Ethyl 5-oxo-L-prolinate

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  • Identifiers

    CAS number
    7149-65-7

    Molecular formula
    C7H11NO3

    SMILES
    CCOC(=O)[C@@H]1CCC(=O)N1

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 54.63%
    Caramellic 52.9%
    Nutty 37.15%
    Fruity 35.84%
    Burnt 30.55%
    Buttery 29.14%
    Roasted 25.39%
    Winey 25.17%
    Ethereal 25.16%
    Odorless 24.98%

     

    Flavor
    Bitter 55.78%
    Odorless 28.54%
    Very mild 25.16%
    Fruity 25.15%
    Sweet-like 20.5%
    Bland 20.38%
    Yeast 20.25%
    Cotton candy 19.85%
    Toffee 19.76%
    Extremely sweet 19.72%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    7.06 (neutral)

    Molecular weight
    157.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    318°C

    Flash point

    • 152.26 ˚C est.

  • Synonyms

    • Ethyl 5-oxo-L-prolinate
    • RefChem:595835
    • 7149-65-7
    • L-Pyroglutamic acid ethyl ester
    • Ethyl L-pyroglutamate
    • ethyl (2S)-5-oxopyrrolidine-2-carboxylate
    • Ethyl pidolate
    • Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate
    • (S)-ethyl 5-oxopyrrolidine-2-carboxylate
    • H-Pyr-OEt
    • MFCD00064497
    • (S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone
    • Ethyl pyroglutamate
    • Ethyl (S)-5-oxopyrrolidine-2-carboxylate
    • CHEMBL4229168
    • 1PS59ES316
    • (+)-L-Pyroglutamic acid ethyl ester
    • pyroglutamic acid ethyl ester
    • UNII-1PS59ES316
    • NSC-72279
    • NSC-166529
    • EINECS 230-480-9
    • NSC 72279
    • NSC 166529
    • ETHYL PCA
    • VAMACTIVE 47
    • SCHEMBL905284
    • orb2940029
    • SCHEMBL1936582
    • ETHYL (S)-PYROGLUTAMATE
    • L-Proline, 5-oxo-, ethyl ester
    • DTXSID201303392
    • AC-708
    • BDBM50460039
    • Ethyl 5-oxo-2-pyrrolidinecarboxylate
    • SBB017516
    • AKOS005259612
    • AKOS015909837
    • CS-W020688
    • DS-1658
    • ethyl (S)-2-pyrrolidone-5-carboxylate
    • ethyl 2-pyrrolidinone-5(s)-carboxylate
    • BP-12288
    • HY-40269
    • SY023258
    • Ethyl (S)-2-oxopyrolidine-5-carboxylate.
    • DB-005490
    • ETHYL L-2-PYRROLIDONE-5-CARBOXYLATE
    • PROLINE, 5-OXO-, ETHYL ESTER, L-
    • NS00080587
    • ethyl (s)-(+)-2-pyrrolidinone-5-carboxylate
    • EN300-185981
    • ETHYL L-2-OXO-5-PYRROLIDINECARBOXYLATE
    • P60063
    • 149P657
    • AQ-405/40679537
    • F404937
    • (S)-(+)-ETHYL 2-PYRROLIDONE-5-CARBOXYLATE
    • Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate, 98%
    • (2S)-5-Oxopyrrolidine-2-carboxylic acid ethyl ester
    • (S)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester
    • Q27252722
    • L-Pyroglutamic acid ethyl ester, puriss., >=98.5% (sum of enantiomers, HPLC)
    • 7149-65-7

  • Applications

    Ethyl 5-oxo-L-prolinate, CAS 7149-65-7, is a convenient lactam-proline-derived ester used as a versatile intermediate in organic synthesis; it is commonly employed as a protected proline derivative and a chiral building block for the synthesis of proline-containing compounds and peptidomimetics, as well as a precursor for the formation of lactam rings and related derivatives; in asymmetric synthesis, it can serve as a source of chirality and a platform for developing catalysts; it finds use in pharmaceutical and fine chemical manufacture and in drug discovery research to assemble proline-containing frameworks; the ester group can be hydrolyzed or functionalized to access diverse proline-based derivatives; its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 386.95
    methanol 1109.24
    isopropanol 208.27
    water 95.32
    ethyl acetate 110.07
    n-propanol 194.63
    acetone 441.45
    n-butanol 148.38
    acetonitrile 514.64
    DMF 1121.89
    toluene 43.24
    isobutanol 145.0
    1,4-dioxane 207.14
    methyl acetate 188.26
    THF 234.85
    2-butanone 194.42
    n-pentanol 139.61
    sec-butanol 154.77
    n-hexane 2.53
    ethylene glycol 203.33
    NMP 671.54
    cyclohexane 2.85
    DMSO 1659.73
    n-butyl acetate 91.05
    n-octanol 47.78
    chloroform 347.14
    n-propyl acetate 100.11
    acetic acid 884.42
    dichloromethane 586.14
    cyclohexanone 241.12
    propylene glycol 153.39
    isopropyl acetate 66.0
    DMAc 809.45
    2-ethoxyethanol 358.23
    isopentanol 137.62
    n-heptane 1.56
    ethyl formate 280.5
    1,2-dichloroethane 283.84
    n-hexanol 63.4
    2-methoxyethanol 544.7
    isobutyl acetate 51.21
    tetrachloromethane 23.3
    n-pentyl acetate 65.78
    transcutol 529.48
    n-heptanol 35.91
    ethylbenzene 36.4
    MIBK 75.62
    2-propoxyethanol 180.38
    tert-butanol 193.98
    MTBE 85.08
    2-butoxyethanol 113.47
    propionic acid 271.0
    o-xylene 41.19
    formic acid 1075.53
    diethyl ether 55.52
    m-xylene 34.01
    p-xylene 55.99
    chlorobenzene 129.53
    dimethyl carbonate 81.69
    n-octane 1.37
    formamide 1225.32
    cyclopentanone 331.32
    2-pentanone 120.32
    anisole 128.27
    cyclopentyl methyl ether 67.91
    gamma-butyrolactone 547.93
    1-methoxy-2-propanol 257.01
    pyridine 311.59
    3-pentanone 78.4
    furfural 729.42
    n-dodecane 2.0
    diethylene glycol 239.19
    diisopropyl ether 13.92
    tert-amyl alcohol 168.44
    acetylacetone 193.73
    n-hexadecane 2.27
    acetophenone 177.17
    methyl propionate 111.98
    isopentyl acetate 75.57
    trichloroethylene 531.11
    n-nonanol 40.49
    cyclohexanol 87.26
    benzyl alcohol 191.38
    2-ethylhexanol 36.16
    isooctanol 32.88
    dipropyl ether 20.8
    1,2-dichlorobenzene 132.68
    ethyl lactate 83.1
    propylene carbonate 268.02
    n-methylformamide 801.75
    2-pentanol 73.92
    n-pentane 2.47
    1-propoxy-2-propanol 91.37
    1-methoxy-2-propyl acetate 87.69
    2-(2-methoxypropoxy) propanol 123.44
    mesitylene 19.84
    ε-caprolactone 228.95
    p-cymene 20.23
    epichlorohydrin 483.75
    1,1,1-trichloroethane 106.05
    2-aminoethanol 286.41
    morpholine-4-carbaldehyde 518.94
    sulfolane 655.57
    2,2,4-trimethylpentane 3.51
    2-methyltetrahydrofuran 147.4
    n-hexyl acetate 91.29
    isooctane 1.92
    2-(2-butoxyethoxy)ethanol 154.51
    sec-butyl acetate 53.13
    tert-butyl acetate 66.8
    decalin 4.43
    glycerin 263.31
    diglyme 294.98
    acrylic acid 356.83
    isopropyl myristate 28.86
    n-butyric acid 253.25
    acetyl acetate 110.82
    di(2-ethylhexyl) phthalate 54.04
    ethyl propionate 73.35
    nitromethane 1273.32
    1,2-diethoxyethane 91.8
    benzonitrile 263.55
    trioctyl phosphate 32.48
    1-bromopropane 75.81
    gamma-valerolactone 506.15
    n-decanol 29.29
    triethyl phosphate 44.48
    4-methyl-2-pentanol 47.33
    propionitrile 199.14
    vinylene carbonate 310.61
    1,1,2-trichlorotrifluoroethane 376.23
    DMS 101.92
    cumene 28.3
    2-octanol 28.68
    2-hexanone 96.86
    octyl acetate 43.53
    limonene 24.52
    1,2-dimethoxyethane 404.8
    ethyl orthosilicate 36.11
    tributyl phosphate 44.58
    diacetone alcohol 121.18
    N,N-dimethylaniline 94.62
    acrylonitrile 431.91
    aniline 130.45
    1,3-propanediol 298.9
    bromobenzene 106.36
    dibromomethane 238.93
    1,1,2,2-tetrachloroethane 312.7
    2-methyl-cyclohexyl acetate 59.95
    tetrabutyl urea 63.11
    diisobutyl methanol 20.71
    2-phenylethanol 96.64
    styrene 56.44
    dioctyl adipate 58.48
    dimethyl sulfate 215.73
    ethyl butyrate 63.2
    methyl lactate 119.87
    butyl lactate 78.21
    diethyl carbonate 57.45
    propanediol butyl ether 144.73
    triethyl orthoformate 43.0
    p-tert-butyltoluene 16.72
    methyl 4-tert-butylbenzoate 102.61
    morpholine 246.57
    tert-butylamine 82.75
    n-dodecanol 21.41
    dimethoxymethane 254.17
    ethylene carbonate 221.0
    cyrene 158.37
    2-ethoxyethyl acetate 106.17
    2-ethylhexyl acetate 52.9
    1,2,4-trichlorobenzene 151.71
    4-methylpyridine 319.95
    dibutyl ether 33.47
    2,6-dimethyl-4-heptanol 20.71
    DEF 228.21
    dimethyl isosorbide 167.56
    tetrachloroethylene 198.22
    eugenol 120.08
    triacetin 116.75
    span 80 90.53
    1,4-butanediol 184.24
    1,1-dichloroethane 168.36
    2-methyl-1-pentanol 128.69
    methyl formate 605.07
    2-methyl-1-butanol 133.68
    n-decane 3.01
    butyronitrile 195.66
    3,7-dimethyl-1-octanol 46.96
    1-chlorooctane 18.7
    1-chlorotetradecane 7.72
    n-nonane 2.51
    undecane 2.39
    tert-butylcyclohexane 3.86
    cyclooctane 1.22
    cyclopentanol 122.62
    tetrahydropyran 94.72
    tert-amyl methyl ether 67.04
    2,5,8-trioxanonane 190.75
    1-hexene 17.55
    2-isopropoxyethanol 181.16
    2,2,2-trifluoroethanol 312.68
    methyl butyrate 142.18

    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