DL-Cycloserine

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  • Identifiers

    CAS number
    68-39-3

    Molecular formula
    C3H6N2O2

    SMILES
    C1C(C(=O)NO1)N

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 71.83%
    Sweet 23.85%
    Fishy 23.31%
    Burnt 20.67%
    Popcorn 19.89%
    Caramellic 19.52%
    Nutty 19.07%
    Roasted 16.77%
    Savory 16.05%
    Malty 13.43%

     

    Flavor
    Bitter 67.19%
    Odorless 25.85%
    Roasted 23.84%
    Sweet-like 21.4%
    Alkaline 20.47%
    Shrimp 19.99%
    Taco 19.97%
    Bouillon 19.71%
    Bread crust 19.64%
    Nitrile 19.5%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.5

    pKa est.
    5.77 (weak acid)

    Molecular weight
    102.09 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    277°C

    Flash point

    • 137.52 ˚C est.

  • Synonyms

    • DL-Cycloserine
    • 4-Aminoisoxazolidin-3-one
    • 68-39-3
    • 4-Amino-3-isoxazolidinone
    • 4-amino-1,2-oxazolidin-3-one
    • rac Cycloserine
    • 3-Isoxazolidinone, 4-amino-
    • DL-4-Aminoisoxazolidin-3-one
    • (+-)-4-Amino-3-isoxazolidinone
    • 4-Amino-3-isoxazolidone
    • C3H6N2O2
    • DTXSID40859074
    • 3-Isoxazolidinone, d-
    • 3-Isoxazolidinone, (R)-
    • 3-Isoxazolidinone, (+)-
    • WLN: T5OMVJ DZ -D
    • Cycloserine, D-
    • .alpha.-Cycloserine
    • NSC154851
    • (+-)-Oxamicina [Italian]
    • (+-)-Oxamicina
    • DL-4-Amino-3-isoxazolidinone
    • EINECS 200-687-9
    • (+-)-4-Amino-3-isossazolidone [Italian]
    • AI3-61058
    • (+-)-4-Amino-3-isossazolidone
    • 3-ISOXAZOLIDINONE, 4-AMINO-, (+-)-
    • Cycloserine, DL-
    • MFCD00064323
    • 3-Isoxazolidinone,4-amino-, (4R)-
    • 4-amino-4,5-dihydro-1,2-oxazol-3-ol
    • DL-Cycloserine crystalline
    • LS6CN6T9ND
    • 4-Amino-isoxazolidin-3-on
    • DL-Cycloserine, crystalline
    • 4-Amino-isoxazolidin-3-one
    • Lopac0_000267
    • SCHEMBL34323
    • 4-amino-2-isoxazoline-3-ol
    • 4-Amino-3-isoxazolidinone #
    • CHEBI:23503
    • CHEBI:27792
    • DTXCID10209224
    • HMS3260F16
    • HMS3370D10
    • HMS3374E09
    • HMS3393C15
    • Pharmakon1600-01506178
    • BCP22967
    • BCP22968
    • NSC76029
    • DL-4-amino-1,2-oxazolidin-3-one
    • Tox21_500267
    • (+/-)-3-Oxoisooxazolidin-4-amine
    • BBL016489
    • NSC760409
    • STK177281
    • STL454326
    • AKOS005410669
    • CCG-204362
    • CS-W008440
    • FR27495
    • LP00267
    • SB23044
    • SDCCGSBI-0050255.P002
    • NCGC00015213-04
    • NCGC00015213-05
    • NCGC00015213-06
    • NCGC00015213-07
    • NCGC00015213-08
    • NCGC00015213-11
    • NCGC00093725-01
    • NCGC00093725-02
    • NCGC00093725-03
    • NCGC00093725-04
    • NCGC00260952-01
    • BP-20174
    • DS-18396
    • SY005636
    • DB-055147
    • DB-055151
    • DB-068913
    • D-Cycloserine; D-4-Amino-3-isoxazolidinone
    • EU-0100267
    • NS00078925
    • NS00079493
    • C 7005
    • C06682
    • EN300-118713
    • SR-01000075776
    • SR-01000075776-1
    • Q27109800
    • Z336087816
    • Cycloserine; Seromycin; Orientomycin; Oxamycin; Seromycin
    • (S)-4-Amino-3-isoxazolidone; (S)-Cycloserine;Levcycloserine
    • 4-Amino-3-isoxazolidinone;(+/-)-3-Oxoisooxazolidin-4-amine;DL-Cycloserine
    • 200-687-9

  • Applications

    DL-Cycloserine is primarily used as a second-line antibiotic for treating drug-resistant tuberculosis, and it is also employed as a research tool in neuroscience and pharmacology to study NMDA receptor function due to its activity at the glycine site. It serves as a chiral building block and synthetic intermediate for the preparation of cycloserine-related pharmaceuticals and other amino acid–derived compounds in medicinal chemistry workflows. In pharmaceutical development and manufacturing, DL-Cycloserine may be used in formulation development, process research, and analytical/quality-control applications, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.67
    methanol 34.8
    isopropanol 1.81
    water 880.19
    ethyl acetate 0.47
    n-propanol 2.24
    acetone 1.6
    n-butanol 1.87
    acetonitrile 2.12
    DMF 41.55
    toluene 0.19
    isobutanol 1.35
    1,4-dioxane 1.71
    methyl acetate 0.57
    THF 2.06
    2-butanone 0.72
    n-pentanol 0.87
    sec-butanol 1.07
    n-hexane 0.05
    ethylene glycol 22.89
    NMP 28.24
    cyclohexane 0.14
    DMSO 45.7
    n-butyl acetate 0.27
    n-octanol 0.33
    chloroform 0.62
    n-propyl acetate 0.29
    acetic acid 44.41
    dichloromethane 0.83
    cyclohexanone 1.73
    propylene glycol 9.48
    isopropyl acetate 0.33
    DMAc 21.33
    2-ethoxyethanol 6.71
    isopentanol 1.39
    n-heptane 0.1
    ethyl formate 2.63
    1,2-dichloroethane 0.49
    n-hexanol 0.53
    2-methoxyethanol 21.97
    isobutyl acetate 0.17
    tetrachloromethane 0.34
    n-pentyl acetate 0.35
    transcutol 10.02
    n-heptanol 0.59
    ethylbenzene 0.12
    MIBK 0.52
    2-propoxyethanol 2.87
    tert-butanol 1.45
    MTBE 0.32
    2-butoxyethanol 3.23
    propionic acid 3.52
    o-xylene 0.32
    formic acid 353.74
    diethyl ether 0.35
    m-xylene 0.23
    p-xylene 0.21
    chlorobenzene 0.18
    dimethyl carbonate 1.13
    n-octane 0.05
    formamide 211.41
    cyclopentanone 2.51
    2-pentanone 0.66
    anisole 0.37
    cyclopentyl methyl ether 0.73
    gamma-butyrolactone 4.15
    1-methoxy-2-propanol 7.28
    pyridine 1.63
    3-pentanone 0.52
    furfural 12.32
    n-dodecane 0.03
    diethylene glycol 9.97
    diisopropyl ether 0.13
    tert-amyl alcohol 1.25
    acetylacetone 1.32
    n-hexadecane 0.03
    acetophenone 0.75
    methyl propionate 0.72
    isopentyl acetate 0.3
    trichloroethylene 0.99
    n-nonanol 0.34
    cyclohexanol 0.96
    benzyl alcohol 1.11
    2-ethylhexanol 0.32
    isooctanol 0.5
    dipropyl ether 0.29
    1,2-dichlorobenzene 0.25
    ethyl lactate 1.07
    propylene carbonate 2.31
    n-methylformamide 28.61
    2-pentanol 0.68
    n-pentane 0.08
    1-propoxy-2-propanol 1.51
    1-methoxy-2-propyl acetate 0.68
    2-(2-methoxypropoxy) propanol 3.26
    mesitylene 0.2
    ε-caprolactone 1.91
    p-cymene 0.2
    epichlorohydrin 2.15
    1,1,1-trichloroethane 0.25
    2-aminoethanol 21.11
    morpholine-4-carbaldehyde 19.25
    sulfolane 13.25
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 0.85
    n-hexyl acetate 0.35
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 4.53
    sec-butyl acetate 0.17
    tert-butyl acetate 0.4
    decalin 0.05
    glycerin 37.58
    diglyme 8.22
    acrylic acid 8.16
    isopropyl myristate 0.17
    n-butyric acid 3.58
    acetyl acetate 0.69
    di(2-ethylhexyl) phthalate 0.65
    ethyl propionate 0.28
    nitromethane 26.67
    1,2-diethoxyethane 0.62
    benzonitrile 0.75
    trioctyl phosphate 0.36
    1-bromopropane 0.18
    gamma-valerolactone 8.59
    n-decanol 0.26
    triethyl phosphate 0.45
    4-methyl-2-pentanol 0.45
    propionitrile 0.82
    vinylene carbonate 2.85
    1,1,2-trichlorotrifluoroethane 9.88
    DMS 0.45
    cumene 0.13
    2-octanol 0.28
    2-hexanone 0.34
    octyl acetate 0.26
    limonene 0.24
    1,2-dimethoxyethane 4.46
    ethyl orthosilicate 0.43
    tributyl phosphate 0.39
    diacetone alcohol 1.9
    N,N-dimethylaniline 0.61
    acrylonitrile 1.94
    aniline 0.76
    1,3-propanediol 15.32
    bromobenzene 0.13
    dibromomethane 0.42
    1,1,2,2-tetrachloroethane 0.76
    2-methyl-cyclohexyl acetate 0.39
    tetrabutyl urea 0.82
    diisobutyl methanol 0.27
    2-phenylethanol 0.71
    styrene 0.12
    dioctyl adipate 0.39
    dimethyl sulfate 3.73
    ethyl butyrate 0.39
    methyl lactate 3.33
    butyl lactate 1.08
    diethyl carbonate 0.3
    propanediol butyl ether 4.06
    triethyl orthoformate 0.46
    p-tert-butyltoluene 0.18
    methyl 4-tert-butylbenzoate 1.56
    morpholine 3.15
    tert-butylamine 0.57
    n-dodecanol 0.19
    dimethoxymethane 4.03
    ethylene carbonate 1.61
    cyrene 6.46
    2-ethoxyethyl acetate 0.73
    2-ethylhexyl acetate 0.23
    1,2,4-trichlorobenzene 0.31
    4-methylpyridine 1.21
    dibutyl ether 0.22
    2,6-dimethyl-4-heptanol 0.27
    DEF 3.06
    dimethyl isosorbide 3.6
    tetrachloroethylene 0.99
    eugenol 2.33
    triacetin 0.95
    span 80 2.54
    1,4-butanediol 5.29
    1,1-dichloroethane 0.23
    2-methyl-1-pentanol 0.78
    methyl formate 14.88
    2-methyl-1-butanol 1.35
    n-decane 0.05
    butyronitrile 0.99
    3,7-dimethyl-1-octanol 0.33
    1-chlorooctane 0.09
    1-chlorotetradecane 0.05
    n-nonane 0.04
    undecane 0.03
    tert-butylcyclohexane 0.03
    cyclooctane 0.07
    cyclopentanol 1.41
    tetrahydropyran 0.64
    tert-amyl methyl ether 0.38
    2,5,8-trioxanonane 6.52
    1-hexene 0.1
    2-isopropoxyethanol 2.26
    2,2,2-trifluoroethanol 25.72
    methyl butyrate 0.57

    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