N-acetyl-9-O-acetylneuraminic acid

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  • Identifiers

    CAS number
    55717-54-9

    Molecular formula
    C13H21NO10

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 73.47%
    Sweet 34.11%
    Savory 27.27%
    Milky 24.35%
    Buttery 22.68%
    Caramellic 19.83%
    Meaty 17.41%
    Cooling 16.92%
    Creamy 16.52%
    Roasted 15.7%

     

    Flavor
    Odorless 57.96%
    Bitter 38.58%
    Very mild 33.42%
    Bland 27.52%
    Sweet-like 26.95%
    Mild 25.41%
    Yeast 20.59%
    Very slight 19.82%
    Toffee 19.39%
    Cotton candy 19.19%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.9

    pKa est.
    4.45 (weak acid)

    Molecular weight
    351.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1998°C

    Flash point

    • 275.21 ˚C est.

  • Synonyms

    • N-Acetyl-9-O-acetylneuraminic acid
    • 9-Anana
    • 55717-54-9
    • 9-O-Acetylsialic acid
    • 9-O-acetyl-N-acetylneuraminic acid
    • D-glycero-D-galacto-2-Nonulosonic acid, 5-(acetylamino)-3,5-dideoxy-, 9-acetate
    • (2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
    • CHEBI:21500
    • (2S,4S,5R,6R)-6-((1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl)-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
    • RefChem:162567
    • GlyTouCan:G53320FT
    • G53320FT
    • (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-3-acetyloxy-1,2-dihydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid
    • (2S,4S,5R,6R)-5-Acetamido-6-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)-2,4-dihydroxytetrahydro-2H-pyran-2-carboxylic acid
    • 81228-99-1
    • C13H21NO10
    • 5-n-acetyl-9-o-acetyl neuraminic acid
    • SCHEMBL420656
    • 9-O-Acetyl-N-acetylneuraminate
    • DTXSID40971088
    • (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-3-acetyloxy-1,2-dihydroxypropyl]-2,4-dihydroxy-2-oxanecarboxylic acid
    • 9-O-Acetyl-N-acetyl-neuraminic acid
    • MA12117
    • NS00123936
    • H37747
    • Q27109402
    • 5-acetamido-9-O-acetyl-3,5-dideoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
    • 9-O-Acetyl-3,5-dideoxy-5-[(1-hydroxyethylidene)amino]non-2-ulopyranosonic acid
    • (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-3-acetoxy-1,2-dihydroxy-propyl]-2,4-dihydroxy-tetrahydropyran-2-carboxylic acid
    • 55717-54-9

  • Applications

    N-acetyl-9-O-acetylneuraminic acid (CAS 55717-54-9) is primarily used as an intermediate for the synthesis of sialic acid–containing glycoconjugates in pharmaceutical research and glycomics; it serves as a substrate or reference standard in enzymatic assays of sialidases and sialyltransferases; it functions as a building block for glycopolymers and other carbohydrate-functionalized materials in polymer science; it may be pursued as a precursor in neuraminidase inhibitor research and related preclinical exploration; and it is used as a reference standard for analytical methods (HPLC/LC-MS) to quantify sialic acids in biological samples.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.35
    methanol 30.87
    isopropanol 2.08
    water 99.36
    ethyl acetate 0.67
    n-propanol 2.66
    acetone 4.35
    n-butanol 1.29
    acetonitrile 0.96
    DMF 180.15
    toluene 0.24
    isobutanol 1.02
    1,4-dioxane 8.63
    methyl acetate 1.05
    THF 9.03
    2-butanone 1.45
    n-pentanol 0.89
    sec-butanol 1.37
    n-hexane 0.12
    ethylene glycol 45.69
    NMP 96.36
    cyclohexane 0.22
    DMSO 351.93
    n-butyl acetate 0.35
    n-octanol 0.61
    chloroform 0.19
    n-propyl acetate 0.44
    acetic acid 20.0
    dichloromethane 0.4
    cyclohexanone 3.48
    propylene glycol 19.45
    isopropyl acetate 0.42
    DMAc 98.02
    2-ethoxyethanol 20.61
    isopentanol 0.83
    n-heptane 0.15
    ethyl formate 2.67
    1,2-dichloroethane 0.54
    n-hexanol 0.63
    2-methoxyethanol 67.15
    isobutyl acetate 0.16
    tetrachloromethane 0.12
    n-pentyl acetate 0.32
    transcutol 10.94
    n-heptanol 0.66
    ethylbenzene 0.2
    MIBK 0.62
    2-propoxyethanol 8.13
    tert-butanol 2.26
    MTBE 0.48
    2-butoxyethanol 4.3
    propionic acid 3.16
    o-xylene 0.38
    formic acid 201.22
    diethyl ether 0.89
    m-xylene 0.21
    p-xylene 0.25
    chlorobenzene 0.08
    dimethyl carbonate 3.88
    n-octane 0.09
    formamide 151.37
    cyclopentanone 6.09
    2-pentanone 1.19
    anisole 0.71
    cyclopentyl methyl ether 2.03
    gamma-butyrolactone 9.08
    1-methoxy-2-propanol 21.12
    pyridine 2.2
    3-pentanone 1.01
    furfural 13.79
    n-dodecane 0.05
    diethylene glycol 25.76
    diisopropyl ether 0.18
    tert-amyl alcohol 1.57
    acetylacetone 3.19
    n-hexadecane 0.05
    acetophenone 1.14
    methyl propionate 1.82
    isopentyl acetate 0.27
    trichloroethylene 0.56
    n-nonanol 0.63
    cyclohexanol 1.64
    benzyl alcohol 1.4
    2-ethylhexanol 0.33
    isooctanol 0.42
    dipropyl ether 0.84
    1,2-dichlorobenzene 0.13
    ethyl lactate 2.12
    propylene carbonate 2.48
    n-methylformamide 50.87
    2-pentanol 0.68
    n-pentane 0.11
    1-propoxy-2-propanol 3.45
    1-methoxy-2-propyl acetate 1.44
    2-(2-methoxypropoxy) propanol 4.95
    mesitylene 0.17
    ε-caprolactone 3.19
    p-cymene 0.14
    epichlorohydrin 4.22
    1,1,1-trichloroethane 0.1
    2-aminoethanol 30.38
    morpholine-4-carbaldehyde 63.8
    sulfolane 43.82
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 2.15
    n-hexyl acetate 0.46
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 6.79
    sec-butyl acetate 0.22
    tert-butyl acetate 0.6
    decalin 0.07
    glycerin 84.2
    diglyme 13.89
    acrylic acid 6.31
    isopropyl myristate 0.22
    n-butyric acid 1.93
    acetyl acetate 0.6
    di(2-ethylhexyl) phthalate 0.5
    ethyl propionate 0.59
    nitromethane 24.99
    1,2-diethoxyethane 1.27
    benzonitrile 0.44
    trioctyl phosphate 0.41
    1-bromopropane 0.18
    gamma-valerolactone 24.71
    n-decanol 0.47
    triethyl phosphate 0.68
    4-methyl-2-pentanol 0.34
    propionitrile 0.57
    vinylene carbonate 2.49
    1,1,2-trichlorotrifluoroethane 15.9
    DMS 0.8
    cumene 0.15
    2-octanol 0.37
    2-hexanone 0.63
    octyl acetate 0.36
    limonene 0.23
    1,2-dimethoxyethane 19.96
    ethyl orthosilicate 0.61
    tributyl phosphate 0.4
    diacetone alcohol 3.89
    N,N-dimethylaniline 1.09
    acrylonitrile 1.34
    aniline 0.88
    1,3-propanediol 21.05
    bromobenzene 0.06
    dibromomethane 0.2
    1,1,2,2-tetrachloroethane 0.71
    2-methyl-cyclohexyl acetate 0.48
    tetrabutyl urea 1.16
    diisobutyl methanol 0.23
    2-phenylethanol 0.82
    styrene 0.17
    dioctyl adipate 0.51
    dimethyl sulfate 14.45
    ethyl butyrate 0.53
    methyl lactate 9.06
    butyl lactate 1.0
    diethyl carbonate 0.4
    propanediol butyl ether 4.66
    triethyl orthoformate 0.77
    p-tert-butyltoluene 0.14
    methyl 4-tert-butylbenzoate 1.65
    morpholine 12.4
    tert-butylamine 0.65
    n-dodecanol 0.35
    dimethoxymethane 27.91
    ethylene carbonate 1.8
    cyrene 12.7
    2-ethoxyethyl acetate 0.77
    2-ethylhexyl acetate 0.22
    1,2,4-trichlorobenzene 0.2
    4-methylpyridine 1.41
    dibutyl ether 0.42
    2,6-dimethyl-4-heptanol 0.23
    DEF 7.63
    dimethyl isosorbide 6.97
    tetrachloroethylene 0.74
    eugenol 2.37
    triacetin 1.11
    span 80 2.9
    1,4-butanediol 7.64
    1,1-dichloroethane 0.13
    2-methyl-1-pentanol 0.57
    methyl formate 30.23
    2-methyl-1-butanol 0.89
    n-decane 0.1
    butyronitrile 0.43
    3,7-dimethyl-1-octanol 0.32
    1-chlorooctane 0.16
    1-chlorotetradecane 0.07
    n-nonane 0.1
    undecane 0.07
    tert-butylcyclohexane 0.04
    cyclooctane 0.1
    cyclopentanol 2.57
    tetrahydropyran 2.08
    tert-amyl methyl ether 0.69
    2,5,8-trioxanonane 11.74
    1-hexene 0.22
    2-isopropoxyethanol 5.44
    2,2,2-trifluoroethanol 12.88
    methyl butyrate 1.0

    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