4-Nitrophenylrhamnoside

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  • Identifiers

    CAS number
    18918-31-5

    Molecular formula
    C12H15NO7

    SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 64.72%
    Sweet 46.73%
    Vanilla 41.82%
    Milky 25.96%
    Creamy 25.27%
    Caramellic 24.64%
    Phenolic 20.87%
    Powdery 20.46%
    Bitter 20.4%
    Burnt 18.83%

     

    Flavor
    Bitter 73.66%
    Odorless 40.31%
    Bland 28.63%
    Sweet-like 26.16%
    Very mild 23.35%
    Fenugreek 19.51%
    Mild 19.45%
    Cedarleaf 19.45%
    Orange flower 19.15%
    Nitrile 19.05%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.1

    pKa est.
    8.23 (weak base)

    Molecular weight
    285.25 g/mol

    Flash point

    • 203.63 ˚C est.

  • Synonyms

    • 18918-31-5
    • 4-Nitrophenylrhamnoside
    • para-Nitrophenyl-alpha-L-rhamnoside
    • DTXSID20172314
    • RefChem:912737
    • DTXCID6094805
    • 4-Nitrophenyl-alpha-L-rhamnoside
    • (2S,3R,4R,5R,6S)-2-methyl-6-(4-nitrophenoxy)oxane-3,4,5-triol
    • 3-Nitrophenyl a-L-rhamnopyranoside
    • 4-Nitrophenyl |A-L-rhamnopyranoside
    • 4-Nitrophenyl alpha-L-rhamnopyranoside
    • alpha-L-Mannopyranoside, 4-nitrophenyl 6-deoxy-
    • 4-Nitrophenyl a-L-rhamnopyranoside
    • p-Nitrophenyl 6-deoxy-alpha-L-mannopyranoside
    • MFCD00069788
    • (2S,3R,4R,5R,6S)-2-Methyl-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol
    • p-NITROPHENYL alpha-L-RHAMNOPYRANOSIDE
    • p-nitrophenyl-alpha-L-rhamnopyranoside
    • pNP-alpha-L-rhamnoside
    • 4-Nitrophenylrhamnoside?
    • orb1146603
    • orb2942000
    • SCHEMBL2296345
    • p-nitrophenyl-alpha-l-rhamnoside
    • 4-Nitrophenyl ?-L-rhamnopyranoside
    • MFCD27665408
    • 4-Nitrophenylalpha-L-Rhamnopyranoside
    • AKOS016009962
    • 4-Nitrophenyl I+/--L-rhamnopyranoside
    • EN06877
    • s11470
    • AS-66058
    • PD126759
    • a-L-Mannopyranoside, 4-nitrophenyl6-deoxy-
    • HY-137815
    • CS-0142221
    • |A-L-Mannopyranoside, 4-nitrophenyl 6-deoxy-
    • (2S,3R,4R,5R,6S)-2-methyl-6-(4-nitrophenoxy)tetrahydropyran-3,4,5-triol
    • (2S,3R,4R,5R,6S)-2-methyl-6-[4-[oxidanyl(oxidanylidene)-$l^4-azanyl]phenoxy]oxane-3,4,5-triol
    • 4-Nitrophenyl 6-Deoxy-a-L-mannopyranoside; p-Nitrophenyl a-L-rhamnopyranoside; p-Nitrophenyl a-L-rhamnoside; p-Nitrophenyl 6-Deoxy-a-L-mannopyranoside
    • RY3
    • 18918-31-5

  • Applications

    4-Nitrophenylrhamnoside, CAS 18918-31-5, is widely used in biochemistry and carbohydrate chemistry as a chromogenic substrate for rhamnosidases and other glycosidases, enabling straightforward colorimetric monitoring of enzyme activity via release of p-nitrophenol; it also serves as a model substrate for kinetic and specificity studies, supports educational laboratory demonstrations, and can function as a glycosyl donor or leaving group in the chemical synthesis of rhamnoside derivatives under appropriate conditions.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.81
    methanol 40.49
    isopropanol 8.03
    water 4.03
    ethyl acetate 3.07
    n-propanol 7.91
    acetone 17.15
    n-butanol 8.96
    acetonitrile 3.93
    DMF 76.07
    toluene 1.69
    isobutanol 3.19
    1,4-dioxane 27.45
    methyl acetate 3.84
    THF 41.98
    2-butanone 7.09
    n-pentanol 4.3
    sec-butanol 6.05
    n-hexane 0.1
    ethylene glycol 32.79
    NMP 39.53
    cyclohexane 0.39
    DMSO 292.93
    n-butyl acetate 1.45
    n-octanol 4.98
    chloroform 0.4
    n-propyl acetate 1.93
    acetic acid 37.02
    dichloromethane 0.61
    cyclohexanone 15.66
    propylene glycol 23.11
    isopropyl acetate 2.43
    DMAc 120.11
    2-ethoxyethanol 59.87
    isopentanol 6.07
    n-heptane 0.33
    ethyl formate 4.14
    1,2-dichloroethane 1.13
    n-hexanol 3.38
    2-methoxyethanol 115.98
    isobutyl acetate 1.05
    tetrachloromethane 0.14
    n-pentyl acetate 2.82
    transcutol 120.86
    n-heptanol 4.76
    ethylbenzene 0.94
    MIBK 5.22
    2-propoxyethanol 26.62
    tert-butanol 10.93
    MTBE 2.81
    2-butoxyethanol 18.37
    propionic acid 7.27
    o-xylene 2.04
    formic acid 115.35
    diethyl ether 3.22
    m-xylene 1.56
    p-xylene 1.26
    chlorobenzene 0.54
    dimethyl carbonate 6.6
    n-octane 0.28
    formamide 167.41
    cyclopentanone 19.27
    2-pentanone 8.21
    anisole 4.38
    cyclopentyl methyl ether 7.34
    gamma-butyrolactone 22.11
    1-methoxy-2-propanol 61.42
    pyridine 8.61
    3-pentanone 4.35
    furfural 23.79
    n-dodecane 0.24
    diethylene glycol 58.23
    diisopropyl ether 0.88
    tert-amyl alcohol 8.84
    acetylacetone 16.74
    n-hexadecane 0.28
    acetophenone 7.22
    methyl propionate 5.03
    isopentyl acetate 2.02
    trichloroethylene 1.98
    n-nonanol 5.42
    cyclohexanol 9.09
    benzyl alcohol 9.1
    2-ethylhexanol 2.19
    isooctanol 3.71
    dipropyl ether 2.87
    1,2-dichlorobenzene 0.72
    ethyl lactate 8.13
    propylene carbonate 6.43
    n-methylformamide 35.65
    2-pentanol 4.54
    n-pentane 0.12
    1-propoxy-2-propanol 14.74
    1-methoxy-2-propyl acetate 7.13
    2-(2-methoxypropoxy) propanol 26.7
    mesitylene 1.16
    ε-caprolactone 11.89
    p-cymene 1.13
    epichlorohydrin 16.6
    1,1,1-trichloroethane 0.34
    2-aminoethanol 34.74
    morpholine-4-carbaldehyde 63.97
    sulfolane 54.38
    2,2,4-trimethylpentane 0.12
    2-methyltetrahydrofuran 9.65
    n-hexyl acetate 4.77
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 36.88
    sec-butyl acetate 1.39
    tert-butyl acetate 4.63
    decalin 0.17
    glycerin 65.02
    diglyme 61.33
    acrylic acid 12.5
    isopropyl myristate 2.64
    n-butyric acid 7.84
    acetyl acetate 3.29
    di(2-ethylhexyl) phthalate 4.41
    ethyl propionate 2.08
    nitromethane 52.24
    1,2-diethoxyethane 11.3
    benzonitrile 2.95
    trioctyl phosphate 3.22
    1-bromopropane 0.37
    gamma-valerolactone 46.29
    n-decanol 4.34
    triethyl phosphate 2.92
    4-methyl-2-pentanol 2.8
    propionitrile 1.85
    vinylene carbonate 6.18
    1,1,2-trichlorotrifluoroethane 29.06
    DMS 5.21
    cumene 0.76
    2-octanol 3.04
    2-hexanone 3.84
    octyl acetate 3.84
    limonene 1.73
    1,2-dimethoxyethane 48.31
    ethyl orthosilicate 2.67
    tributyl phosphate 3.28
    diacetone alcohol 19.86
    N,N-dimethylaniline 4.6
    acrylonitrile 4.08
    aniline 4.8
    1,3-propanediol 47.27
    bromobenzene 0.36
    dibromomethane 0.35
    1,1,2,2-tetrachloroethane 2.2
    2-methyl-cyclohexyl acetate 3.65
    tetrabutyl urea 7.32
    diisobutyl methanol 2.11
    2-phenylethanol 6.0
    styrene 0.9
    dioctyl adipate 5.73
    dimethyl sulfate 17.89
    ethyl butyrate 2.25
    methyl lactate 19.37
    butyl lactate 6.55
    diethyl carbonate 1.78
    propanediol butyl ether 22.79
    triethyl orthoformate 3.25
    p-tert-butyltoluene 1.15
    methyl 4-tert-butylbenzoate 11.46
    morpholine 37.73
    tert-butylamine 2.41
    n-dodecanol 3.24
    dimethoxymethane 41.92
    ethylene carbonate 4.62
    cyrene 28.19
    2-ethoxyethyl acetate 7.37
    2-ethylhexyl acetate 1.39
    1,2,4-trichlorobenzene 1.28
    4-methylpyridine 5.66
    dibutyl ether 3.33
    2,6-dimethyl-4-heptanol 2.11
    DEF 17.61
    dimethyl isosorbide 30.5
    tetrachloroethylene 1.77
    eugenol 13.85
    triacetin 10.6
    span 80 16.92
    1,4-butanediol 18.91
    1,1-dichloroethane 0.29
    2-methyl-1-pentanol 4.07
    methyl formate 23.48
    2-methyl-1-butanol 5.2
    n-decane 0.44
    butyronitrile 2.26
    3,7-dimethyl-1-octanol 4.13
    1-chlorooctane 1.19
    1-chlorotetradecane 0.61
    n-nonane 0.36
    undecane 0.32
    tert-butylcyclohexane 0.12
    cyclooctane 0.23
    cyclopentanol 7.4
    tetrahydropyran 8.77
    tert-amyl methyl ether 3.86
    2,5,8-trioxanonane 53.0
    1-hexene 0.38
    2-isopropoxyethanol 23.05
    2,2,2-trifluoroethanol 16.48
    methyl butyrate 3.32

    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