Proline

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  • Identifiers

    CAS number
    147-85-3

    Molecular formula
    C5H9NO2

    SMILES
    C1C[C@H](NC1)C(=O)O

  • Odor profile

    Fragrance
    Odorless 75.05%
    Sweet 27.28%
    Nutty 24.94%
    Popcorn 22.11%
    Caramellic 20.03%
    Fishy 19.43%
    Savory 18.94%
    Roasted 16.89%
    Buttery 16.54%
    Bitter 16.41%

     

    Flavor
    Odorless 48.32%
    Bitter 44.52%
    Mild 22.08%
    Very mild 22.03%
    Sweet-like 21.79%
    Yeast 20.9%
    Bland 20.28%
    Alkaline 20.25%
    Taco 20.2%
    Urine 19.94%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.5

    pKa est.
    8.01 (weak base)

    Molecular weight
    115.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    240°C

    Melting point expt.

    • 221 dec °C
    • 220-222 °C, decomposes
    • MP: 215-220 °C with decomposition /D(+)-Proline/
    • MP: 205 °C with decomposition /DL-Proline/
    • 221 °C

    Flash point

    • 139.39 ˚C est.

    Solubility expt.

    • 162000 mg/L (at 25 °C)
    • Solubility in 100 mL of water: 127 g at 0 °C; 162 g at 25 °C; 206.7 g at 50 °C; 239 g at 65 °C
    • Solubility in alcohol: 1.55% at 35 °C; insoluble in ether, butanol, isopropanol
    • Very soluble in water, alcohol; insoluble in ether
    • Very soluble in water; slightly soluble in ethanol, acetone, benzene; insoluble in ether, propanol
    • 162.0 mg/mL
    • Soluble in water; Insoluble in ether
    • Soluble (in ethanol)

  • Synonyms

    • L-proline
    • proline
    • 147-85-3
    • L-(-)-Proline
    • (2S)-pyrrolidine-2-carboxylic acid
    • (S)-Pyrrolidine-2-carboxylic acid
    • H-Pro-OH
    • 2-pyrrolidinecarboxylic acid
    • (-)-Proline
    • (-)-(S)-Proline
    • prolina
    • Prolinum
    • (S)-2-Pyrrolidinecarboxylic acid
    • (-)-2-Pyrrolidinecarboxylic acid
    • (S)-Proline
    • L-Pyrrolidine-2-carboxylic acid
    • L-alpha-Pyrrolidinecarboxylic acid
    • (S)-2-Carboxypyrrolidine
    • L-Prolin
    • Prolinum [Latin]
    • Prolina [Spanish]
    • Proline, L-
    • Proline (VAN)
    • (L)-PROLINE
    • FEMA No. 3319
    • Proline [USAN:INN]
    • FEMA Number 3319
    • 2-Pyrrolidinecarboxylic acid, (S)-
    • PRO (IUPAC abbreviation)
    • CB 1707
    • HSDB 1210
    • AI3-26710
    • (S)-(-)-Proline
    • UNII-9DLQ4CIU6V
    • 9DLQ4CIU6V
    • EINECS 205-702-2
    • MFCD00064318
    • NSC 46703
    • pro
    • CHEBI:17203
    • NSC-46703
    • 37159-97-0
    • CHEMBL54922
    • L-2-pyrrolidinecarboxylic acid
    • DTXSID5044021
    • EC 205-702-2
    • Prolinum (Latin)
    • prol
    • 4305-67-3
    • Proline (L-Proline)
    • PROLINE (II)
    • PROLINE [II]
    • PROLINE (MART.)
    • PROLINE [MART.]
    • PROLINE (EP MONOGRAPH)
    • PROLINE [EP MONOGRAPH]
    • PROLINE (USP MONOGRAPH)
    • PROLINE [USP MONOGRAPH]
    • Carboxypyrrolidine
    • L-(2,3-3H)Proline
    • Proline (USP)
    • L-Proline, labeled with carbon-14
    • racemic proline
    • rac-proline
    • NSC46703
    • s-proline
    • 3h-l-proline
    • Proline, (S)-pyrrolidine-2-carboxylic acid, (-)-2-Pyrrolidinecarboxylic acid, (-)-Proline, (S)-(-)-Proline, (S)-2-Carboxypyrrolidine, (S)-2-Pyrrolidinecarboxylic acid, (S)-Proline, 2-Pyrrolidinecarboxylic acid, Carboxypyrrolidine, L-(-)-Proline, L-Pyrrolidine-2-carboxylic acid, L-alpha-Pyrrolidinecarboxylic acid, NSC 46703
    • H-Pro
    • (2S)-proline
    • Pro-OH
    • L-Pro-OH
    • (-)-Proline (S)-2-Carboxypyrrolidine
    • L-Proline (Standard)
    • 2-Pyrrolidinecarboxylate
    • L-Proline (JP18)
    • PROLINE [VANDF]
    • PROLINE [HSDB]
    • PROLINE [USAN]
    • PROLINE [INN]
    • PROLINE [MI]
    • L-PROLINE [FCC]
    • L-PROLINE [JAN]
    • L-PROLINE [FHFI]
    • PROLINE [WHO-DD]
    • bmse000047
    • bmse000947
    • (2S)-2-carboxypyrrolidine
    • SCHEMBL7792
    • L-PROLINE [USP-RS]
    • (S)-2-Pyrralidinecarboxylate
    • (S)-2-Pyrrolidinecarboxylate
    • (-)-2-Pyrrolidinecarboxylate
    • (S)-(-)-PROLIN
    • GTPL3314
    • DTXCID3024021
    • HY-Y0252R
    • L-Proline, 99%, FCC, FG
    • (S)-2-Pyrralidinecarboxylic acid
    • pyrrolidin-2-(S)-carboxylic acid
    • Pharmakon1600-01301007
    • pyrrolidine-2-(S)-carboxylic acid
    • BCP25292
    • HY-Y0252
    • (S) -pyrrolidine-2-carboxylic acid
    • L-Proline, >=99.0% (NT)
    • (S)-(-)-Pyrrolidine-2-carboxylate
    • BDBM50000100
    • NCGC00014017
    • NSC760114
    • s5629
    • (2S)-pyrrolidin-1-ium-2-carboxylate
    • AKOS010372120
    • AKOS015856025
    • CCG-214709
    • CS-W019861
    • DB00172
    • FP02713
    • NSC-760114
    • (S)-(-)-Pyrrolidine-2-carboxylic acid
    • NCGC00014017-02
    • NCGC00014017-03
    • NCGC00097126-01
    • AC-11190
    • AS-10803
    • L-Proline, BioUltra, >=99.5% (NT)
    • DB-029981
    • L-Proline, SAJ special grade, >=99.0%

  • Applications

    L-Proline (CAS 147-85-3) is a naturally occurring amino acid with diverse applications: nutritional supplement in pharmaceuticals, foods and animal feed to enhance growth and tissue repair; flavor enhancer for soups, meats and beverages due to its mild savory note; moisturizing and anti-aging agent in cosmetics that supports collagen remodeling; osmoprotectant for cell culture, cryopreservation and lyophilization; biochemical buffer to stabilize proteins and enzymes; backbone unit in peptide synthesis and chiral auxiliary for high-optical-purity drug intermediates; benchmark organocatalyst enabling green, stereoselective Aldol, Mannich, Michael and α-aminoxylation reactions in industrial organic synthesis; agrochemical adjuvant and foliar fertilizer improving plant tolerance to salinity, drought and frost; component of electrochemical solvents, functional polymers and metal-coating formulations; reference standard in analytical chemistry, protein structure studies and proteomics techniques.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.09
    methanol 180.75
    isopropanol 1.64
    water 560.21
    ethyl acetate 2.17
    n-propanol 4.02
    acetone 1.29
    n-butanol 3.23
    acetonitrile 0.59
    DMF 11.6
    toluene 0.35
    isobutanol 2.98
    1,4-dioxane 3.65
    methyl acetate 0.9
    THF 10.78
    2-butanone 0.86
    n-pentanol 3.09
    sec-butanol 1.48
    n-hexane 0.14
    ethylene glycol 113.49
    NMP 91.65
    cyclohexane 0.12
    DMSO 103.62
    n-butyl acetate 5.73
    n-octanol 5.02
    chloroform 2.08
    n-propyl acetate 2.2
    acetic acid 196.13
    dichloromethane 3.04
    cyclohexanone 8.67
    propylene glycol 38.74
    isopropyl acetate 2.41
    DMAc 14.39
    2-ethoxyethanol 24.87
    isopentanol 4.64
    n-heptane 0.35
    ethyl formate 5.02
    1,2-dichloroethane 1.76
    n-hexanol 8.75
    2-methoxyethanol 53.58
    isobutyl acetate 2.08
    tetrachloromethane 0.72
    n-pentyl acetate 4.5
    transcutol 109.91
    n-heptanol 7.08
    ethylbenzene 0.36
    MIBK 3.66
    2-propoxyethanol 37.03
    tert-butanol 3.94
    MTBE 0.62
    2-butoxyethanol 24.7
    propionic acid 26.82
    o-xylene 0.81
    formic acid 733.72
    diethyl ether 0.46
    m-xylene 1.14
    p-xylene 0.6
    chlorobenzene 1.31
    dimethyl carbonate 2.54
    n-octane 0.2
    formamide 296.73
    cyclopentanone 12.88
    2-pentanone 1.68
    anisole 1.38
    cyclopentyl methyl ether 3.77
    gamma-butyrolactone 35.49
    1-methoxy-2-propanol 21.88
    pyridine 2.44
    3-pentanone 0.95
    furfural 55.29
    n-dodecane 0.19
    diethylene glycol 88.07
    diisopropyl ether 0.6
    tert-amyl alcohol 4.38
    acetylacetone 7.39
    n-hexadecane 0.2
    acetophenone 4.48
    methyl propionate 2.32
    isopentyl acetate 6.63
    trichloroethylene 4.75
    n-nonanol 4.81
    cyclohexanol 4.68
    benzyl alcohol 5.45
    2-ethylhexanol 5.53
    isooctanol 6.35
    dipropyl ether 1.75
    1,2-dichlorobenzene 2.88
    ethyl lactate 9.44
    propylene carbonate 23.9
    n-methylformamide 23.96
    2-pentanol 1.73
    n-pentane 0.1
    1-propoxy-2-propanol 21.5
    1-methoxy-2-propyl acetate 12.11
    2-(2-methoxypropoxy) propanol 30.62
    mesitylene 1.27
    ε-caprolactone 15.44
    p-cymene 1.73
    epichlorohydrin 12.31
    1,1,1-trichloroethane 0.89
    2-aminoethanol 77.56
    morpholine-4-carbaldehyde 58.12
    sulfolane 103.87
    2,2,4-trimethylpentane 0.22
    2-methyltetrahydrofuran 4.11
    n-hexyl acetate 6.86
    isooctane 0.3
    2-(2-butoxyethoxy)ethanol 41.5
    sec-butyl acetate 1.73
    tert-butyl acetate 4.71
    decalin 0.23
    glycerin 137.41
    diglyme 45.82
    acrylic acid 59.68
    isopropyl myristate 3.15
    n-butyric acid 24.07
    acetyl acetate 4.41
    di(2-ethylhexyl) phthalate 11.19
    ethyl propionate 1.99
    nitromethane 47.42
    1,2-diethoxyethane 4.57
    benzonitrile 4.2
    trioctyl phosphate 7.6
    1-bromopropane 0.43
    gamma-valerolactone 41.82
    n-decanol 3.66
    triethyl phosphate 4.83
    4-methyl-2-pentanol 3.43
    propionitrile 0.67
    vinylene carbonate 20.11
    1,1,2-trichlorotrifluoroethane 57.04
    DMS 6.88
    cumene 0.76
    2-octanol 3.51
    2-hexanone 1.74
    octyl acetate 4.61
    limonene 2.01
    1,2-dimethoxyethane 9.55
    ethyl orthosilicate 4.22
    tributyl phosphate 8.31
    diacetone alcohol 18.34
    N,N-dimethylaniline 2.42
    acrylonitrile 2.04
    aniline 2.19
    1,3-propanediol 48.07
    bromobenzene 0.91
    dibromomethane 1.42
    1,1,2,2-tetrachloroethane 4.05
    2-methyl-cyclohexyl acetate 7.29
    tetrabutyl urea 11.56
    diisobutyl methanol 4.18
    2-phenylethanol 9.38
    styrene 0.33
    dioctyl adipate 6.7
    dimethyl sulfate 12.57
    ethyl butyrate 3.94
    methyl lactate 17.49
    butyl lactate 14.78
    diethyl carbonate 2.94
    propanediol butyl ether 37.94
    triethyl orthoformate 4.45
    p-tert-butyltoluene 1.72
    methyl 4-tert-butylbenzoate 17.02
    morpholine 5.17
    tert-butylamine 1.46
    n-dodecanol 2.82
    dimethoxymethane 6.08
    ethylene carbonate 12.75
    cyrene 42.08
    2-ethoxyethyl acetate 8.5
    2-ethylhexyl acetate 4.66
    1,2,4-trichlorobenzene 4.01
    4-methylpyridine 1.85
    dibutyl ether 1.52
    2,6-dimethyl-4-heptanol 4.18
    DEF 4.61
    dimethyl isosorbide 45.93
    tetrachloroethylene 4.98
    eugenol 23.61
    triacetin 14.11
    span 80 32.34
    1,4-butanediol 24.06
    1,1-dichloroethane 0.51
    2-methyl-1-pentanol 4.13
    methyl formate 16.87
    2-methyl-1-butanol 3.67
    n-decane 0.26
    butyronitrile 1.01
    3,7-dimethyl-1-octanol 5.95
    1-chlorooctane 1.03
    1-chlorotetradecane 0.58
    n-nonane 0.23
    undecane 0.22
    tert-butylcyclohexane 0.27
    cyclooctane 0.13
    cyclopentanol 8.59
    tetrahydropyran 1.24
    tert-amyl methyl ether 1.1
    2,5,8-trioxanonane 45.31
    1-hexene 0.29
    2-isopropoxyethanol 12.64
    2,2,2-trifluoroethanol 81.38
    methyl butyrate 3.11

    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