4-[(2S)-2-Carboxyazetidin-1-yl]-N-[(3S)-3-carboxy-3-hydroxypropyl]-D-threonine

Overview IFRA Request a quote

  • Identifiers

    CAS number
    74281-81-5

    Molecular formula
    C12H20N2O8

    SMILES
    C1CN([C@@H]1C(=O)O)C[C@@H]([C@H](C(=O)O)NCC[C@@H](C(=O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 72.32%
    Sweet 40.31%
    Savory 30.91%
    Alcoholic 19.15%
    Cooling 19.14%
    Milky 18.38%
    Fishy 17.43%
    Buttery 16.65%
    Meaty 15.95%
    Bitter 15.17%

     

    Flavor
    Odorless 68.71%
    Bitter 50.32%
    Bland 35.76%
    Mild 29.8%
    Very mild 29.46%
    Sweet-like 26.57%
    Yeast 22.41%
    Faint 19.8%
    Nitrile 19.17%
    Oriental 18.71%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -6.7

    pKa est.
    5.3 (weak acid)

    Molecular weight
    320.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    577°C

    Flash point

    • 299.21 ˚C est.

  • Synonyms

    • DTXSID501116055
    • 4-[(2S)-2-Carboxyazetidin-1-yl]-N-[(3S)-3-carboxy-3-hydroxypropyl]-D-threonine
    • (I+/-R,I(2)S,2S)-2-Carboxy-I+/--[[(3S)-3-carboxy-3-hydroxypropyl]amino]-I(2)-hydroxy-1-azetidinebutanoic acid
    • 74281-81-5
    • 74281-81-5

  • Applications

    Chemical name: 4-[(2S)-2-Carboxyazetidin-1-yl]-N-[(3S)-3-carboxy-3-hydroxypropyl]-D-threonine; CAS number: 74281-81-5. This non-natural amino acid derivative is used as a building block in medicinal chemistry for peptidomimetics and constrained peptides, enabling conformational control in drug discovery. It also serves as an intermediate for synthesizing azetidine-containing amino acid derivatives and related structural scaffolds for drug development research, and may be employed as a non-natural amino acid building block in solid-phase peptide synthesis and library construction.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.65
    methanol 3.18
    isopropanol 0.42
    water 324.36
    ethyl acetate 0.64
    n-propanol 0.51
    acetone 0.83
    n-butanol 0.49
    acetonitrile 0.31
    DMF 34.48
    toluene 0.46
    isobutanol 0.36
    1,4-dioxane 1.34
    methyl acetate 0.31
    THF 1.54
    2-butanone 0.52
    n-pentanol 0.34
    sec-butanol 0.45
    n-hexane 0.16
    ethylene glycol 27.26
    NMP 62.25
    cyclohexane 0.37
    DMSO 115.08
    n-butyl acetate 0.3
    n-octanol 0.22
    chloroform 0.11
    n-propyl acetate 0.24
    acetic acid 6.35
    dichloromethane 0.19
    cyclohexanone 2.3
    propylene glycol 10.28
    isopropyl acetate 0.46
    DMAc 37.15
    2-ethoxyethanol 4.97
    isopentanol 0.48
    n-heptane 0.32
    ethyl formate 0.63
    1,2-dichloroethane 0.31
    n-hexanol 0.62
    2-methoxyethanol 16.3
    isobutyl acetate 0.09
    tetrachloromethane 0.1
    n-pentyl acetate 0.22
    transcutol 4.55
    n-heptanol 0.49
    ethylbenzene 0.26
    MIBK 0.63
    2-propoxyethanol 4.86
    tert-butanol 0.77
    MTBE 0.21
    2-butoxyethanol 2.04
    propionic acid 1.84
    o-xylene 0.83
    formic acid 111.12
    diethyl ether 0.33
    m-xylene 0.6
    p-xylene 0.29
    chlorobenzene 0.09
    dimethyl carbonate 2.15
    n-octane 0.14
    formamide 69.22
    cyclopentanone 2.42
    2-pentanone 1.02
    anisole 0.29
    cyclopentyl methyl ether 1.46
    gamma-butyrolactone 3.86
    1-methoxy-2-propanol 9.67
    pyridine 0.94
    3-pentanone 1.08
    furfural 5.6
    n-dodecane 0.05
    diethylene glycol 18.39
    diisopropyl ether 0.23
    tert-amyl alcohol 0.82
    acetylacetone 2.54
    n-hexadecane 0.05
    acetophenone 0.75
    methyl propionate 1.46
    isopentyl acetate 0.23
    trichloroethylene 0.35
    n-nonanol 0.25
    cyclohexanol 1.58
    benzyl alcohol 0.78
    2-ethylhexanol 0.41
    isooctanol 0.33
    dipropyl ether 0.63
    1,2-dichlorobenzene 0.13
    ethyl lactate 1.51
    propylene carbonate 1.24
    n-methylformamide 11.1
    2-pentanol 0.55
    n-pentane 0.16
    1-propoxy-2-propanol 2.5
    1-methoxy-2-propyl acetate 1.3
    2-(2-methoxypropoxy) propanol 2.11
    mesitylene 0.48
    ε-caprolactone 1.99
    p-cymene 0.29
    epichlorohydrin 1.27
    1,1,1-trichloroethane 0.09
    2-aminoethanol 11.75
    morpholine-4-carbaldehyde 24.97
    sulfolane 28.7
    2,2,4-trimethylpentane 0.08
    2-methyltetrahydrofuran 0.72
    n-hexyl acetate 0.22
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 2.82
    sec-butyl acetate 0.18
    tert-butyl acetate 0.54
    decalin 0.11
    glycerin 75.11
    diglyme 4.09
    acrylic acid 4.4
    isopropyl myristate 0.13
    n-butyric acid 1.5
    acetyl acetate 0.52
    di(2-ethylhexyl) phthalate 0.25
    ethyl propionate 0.46
    nitromethane 6.12
    1,2-diethoxyethane 0.48
    benzonitrile 0.27
    trioctyl phosphate 0.27
    1-bromopropane 0.13
    gamma-valerolactone 8.95
    n-decanol 0.22
    triethyl phosphate 0.48
    4-methyl-2-pentanol 0.37
    propionitrile 0.25
    vinylene carbonate 1.26
    1,1,2-trichlorotrifluoroethane 9.63
    DMS 0.58
    cumene 0.21
    2-octanol 0.26
    2-hexanone 0.29
    octyl acetate 0.19
    limonene 0.43
    1,2-dimethoxyethane 2.6
    ethyl orthosilicate 0.42
    tributyl phosphate 0.23
    diacetone alcohol 3.31
    N,N-dimethylaniline 0.65
    acrylonitrile 0.61
    aniline 0.88
    1,3-propanediol 6.63
    bromobenzene 0.08
    dibromomethane 0.13
    1,1,2,2-tetrachloroethane 0.5
    2-methyl-cyclohexyl acetate 0.35
    tetrabutyl urea 0.64
    diisobutyl methanol 0.34
    2-phenylethanol 0.69
    styrene 0.18
    dioctyl adipate 0.21
    dimethyl sulfate 9.18
    ethyl butyrate 0.4
    methyl lactate 8.1
    butyl lactate 0.75
    diethyl carbonate 0.23
    propanediol butyl ether 2.33
    triethyl orthoformate 0.47
    p-tert-butyltoluene 0.27
    methyl 4-tert-butylbenzoate 1.18
    morpholine 2.29
    tert-butylamine 0.35
    n-dodecanol 0.19
    dimethoxymethane 6.58
    ethylene carbonate 0.9
    cyrene 7.44
    2-ethoxyethyl acetate 0.43
    2-ethylhexyl acetate 0.2
    1,2,4-trichlorobenzene 0.17
    4-methylpyridine 0.71
    dibutyl ether 0.17
    2,6-dimethyl-4-heptanol 0.34
    DEF 4.54
    dimethyl isosorbide 3.69
    tetrachloroethylene 0.61
    eugenol 1.48
    triacetin 0.58
    span 80 1.91
    1,4-butanediol 2.91
    1,1-dichloroethane 0.09
    2-methyl-1-pentanol 0.32
    methyl formate 5.67
    2-methyl-1-butanol 0.49
    n-decane 0.09
    butyronitrile 0.21
    3,7-dimethyl-1-octanol 0.19
    1-chlorooctane 0.11
    1-chlorotetradecane 0.06
    n-nonane 0.1
    undecane 0.06
    tert-butylcyclohexane 0.06
    cyclooctane 0.29
    cyclopentanol 1.37
    tetrahydropyran 0.58
    tert-amyl methyl ether 0.48
    2,5,8-trioxanonane 4.28
    1-hexene 0.18
    2-isopropoxyethanol 1.73
    2,2,2-trifluoroethanol 8.4
    methyl butyrate 0.54

    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