1,2:3,5-Di-O-isopropylidene-alpha-D-apiose

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  • Identifiers

    CAS number
    25904-06-7

    Molecular formula
    C11H18O5

    SMILES
    CC1(OCC2(O1)COC3C2OC(O3)(C)C)C

    Safety labels

  • Odor profile

    Fragrance
    Fruity 58.6%
    Woody 39.09%
    Green 37.46%
    Sweet 28.81%
    Fresh 27.82%
    Ethereal 23.15%
    Fatty 22.36%
    Earthy 21.92%
    Herbal 21.69%
    Tropical 21.03%

     

    Flavor
    Green 63.34%
    Earthy 51.91%
    Vegetable 43.94%
    Potato 28.33%
    Raw 27.68%
    Earth 26.38%
    Nutty 24.91%
    Pepper 23.41%
    Musty 23.39%
    Metallic 23.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    7.26 (neutral)

    Molecular weight
    230.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    270°C

    Flash point

    • 100.62 ˚C est.

  • Synonyms

    • 25904-06-7
    • 1,2:3,5-Di-O-isopropylidene-alpha-D-apiose
    • 1,2:3,5-Di-O-isopropylidene-|A-D-apiose
    • 2,3-O-Isopropylidene-D-apiose
    • D-Apio-a-D-furanose, 1,2:3,5-bis-O-(1-methylethylidene)-
    • 94943-41-6
    • orb2939445
    • HY-W145653
    • CS-0226082
    • D-Apio-|A-D-furanose, 1,2:3,5-bis-O-(1-methylethylidene)-
    • 25904-06-7

  • Applications

    Chemical name: 1,2:3,5-Di-O-isopropylidene-alpha-D-apiose; CAS number: 25904-06-7. It serves primarily as a protected sugar building block in organic synthesis. It is commonly used as an intermediate and as a glycosyl donor/acceptor for the construction of oligosaccharides and glycosides, enabling selective installation of apiose units in drug discovery and natural product synthesis. In pharmaceutical research, it provides a protected apiose framework for elaboration toward sugar-containing drug candidates and bioactive glycosides. In polymer and materials chemistry, it supports the preparation of carbohydrate-functionalized polymers and glycosylated materials. In agrochemical research, it is employed to assemble sugar-bearing scaffolds used in bioactive molecule development. Its role is confined to synthetic chemistry, with handling governed by protecting-group strategies and regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 579.74
    methanol 1084.92
    isopropanol 462.05
    water 220.27
    ethyl acetate 771.41
    n-propanol 449.49
    acetone 1046.34
    n-butanol 362.0
    acetonitrile 871.07
    DMF 2117.69
    toluene 303.86
    isobutanol 330.85
    1,4-dioxane 1018.02
    methyl acetate 903.61
    THF 1291.41
    2-butanone 667.47
    n-pentanol 222.4
    sec-butanol 352.7
    n-hexane 30.15
    ethylene glycol 414.44
    NMP 1607.81
    cyclohexane 59.69
    DMSO 1365.01
    n-butyl acetate 288.89
    n-octanol 160.02
    chloroform 2666.61
    n-propyl acetate 410.92
    acetic acid 1627.58
    dichloromethane 2021.45
    cyclohexanone 785.36
    propylene glycol 367.4
    isopropyl acetate 456.52
    DMAc 1984.44
    2-ethoxyethanol 697.62
    isopentanol 273.12
    n-heptane 20.06
    ethyl formate 872.34
    1,2-dichloroethane 927.72
    n-hexanol 182.86
    2-methoxyethanol 1402.64
    isobutyl acetate 284.74
    tetrachloromethane 414.38
    n-pentyl acetate 219.75
    transcutol 733.81
    n-heptanol 120.38
    ethylbenzene 143.84
    MIBK 297.77
    2-propoxyethanol 664.24
    tert-butanol 409.79
    MTBE 324.73
    2-butoxyethanol 372.94
    propionic acid 817.39
    o-xylene 198.6
    formic acid 1678.28
    diethyl ether 401.98
    m-xylene 209.9
    p-xylene 219.93
    chlorobenzene 475.97
    dimethyl carbonate 708.14
    n-octane 12.83
    formamide 1637.61
    cyclopentanone 1070.6
    2-pentanone 499.58
    anisole 381.87
    cyclopentyl methyl ether 528.59
    gamma-butyrolactone 1800.22
    1-methoxy-2-propanol 894.47
    pyridine 865.9
    3-pentanone 441.05
    furfural 1692.24
    n-dodecane 17.4
    diethylene glycol 710.23
    diisopropyl ether 133.29
    tert-amyl alcohol 311.46
    acetylacetone 868.83
    n-hexadecane 19.75
    acetophenone 438.59
    methyl propionate 744.37
    isopentyl acetate 264.3
    trichloroethylene 2115.81
    n-nonanol 146.09
    cyclohexanol 355.49
    benzyl alcohol 357.0
    2-ethylhexanol 111.5
    isooctanol 101.12
    dipropyl ether 151.91
    1,2-dichlorobenzene 492.05
    ethyl lactate 355.85
    propylene carbonate 1079.91
    n-methylformamide 1449.13
    2-pentanol 229.98
    n-pentane 34.07
    1-propoxy-2-propanol 332.62
    1-methoxy-2-propyl acetate 458.64
    2-(2-methoxypropoxy) propanol 323.32
    mesitylene 127.65
    ε-caprolactone 922.85
    p-cymene 88.12
    epichlorohydrin 1537.32
    1,1,1-trichloroethane 921.42
    2-aminoethanol 496.85
    morpholine-4-carbaldehyde 1617.73
    sulfolane 1275.66
    2,2,4-trimethylpentane 24.55
    2-methyltetrahydrofuran 756.07
    n-hexyl acetate 336.52
    isooctane 17.18
    2-(2-butoxyethoxy)ethanol 376.58
    sec-butyl acetate 299.54
    tert-butyl acetate 366.29
    decalin 36.14
    glycerin 742.75
    diglyme 828.46
    acrylic acid 973.07
    isopropyl myristate 133.64
    n-butyric acid 814.58
    acetyl acetate 793.01
    di(2-ethylhexyl) phthalate 143.86
    ethyl propionate 467.03
    nitromethane 3215.38
    1,2-diethoxyethane 252.6
    benzonitrile 448.82
    trioctyl phosphate 107.71
    1-bromopropane 404.56
    gamma-valerolactone 1794.31
    n-decanol 104.94
    triethyl phosphate 197.82
    4-methyl-2-pentanol 143.45
    propionitrile 535.67
    vinylene carbonate 1271.87
    1,1,2-trichlorotrifluoroethane 1501.05
    DMS 470.51
    cumene 104.56
    2-octanol 90.82
    2-hexanone 270.67
    octyl acetate 170.48
    limonene 105.56
    1,2-dimethoxyethane 1051.84
    ethyl orthosilicate 175.95
    tributyl phosphate 140.02
    diacetone alcohol 393.0
    N,N-dimethylaniline 250.67
    acrylonitrile 830.59
    aniline 384.83
    1,3-propanediol 630.3
    bromobenzene 476.98
    dibromomethane 1118.89
    1,1,2,2-tetrachloroethane 1502.99
    2-methyl-cyclohexyl acetate 221.45
    tetrabutyl urea 173.5
    diisobutyl methanol 74.98
    2-phenylethanol 245.53
    styrene 180.42
    dioctyl adipate 190.29
    dimethyl sulfate 1153.59
    ethyl butyrate 259.32
    methyl lactate 576.62
    butyl lactate 216.64
    diethyl carbonate 249.23
    propanediol butyl ether 298.41
    triethyl orthoformate 225.01
    p-tert-butyltoluene 90.62
    methyl 4-tert-butylbenzoate 299.15
    morpholine 1042.18
    tert-butylamine 228.39
    n-dodecanol 80.75
    dimethoxymethane 1252.16
    ethylene carbonate 995.72
    cyrene 403.22
    2-ethoxyethyl acetate 334.18
    2-ethylhexyl acetate 222.69
    1,2,4-trichlorobenzene 591.87
    4-methylpyridine 798.13
    dibutyl ether 142.72
    2,6-dimethyl-4-heptanol 74.98
    DEF 743.3
    dimethyl isosorbide 524.13
    tetrachloroethylene 1007.89
    eugenol 281.3
    triacetin 442.73
    span 80 236.02
    1,4-butanediol 248.65
    1,1-dichloroethane 910.31
    2-methyl-1-pentanol 179.32
    methyl formate 1408.49
    2-methyl-1-butanol 279.96
    n-decane 26.69
    butyronitrile 447.34
    3,7-dimethyl-1-octanol 135.13
    1-chlorooctane 105.78
    1-chlorotetradecane 48.56
    n-nonane 23.36
    undecane 20.84
    tert-butylcyclohexane 31.21
    cyclooctane 24.39
    cyclopentanol 465.54
    tetrahydropyran 634.46
    tert-amyl methyl ether 266.06
    2,5,8-trioxanonane 547.07
    1-hexene 92.67
    2-isopropoxyethanol 403.55
    2,2,2-trifluoroethanol 1205.78
    methyl butyrate 539.9

    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