p-Nitrophenyl beta-D-glucopyranoside

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  • Identifiers

    CAS number
    2492-87-7

    Molecular formula
    C12H15NO8

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

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 67.18%
    Sweet 50.27%
    Vanilla 36.58%
    Milky 23.08%
    Bitter 21.96%
    Creamy 21.77%
    Caramellic 21.52%
    Balsamic 19.98%
    Powdery 19.38%
    Phenolic 19.06%

     

    Flavor
    Bitter 71.05%
    Odorless 45.01%
    Bland 29.57%
    Sweet-like 27.7%
    Very mild 25.33%
    Mild 20.61%
    Sweet 19.69%
    Very slight 19.52%
    Fenugreek 19.5%
    Cedarleaf 19.23%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.4

    pKa est.
    8.07 (weak base)

    Molecular weight
    301.25 g/mol

    Flash point

    • 243.49 ˚C est.

  • Synonyms

    • 2492-87-7
    • 4-Nitrophenyl beta-D-glucopyranoside
    • p-Nitrophenyl beta-D-glucopyranoside
    • beta-D-Glucopyranoside, 4-nitrophenyl
    • 4-Nitrophenyl beta-D-glucoside
    • p-Nitrophenyl-beta-glucoside
    • 1-O-p-Nitrophenyl-D-glucose
    • CHEBI:90259
    • DTXSID40883854
    • PNP-beta-Glu
    • 4-nitrophenylglucoside
    • RefChem:525987
    • para-nitrophenyl beta-D-glucoside
    • DTXCID801023338
    • 219-661-3
    • 4-Nitrophenyl-beta-D-glucopyranoside
    • p-nitrophenyl-beta-D-glucoside
    • MFCD00006593
    • p-Nitrophenyl beta-D-glucoside
    • (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
    • .beta.-D-glucopyranoside, 4-nitrophenyl
    • Glucoside, p-nitrophenyl
    • (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol
    • (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydropyran-3,4,5-triol
    • 4-nitrophenyl |A-d-glucopyranoside
    • 4-Nitrophenyl beta-D-glucopyranoside monohydrate
    • EN03181
    • p-Nitrophenyl glucopyranoside
    • 4-Nitrophenyl hexopyranoside #
    • p-Nitrophenyl beta-glucoside
    • p-Nitrophenyl ?-D-Glucopyranoside
    • pNPbetaGlu
    • 4-nitrophenyl-beta-D-glucoside
    • PNP-glucoside
    • 4-nitrophenyl b-d-glucopyranoside
    • PNW
    • EINECS 219-661-3
    • PNP-beta-D-Glc
    • SCHEMBL78954
    • p-Nitrophenol beta-D-glucoside
    • CHEMBL152723
    • orb1306992
    • BDBM84613
    • p-Nitrophenyl b-D-Glucopyranoside
    • para-Nitrophenyl b-D-glucopyranoside
    • |A-D-Glucopyranoside, 4-nitrophenyl
    • 4-Nitrophenyl-I(2)-D-glucopyranoside
    • AKOS003631966
    • AKOS016015681
    • AKOS040744347
    • CCG-233291
    • GS-6255
    • 4-Nitrophenyl- beta -D- glucopyranoside
    • HY-15927
    • PD012495
    • SY024305
    • N0235
    • NS00081700
    • beta-D-Glucopyranoside, 4-nitrophenyl (9CI)
    • H10200
    • N-4400
    • 492N877
    • F235558
    • 4-Nitrophenyl beta-D-glucopyranoside, >=98% (TLC)
    • Q27162435
    • Glucopyranoside, p-nitrophenyl, beta-D- (6CI,7CI,8CI)
    • 2492-87-7

  • Applications

    p-Nitrophenyl beta-D-glucopyranoside is widely used as a chromogenic substrate in enzymology to assay beta-glucosidase and related glycosidases, releasing p-nitrophenol upon hydrolysis and providing a convenient colorimetric readout for activity and kinetic studies. It serves as a common tool in pharmaceutical and biotechnology research for inhibitor screening and assay development, enabling high-throughput formats to monitor glycosidase function. The compound is also employed in academic teaching laboratories to illustrate enzyme kinetics and substrate specificity, and may be used as a model substrate in method development for biocatalysis and process analytics. Usage is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 12.16
    methanol 38.88
    isopropanol 5.74
    water 21.65
    ethyl acetate 1.26
    n-propanol 5.45
    acetone 9.38
    n-butanol 6.25
    acetonitrile 2.49
    DMF 125.85
    toluene 0.84
    isobutanol 1.84
    1,4-dioxane 14.15
    methyl acetate 1.53
    THF 18.42
    2-butanone 3.25
    n-pentanol 1.93
    sec-butanol 3.63
    n-hexane 0.07
    ethylene glycol 71.29
    NMP 59.09
    cyclohexane 0.35
    DMSO 487.85
    n-butyl acetate 0.59
    n-octanol 2.46
    chloroform 0.08
    n-propyl acetate 0.71
    acetic acid 32.99
    dichloromethane 0.13
    cyclohexanone 7.43
    propylene glycol 32.9
    isopropyl acetate 1.05
    DMAc 123.76
    2-ethoxyethanol 46.56
    isopentanol 3.32
    n-heptane 0.29
    ethyl formate 2.17
    1,2-dichloroethane 0.36
    n-hexanol 1.7
    2-methoxyethanol 123.41
    isobutyl acetate 0.28
    tetrachloromethane 0.06
    n-pentyl acetate 1.13
    transcutol 72.54
    n-heptanol 2.64
    ethylbenzene 0.35
    MIBK 2.26
    2-propoxyethanol 16.8
    tert-butanol 5.92
    MTBE 1.22
    2-butoxyethanol 11.81
    propionic acid 4.98
    o-xylene 0.98
    formic acid 166.06
    diethyl ether 1.81
    m-xylene 0.71
    p-xylene 0.41
    chlorobenzene 0.15
    dimethyl carbonate 4.8
    n-octane 0.2
    formamide 205.62
    cyclopentanone 11.01
    2-pentanone 3.86
    anisole 1.66
    cyclopentyl methyl ether 4.35
    gamma-butyrolactone 12.21
    1-methoxy-2-propanol 58.42
    pyridine 4.35
    3-pentanone 2.3
    furfural 14.49
    n-dodecane 0.14
    diethylene glycol 50.04
    diisopropyl ether 0.47
    tert-amyl alcohol 4.25
    acetylacetone 8.59
    n-hexadecane 0.16
    acetophenone 2.96
    methyl propionate 2.81
    isopentyl acetate 0.68
    trichloroethylene 0.49
    n-nonanol 2.66
    cyclohexanol 5.49
    benzyl alcohol 3.84
    2-ethylhexanol 1.0
    isooctanol 1.83
    dipropyl ether 1.97
    1,2-dichlorobenzene 0.19
    ethyl lactate 5.06
    propylene carbonate 3.11
    n-methylformamide 43.56
    2-pentanol 2.68
    n-pentane 0.12
    1-propoxy-2-propanol 9.76
    1-methoxy-2-propyl acetate 3.78
    2-(2-methoxypropoxy) propanol 16.6
    mesitylene 0.52
    ε-caprolactone 5.83
    p-cymene 0.51
    epichlorohydrin 6.17
    1,1,1-trichloroethane 0.09
    2-aminoethanol 49.42
    morpholine-4-carbaldehyde 67.49
    sulfolane 49.68
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 4.49
    n-hexyl acetate 1.91
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 23.79
    sec-butyl acetate 0.46
    tert-butyl acetate 1.98
    decalin 0.08
    glycerin 105.89
    diglyme 40.91
    acrylic acid 10.06
    isopropyl myristate 1.06
    n-butyric acid 4.69
    acetyl acetate 1.38
    di(2-ethylhexyl) phthalate 1.92
    ethyl propionate 0.9
    nitromethane 39.87
    1,2-diethoxyethane 5.16
    benzonitrile 1.08
    trioctyl phosphate 1.54
    1-bromopropane 0.16
    gamma-valerolactone 32.62
    n-decanol 2.15
    triethyl phosphate 1.44
    4-methyl-2-pentanol 1.28
    propionitrile 1.08
    vinylene carbonate 3.16
    1,1,2-trichlorotrifluoroethane 20.5
    DMS 2.34
    cumene 0.27
    2-octanol 1.52
    2-hexanone 1.28
    octyl acetate 1.7
    limonene 0.85
    1,2-dimethoxyethane 28.84
    ethyl orthosilicate 1.3
    tributyl phosphate 1.36
    diacetone alcohol 12.16
    N,N-dimethylaniline 2.08
    acrylonitrile 2.45
    aniline 2.55
    1,3-propanediol 53.82
    bromobenzene 0.1
    dibromomethane 0.08
    1,1,2,2-tetrachloroethane 0.66
    2-methyl-cyclohexyl acetate 1.34
    tetrabutyl urea 4.0
    diisobutyl methanol 0.98
    2-phenylethanol 2.59
    styrene 0.32
    dioctyl adipate 2.4
    dimethyl sulfate 15.55
    ethyl butyrate 1.02
    methyl lactate 18.48
    butyl lactate 3.63
    diethyl carbonate 0.82
    propanediol butyl ether 16.79
    triethyl orthoformate 1.67
    p-tert-butyltoluene 0.53
    methyl 4-tert-butylbenzoate 6.1
    morpholine 24.42
    tert-butylamine 1.38
    n-dodecanol 1.59
    dimethoxymethane 35.61
    ethylene carbonate 2.32
    cyrene 21.54
    2-ethoxyethyl acetate 2.94
    2-ethylhexyl acetate 0.48
    1,2,4-trichlorobenzene 0.37
    4-methylpyridine 2.61
    dibutyl ether 1.56
    2,6-dimethyl-4-heptanol 0.98
    DEF 13.45
    dimethyl isosorbide 18.01
    tetrachloroethylene 0.58
    eugenol 7.78
    triacetin 5.2
    span 80 10.92
    1,4-butanediol 17.72
    1,1-dichloroethane 0.09
    2-methyl-1-pentanol 1.44
    methyl formate 21.22
    2-methyl-1-butanol 2.67
    n-decane 0.27
    butyronitrile 1.15
    3,7-dimethyl-1-octanol 1.72
    1-chlorooctane 0.53
    1-chlorotetradecane 0.26
    n-nonane 0.24
    undecane 0.19
    tert-butylcyclohexane 0.05
    cyclooctane 0.2
    cyclopentanol 5.31
    tetrahydropyran 4.79
    tert-amyl methyl ether 1.74
    2,5,8-trioxanonane 34.9
    1-hexene 0.18
    2-isopropoxyethanol 13.97
    2,2,2-trifluoroethanol 15.52
    methyl butyrate 1.36

    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