Sambunigrin

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  • Identifiers

    CAS number
    99-19-4

    Molecular formula
    C14H17NO6

    SMILES
    C1=CC=C(C=C1)[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
    Sweet 51.87%
    Odorless 47.9%
    Bitter 27.47%
    Vanilla 27.18%
    Spicy 24.29%
    Almond 19.55%
    Balsamic 19.35%
    Powdery 19.24%
    Woody 17.29%
    Dry 16.92%

     

    Flavor
    Bitter 77.18%
    Odorless 37.22%
    Sweet-like 25.83%
    Bland 25.38%
    Cedarleaf 19.46%
    Nitrile 19.13%
    Mild 18.82%
    Alkaline 18.77%
    Very slight 18.74%
    Naphthalic 18.56%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    5.04 (weak acid)

    Molecular weight
    295.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1304°C

    Melting point expt.

    • 151 - 152 °C

    Flash point

    • 238.75 ˚C est.

  • Synonyms

    • Sambunigrin
    • (S)-prunasin
    • 99-19-4
    • (S)-Mandelonitrile beta-D-glucoside
    • 9UZJ2ZO1HS
    • (2S)-(beta-D-glucopyranosyloxy)(phenyl)acetonitrile
    • CHEBI:27761
    • DTXSID00912912
    • (2S)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
    • (2S)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
    • Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-, (alphaS)-
    • (2S)-2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)acetonitrile
    • (2S)-2-phenyl-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyacetonitrile
    • RefChem:181090
    • DTXCID501341925
    • L-Prunasin
    • (2S)-Sambunigrin
    • Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-, (aS)-
    • (S)-2-Phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile
    • UNII-9UZJ2ZO1HS
    • S-Prunasin
    • (aS)-a-(ss-D-Glucopyranosyloxy)benzeneacetonitrile; L-Prunasin; Sambunigrin; (2S)-Sambunigrin;
    • Sambunigrin ((S)-Prunasin)
    • orb1695316
    • ZKSZEJFBGODIJW-YOVYLDAJSA-N
    • (alphaS)-alpha-(beta-D-Glucopyranosyloxy)benzeneacetonitrile
    • NSC782175
    • AKOS030531714
    • MANDELONITRILE GLUCOSIDE L-FORM
    • NSC-782175
    • XP175789
    • MANDELONITRILE GLUCOSIDE L-FORM [MI]
    • NS00094438
    • C04273
    • Q2217000
    • BENZENEACETONITRILE, .ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-, (.ALPHA.S)-
    • (2S)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-acetonitrile
    • 99-19-4

  • Applications

    Sambunigrin (CAS 99-19-4) is primarily used in scientific research and analytical chemistry as a cyanogenic glycoside reference material: it serves as a standard for developing and validating analytical methods to detect and quantify cyanogenic glycosides and their hydrolysis products; it is employed in enzymatic hydrolysis studies to probe beta-glucosidase–mediated release of hydrogen cyanide and to investigate reaction mechanisms; it supports natural product isolation and structural confirmation from plant sources containing sambunigrin; it is utilized in plant physiology and toxicology research to understand the distribution, biosynthesis, and safety considerations of cyanogenic glycosides in agricultural crops; and it is used as a reference in method development for food safety and environmental testing where cyanogenic compounds are a concern, subject to local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.58
    methanol 22.41
    isopropanol 2.06
    water 49.31
    ethyl acetate 2.34
    n-propanol 2.57
    acetone 7.5
    n-butanol 2.49
    acetonitrile 4.11
    DMF 91.45
    toluene 1.02
    isobutanol 1.07
    1,4-dioxane 6.71
    methyl acetate 2.52
    THF 9.38
    2-butanone 2.42
    n-pentanol 1.07
    sec-butanol 1.21
    n-hexane 0.08
    ethylene glycol 62.54
    NMP 64.98
    cyclohexane 0.48
    DMSO 361.37
    n-butyl acetate 1.16
    n-octanol 1.85
    chloroform 1.01
    n-propyl acetate 1.3
    acetic acid 56.2
    dichloromethane 1.36
    cyclohexanone 6.3
    propylene glycol 18.27
    isopropyl acetate 1.69
    DMAc 77.69
    2-ethoxyethanol 18.53
    isopentanol 1.56
    n-heptane 0.38
    ethyl formate 3.9
    1,2-dichloroethane 1.63
    n-hexanol 1.71
    2-methoxyethanol 48.74
    isobutyl acetate 0.68
    tetrachloromethane 0.32
    n-pentyl acetate 1.51
    transcutol 41.83
    n-heptanol 2.42
    ethylbenzene 0.5
    MIBK 1.92
    2-propoxyethanol 13.4
    tert-butanol 2.28
    MTBE 0.65
    2-butoxyethanol 9.92
    propionic acid 7.99
    o-xylene 1.1
    formic acid 219.06
    diethyl ether 1.17
    m-xylene 0.98
    p-xylene 0.52
    chlorobenzene 0.66
    dimethyl carbonate 9.85
    n-octane 0.23
    formamide 206.95
    cyclopentanone 10.77
    2-pentanone 2.79
    anisole 1.75
    cyclopentyl methyl ether 3.61
    gamma-butyrolactone 17.95
    1-methoxy-2-propanol 22.1
    pyridine 5.71
    3-pentanone 2.24
    furfural 24.62
    n-dodecane 0.15
    diethylene glycol 39.08
    diisopropyl ether 0.47
    tert-amyl alcohol 1.54
    acetylacetone 10.74
    n-hexadecane 0.17
    acetophenone 3.99
    methyl propionate 4.66
    isopentyl acetate 1.13
    trichloroethylene 3.11
    n-nonanol 2.0
    cyclohexanol 2.88
    benzyl alcohol 3.82
    2-ethylhexanol 1.09
    isooctanol 1.76
    dipropyl ether 1.65
    1,2-dichlorobenzene 0.89
    ethyl lactate 6.31
    propylene carbonate 8.37
    n-methylformamide 42.92
    2-pentanol 1.22
    n-pentane 0.14
    1-propoxy-2-propanol 7.4
    1-methoxy-2-propyl acetate 5.4
    2-(2-methoxypropoxy) propanol 11.98
    mesitylene 0.74
    ε-caprolactone 6.92
    p-cymene 0.83
    epichlorohydrin 9.15
    1,1,1-trichloroethane 0.56
    2-aminoethanol 29.1
    morpholine-4-carbaldehyde 52.96
    sulfolane 64.26
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 2.75
    n-hexyl acetate 1.93
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 16.23
    sec-butyl acetate 0.8
    tert-butyl acetate 2.16
    decalin 0.13
    glycerin 76.49
    diglyme 29.19
    acrylic acid 20.43
    isopropyl myristate 1.22
    n-butyric acid 6.57
    acetyl acetate 4.23
    di(2-ethylhexyl) phthalate 2.62
    ethyl propionate 1.6
    nitromethane 68.57
    1,2-diethoxyethane 3.51
    benzonitrile 2.16
    trioctyl phosphate 2.13
    1-bromopropane 0.44
    gamma-valerolactone 25.39
    n-decanol 1.61
    triethyl phosphate 2.44
    4-methyl-2-pentanol 0.86
    propionitrile 1.66
    vinylene carbonate 9.33
    1,1,2-trichlorotrifluoroethane 33.55
    DMS 4.12
    cumene 0.41
    2-octanol 1.21
    2-hexanone 1.14
    octyl acetate 1.84
    limonene 1.16
    1,2-dimethoxyethane 13.29
    ethyl orthosilicate 1.99
    tributyl phosphate 1.93
    diacetone alcohol 8.28
    N,N-dimethylaniline 2.18
    acrylonitrile 4.76
    aniline 2.76
    1,3-propanediol 22.09
    bromobenzene 0.49
    dibromomethane 0.69
    1,1,2,2-tetrachloroethane 2.78
    2-methyl-cyclohexyl acetate 2.12
    tetrabutyl urea 3.79
    diisobutyl methanol 0.96
    2-phenylethanol 3.46
    styrene 0.51
    dioctyl adipate 3.24
    dimethyl sulfate 30.54
    ethyl butyrate 1.85
    methyl lactate 20.34
    butyl lactate 4.29
    diethyl carbonate 1.89
    propanediol butyl ether 12.05
    triethyl orthoformate 2.24
    p-tert-butyltoluene 0.85
    methyl 4-tert-butylbenzoate 7.89
    morpholine 10.12
    tert-butylamine 0.81
    n-dodecanol 1.28
    dimethoxymethane 21.98
    ethylene carbonate 6.25
    cyrene 20.2
    2-ethoxyethyl acetate 3.64
    2-ethylhexyl acetate 0.81
    1,2,4-trichlorobenzene 1.38
    4-methylpyridine 2.92
    dibutyl ether 1.03
    2,6-dimethyl-4-heptanol 0.96
    DEF 9.92
    dimethyl isosorbide 19.22
    tetrachloroethylene 2.65
    eugenol 9.23
    triacetin 7.32
    span 80 10.2
    1,4-butanediol 9.02
    1,1-dichloroethane 0.51
    2-methyl-1-pentanol 0.91
    methyl formate 31.6
    2-methyl-1-butanol 1.32
    n-decane 0.25
    butyronitrile 1.39
    3,7-dimethyl-1-octanol 1.33
    1-chlorooctane 0.57
    1-chlorotetradecane 0.33
    n-nonane 0.23
    undecane 0.19
    tert-butylcyclohexane 0.08
    cyclooctane 0.29
    cyclopentanol 3.19
    tetrahydropyran 2.47
    tert-amyl methyl ether 0.94
    2,5,8-trioxanonane 27.31
    1-hexene 0.18
    2-isopropoxyethanol 7.28
    2,2,2-trifluoroethanol 35.12
    methyl butyrate 2.13

    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