Amygdalin

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  • Identifiers

    CAS number
    29883-15-6

    Molecular formula
    C20H27NO11

    SMILES
    C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 61.19%
    Sweet 50.08%
    Vanilla 24.49%
    Bitter 22.99%
    Spicy 19.13%
    Woody 18.5%
    Savory 17.4%
    Milky 16.78%
    Balsamic 16.39%
    Warm 16.17%

     

    Flavor
    Bitter 68.27%
    Odorless 40.97%
    Sweet 31.38%
    Sweet-like 29.15%
    Bland 26.26%
    Very slight 19.74%
    Alkaline 19.55%
    Cauliflower 19.52%
    Cedarleaf 19.42%
    Naphthalic 19.24%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.7

    pKa est.
    4.24 (weak acid)

    Molecular weight
    457.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3784°C

    Melting point expt.

    • 223-226 °C

    Flash point

    • 264.44 ˚C est.

    Solubility expt.

    • VERY SOL IN HOT WATER; SLIGHTLY SOL IN ALCOHOL; INSOL IN ETHER, CHLOROFORM; SOL IN HOT ALCOHOL

  • Synonyms

    • amygdalin
    • 29883-15-6
    • (R)-Amygdalin
    • D-Amygdalin
    • (R)-Laenitrile
    • (R)-Amygdaloside
    • R-Amygdalin
    • NSC-15780
    • D(-)-Mandelonitrile-beta-D-gentiobioside
    • D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside
    • 214UUQ9N0H
    • NSC 15780
    • Glucoprunasin
    • CHEBI:17019
    • DTXSID00897159
    • (-)-D-mandelonitrile beta-D-gentiobioside
    • (2R)-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy](phenyl)acetonitrile
    • (R)-alpha-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile
    • Benzeneacetonitrile, alpha-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (R)-
    • (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
    • CHEBI:27613
    • NSC251222
    • (2R)-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile
    • (2R)-2-phenyl-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)oxan-2-yl)oxyacetonitrile
    • RefChem:5553
    • Mandelonitrile beta Gentiobioside
    • DTXCID701326581
    • 2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)methyl)oxan-2-yl)oxy)acetonitrile
    • 249-925-3
    • ((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile
    • NSC15780
    • Amygdaloside
    • (R)-2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile
    • Benzeneacetonitrile,a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-, (aR)-
    • MFCD00006598
    • C20H27NO11
    • (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
    • amygdaline
    • UNII-214UUQ9N0H
    • MFCD00866428
    • HSDB 3559
    • EINECS 249-925-3
    • BRN 0066856
    • Amygdalin/Vitamin B17
    • AMYGDALIN [MI]
    • AMYGDALIN [HSDB]
    • bmse000139
    • AMYGDALIN [WHO-DD]
    • 5-17-08-00118 (Beilstein Handbook Reference)
    • MLS002473175
    • SCHEMBL131406
    • CHEMBL461727
    • orb1305010
    • MSK1532
    • HMS2205O07
    • HY-N0190
    • s2260
    • AKOS016034288
    • CCG-269308
    • CS-6162
    • DS-7377
    • EBC-617148
    • SMP1_000103
    • (2R)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile
    • AC-27315
    • SMR001397267
    • SY067870
    • D-(-)-mandelonitrile-beta-D-gentiobioside
    • NS00015336
    • C08325
    • Q410215
    • BRD-K03504028-001-07-6
    • (2R)-((6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)(PHENYL)ACETONITRILE
    • (R)-alpha-((6-O-beta-D-glucopyranosyl-beta-D- glucopyranosyl)oxy)benzeneacetonitrile
    • (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneaceto
    • Benzeneacetonitrile, alpha-[(6-O-.beta.-D-glucopyransoyl-.beta.-D-glucopyranosyl)oxy]-, (R)-
    • 29883-15-6

  • Applications

    Amygdalin (CAS 29883-15-6) is a cyanogenic glycoside found in bitter almonds and other plants. Real-world applications are mainly in phytochemistry research and analytical work on cyanogenic glycosides; it is used as a reference standard for quantifying amygdalin in plant material, seeds, and agricultural products to assess cyanogenic content; studies of enzymatic hydrolysis to release benzaldehyde and hydrogen cyanide help elucidate flavor formation and safety aspects of samples; it is used as a model compound for cyanogenic glycosides in organic synthesis and related chemical research; and it may be considered in the context of food safety evaluations related to cyanogenic glycoside levels.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.01
    methanol 13.85
    isopropanol 1.11
    water 22.39
    ethyl acetate 0.88
    n-propanol 1.65
    acetone 3.14
    n-butanol 1.16
    acetonitrile 1.4
    DMF 31.63
    toluene 0.33
    isobutanol 0.49
    1,4-dioxane 3.31
    methyl acetate 0.96
    THF 4.51
    2-butanone 1.25
    n-pentanol 0.49
    sec-butanol 0.64
    n-hexane 0.02
    ethylene glycol 17.48
    NMP 29.28
    cyclohexane 0.09
    DMSO 130.46
    n-butyl acetate 0.28
    n-octanol 0.61
    chloroform 0.38
    n-propyl acetate 0.31
    acetic acid 19.41
    dichloromethane 0.56
    cyclohexanone 2.26
    propylene glycol 8.38
    isopropyl acetate 0.47
    DMAc 25.41
    2-ethoxyethanol 7.04
    isopentanol 0.42
    n-heptane 0.09
    ethyl formate 1.37
    1,2-dichloroethane 0.51
    n-hexanol 0.42
    2-methoxyethanol 22.1
    isobutyl acetate 0.12
    tetrachloromethane 0.1
    n-pentyl acetate 0.52
    transcutol 12.23
    n-heptanol 0.8
    ethylbenzene 0.11
    MIBK 0.48
    2-propoxyethanol 4.41
    tert-butanol 0.54
    MTBE 0.2
    2-butoxyethanol 3.8
    propionic acid 2.87
    o-xylene 0.28
    formic acid 76.12
    diethyl ether 0.61
    m-xylene 0.23
    p-xylene 0.11
    chlorobenzene 0.15
    dimethyl carbonate 3.09
    n-octane 0.06
    formamide 61.13
    cyclopentanone 4.33
    2-pentanone 1.33
    anisole 0.39
    cyclopentyl methyl ether 1.44
    gamma-butyrolactone 6.27
    1-methoxy-2-propanol 9.71
    pyridine 2.32
    3-pentanone 0.95
    furfural 8.21
    n-dodecane 0.04
    diethylene glycol 12.27
    diisopropyl ether 0.12
    tert-amyl alcohol 0.42
    acetylacetone 3.08
    n-hexadecane 0.04
    acetophenone 0.82
    methyl propionate 1.83
    isopentyl acetate 0.2
    trichloroethylene 0.87
    n-nonanol 0.62
    cyclohexanol 0.92
    benzyl alcohol 0.95
    2-ethylhexanol 0.2
    isooctanol 0.43
    dipropyl ether 0.52
    1,2-dichlorobenzene 0.15
    ethyl lactate 1.47
    propylene carbonate 1.88
    n-methylformamide 15.25
    2-pentanol 0.47
    n-pentane 0.05
    1-propoxy-2-propanol 2.41
    1-methoxy-2-propyl acetate 1.39
    2-(2-methoxypropoxy) propanol 3.1
    mesitylene 0.14
    ε-caprolactone 2.2
    p-cymene 0.13
    epichlorohydrin 3.26
    1,1,1-trichloroethane 0.14
    2-aminoethanol 10.88
    morpholine-4-carbaldehyde 23.0
    sulfolane 22.76
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.23
    n-hexyl acetate 0.58
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 5.12
    sec-butyl acetate 0.17
    tert-butyl acetate 0.41
    decalin 0.02
    glycerin 30.86
    diglyme 8.86
    acrylic acid 6.67
    isopropyl myristate 0.23
    n-butyric acid 2.2
    acetyl acetate 0.97
    di(2-ethylhexyl) phthalate 0.48
    ethyl propionate 0.41
    nitromethane 22.11
    1,2-diethoxyethane 1.13
    benzonitrile 0.47
    trioctyl phosphate 0.41
    1-bromopropane 0.19
    gamma-valerolactone 12.13
    n-decanol 0.44
    triethyl phosphate 0.42
    4-methyl-2-pentanol 0.18
    propionitrile 0.61
    vinylene carbonate 2.32
    1,1,2-trichlorotrifluoroethane 10.68
    DMS 0.96
    cumene 0.07
    2-octanol 0.39
    2-hexanone 0.35
    octyl acetate 0.44
    limonene 0.21
    1,2-dimethoxyethane 3.98
    ethyl orthosilicate 0.35
    tributyl phosphate 0.3
    diacetone alcohol 2.14
    N,N-dimethylaniline 0.44
    acrylonitrile 1.58
    aniline 0.95
    1,3-propanediol 9.21
    bromobenzene 0.11
    dibromomethane 0.27
    1,1,2,2-tetrachloroethane 0.78
    2-methyl-cyclohexyl acetate 0.32
    tetrabutyl urea 0.73
    diisobutyl methanol 0.15
    2-phenylethanol 0.67
    styrene 0.12
    dioctyl adipate 0.6
    dimethyl sulfate 9.85
    ethyl butyrate 0.41
    methyl lactate 6.98
    butyl lactate 1.32
    diethyl carbonate 0.31
    propanediol butyl ether 5.02
    triethyl orthoformate 0.5
    p-tert-butyltoluene 0.14
    methyl 4-tert-butylbenzoate 1.79
    morpholine 5.49
    tert-butylamine 0.17
    n-dodecanol 0.3
    dimethoxymethane 9.65
    ethylene carbonate 1.42
    cyrene 6.17
    2-ethoxyethyl acetate 1.38
    2-ethylhexyl acetate 0.15
    1,2,4-trichlorobenzene 0.25
    4-methylpyridine 1.11
    dibutyl ether 0.3
    2,6-dimethyl-4-heptanol 0.15
    DEF 3.47
    dimethyl isosorbide 4.45
    tetrachloroethylene 0.66
    eugenol 2.17
    triacetin 1.88
    span 80 3.07
    1,4-butanediol 3.1
    1,1-dichloroethane 0.19
    2-methyl-1-pentanol 0.22
    methyl formate 10.86
    2-methyl-1-butanol 0.45
    n-decane 0.07
    butyronitrile 0.49
    3,7-dimethyl-1-octanol 0.25
    1-chlorooctane 0.17
    1-chlorotetradecane 0.07
    n-nonane 0.07
    undecane 0.05
    tert-butylcyclohexane 0.01
    cyclooctane 0.06
    cyclopentanol 1.43
    tetrahydropyran 1.25
    tert-amyl methyl ether 0.3
    2,5,8-trioxanonane 7.45
    1-hexene 0.06
    2-isopropoxyethanol 2.19
    2,2,2-trifluoroethanol 11.32
    methyl butyrate 0.53

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
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Rinse-off products applied to the hair with some hand contact
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Category 2
Products applied to the axillae
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Leave-on products applied to the hair with some hand contact
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Category 3
Products applied to the face/body using fingertips
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Products with significant anogenital exposure
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Category 4
Products related to fine fragrance
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Products with body and hand exposure, primarily rinse off
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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
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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
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Category 5D
Baby Creams, baby Oils and baby talc
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Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
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Category 6
Products with oral and lip exposure
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Products not intended for direct skin contact, minimal or insignificant transfer to skin
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