{4-[(3-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]phenyl}acetonitrile

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  • Identifiers

    CAS number
    159397-73-6

    Molecular formula
    C16H19NO6

    SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)CC#N)O)OC(=O)C)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 46.96%
    Sweet 35.34%
    Vanilla 31.35%
    Floral 30.81%
    Milky 21.13%
    Powdery 20.99%
    Spicy 20.91%
    Creamy 19.89%
    Bitter 17.65%
    Balsamic 17.37%

     

    Flavor
    Bitter 73.24%
    Odorless 31.25%
    Mild 25.45%
    Fruity 24.69%
    Bland 23.18%
    Sweet 21.88%
    Sweet-like 21.66%
    Orange blossom 19.56%
    Orange flower 19.49%
    Parsley 18.96%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    6.33 (neutral)

    Molecular weight
    321.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    683°C

    Flash point

    • 189.46 ˚C est.

  • Synonyms

    • DTXSID601167520
    • {4-[(3-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]phenyl}acetonitrile
    • 4-[(3-O-Acetyl-6-deoxy-I+/--L-mannopyranosyl)oxy]benzeneacetonitrile
    • 159397-73-6
    • 159397-73-6

  • Applications

    The compound {4-[(3-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]phenyl}acetonitrile (CAS 159397-73-6) is typically used as a protected glycosylated aryl building block in organic synthesis. In pharmaceutical and medicinal chemistry, it serves as an intermediate for the preparation of glycosylated aromatic compounds and glycoconjugates, enabling exploration of structure–activity relationships. As a protected sugar donor, it supports carbohydrate-chemistry workflows such as selective deprotection and subsequent glycosylation to access oligosaccharide analogs. In chemical biology and materials science, it may be employed as a starting material for glycosylated probes or as a monomeric precursor in the synthesis of sugar-containing polymers or functional materials with increased hydrophilicity. Additionally, it can function as a synthetic intermediate for proteoglycan mimetics and other glycoconjugate architectures in research settings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 22.55
    methanol 67.55
    isopropanol 8.67
    water 8.53
    ethyl acetate 16.3
    n-propanol 11.65
    acetone 91.08
    n-butanol 7.24
    acetonitrile 31.28
    DMF 207.67
    toluene 2.69
    isobutanol 5.88
    1,4-dioxane 45.59
    methyl acetate 21.52
    THF 92.48
    2-butanone 22.79
    n-pentanol 7.99
    sec-butanol 5.52
    n-hexane 0.17
    ethylene glycol 44.73
    NMP 112.42
    cyclohexane 0.48
    DMSO 877.05
    n-butyl acetate 6.18
    n-octanol 6.44
    chloroform 12.83
    n-propyl acetate 10.74
    acetic acid 119.07
    dichloromethane 21.18
    cyclohexanone 42.76
    propylene glycol 20.78
    isopropyl acetate 8.38
    DMAc 259.15
    2-ethoxyethanol 58.16
    isopentanol 5.88
    n-heptane 0.37
    ethyl formate 22.23
    1,2-dichloroethane 17.48
    n-hexanol 5.37
    2-methoxyethanol 95.86
    isobutyl acetate 5.91
    tetrachloromethane 1.49
    n-pentyl acetate 5.66
    transcutol 71.64
    n-heptanol 5.74
    ethylbenzene 2.13
    MIBK 8.91
    2-propoxyethanol 34.87
    tert-butanol 8.67
    MTBE 2.82
    2-butoxyethanol 22.06
    propionic acid 22.39
    o-xylene 2.41
    formic acid 193.05
    diethyl ether 5.43
    m-xylene 1.98
    p-xylene 3.13
    chlorobenzene 4.83
    dimethyl carbonate 25.65
    n-octane 0.31
    formamide 205.71
    cyclopentanone 67.88
    2-pentanone 16.54
    anisole 10.07
    cyclopentyl methyl ether 12.06
    gamma-butyrolactone 85.68
    1-methoxy-2-propanol 42.22
    pyridine 27.23
    3-pentanone 12.36
    furfural 75.6
    n-dodecane 0.37
    diethylene glycol 63.76
    diisopropyl ether 1.24
    tert-amyl alcohol 5.68
    acetylacetone 44.6
    n-hexadecane 0.42
    acetophenone 17.69
    methyl propionate 19.83
    isopentyl acetate 6.39
    trichloroethylene 27.58
    n-nonanol 6.85
    cyclohexanol 7.45
    benzyl alcohol 16.02
    2-ethylhexanol 3.64
    isooctanol 4.67
    dipropyl ether 4.75
    1,2-dichlorobenzene 5.61
    ethyl lactate 17.13
    propylene carbonate 32.04
    n-methylformamide 83.74
    2-pentanol 2.91
    n-pentane 0.13
    1-propoxy-2-propanol 17.7
    1-methoxy-2-propyl acetate 15.06
    2-(2-methoxypropoxy) propanol 28.06
    mesitylene 1.45
    ε-caprolactone 30.59
    p-cymene 2.02
    epichlorohydrin 64.83
    1,1,1-trichloroethane 5.88
    2-aminoethanol 34.1
    morpholine-4-carbaldehyde 101.11
    sulfolane 151.3
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 18.81
    n-hexyl acetate 8.87
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 34.23
    sec-butyl acetate 5.61
    tert-butyl acetate 8.51
    decalin 0.32
    glycerin 58.96
    diglyme 68.18
    acrylic acid 36.63
    isopropyl myristate 5.08
    n-butyric acid 20.78
    acetyl acetate 20.84
    di(2-ethylhexyl) phthalate 9.19
    ethyl propionate 10.33
    nitromethane 192.9
    1,2-diethoxyethane 14.06
    benzonitrile 13.81
    trioctyl phosphate 6.43
    1-bromopropane 3.67
    gamma-valerolactone 94.13
    n-decanol 5.33
    triethyl phosphate 8.2
    4-methyl-2-pentanol 2.5
    propionitrile 12.57
    vinylene carbonate 31.36
    1,1,2-trichlorotrifluoroethane 74.09
    DMS 13.97
    cumene 1.66
    2-octanol 3.27
    2-hexanone 11.44
    octyl acetate 7.32
    limonene 2.62
    1,2-dimethoxyethane 69.29
    ethyl orthosilicate 6.95
    tributyl phosphate 7.11
    diacetone alcohol 21.13
    N,N-dimethylaniline 8.73
    acrylonitrile 24.62
    aniline 8.3
    1,3-propanediol 34.44
    bromobenzene 3.67
    dibromomethane 9.81
    1,1,2,2-tetrachloroethane 21.26
    2-methyl-cyclohexyl acetate 9.65
    tetrabutyl urea 13.12
    diisobutyl methanol 2.52
    2-phenylethanol 11.59
    styrene 2.5
    dioctyl adipate 11.93
    dimethyl sulfate 61.67
    ethyl butyrate 8.38
    methyl lactate 31.95
    butyl lactate 9.98
    diethyl carbonate 8.12
    propanediol butyl ether 20.69
    triethyl orthoformate 8.17
    p-tert-butyltoluene 1.73
    methyl 4-tert-butylbenzoate 17.66
    morpholine 46.1
    tert-butylamine 2.46
    n-dodecanol 4.09
    dimethoxymethane 75.65
    ethylene carbonate 25.88
    cyrene 41.91
    2-ethoxyethyl acetate 12.69
    2-ethylhexyl acetate 4.63
    1,2,4-trichlorobenzene 7.78
    4-methylpyridine 18.4
    dibutyl ether 4.83
    2,6-dimethyl-4-heptanol 2.52
    DEF 32.3
    dimethyl isosorbide 40.81
    tetrachloroethylene 13.96
    eugenol 20.63
    triacetin 20.6
    span 80 19.34
    1,4-butanediol 21.0
    1,1-dichloroethane 6.73
    2-methyl-1-pentanol 6.22
    methyl formate 82.96
    2-methyl-1-butanol 5.1
    n-decane 0.57
    butyronitrile 10.23
    3,7-dimethyl-1-octanol 4.99
    1-chlorooctane 2.36
    1-chlorotetradecane 1.22
    n-nonane 0.47
    undecane 0.45
    tert-butylcyclohexane 0.22
    cyclooctane 0.21
    cyclopentanol 12.4
    tetrahydropyran 16.21
    tert-amyl methyl ether 3.26
    2,5,8-trioxanonane 58.38
    1-hexene 0.91
    2-isopropoxyethanol 27.87
    2,2,2-trifluoroethanol 56.75
    methyl butyrate 14.92

    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