beta-D-Glucopyranose, 1,2,3,4-tetraacetate

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  • Identifiers

    CAS number
    13100-46-4

    Molecular formula
    C14H20O10

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 76.77%
    Clean 19.52%
    Sour 19.35%
    Alcoholic 18.78%
    Ethereal 18.69%
    Winey 17.19%
    Milky 16.99%
    Creamy 15.74%
    Burnt 15.71%
    Cooked 15.29%

     

    Flavor
    Fruity 61.99%
    Bitter 46.01%
    Odorless 34.7%
    Mild 32.31%
    Tropical 29.45%
    Sweet 27.69%
    Creamy 24.96%
    Grape 23.4%
    Very mild 22.58%
    Toffee 22.12%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.1

    pKa est.
    3.83 (weak acid)

    Molecular weight
    348.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    358°C

    Flash point

    • 199.91 ˚C est.

  • Synonyms

    • 13100-46-4
    • beta-D-Glucopyranose, 1,2,3,4-tetraacetate
    • 1,2,3,4-Tetra-O-acetylglucopyranose
    • 4AcOGlc
    • RefChem:71287
    • 236-018-2
    • 1,2,3,4-Tetra-O-acetyl-beta-D-glucopyranose
    • MFCD00063260
    • beta-d-glucose-2,3,4,5-tetraacetate
    • 1,2,3,4-Tetra-O-acetyl-|A-D-glucopyranose
    • 1,2,3,4-Tetra-O-acetyl-b-D-glucopyranose
    • beta-D-Glucose 1,2,3,4-tetraacetate
    • EINECS 236-018-2
    • 1,2,3,4-tetra-O-acetyl--d-glucopyranose
    • AI3-19572
    • |A-d-glucopyranose, 1,2,3,4-tetraacetate
    • (2S,3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
    • SCHEMBL314060
    • orb2941968
    • AKOS003628644
    • FS-5088
    • HY-W039854
    • MT05432
    • NSC 409250
    • 1,2,3,4-tetra-o-acetyl-beta-d-glucose
    • SY066505
    • |_-D-Glucopyranose, 1,2,3,4-tetraacetate
    • 1,2,3,4-Tetra-O-acetyl-?-D-glucopyranose
    • 1,2,3,4-Tetra-O-acetyl-ss-D-glucopyranose
    • B-D-GLUCOPYRANOSE,1,2,3,4-TETRAACETATE
    • 1,2,3,4-Tetra-O-acetyl- beta -D-glucopyranose
    • CS-002/03845062
    • F095602
    • 1,2,3,4-Tetra-O-acetyl-|A-D-glucopyranose, 96%
    • A1-01508
    • 1,2,3,4-Tetra-O-acetyl-beta-D-glucopyranose, 98%
    • 2,3,5-tris(acetyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl acetate
    • [(2R,3R,4S,5R,6S)-4,5,6-triacetoxy-2-(hydroxymethyl)tetrahydropyran-3-yl] acetate
    • 13100-46-4

  • Applications

    beta-D-Glucopyranose, 1,2,3,4-tetraacetate (13100-46-4) is mainly used as an intermediate and protecting group in carbohydrate synthesis. In carbohydrate chemistry, it protects simultaneously the OH groups on the glucose ring to enable subsequent glycosylation steps. It serves as a building block for preparing acetylated glycosides and other protected sugar derivatives used in pharmaceutical research and drug development. It is also employed as a precursor in polymer chemistry, where protected sugar units are incorporated into polymers or used to introduce sugar functionalities, with deprotection to unveil the sugar in the final material. Additionally, it is used in studies on glycosyl donor/acceptor synthesis in medicinal chemistry research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 45.54
    methanol 94.88
    isopropanol 22.69
    water 13.47
    ethyl acetate 33.47
    n-propanol 22.32
    acetone 99.63
    n-butanol 13.09
    acetonitrile 41.44
    DMF 383.05
    toluene 3.64
    isobutanol 11.42
    1,4-dioxane 64.14
    methyl acetate 62.98
    THF 113.45
    2-butanone 46.9
    n-pentanol 8.89
    sec-butanol 14.2
    n-hexane 0.75
    ethylene glycol 30.22
    NMP 585.08
    cyclohexane 0.89
    DMSO 805.93
    n-butyl acetate 18.8
    n-octanol 3.77
    chloroform 32.8
    n-propyl acetate 23.69
    acetic acid 195.79
    dichloromethane 62.27
    cyclohexanone 67.37
    propylene glycol 23.88
    isopropyl acetate 14.68
    DMAc 579.06
    2-ethoxyethanol 78.43
    isopentanol 8.59
    n-heptane 0.36
    ethyl formate 72.99
    1,2-dichloroethane 42.53
    n-hexanol 4.27
    2-methoxyethanol 161.81
    isobutyl acetate 8.78
    tetrachloromethane 4.29
    n-pentyl acetate 6.95
    transcutol 77.77
    n-heptanol 2.5
    ethylbenzene 3.43
    MIBK 10.16
    2-propoxyethanol 43.79
    tert-butanol 19.92
    MTBE 9.99
    2-butoxyethanol 20.34
    propionic acid 64.31
    o-xylene 4.36
    formic acid 284.87
    diethyl ether 12.7
    m-xylene 2.12
    p-xylene 5.34
    chlorobenzene 8.12
    dimethyl carbonate 52.97
    n-octane 0.21
    formamide 351.17
    cyclopentanone 120.05
    2-pentanone 24.98
    anisole 18.34
    cyclopentyl methyl ether 19.8
    gamma-butyrolactone 255.07
    1-methoxy-2-propanol 65.3
    pyridine 56.32
    3-pentanone 22.92
    furfural 254.55
    n-dodecane 0.22
    diethylene glycol 56.86
    diisopropyl ether 1.92
    tert-amyl alcohol 15.56
    acetylacetone 50.78
    n-hexadecane 0.25
    acetophenone 32.7
    methyl propionate 49.56
    isopentyl acetate 13.66
    trichloroethylene 67.22
    n-nonanol 3.79
    cyclohexanol 11.24
    benzyl alcohol 21.12
    2-ethylhexanol 3.19
    isooctanol 2.01
    dipropyl ether 7.56
    1,2-dichlorobenzene 11.92
    ethyl lactate 24.74
    propylene carbonate 108.65
    n-methylformamide 201.81
    2-pentanol 5.45
    n-pentane 0.53
    1-propoxy-2-propanol 23.93
    1-methoxy-2-propyl acetate 26.66
    2-(2-methoxypropoxy) propanol 39.41
    mesitylene 1.44
    ε-caprolactone 89.5
    p-cymene 2.18
    epichlorohydrin 152.94
    1,1,1-trichloroethane 15.71
    2-aminoethanol 38.06
    morpholine-4-carbaldehyde 321.35
    sulfolane 420.36
    2,2,4-trimethylpentane 0.31
    2-methyltetrahydrofuran 47.17
    n-hexyl acetate 9.99
    isooctane 0.11
    2-(2-butoxyethoxy)ethanol 34.39
    sec-butyl acetate 10.83
    tert-butyl acetate 13.18
    decalin 0.68
    glycerin 71.78
    diglyme 83.14
    acrylic acid 87.74
    isopropyl myristate 4.31
    n-butyric acid 46.56
    acetyl acetate 30.45
    di(2-ethylhexyl) phthalate 10.17
    ethyl propionate 27.42
    nitromethane 371.76
    1,2-diethoxyethane 17.55
    benzonitrile 18.74
    trioctyl phosphate 5.47
    1-bromopropane 10.13
    gamma-valerolactone 254.81
    n-decanol 2.76
    triethyl phosphate 21.2
    4-methyl-2-pentanol 2.61
    propionitrile 19.97
    vinylene carbonate 108.97
    1,1,2-trichlorotrifluoroethane 160.01
    DMS 25.63
    cumene 2.52
    2-octanol 1.64
    2-hexanone 17.7
    octyl acetate 6.36
    limonene 3.07
    1,2-dimethoxyethane 136.54
    ethyl orthosilicate 15.84
    tributyl phosphate 9.82
    diacetone alcohol 26.49
    N,N-dimethylaniline 18.32
    acrylonitrile 41.06
    aniline 14.29
    1,3-propanediol 48.38
    bromobenzene 6.12
    dibromomethane 28.12
    1,1,2,2-tetrachloroethane 50.91
    2-methyl-cyclohexyl acetate 15.72
    tetrabutyl urea 17.73
    diisobutyl methanol 1.96
    2-phenylethanol 9.41
    styrene 4.22
    dioctyl adipate 12.53
    dimethyl sulfate 163.2
    ethyl butyrate 20.51
    methyl lactate 53.82
    butyl lactate 12.49
    diethyl carbonate 20.55
    propanediol butyl ether 18.37
    triethyl orthoformate 17.36
    p-tert-butyltoluene 1.88
    methyl 4-tert-butylbenzoate 22.65
    morpholine 86.78
    tert-butylamine 7.04
    n-dodecanol 2.06
    dimethoxymethane 113.87
    ethylene carbonate 79.68
    cyrene 62.81
    2-ethoxyethyl acetate 16.36
    2-ethylhexyl acetate 11.06
    1,2,4-trichlorobenzene 20.03
    4-methylpyridine 49.75
    dibutyl ether 5.27
    2,6-dimethyl-4-heptanol 1.96
    DEF 82.79
    dimethyl isosorbide 65.2
    tetrachloroethylene 31.6
    eugenol 20.59
    triacetin 25.53
    span 80 18.6
    1,4-butanediol 18.42
    1,1-dichloroethane 18.53
    2-methyl-1-pentanol 7.2
    methyl formate 181.67
    2-methyl-1-butanol 9.95
    n-decane 0.37
    butyronitrile 14.88
    3,7-dimethyl-1-octanol 3.38
    1-chlorooctane 1.74
    1-chlorotetradecane 0.8
    n-nonane 0.32
    undecane 0.28
    tert-butylcyclohexane 0.44
    cyclooctane 0.26
    cyclopentanol 21.1
    tetrahydropyran 25.65
    tert-amyl methyl ether 9.63
    2,5,8-trioxanonane 63.85
    1-hexene 2.51
    2-isopropoxyethanol 33.62
    2,2,2-trifluoroethanol 123.91
    methyl butyrate 41.05

    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