N-Acetyl-4-O-acetylneuraminic acid

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  • Identifiers

    CAS number
    16655-75-7

    Molecular formula
    C13H21NO10

    SMILES
    CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)OC(=O)C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 74.89%
    Sweet 31.58%
    Savory 27.8%
    Milky 23.95%
    Buttery 21.71%
    Caramellic 18.56%
    Meaty 17.83%
    Cooling 17.32%
    Creamy 15.88%
    Roasted 15.8%

     

    Flavor
    Odorless 60.04%
    Bitter 35.1%
    Very mild 33.78%
    Bland 27.59%
    Sweet-like 26.9%
    Mild 25.22%
    Yeast 20.59%
    Very slight 19.7%
    Toffee 19.08%
    Cotton candy 18.94%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.9

    pKa est.
    4.4 (weak acid)

    Molecular weight
    351.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1560°C

    Flash point

    • 285.75 ˚C est.

  • Synonyms

    • N-acetyl-4-O-acetylneuraminic acid
    • 16655-75-7
    • 4-O-Acetyl-N-acetylneuraminic acid
    • (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
    • CHEBI:32844
    • (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
    • RefChem:927002
    • GlyTouCan:G14558QS
    • G14558QS
    • (2S,4S,5R,6R)-5-Acetamido-4-acetoxy-2-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
    • SCHEMBL2932173
    • DTXSID50937216
    • NS00123317
    • Q27104239
    • 4-O-Acetyl-3,5-dideoxy-5-[(1-hydroxyethylidene)amino]non-2-ulopyranosonic acid
    • 5-acetamido-4-O-acetyl-3,5-dideoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
    • (2S,4S,5R,6R)-5-acetamido-4-acetoxy-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid
    • 16655-75-7

  • Applications

    N-Acetyl-4-O-acetylneuraminic acid (CAS 16655-75-7) is primarily used as a synthetic intermediate and building block in glycoconjugate chemistry, notably for the preparation of sialylated glycans and glycoproteins in pharmaceutical and biotech research. It serves as a key carbohydrate chemistry building block for library development and structure-activity studies of sialic acid-containing structures. In analytical contexts, it is employed as a reference material or reagent for glycobiology assays and for calibrating chromatography and mass spectrometry workflows. It is also used as a precursor in chemoenzymatic routes to neuraminic acid derivatives and related glycoconjugates, supporting enzymatic synthesis and glycan-focused diagnostics and biomarker research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.58
    methanol 86.21
    isopropanol 3.64
    water 174.22
    ethyl acetate 1.17
    n-propanol 5.34
    acetone 6.98
    n-butanol 2.11
    acetonitrile 1.51
    DMF 446.87
    toluene 0.33
    isobutanol 1.79
    1,4-dioxane 9.12
    methyl acetate 2.14
    THF 11.01
    2-butanone 2.41
    n-pentanol 1.09
    sec-butanol 2.14
    n-hexane 0.13
    ethylene glycol 114.59
    NMP 245.47
    cyclohexane 0.27
    DMSO 529.58
    n-butyl acetate 0.61
    n-octanol 0.66
    chloroform 0.41
    n-propyl acetate 0.64
    acetic acid 82.29
    dichloromethane 0.83
    cyclohexanone 5.18
    propylene glycol 51.19
    isopropyl acetate 0.7
    DMAc 186.4
    2-ethoxyethanol 30.3
    isopentanol 1.1
    n-heptane 0.16
    ethyl formate 6.15
    1,2-dichloroethane 0.96
    n-hexanol 0.88
    2-methoxyethanol 130.33
    isobutyl acetate 0.21
    tetrachloromethane 0.24
    n-pentyl acetate 0.51
    transcutol 20.27
    n-heptanol 0.77
    ethylbenzene 0.2
    MIBK 0.85
    2-propoxyethanol 13.28
    tert-butanol 3.5
    MTBE 0.71
    2-butoxyethanol 6.19
    propionic acid 10.72
    o-xylene 0.53
    formic acid 638.41
    diethyl ether 1.02
    m-xylene 0.27
    p-xylene 0.23
    chlorobenzene 0.14
    dimethyl carbonate 9.79
    n-octane 0.08
    formamide 475.42
    cyclopentanone 10.24
    2-pentanone 1.67
    anisole 0.86
    cyclopentyl methyl ether 2.83
    gamma-butyrolactone 20.41
    1-methoxy-2-propanol 40.21
    pyridine 3.59
    3-pentanone 1.61
    furfural 30.62
    n-dodecane 0.04
    diethylene glycol 46.15
    diisopropyl ether 0.21
    tert-amyl alcohol 2.52
    acetylacetone 4.96
    n-hexadecane 0.04
    acetophenone 1.57
    methyl propionate 3.68
    isopentyl acetate 0.44
    trichloroethylene 1.35
    n-nonanol 0.68
    cyclohexanol 2.23
    benzyl alcohol 1.87
    2-ethylhexanol 0.44
    isooctanol 0.48
    dipropyl ether 0.98
    1,2-dichlorobenzene 0.23
    ethyl lactate 3.94
    propylene carbonate 6.69
    n-methylformamide 153.44
    2-pentanol 0.92
    n-pentane 0.14
    1-propoxy-2-propanol 5.63
    1-methoxy-2-propyl acetate 2.57
    2-(2-methoxypropoxy) propanol 7.57
    mesitylene 0.22
    ε-caprolactone 5.71
    p-cymene 0.19
    epichlorohydrin 7.45
    1,1,1-trichloroethane 0.22
    2-aminoethanol 78.0
    morpholine-4-carbaldehyde 126.65
    sulfolane 90.47
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 2.75
    n-hexyl acetate 0.68
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 10.18
    sec-butyl acetate 0.31
    tert-butyl acetate 0.95
    decalin 0.08
    glycerin 212.13
    diglyme 20.92
    acrylic acid 23.69
    isopropyl myristate 0.27
    n-butyric acid 5.41
    acetyl acetate 1.28
    di(2-ethylhexyl) phthalate 0.84
    ethyl propionate 0.91
    nitromethane 73.34
    1,2-diethoxyethane 1.44
    benzonitrile 0.59
    trioctyl phosphate 0.68
    1-bromopropane 0.25
    gamma-valerolactone 45.97
    n-decanol 0.5
    triethyl phosphate 1.12
    4-methyl-2-pentanol 0.47
    propionitrile 0.89
    vinylene carbonate 7.0
    1,1,2-trichlorotrifluoroethane 38.77
    DMS 1.68
    cumene 0.16
    2-octanol 0.39
    2-hexanone 0.72
    octyl acetate 0.48
    limonene 0.33
    1,2-dimethoxyethane 25.94
    ethyl orthosilicate 0.92
    tributyl phosphate 0.7
    diacetone alcohol 6.0
    N,N-dimethylaniline 1.44
    acrylonitrile 2.64
    aniline 1.33
    1,3-propanediol 43.45
    bromobenzene 0.09
    dibromomethane 0.35
    1,1,2,2-tetrachloroethane 1.57
    2-methyl-cyclohexyl acetate 0.74
    tetrabutyl urea 1.77
    diisobutyl methanol 0.32
    2-phenylethanol 1.05
    styrene 0.19
    dioctyl adipate 0.78
    dimethyl sulfate 36.59
    ethyl butyrate 0.78
    methyl lactate 22.27
    butyl lactate 2.04
    diethyl carbonate 0.65
    propanediol butyl ether 8.55
    triethyl orthoformate 1.13
    p-tert-butyltoluene 0.2
    methyl 4-tert-butylbenzoate 2.75
    morpholine 16.6
    tert-butylamine 0.99
    n-dodecanol 0.37
    dimethoxymethane 50.55
    ethylene carbonate 4.4
    cyrene 21.81
    2-ethoxyethyl acetate 1.4
    2-ethylhexyl acetate 0.34
    1,2,4-trichlorobenzene 0.39
    4-methylpyridine 2.12
    dibutyl ether 0.38
    2,6-dimethyl-4-heptanol 0.32
    DEF 13.85
    dimethyl isosorbide 11.07
    tetrachloroethylene 1.64
    eugenol 3.87
    triacetin 2.16
    span 80 5.15
    1,4-butanediol 12.82
    1,1-dichloroethane 0.24
    2-methyl-1-pentanol 0.7
    methyl formate 90.02
    2-methyl-1-butanol 1.4
    n-decane 0.08
    butyronitrile 0.61
    3,7-dimethyl-1-octanol 0.4
    1-chlorooctane 0.15
    1-chlorotetradecane 0.07
    n-nonane 0.08
    undecane 0.06
    tert-butylcyclohexane 0.04
    cyclooctane 0.12
    cyclopentanol 3.8
    tetrahydropyran 2.14
    tert-amyl methyl ether 0.98
    2,5,8-trioxanonane 16.65
    1-hexene 0.21
    2-isopropoxyethanol 7.07
    2,2,2-trifluoroethanol 43.51
    methyl butyrate 1.66

    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