D-Asparagine

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  • Identifiers

    CAS number
    2058-58-4

    Molecular formula
    C4H8N2O3

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 77.07%
    Savory 34.18%
    Sweet 30.21%
    Meaty 21.96%
    Fishy 18.56%
    Cooked 18.04%
    Cocoa 17.12%
    Milky 16.94%
    Bitter 15.82%
    Cooling 15.36%

     

    Flavor
    Odorless 66.69%
    Mild 32.31%
    Bland 26.42%
    Very mild 25.26%
    Yeast 23.23%
    Bitter 22.4%
    Faint 21.33%
    Sweet-like 21.33%
    Sour 20.15%
    Cooked 20.07%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -3.4

    pKa est.
    5.58 (weak acid)

    Molecular weight
    132.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    372°C

    Melting point expt.

    • 234 - 235 °C

    Flash point

    • 185.71 ˚C est.

  • Synonyms

    • D-Asparagine
    • 2058-58-4
    • (2R)-2,4-diamino-4-oxobutanoic acid
    • (2R)-2-amino-3-carbamoylpropanoic acid
    • Asparagine, D-
    • D-2-aminosuccinamic acid
    • D-Asparagin
    • D-aspartic acid beta-amide
    • UNII-T6QV1010K6
    • (2R)-4-amino-2-ammonio-4-oxobutanoate
    • EINECS 218-163-3
    • (R)-2-amino-3-carbamoylpropanoic acid
    • CHEBI:28159
    • DTXSID30872479
    • D-asparagine zwitterion
    • CHEBI:74337
    • (2R)-4-amino-2-azaniumyl-4-oxobutanoate
    • RefChem:130509
    • DTXCID70820136
    • 218-163-3
    • DCXYFEDJOCDNAF-UWTATZPHSA-N
    • H-D-Asn-OH
    • Asparagine D-form
    • (R)-2,4-Diamino-4-oxobutanoic acid
    • H-D-Asn-OH.H2O
    • MFCD00008036
    • T6QV1010K6
    • Asparagine #
    • NCGC00163330-01
    • D-Asn
    • d-asn11
    • D-Asparagine, 99%
    • starbld0005099
    • D-Aspartic acid 4-amide
    • (R)-2-Aminosuccinamic acid
    • SCHEMBL92738
    • orb1297111
    • ASPARAGINE D-FORM [MI]
    • CHEMBL1232369
    • (R)-2-Aminosuccinic acid 4-amide
    • EBC-44109
    • SBB058629
    • AKOS022186061
    • CS-W011094
    • DB03943
    • FA39328
    • HY-W010378
    • AS-12167
    • SY008178
    • A0543
    • NS00068513
    • ST51036369
    • EN300-72273
    • C01905
    • 058A584
    • F791085
    • D-Asparagine, puriss., anhydrous, >=99.0% (NT)
    • Q27094804
    • Z1147451758
    • (R)-2-Aminosuccinamic acid (R)-2-Aminosuccinic acid 4-amide D-Aspartic acid 4-amide
    • 2058-58-4

  • Applications

    D-Asparagine (CAS 2058-58-4) is primarily used as a chiral building block and synthetic intermediate in pharmaceutical and agrochemical production; it serves as a starting material for the preparation of D-Asparagine derivatives and can be incorporated into peptide synthesis to introduce D-amino acid residues. In biochemical and enzymology research, D-Asparagine is commonly used as a substrate or reference compound for assays involving D-amino acid oxidase and related enzymes, aiding the study of stereochemical recognition. In materials and polymer science, it may be used as a component of peptidomimetics or amino acid–based derivatives to enhance protease resistance and thermal properties of materials. It is also evaluated as a nitrogen source in microbial culture media for research and fermentation processes, depending on regulatory and formulation requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.09
    methanol 0.14
    isopropanol 0.05
    water 4.96
    ethyl acetate 0.12
    n-propanol 0.05
    acetone 0.45
    n-butanol 0.04
    acetonitrile 0.12
    DMF 3.56
    toluene 0.06
    isobutanol 0.04
    1,4-dioxane 0.78
    methyl acetate 0.12
    THF 0.65
    2-butanone 0.14
    n-pentanol 0.05
    sec-butanol 0.05
    n-hexane 0.04
    ethylene glycol 1.47
    NMP 7.07
    cyclohexane 0.03
    DMSO 5.36
    n-butyl acetate 0.11
    n-octanol 0.07
    chloroform 0.06
    n-propyl acetate 0.07
    acetic acid 1.07
    dichloromethane 0.08
    cyclohexanone 0.44
    propylene glycol 0.62
    isopropyl acetate 0.1
    DMAc 4.52
    2-ethoxyethanol 0.66
    isopentanol 0.06
    n-heptane 0.06
    ethyl formate 0.42
    1,2-dichloroethane 0.07
    n-hexanol 0.11
    2-methoxyethanol 1.39
    isobutyl acetate 0.04
    tetrachloromethane 0.09
    n-pentyl acetate 0.08
    transcutol 0.67
    n-heptanol 0.12
    ethylbenzene 0.07
    MIBK 0.14
    2-propoxyethanol 0.83
    tert-butanol 0.16
    MTBE 0.08
    2-butoxyethanol 0.56
    propionic acid 0.22
    o-xylene 0.13
    formic acid 8.19
    diethyl ether 0.06
    m-xylene 0.09
    p-xylene 0.1
    chlorobenzene 0.03
    dimethyl carbonate 0.32
    n-octane 0.03
    formamide 3.44
    cyclopentanone 0.72
    2-pentanone 0.14
    anisole 0.14
    cyclopentyl methyl ether 0.26
    gamma-butyrolactone 1.2
    1-methoxy-2-propanol 0.68
    pyridine 0.21
    3-pentanone 0.14
    furfural 3.06
    n-dodecane 0.01
    diethylene glycol 2.65
    diisopropyl ether 0.04
    tert-amyl alcohol 0.16
    acetylacetone 0.64
    n-hexadecane 0.01
    acetophenone 0.26
    methyl propionate 0.17
    isopentyl acetate 0.11
    trichloroethylene 0.12
    n-nonanol 0.07
    cyclohexanol 0.11
    benzyl alcohol 0.16
    2-ethylhexanol 0.11
    isooctanol 0.11
    dipropyl ether 0.14
    1,2-dichlorobenzene 0.06
    ethyl lactate 0.32
    propylene carbonate 0.7
    n-methylformamide 1.1
    2-pentanol 0.04
    n-pentane 0.02
    1-propoxy-2-propanol 0.48
    1-methoxy-2-propyl acetate 0.35
    2-(2-methoxypropoxy) propanol 0.86
    mesitylene 0.1
    ε-caprolactone 0.48
    p-cymene 0.1
    epichlorohydrin 0.39
    1,1,1-trichloroethane 0.06
    2-aminoethanol 0.68
    morpholine-4-carbaldehyde 5.22
    sulfolane 4.57
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 0.25
    n-hexyl acetate 0.09
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 0.76
    sec-butyl acetate 0.05
    tert-butyl acetate 0.18
    decalin 0.03
    glycerin 4.61
    diglyme 1.59
    acrylic acid 0.48
    isopropyl myristate 0.05
    n-butyric acid 0.21
    acetyl acetate 0.19
    di(2-ethylhexyl) phthalate 0.17
    ethyl propionate 0.11
    nitromethane 1.68
    1,2-diethoxyethane 0.13
    benzonitrile 0.12
    trioctyl phosphate 0.12
    1-bromopropane 0.02
    gamma-valerolactone 2.46
    n-decanol 0.06
    triethyl phosphate 0.26
    4-methyl-2-pentanol 0.06
    propionitrile 0.06
    vinylene carbonate 0.56
    1,1,2-trichlorotrifluoroethane 2.15
    DMS 0.16
    cumene 0.08
    2-octanol 0.07
    2-hexanone 0.1
    octyl acetate 0.07
    limonene 0.11
    1,2-dimethoxyethane 1.36
    ethyl orthosilicate 0.23
    tributyl phosphate 0.12
    diacetone alcohol 0.72
    N,N-dimethylaniline 0.29
    acrylonitrile 0.13
    aniline 0.1
    1,3-propanediol 0.47
    bromobenzene 0.03
    dibromomethane 0.05
    1,1,2,2-tetrachloroethane 0.14
    2-methyl-cyclohexyl acetate 0.17
    tetrabutyl urea 0.3
    diisobutyl methanol 0.12
    2-phenylethanol 0.2
    styrene 0.05
    dioctyl adipate 0.1
    dimethyl sulfate 1.53
    ethyl butyrate 0.15
    methyl lactate 0.76
    butyl lactate 0.26
    diethyl carbonate 0.12
    propanediol butyl ether 0.55
    triethyl orthoformate 0.21
    p-tert-butyltoluene 0.1
    methyl 4-tert-butylbenzoate 0.56
    morpholine 0.52
    tert-butylamine 0.07
    n-dodecanol 0.06
    dimethoxymethane 0.96
    ethylene carbonate 0.37
    cyrene 2.19
    2-ethoxyethyl acetate 0.14
    2-ethylhexyl acetate 0.09
    1,2,4-trichlorobenzene 0.08
    4-methylpyridine 0.23
    dibutyl ether 0.06
    2,6-dimethyl-4-heptanol 0.12
    DEF 0.62
    dimethyl isosorbide 1.86
    tetrachloroethylene 0.18
    eugenol 0.74
    triacetin 0.23
    span 80 0.57
    1,4-butanediol 0.28
    1,1-dichloroethane 0.03
    2-methyl-1-pentanol 0.07
    methyl formate 1.52
    2-methyl-1-butanol 0.06
    n-decane 0.02
    butyronitrile 0.06
    3,7-dimethyl-1-octanol 0.07
    1-chlorooctane 0.03
    1-chlorotetradecane 0.02
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.03
    cyclooctane 0.03
    cyclopentanol 0.17
    tetrahydropyran 0.12
    tert-amyl methyl ether 0.12
    2,5,8-trioxanonane 1.67
    1-hexene 0.04
    2-isopropoxyethanol 0.33
    2,2,2-trifluoroethanol 1.71
    methyl butyrate 0.18

    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