N-acetyl-9-O-lactoylneuraminic acid

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  • Identifiers

    CAS number
    92935-30-3

    Molecular formula
    C14H23NO11

    SMILES
    CC(C(=O)OC[C@H]([C@H]([C@H]1[C@@H]([C@H](C[C@](O1)(C(=O)O)O)O)NC(=O)C)O)O)O

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  • Odor profile

    Fragrance
    Odorless 68.93%
    Sweet 42.77%
    Buttery 28.89%
    Savory 28.38%
    Caramellic 26.05%
    Milky 25.85%
    Creamy 18.83%
    Dairy 16.72%
    Meaty 15.98%
    Lactonic 15.04%

     

    Flavor
    Odorless 61.17%
    Very mild 35.75%
    Bitter 34.32%
    Bland 29.12%
    Sweet-like 28.41%
    Mild 23.53%
    Yeast 20.79%
    Very slight 19.72%
    Toffee 18.8%
    Cotton candy 18.69%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -3.1

    pKa est.
    4.17 (weak acid)

    Molecular weight
    381.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2670°C

    Flash point

    • 286.36 ˚C est.

  • Synonyms

    • N-Acetyl-9-O-lactoylneuraminic acid
    • Neu5Ac9Lt
    • 9-O-Lactoyl-N-acetylneuraminic acid
    • (2S,4S,5R,6R)-6-((1R,2R)-1,2-dihydroxy-3-((2-hydroxypropanoyl)oxy)propyl)-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
    • (2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
    • RefChem:108050
    • 92935-30-3
    • (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-(2-hydroxypropanoyloxy)propyl]-2,4-dihydroxyoxane-2-carboxylic acid
    • Neu5,8Ac29
    • SCHEMBL8662575
    • N-Acetyl-9-O-lactoylneuraminate
    • DTXSID30918861
    • CHEBI:165243
    • NS00126781
    • 5-(acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate
    • 5-(acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoic acid
    • 5-(acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-Nonulosonate
    • 5-(acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-Nonulosonic acid
    • 3,5-Dideoxy-5-[(1-hydroxyethylidene)amino]-9-O-(2-hydroxypropanoyl)non-2-ulopyranosonic acid
    • 5-Acetamido-3,5-dideoxy-9-O-(2-hydroxypropanoyl)-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
    • 92935-30-3

  • Applications

    N-acetyl-9-O-lactoylneuraminic acid (CAS 92935-30-3) is commonly used as a building block and intermediate for the synthesis of sialic acid-containing glycoconjugates and oligosaccharides in pharmaceutical and biotech research; it may also serve as a substrate or standard for enzymes such as neuraminidases and sialyltransferases in biochemical and enzymology studies. In analytical chemistry, it is used as a reference material for glycan analysis by HPLC/LC-MS. In polymer science, it can be used as a functional carbohydrate monomer unit or precursor for carbohydrate-based polymers. In organic synthesis, it functions as an intermediate for the preparation of sialylated compounds or glycoconjugates to support drug discovery and glyco-related materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.93
    methanol 44.53
    isopropanol 2.83
    water 196.05
    ethyl acetate 1.06
    n-propanol 3.43
    acetone 6.97
    n-butanol 1.93
    acetonitrile 1.42
    DMF 229.78
    toluene 0.38
    isobutanol 1.31
    1,4-dioxane 10.17
    methyl acetate 1.33
    THF 8.48
    2-butanone 1.98
    n-pentanol 1.09
    sec-butanol 1.74
    n-hexane 0.13
    ethylene glycol 78.08
    NMP 110.3
    cyclohexane 0.32
    DMSO 506.54
    n-butyl acetate 0.39
    n-octanol 0.78
    chloroform 0.23
    n-propyl acetate 0.47
    acetic acid 35.35
    dichloromethane 0.54
    cyclohexanone 4.05
    propylene glycol 32.62
    isopropyl acetate 0.67
    DMAc 112.21
    2-ethoxyethanol 24.82
    isopentanol 1.13
    n-heptane 0.21
    ethyl formate 3.14
    1,2-dichloroethane 0.69
    n-hexanol 0.81
    2-methoxyethanol 93.95
    isobutyl acetate 0.17
    tetrachloromethane 0.14
    n-pentyl acetate 0.43
    transcutol 16.7
    n-heptanol 0.9
    ethylbenzene 0.22
    MIBK 0.87
    2-propoxyethanol 9.68
    tert-butanol 2.63
    MTBE 0.63
    2-butoxyethanol 5.23
    propionic acid 4.39
    o-xylene 0.53
    formic acid 311.53
    diethyl ether 1.24
    m-xylene 0.31
    p-xylene 0.24
    chlorobenzene 0.11
    dimethyl carbonate 5.58
    n-octane 0.13
    formamide 225.6
    cyclopentanone 6.44
    2-pentanone 1.96
    anisole 0.75
    cyclopentyl methyl ether 2.51
    gamma-butyrolactone 9.4
    1-methoxy-2-propanol 30.41
    pyridine 2.69
    3-pentanone 1.5
    furfural 15.26
    n-dodecane 0.06
    diethylene glycol 34.92
    diisopropyl ether 0.27
    tert-amyl alcohol 1.86
    acetylacetone 5.14
    n-hexadecane 0.07
    acetophenone 1.27
    methyl propionate 2.55
    isopentyl acetate 0.28
    trichloroethylene 0.78
    n-nonanol 0.79
    cyclohexanol 2.33
    benzyl alcohol 1.62
    2-ethylhexanol 0.39
    isooctanol 0.52
    dipropyl ether 1.03
    1,2-dichlorobenzene 0.16
    ethyl lactate 2.41
    propylene carbonate 2.54
    n-methylformamide 62.54
    2-pentanol 1.02
    n-pentane 0.16
    1-propoxy-2-propanol 4.23
    1-methoxy-2-propyl acetate 1.87
    2-(2-methoxypropoxy) propanol 5.41
    mesitylene 0.23
    ε-caprolactone 3.4
    p-cymene 0.17
    epichlorohydrin 4.65
    1,1,1-trichloroethane 0.13
    2-aminoethanol 47.19
    morpholine-4-carbaldehyde 80.47
    sulfolane 50.66
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 2.3
    n-hexyl acetate 0.57
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 8.42
    sec-butyl acetate 0.26
    tert-butyl acetate 0.8
    decalin 0.08
    glycerin 142.71
    diglyme 17.18
    acrylic acid 9.57
    isopropyl myristate 0.26
    n-butyric acid 3.14
    acetyl acetate 0.97
    di(2-ethylhexyl) phthalate 0.53
    ethyl propionate 0.68
    nitromethane 36.23
    1,2-diethoxyethane 1.74
    benzonitrile 0.47
    trioctyl phosphate 0.47
    1-bromopropane 0.24
    gamma-valerolactone 28.49
    n-decanol 0.6
    triethyl phosphate 0.65
    4-methyl-2-pentanol 0.44
    propionitrile 0.71
    vinylene carbonate 2.67
    1,1,2-trichlorotrifluoroethane 20.38
    DMS 1.03
    cumene 0.16
    2-octanol 0.5
    2-hexanone 0.67
    octyl acetate 0.46
    limonene 0.29
    1,2-dimethoxyethane 19.7
    ethyl orthosilicate 0.58
    tributyl phosphate 0.39
    diacetone alcohol 5.03
    N,N-dimethylaniline 1.16
    acrylonitrile 1.68
    aniline 1.29
    1,3-propanediol 32.34
    bromobenzene 0.08
    dibromomethane 0.25
    1,1,2,2-tetrachloroethane 0.96
    2-methyl-cyclohexyl acetate 0.45
    tetrabutyl urea 1.24
    diisobutyl methanol 0.27
    2-phenylethanol 0.93
    styrene 0.2
    dioctyl adipate 0.57
    dimethyl sulfate 20.86
    ethyl butyrate 0.53
    methyl lactate 13.64
    butyl lactate 1.24
    diethyl carbonate 0.38
    propanediol butyl ether 6.75
    triethyl orthoformate 0.79
    p-tert-butyltoluene 0.17
    methyl 4-tert-butylbenzoate 1.89
    morpholine 14.87
    tert-butylamine 0.75
    n-dodecanol 0.45
    dimethoxymethane 38.44
    ethylene carbonate 1.86
    cyrene 13.2
    2-ethoxyethyl acetate 1.12
    2-ethylhexyl acetate 0.22
    1,2,4-trichlorobenzene 0.25
    4-methylpyridine 1.71
    dibutyl ether 0.5
    2,6-dimethyl-4-heptanol 0.27
    DEF 10.0
    dimethyl isosorbide 6.79
    tetrachloroethylene 0.99
    eugenol 2.66
    triacetin 1.44
    span 80 3.7
    1,4-butanediol 10.44
    1,1-dichloroethane 0.18
    2-methyl-1-pentanol 0.67
    methyl formate 36.73
    2-methyl-1-butanol 1.2
    n-decane 0.13
    butyronitrile 0.54
    3,7-dimethyl-1-octanol 0.36
    1-chlorooctane 0.21
    1-chlorotetradecane 0.09
    n-nonane 0.13
    undecane 0.09
    tert-butylcyclohexane 0.04
    cyclooctane 0.16
    cyclopentanol 3.17
    tetrahydropyran 2.39
    tert-amyl methyl ether 0.88
    2,5,8-trioxanonane 13.97
    1-hexene 0.23
    2-isopropoxyethanol 6.55
    2,2,2-trifluoroethanol 19.24
    methyl butyrate 1.04

    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