(alphaR)-alpha-((6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile

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  • Identifiers

    CAS number
    1392-28-5

    Molecular formula
    C19H25NO10

    SMILES
    C1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H](C#N)C3=CC=CC=C3)O)O)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 56.18%
    Sweet 53.14%
    Vanilla 26.62%
    Bitter 23.18%
    Spicy 22.67%
    Woody 21.76%
    Powdery 17.67%
    Balsamic 17.63%
    Warm 17.41%
    Caramellic 17.07%

     

    Flavor
    Bitter 71.26%
    Odorless 37.63%
    Sweet-like 28.24%
    Bland 26.68%
    Sweet 25.9%
    Cedarleaf 19.4%
    Alkaline 19.35%
    Very slight 19.24%
    Cauliflower 19.1%
    Naphthalic 19.02%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.6

    pKa est.
    4.3 (weak acid)

    Molecular weight
    427.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3145°C

    Flash point

    • 254.61 ˚C est.

  • Synonyms

    • Lucumin
    • Lucumine
    • 1392-28-5
    • CHEBI:6559
    • (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
    • (2R)-phenyl{[6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranosyl]oxy}acetonitrile
    • (2R)-phenyl((6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranosyl)oxy)acetonitrile
    • (2R)-2-phenyl-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxymethyl)oxan-2-yl)oxyacetonitrile
    • RefChem:1050790
    • (alphaR)-alpha-((6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile
    • Mandelonitrile primeveroside
    • Benzeneacetonitrile, alpha-((6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy)-, (R)-
    • orb1696185
    • SCHEMBL20973857
    • DTXSID40930392
    • AKOS040752924
    • (R)-mandelonitrile-beta-D-primeveroside
    • C08335
    • Q27107242
    • [(6-O-Pentopyranosylhexopyranosyl)oxy](phenyl)acetonitrile
    • (2R)-Phenyl[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]acetonitrile
    • Benzeneacetonitrile,alpha-((6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy)-,(R)-
    • 1392-28-5

  • Applications

    For the compound (alphaR)-alpha-((6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile (CAS 1392-28-5), potential applications include its use as an intermediate in the synthesis of glycosyl aryl derivatives for pharmaceutical research; as a building block in medicinal chemistry SAR studies; as a solubility-enhancing component in cosmetics and personal care formulations; as a model substrate in carbohydrate chemistry and enzymology studies; and as a precursor for specialty dyes or coatings in materials research. Its use is typically governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.7
    methanol 16.75
    isopropanol 1.31
    water 28.89
    ethyl acetate 1.05
    n-propanol 1.97
    acetone 3.66
    n-butanol 1.47
    acetonitrile 1.83
    DMF 41.18
    toluene 0.42
    isobutanol 0.62
    1,4-dioxane 3.6
    methyl acetate 1.1
    THF 5.09
    2-butanone 1.39
    n-pentanol 0.61
    sec-butanol 0.8
    n-hexane 0.03
    ethylene glycol 23.33
    NMP 35.75
    cyclohexane 0.12
    DMSO 155.47
    n-butyl acetate 0.34
    n-octanol 0.79
    chloroform 0.46
    n-propyl acetate 0.37
    acetic acid 27.35
    dichloromethane 0.63
    cyclohexanone 2.7
    propylene glycol 10.98
    isopropyl acetate 0.6
    DMAc 32.1
    2-ethoxyethanol 9.16
    isopentanol 0.56
    n-heptane 0.12
    ethyl formate 1.67
    1,2-dichloroethane 0.58
    n-hexanol 0.54
    2-methoxyethanol 28.59
    isobutyl acetate 0.15
    tetrachloromethane 0.12
    n-pentyl acetate 0.63
    transcutol 17.77
    n-heptanol 1.03
    ethylbenzene 0.14
    MIBK 0.64
    2-propoxyethanol 5.84
    tert-butanol 0.7
    MTBE 0.25
    2-butoxyethanol 5.0
    propionic acid 3.69
    o-xylene 0.37
    formic acid 111.43
    diethyl ether 0.68
    m-xylene 0.31
    p-xylene 0.14
    chlorobenzene 0.19
    dimethyl carbonate 4.03
    n-octane 0.08
    formamide 87.17
    cyclopentanone 5.19
    2-pentanone 1.59
    anisole 0.52
    cyclopentyl methyl ether 1.78
    gamma-butyrolactone 7.54
    1-methoxy-2-propanol 13.27
    pyridine 2.78
    3-pentanone 1.13
    furfural 10.35
    n-dodecane 0.05
    diethylene glycol 16.67
    diisopropyl ether 0.16
    tert-amyl alcohol 0.56
    acetylacetone 3.97
    n-hexadecane 0.05
    acetophenone 1.1
    methyl propionate 2.2
    isopentyl acetate 0.26
    trichloroethylene 1.07
    n-nonanol 0.81
    cyclohexanol 1.23
    benzyl alcohol 1.31
    2-ethylhexanol 0.28
    isooctanol 0.59
    dipropyl ether 0.65
    1,2-dichlorobenzene 0.2
    ethyl lactate 2.07
    propylene carbonate 2.45
    n-methylformamide 20.38
    2-pentanol 0.6
    n-pentane 0.06
    1-propoxy-2-propanol 3.25
    1-methoxy-2-propyl acetate 1.88
    2-(2-methoxypropoxy) propanol 4.58
    mesitylene 0.19
    ε-caprolactone 2.7
    p-cymene 0.18
    epichlorohydrin 3.91
    1,1,1-trichloroethane 0.17
    2-aminoethanol 14.47
    morpholine-4-carbaldehyde 29.16
    sulfolane 28.12
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 1.42
    n-hexyl acetate 0.74
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 7.27
    sec-butyl acetate 0.22
    tert-butyl acetate 0.57
    decalin 0.03
    glycerin 41.11
    diglyme 12.32
    acrylic acid 8.82
    isopropyl myristate 0.32
    n-butyric acid 3.03
    acetyl acetate 1.27
    di(2-ethylhexyl) phthalate 0.69
    ethyl propionate 0.51
    nitromethane 30.09
    1,2-diethoxyethane 1.45
    benzonitrile 0.62
    trioctyl phosphate 0.57
    1-bromopropane 0.22
    gamma-valerolactone 15.02
    n-decanol 0.58
    triethyl phosphate 0.59
    4-methyl-2-pentanol 0.26
    propionitrile 0.74
    vinylene carbonate 3.03
    1,1,2-trichlorotrifluoroethane 13.9
    DMS 1.24
    cumene 0.09
    2-octanol 0.5
    2-hexanone 0.42
    octyl acetate 0.61
    limonene 0.29
    1,2-dimethoxyethane 4.96
    ethyl orthosilicate 0.49
    tributyl phosphate 0.44
    diacetone alcohol 2.98
    N,N-dimethylaniline 0.61
    acrylonitrile 1.99
    aniline 1.25
    1,3-propanediol 12.35
    bromobenzene 0.13
    dibromomethane 0.31
    1,1,2,2-tetrachloroethane 0.99
    2-methyl-cyclohexyl acetate 0.44
    tetrabutyl urea 1.02
    diisobutyl methanol 0.21
    2-phenylethanol 0.92
    styrene 0.16
    dioctyl adipate 0.85
    dimethyl sulfate 12.33
    ethyl butyrate 0.53
    methyl lactate 9.67
    butyl lactate 1.81
    diethyl carbonate 0.43
    propanediol butyl ether 6.83
    triethyl orthoformate 0.68
    p-tert-butyltoluene 0.19
    methyl 4-tert-butylbenzoate 2.52
    morpholine 6.4
    tert-butylamine 0.22
    n-dodecanol 0.41
    dimethoxymethane 12.37
    ethylene carbonate 1.83
    cyrene 8.28
    2-ethoxyethyl acetate 1.7
    2-ethylhexyl acetate 0.2
    1,2,4-trichlorobenzene 0.34
    4-methylpyridine 1.35
    dibutyl ether 0.39
    2,6-dimethyl-4-heptanol 0.21
    DEF 4.33
    dimethyl isosorbide 6.39
    tetrachloroethylene 0.83
    eugenol 3.09
    triacetin 2.61
    span 80 4.34
    1,4-butanediol 4.11
    1,1-dichloroethane 0.23
    2-methyl-1-pentanol 0.3
    methyl formate 13.99
    2-methyl-1-butanol 0.6
    n-decane 0.09
    butyronitrile 0.6
    3,7-dimethyl-1-octanol 0.36
    1-chlorooctane 0.21
    1-chlorotetradecane 0.1
    n-nonane 0.09
    undecane 0.06
    tert-butylcyclohexane 0.02
    cyclooctane 0.08
    cyclopentanol 1.77
    tetrahydropyran 1.41
    tert-amyl methyl ether 0.38
    2,5,8-trioxanonane 10.55
    1-hexene 0.07
    2-isopropoxyethanol 2.92
    2,2,2-trifluoroethanol 15.3
    methyl butyrate 0.66

    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