Dhurrin

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  • Identifiers

    CAS number
    499-20-7

    Molecular formula
    C14H17NO7

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 59.81%
    Sweet 44.46%
    Vanilla 33.43%
    Bitter 24.47%
    Spicy 22.73%
    Phenolic 21.44%
    Savory 20.56%
    Smoky 20.16%
    Milky 19.33%
    Creamy 18.36%

     

    Flavor
    Bitter 79.41%
    Odorless 40.82%
    Bland 29.1%
    Sweet-like 26.62%
    Cedarleaf 19.38%
    Mild 19.09%
    Nitrile 18.93%
    Very slight 18.6%
    Alkaline 18.44%
    Bouillon 18.32%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.9

    pKa est.
    6.03 (neutral)

    Molecular weight
    311.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1620°C

    Flash point

    • 256.7 ˚C est.

  • Synonyms

    • Dhurrin
    • 499-20-7
    • P5999IY65C
    • (S)-4-Hydroxymandelonitrile beta-D-glucoside
    • (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
    • (2S)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
    • CHEBI:27826
    • DTXSID90198142
    • (alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
    • (S)-p-Hydroxymandelnitrile-beta-D-glucopyranoside
    • (2S)-2-(4-hydroxyphenyl)-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyacetonitrile
    • RefChem:132456
    • DTXCID20120633
    • 207-878-6
    • (S)-(beta-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
    • C14H17NO7
    • MFCD18632527
    • UNII-P5999IY65C
    • EINECS 207-878-6
    • DHURRIN [MI]
    • SCHEMBL50174
    • orb1684649
    • Dhurrin, >=95% (HPLC)
    • 1e55
    • HY-N8433
    • MSK158578
    • 4-Hydroxymandelonitrile-?-D-glucoside
    • AKOS040760368
    • FD71615
    • CS-0144166
    • NS00031982
    • (S)-4-hydroxymandelonitrile-beta-D-glucoside
    • C05143
    • p-hydroxy-S-mandelonitrile-beta-D-glucopyranoside
    • Q908811
    • beta-D-glucopyranosyloxy-(S)-p-hydroxymandelonitrile
    • .BETA.-D-GLUCOPYRANOSYLOXY-L-P-HYDROXYMANDELONITRILE
    • Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-4-hydroxy-, (alphaS)-
    • (.ALPHA.S)-.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-4-HYDROXYBENZENEACETONITRILE
    • (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-acetonitrile
    • (2s)-2-(4-hydroxyphenyl)-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]acetonitrile
    • (S)-2-(4-hydroxyphenyl)-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile
    • 499-20-7

  • Applications

    Dhurrin is a cyanogenic glucoside primarily studied as a model substrate in plant biochemistry; its hydrolysis by specific glucosidases releases cyanide, making it a useful tool for investigating cyanogenesis pathways and enzyme kinetics. In agricultural science, it informs understanding of sorghum plant defense and can guide breeding and agricultural management studies aimed at modulating cyanogenic potential. In analytical chemistry, dhurrin serves as a reference compound for method development and calibration for cyanogenic glucosides in plant materials. In food science and safety research, it is used to assess cyanide potential and the impact of processing on cyanogenic content in sorghum-based ingredients. In toxicology and environmental studies, researchers examine cyanide release kinetics and toxicological implications of cyanogenic glycosides under various conditions.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.01
    methanol 22.79
    isopropanol 2.03
    water 51.92
    ethyl acetate 1.34
    n-propanol 2.34
    acetone 6.84
    n-butanol 1.89
    acetonitrile 2.84
    DMF 107.06
    toluene 0.56
    isobutanol 0.76
    1,4-dioxane 5.1
    methyl acetate 1.38
    THF 8.01
    2-butanone 1.73
    n-pentanol 0.76
    sec-butanol 1.01
    n-hexane 0.05
    ethylene glycol 63.95
    NMP 61.72
    cyclohexane 0.24
    DMSO 417.14
    n-butyl acetate 0.55
    n-octanol 1.07
    chloroform 0.26
    n-propyl acetate 0.66
    acetic acid 45.33
    dichloromethane 0.32
    cyclohexanone 3.61
    propylene glycol 23.78
    isopropyl acetate 0.91
    DMAc 74.75
    2-ethoxyethanol 19.15
    isopentanol 0.97
    n-heptane 0.25
    ethyl formate 2.3
    1,2-dichloroethane 0.52
    n-hexanol 0.96
    2-methoxyethanol 56.23
    isobutyl acetate 0.29
    tetrachloromethane 0.12
    n-pentyl acetate 0.81
    transcutol 26.88
    n-heptanol 1.49
    ethylbenzene 0.22
    MIBK 1.13
    2-propoxyethanol 11.15
    tert-butanol 1.72
    MTBE 0.41
    2-butoxyethanol 7.55
    propionic acid 5.04
    o-xylene 0.53
    formic acid 233.87
    diethyl ether 0.91
    m-xylene 0.47
    p-xylene 0.24
    chlorobenzene 0.2
    dimethyl carbonate 6.51
    n-octane 0.15
    formamide 200.5
    cyclopentanone 7.5
    2-pentanone 1.99
    anisole 0.87
    cyclopentyl methyl ether 2.49
    gamma-butyrolactone 11.52
    1-methoxy-2-propanol 25.07
    pyridine 3.42
    3-pentanone 1.45
    furfural 15.46
    n-dodecane 0.09
    diethylene glycol 37.32
    diisopropyl ether 0.28
    tert-amyl alcohol 1.03
    acetylacetone 7.4
    n-hexadecane 0.1
    acetophenone 1.93
    methyl propionate 2.73
    isopentyl acetate 0.5
    trichloroethylene 0.88
    n-nonanol 1.18
    cyclohexanol 1.79
    benzyl alcohol 2.06
    2-ethylhexanol 0.55
    isooctanol 0.98
    dipropyl ether 1.22
    1,2-dichlorobenzene 0.25
    ethyl lactate 4.14
    propylene carbonate 3.86
    n-methylformamide 41.39
    2-pentanol 0.87
    n-pentane 0.09
    1-propoxy-2-propanol 5.69
    1-methoxy-2-propyl acetate 3.08
    2-(2-methoxypropoxy) propanol 8.76
    mesitylene 0.33
    ε-caprolactone 3.53
    p-cymene 0.34
    epichlorohydrin 4.78
    1,1,1-trichloroethane 0.18
    2-aminoethanol 30.55
    morpholine-4-carbaldehyde 47.86
    sulfolane 50.08
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.97
    n-hexyl acetate 1.02
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 12.31
    sec-butyl acetate 0.37
    tert-butyl acetate 1.17
    decalin 0.06
    glycerin 89.51
    diglyme 21.21
    acrylic acid 12.84
    isopropyl myristate 0.6
    n-butyric acid 4.05
    acetyl acetate 1.85
    di(2-ethylhexyl) phthalate 1.27
    ethyl propionate 0.82
    nitromethane 57.62
    1,2-diethoxyethane 2.16
    benzonitrile 0.87
    trioctyl phosphate 1.09
    1-bromopropane 0.19
    gamma-valerolactone 21.44
    n-decanol 0.95
    triethyl phosphate 1.17
    4-methyl-2-pentanol 0.46
    propionitrile 0.9
    vinylene carbonate 4.27
    1,1,2-trichlorotrifluoroethane 21.96
    DMS 2.01
    cumene 0.16
    2-octanol 0.74
    2-hexanone 0.66
    octyl acetate 0.98
    limonene 0.52
    1,2-dimethoxyethane 10.91
    ethyl orthosilicate 0.94
    tributyl phosphate 0.89
    diacetone alcohol 6.14
    N,N-dimethylaniline 1.14
    acrylonitrile 2.42
    aniline 1.5
    1,3-propanediol 23.87
    bromobenzene 0.14
    dibromomethane 0.19
    1,1,2,2-tetrachloroethane 0.96
    2-methyl-cyclohexyl acetate 0.91
    tetrabutyl urea 2.16
    diisobutyl methanol 0.48
    2-phenylethanol 1.7
    styrene 0.22
    dioctyl adipate 1.53
    dimethyl sulfate 20.76
    ethyl butyrate 0.93
    methyl lactate 16.55
    butyl lactate 2.55
    diethyl carbonate 0.85
    propanediol butyl ether 9.42
    triethyl orthoformate 1.17
    p-tert-butyltoluene 0.36
    methyl 4-tert-butylbenzoate 4.37
    morpholine 9.22
    tert-butylamine 0.48
    n-dodecanol 0.73
    dimethoxymethane 22.57
    ethylene carbonate 2.64
    cyrene 14.73
    2-ethoxyethyl acetate 2.1
    2-ethylhexyl acetate 0.34
    1,2,4-trichlorobenzene 0.41
    4-methylpyridine 1.73
    dibutyl ether 0.62
    2,6-dimethyl-4-heptanol 0.48
    DEF 7.1
    dimethyl isosorbide 12.13
    tetrachloroethylene 0.9
    eugenol 5.49
    triacetin 3.88
    span 80 7.21
    1,4-butanediol 8.2
    1,1-dichloroethane 0.18
    2-methyl-1-pentanol 0.47
    methyl formate 26.33
    2-methyl-1-butanol 0.79
    n-decane 0.16
    butyronitrile 0.8
    3,7-dimethyl-1-octanol 0.68
    1-chlorooctane 0.3
    1-chlorotetradecane 0.16
    n-nonane 0.15
    undecane 0.12
    tert-butylcyclohexane 0.03
    cyclooctane 0.15
    cyclopentanol 2.36
    tetrahydropyran 1.87
    tert-amyl methyl ether 0.57
    2,5,8-trioxanonane 19.14
    1-hexene 0.11
    2-isopropoxyethanol 5.95
    2,2,2-trifluoroethanol 24.72
    methyl butyrate 1.14

    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