(R)-(beta-D-Glucopyranosyloxy)(3-hydroxyphenyl)acetonitrile

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  • Identifiers

    CAS number
    41753-54-2

    Molecular formula
    C14H17NO7

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 62.3%
    Sweet 40.05%
    Vanilla 28.84%
    Bitter 23.82%
    Savory 21.21%
    Spicy 20.83%
    Phenolic 19.17%
    Milky 19.0%
    Smoky 18.08%
    Creamy 16.84%

     

    Flavor
    Bitter 80.42%
    Odorless 40.71%
    Bland 30.6%
    Sweet-like 26.43%
    Cedarleaf 19.7%
    Nitrile 19.04%
    Mild 18.77%
    Very slight 18.47%
    Alkaline 18.38%
    Parsley 18.27%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.9

    pKa est.
    6.04 (neutral)

    Molecular weight
    311.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1741°C

    Flash point

    • 256.21 ˚C est.

  • Synonyms

    • 41753-54-2
    • (R)-(beta-D-Glucopyranosyloxy)(3-hydroxyphenyl)acetonitrile
    • HOLOCALIN
    • EINECS 255-533-3
    • SCHEMBL28470494
    • DTXSID10961956
    • NS00056599
    • (Hexopyranosyloxy)(3-hydroxyphenyl)acetonitrile
    • (2R)-(beta-D-Glucopyranosyloxy)(3-hydroxyphenyl)acetonitrile
    • (R)-2-(3-Hydroxyphenyl)-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile
    • 41753-54-2

  • Applications

    Chemical name: (R)-(beta-D-Glucopyranosyloxy)(3-hydroxyphenyl)acetonitrile, CAS 41753-54-2. It is typically used as an aroma-related intermediate in fragrance chemistry; as a glucoside it can function as a pro-fragrance, releasing the aglycone 3-hydroxyphenylacetonitrile upon enzymatic or acid hydrolysis to contribute characteristic aroma notes. In cosmetic and personal-care formulations, it may be employed as a fragrance ingredient or pro-fragrance, aiding scent delivery and potentially improving solubility due to the glucose moiety. In household cleaning products, it can serve as a fragrance additive to impart and stabilize aroma in detergents and cleaners. In industrial manufacturing, it can be used as an intermediate in the synthesis of aroma compounds and related nitrile-containing aromatics, or as a chiral building block in synthetic routes. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.46
    methanol 20.65
    isopropanol 1.73
    water 48.71
    ethyl acetate 0.99
    n-propanol 2.08
    acetone 5.44
    n-butanol 1.42
    acetonitrile 2.36
    DMF 96.65
    toluene 0.47
    isobutanol 0.69
    1,4-dioxane 4.63
    methyl acetate 1.19
    THF 6.91
    2-butanone 1.44
    n-pentanol 0.67
    sec-butanol 0.81
    n-hexane 0.04
    ethylene glycol 64.99
    NMP 65.45
    cyclohexane 0.21
    DMSO 368.27
    n-butyl acetate 0.57
    n-octanol 1.08
    chloroform 0.23
    n-propyl acetate 0.65
    acetic acid 44.88
    dichloromethane 0.28
    cyclohexanone 3.28
    propylene glycol 21.86
    isopropyl acetate 0.74
    DMAc 68.73
    2-ethoxyethanol 18.09
    isopentanol 0.79
    n-heptane 0.24
    ethyl formate 2.02
    1,2-dichloroethane 0.46
    n-hexanol 0.98
    2-methoxyethanol 49.42
    isobutyl acetate 0.3
    tetrachloromethane 0.11
    n-pentyl acetate 0.82
    transcutol 25.67
    n-heptanol 1.49
    ethylbenzene 0.2
    MIBK 0.94
    2-propoxyethanol 11.25
    tert-butanol 1.57
    MTBE 0.35
    2-butoxyethanol 7.56
    propionic acid 4.84
    o-xylene 0.46
    formic acid 235.81
    diethyl ether 0.67
    m-xylene 0.42
    p-xylene 0.23
    chlorobenzene 0.19
    dimethyl carbonate 5.96
    n-octane 0.14
    formamide 196.74
    cyclopentanone 6.83
    2-pentanone 1.42
    anisole 0.85
    cyclopentyl methyl ether 2.12
    gamma-butyrolactone 11.37
    1-methoxy-2-propanol 21.24
    pyridine 3.21
    3-pentanone 1.15
    furfural 15.62
    n-dodecane 0.09
    diethylene glycol 37.19
    diisopropyl ether 0.24
    tert-amyl alcohol 0.9
    acetylacetone 6.02
    n-hexadecane 0.1
    acetophenone 1.99
    methyl propionate 2.27
    isopentyl acetate 0.51
    trichloroethylene 0.82
    n-nonanol 1.18
    cyclohexanol 1.46
    benzyl alcohol 2.01
    2-ethylhexanol 0.55
    isooctanol 1.0
    dipropyl ether 1.15
    1,2-dichlorobenzene 0.24
    ethyl lactate 4.21
    propylene carbonate 3.89
    n-methylformamide 39.51
    2-pentanol 0.64
    n-pentane 0.08
    1-propoxy-2-propanol 5.79
    1-methoxy-2-propyl acetate 3.13
    2-(2-methoxypropoxy) propanol 8.99
    mesitylene 0.3
    ε-caprolactone 3.44
    p-cymene 0.35
    epichlorohydrin 4.57
    1,1,1-trichloroethane 0.16
    2-aminoethanol 30.55
    morpholine-4-carbaldehyde 47.53
    sulfolane 49.76
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.72
    n-hexyl acetate 1.02
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 12.31
    sec-butyl acetate 0.35
    tert-butyl acetate 1.06
    decalin 0.05
    glycerin 83.26
    diglyme 20.63
    acrylic acid 12.82
    isopropyl myristate 0.62
    n-butyric acid 3.22
    acetyl acetate 1.57
    di(2-ethylhexyl) phthalate 1.37
    ethyl propionate 0.77
    nitromethane 52.79
    1,2-diethoxyethane 2.04
    benzonitrile 0.87
    trioctyl phosphate 1.16
    1-bromopropane 0.16
    gamma-valerolactone 20.25
    n-decanol 0.96
    triethyl phosphate 1.23
    4-methyl-2-pentanol 0.39
    propionitrile 0.79
    vinylene carbonate 4.3
    1,1,2-trichlorotrifluoroethane 22.5
    DMS 2.08
    cumene 0.16
    2-octanol 0.72
    2-hexanone 0.61
    octyl acetate 1.02
    limonene 0.52
    1,2-dimethoxyethane 10.3
    ethyl orthosilicate 0.96
    tributyl phosphate 0.93
    diacetone alcohol 5.54
    N,N-dimethylaniline 1.11
    acrylonitrile 2.26
    aniline 1.35
    1,3-propanediol 20.42
    bromobenzene 0.13
    dibromomethane 0.17
    1,1,2,2-tetrachloroethane 0.85
    2-methyl-cyclohexyl acetate 1.0
    tetrabutyl urea 2.26
    diisobutyl methanol 0.46
    2-phenylethanol 1.8
    styrene 0.21
    dioctyl adipate 1.62
    dimethyl sulfate 19.58
    ethyl butyrate 0.98
    methyl lactate 15.21
    butyl lactate 2.63
    diethyl carbonate 0.88
    propanediol butyl ether 9.17
    triethyl orthoformate 1.2
    p-tert-butyltoluene 0.37
    methyl 4-tert-butylbenzoate 4.59
    morpholine 8.4
    tert-butylamine 0.46
    n-dodecanol 0.74
    dimethoxymethane 19.32
    ethylene carbonate 2.58
    cyrene 15.46
    2-ethoxyethyl acetate 2.07
    2-ethylhexyl acetate 0.37
    1,2,4-trichlorobenzene 0.41
    4-methylpyridine 1.53
    dibutyl ether 0.58
    2,6-dimethyl-4-heptanol 0.46
    DEF 5.82
    dimethyl isosorbide 12.98
    tetrachloroethylene 0.84
    eugenol 5.77
    triacetin 3.96
    span 80 7.55
    1,4-butanediol 7.52
    1,1-dichloroethane 0.15
    2-methyl-1-pentanol 0.43
    methyl formate 24.69
    2-methyl-1-butanol 0.65
    n-decane 0.15
    butyronitrile 0.63
    3,7-dimethyl-1-octanol 0.7
    1-chlorooctane 0.29
    1-chlorotetradecane 0.16
    n-nonane 0.14
    undecane 0.11
    tert-butylcyclohexane 0.03
    cyclooctane 0.13
    cyclopentanol 2.05
    tetrahydropyran 1.56
    tert-amyl methyl ether 0.48
    2,5,8-trioxanonane 19.29
    1-hexene 0.1
    2-isopropoxyethanol 5.7
    2,2,2-trifluoroethanol 25.0
    methyl butyrate 1.09

    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