134.48
    NMP 208.06
    cyclohexane 0.21
    DMSO 328.64
    n-butyl acetate 7.6
    n-octanol 8.7
    chloroform 3.45
    n-propyl acetate 6.36
    acetic acid 204.16
    dichloromethane 5.72
    cyclohexanone 25.7
    propylene glycol 81.43
    isopropyl acetate 6.43
    DMAc 99.92
    2-ethoxyethanol 71.94
    isopentanol 15.76
    n-heptane 0.45
    ethyl formate 14.31
    1,2-dichloroethane 4.7
    n-hexanol 13.42
    2-methoxyethanol 144.78
    isobutyl acetate 4.68
    tetrachloromethane 1.0
    n-pentyl acetate 7.23
    transcutol 150.7
    n-heptanol 9.47
    ethylbenzene 0.85
    MIBK 13.97
    2-propoxyethanol 57.37
    tert-butanol 22.25
    MTBE 3.18
    2-butoxyethanol 31.3
    propionic acid 53.39
    o-xylene 1.89
    formic acid 518.71
    diethyl ether 2.13
    m-xylene 2.42
    p-xylene 1.45
    chlorobenzene 2.26
    dimethyl carbonate 8.48
    n-octane 0.25
    formamide 345.24
    cyclopentanone 43.42
    2-pentanone 10.73
    anisole 4.19
    cyclopentyl methyl ether 12.36
    gamma-butyrolactone 92.67
    1-methoxy-2-propanol 81.24
    pyridine 7.55
    3-pentanone 5.71
    furfural 84.44
    n-dodecane 0.27
    diethylene glycol 107.38
    diisopropyl ether 1.62
    tert-amyl alcohol 15.56
    acetylacetone 24.1
    n-hexadecane 0.29
    acetophenone 10.73
    methyl propionate 10.79
    isopentyl acetate 7.93
    trichloroethylene 10.03
    n-nonanol 7.97
    cyclohexanol 11.48
    benzyl alcohol 11.5
    2-ethylhexanol 6.95
    isooctanol 8.29
    dipropyl ether 3.73
    1,2-dichlorobenzene 3.73
    ethyl lactate 17.84
    propylene carbonate 36.69
    n-methylformamide 115.92
    2-pentanol 7.91
    n-pentane 0.24
    1-propoxy-2-propanol 32.95
    1-methoxy-2-propyl acetate 18.43
    2-(2-methoxypropoxy) propanol 38.17
    mesitylene 2.22
    ε-caprolactone 32.39
    p-cymene 2.34
    epichlorohydrin 43.49
    1,1,1-trichloroethane 2.72
    2-aminoethanol 130.67
    morpholine-4-carbaldehyde 125.01
    sulfolane 157.9
    2,2,4-trimethylpentane 0.37
    2-methyltetrahydrofuran 17.32
    n-hexyl acetate 11.26
    isooctane 0.44
    2-(2-butoxyethoxy)ethanol 55.47
    sec-butyl acetate 4.08
    tert-butyl acetate 10.58
    decalin 0.34
    glycerin 180.67
    diglyme 70.07
    acrylic acid 83.17
    isopropyl myristate 4.79
    n-butyric acid 40.85
    acetyl acetate 8.84
    di(2-ethylhexyl) phthalate 11.7
    ethyl propionate 6.18
    nitromethane 144.04
    1,2-diethoxyethane 10.23
    benzonitrile 9.1
    trioctyl phosphate 8.54
    1-bromopropane 1.31
    gamma-valerolactone 102.02
    n-decanol 5.86
    triethyl phosphate 6.71
    4-methyl-2-pentanol 9.22
    propionitrile 5.53
    vinylene carbonate 32.01
    1,1,2-trichlorotrifluoroethane 76.83
    DMS 11.46
    cumene 1.35
    2-octanol 5.41
    2-hexanone 7.0
    octyl acetate 7.44
    limonene 3.02
    1,2-dimethoxyethane 37.16
    ethyl orthosilicate 5.55
    tributyl phosphate 9.35
    diacetone alcohol 38.99
    N,N-dimethylaniline 5.81
    acrylonitrile 12.82
    aniline 4.46
    1,3-propanediol 95.39
    bromobenzene 1.5
    dibromomethane 2.7
    1,1,2,2-tetrachloroethane 8.46
    2-methyl-cyclohexyl acetate 9.12
    tetrabutyl urea 14.54
    diisobutyl methanol 5.62
    2-phenylethanol 12.49
    styrene 0.81
    dioctyl adipate 10.23
    dimethyl sulfate 34.08
    ethyl butyrate 6.66
    methyl lactate 34.94
    butyl lactate 17.0
    diethyl carbonate 4.67
    propanediol butyl ether 49.9
    triethyl orthoformate 6.25
    p-tert-butyltoluene 2.28
    methyl 4-tert-butylbenzoate 21.87
    morpholine 30.48
    tert-butylamine 6.42
    n-dodecanol 4.26
    dimethoxymethane 36.17
    ethylene carbonate 20.36
    cyrene 58.81
    2-ethoxyethyl acetate 12.71
    2-ethylhexyl acetate 5.6
    1,2,4-trichlorobenzene 5.91
    4-methylpyridine 7.09
    dibutyl ether 3.47
    2,6-dimethyl-4-heptanol 5.62
    DEF 23.81
    dimethyl isosorbide 56.87
    tetrachloroethylene 6.41
    eugenol 27.72
    triacetin 20.56
    span 80 34.69
    1,4-butanediol 50.16
    1,1-dichloroethane 2.16
    2-methyl-1-pentanol 10.96
    methyl formate 65.7
    2-methyl-1-butanol 12.48
    n-decane 0.38
    butyronitrile 5.71
    3,7-dimethyl-1-octanol 9.06
    1-chlorooctane 1.79
    1-chlorotetradecane 0.9
    n-nonane 0.33
    undecane 0.31
    tert-butylcyclohexane 0.4
    cyclooctane 0.19
    cyclopentanol 22.76
    tetrahydropyran 5.94
    tert-amyl methyl ether 4.23
    2,5,8-trioxanonane 60.07
    1-hexene 0.77
    2-isopropoxyethanol 33.3
    2,2,2-trifluoroethanol 90.56
    methyl butyrate 9.71

    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