Linamarin

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  • Identifiers

    CAS number
    554-35-8

    Molecular formula
    C10H17NO6

    SMILES
    CC(C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 62.37%
    Sweet 28.38%
    Woody 24.4%
    Milky 19.7%
    Dry 19.6%
    Vanilla 17.31%
    Mint 17.17%
    Savory 17.06%
    Creamy 16.86%
    Cooling 16.68%

     

    Flavor
    Bitter 72.62%
    Odorless 38.44%
    Sweet-like 26.07%
    Bland 25.92%
    Cedarleaf 20.43%
    Very slight 19.85%
    Bouillon 19.29%
    Yeasty 19.0%
    Cauliflower 18.99%
    Alkaline 18.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.8

    pKa est.
    5.7 (weak acid)

    Molecular weight
    247.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    990°C

    Melting point expt.

    • 142-143 °C
    • 143 - 144 °C

    Flash point

    • 196.75 ˚C est.

    Solubility expt.

    • FREELY SOL IN WATER, COLD ALCOHOL, HOT ACETONE; SLIGHTLY SOL IN HOT ETHYL ACETATE, ETHER, BENZENE, CHLOROFORM; PRACTICALLY INSOL IN PETROLEUM ETHER

  • Synonyms

    • LINAMARIN
    • Phaseolunatin
    • 554-35-8
    • 2-(beta-D-Glucopyranosyloxy)-2-methylpropanenitrile
    • H3V9RP3WLO
    • alpha-Hydroxyisobutyronitrile-beta-D-glucose
    • 1-cyano-1-methylethyl beta-D-glucoside
    • 2-(beta-D-Glucopyranosyloxy)isobutyronitrile
    • Propanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-
    • DTXSID8052857
    • CHEBI:16441
    • 2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile
    • 2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile
    • 2-methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)propanenitrile
    • 2-methyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxypropanenitrile
    • RefChem:153488
    • DTXCID5031268
    • 2-Methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propanenitrile
    • HSDB 3507
    • UNII-H3V9RP3WLO
    • BRN 0019237
    • Manihotoxin
    • Linamarin min. 99%
    • Spectrum_001946
    • SpecPlus_000936
    • LINAMARIN [MI]
    • LINAMARIN [HSDB]
    • Spectrum2_001972
    • Spectrum3_001622
    • Spectrum4_001668
    • Spectrum5_000575
    • SCHEMBL42021
    • BSPBio_003283
    • KBioGR_002195
    • KBioSS_002500
    • 5-17-07-00397 (Beilstein Handbook Reference)
    • DivK1c_007032
    • SPECTRUM1504124
    • SPBio_002123
    • orb3029179
    • CHEMBL3039425
    • KBio1_001976
    • KBio2_002492
    • KBio2_005060
    • KBio2_007628
    • KBio3_002503
    • QLTCHMYAEJEXBT-ZEBDFXRSSA-N
    • CCG-39428
    • MFCD00036209
    • MSK005033
    • a-Hydroxyisobutyronitrile ?-D-glucose
    • AKOS030242445
    • ML04551
    • SDCCGMLS-0066829.P001
    • NCGC00178164-01
    • HY-123114
    • CS-0081441
    • NS00094824
    • C01594
    • G79760
    • 2-beta-d-glucopyranosyloxy-2-methylpropanenitrile
    • Q425157
    • SR-05000002494
    • 2-(?-D-Glucopyranosyloxy)-2-methyl-propanenitrile
    • alpha-Hydroxyisobutyronitrile beta-D-glucopyranoside
    • SR-05000002494-1
    • 2-(beta-D-Glucopyranosyloxy)-2-methyl-Propanenitrile
    • 2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9CI
    • 2-(.BETA.-D-GLUCOPYRANOSYLOXY)-2-METHYLPROPANENITRILE
    • alpha-Hydroxyisobutyronitrile beta-D-glucopyranoside, >=98.0% (HPLC)
    • 2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propanenitrile
    • Linamarin

  • Applications

    Linamarin (CAS 554-35-8) is a natural cyanogenic glycoside found in cassava and other plants. Real-world applications are mainly in research and food safety: it is used as a model substrate to study enzymatic hydrolysis of cyanogenic glycosides and the mechanisms of cyanide release and detoxification; it supports plant biochemistry and breeding studies aimed at reducing cyanogenic potential in crops; it is examined in cassava processing to assess detoxification strategies and safe preparation of products; and it serves as an analytical/model compound in environmental and agricultural chemistry research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 12.53
    methanol 72.55
    isopropanol 2.86
    water 469.9
    ethyl acetate 2.03
    n-propanol 3.95
    acetone 5.2
    n-butanol 2.28
    acetonitrile 2.7
    DMF 179.42
    toluene 0.63
    isobutanol 1.69
    1,4-dioxane 10.47
    methyl acetate 1.92
    THF 12.3
    2-butanone 2.0
    n-pentanol 1.51
    sec-butanol 1.89
    n-hexane 0.12
    ethylene glycol 117.59
    NMP 169.54
    cyclohexane 0.67
    DMSO 584.71
    n-butyl acetate 1.6
    n-octanol 2.16
    chloroform 1.33
    n-propyl acetate 1.58
    acetic acid 78.93
    dichloromethane 2.22
    cyclohexanone 9.37
    propylene glycol 40.23
    isopropyl acetate 1.5
    DMAc 97.55
    2-ethoxyethanol 27.07
    isopentanol 1.58
    n-heptane 0.48
    ethyl formate 5.87
    1,2-dichloroethane 1.9
    n-hexanol 2.16
    2-methoxyethanol 75.72
    isobutyl acetate 0.87
    tetrachloromethane 0.6
    n-pentyl acetate 1.76
    transcutol 31.06
    n-heptanol 2.48
    ethylbenzene 0.54
    MIBK 1.76
    2-propoxyethanol 16.85
    tert-butanol 2.99
    MTBE 0.7
    2-butoxyethanol 11.3
    propionic acid 11.91
    o-xylene 1.16
    formic acid 517.16
    diethyl ether 0.96
    m-xylene 0.81
    p-xylene 0.73
    chlorobenzene 0.73
    dimethyl carbonate 8.03
    n-octane 0.24
    formamide 338.37
    cyclopentanone 14.66
    2-pentanone 2.02
    anisole 1.86
    cyclopentyl methyl ether 3.83
    gamma-butyrolactone 29.18
    1-methoxy-2-propanol 28.71
    pyridine 5.45
    3-pentanone 1.91
    furfural 42.31
    n-dodecane 0.16
    diethylene glycol 55.56
    diisopropyl ether 0.41
    tert-amyl alcohol 2.42
    acetylacetone 8.56
    n-hexadecane 0.18
    acetophenone 4.77
    methyl propionate 4.33
    isopentyl acetate 1.56
    trichloroethylene 3.7
    n-nonanol 2.14
    cyclohexanol 4.09
    benzyl alcohol 4.94
    2-ethylhexanol 1.54
    isooctanol 1.95
    dipropyl ether 1.55
    1,2-dichlorobenzene 1.21
    ethyl lactate 8.26
    propylene carbonate 13.84
    n-methylformamide 85.79
    2-pentanol 1.15
    n-pentane 0.17
    1-propoxy-2-propanol 9.0
    1-methoxy-2-propyl acetate 5.7
    2-(2-methoxypropoxy) propanol 13.72
    mesitylene 0.82
    ε-caprolactone 11.11
    p-cymene 1.08
    epichlorohydrin 10.75
    1,1,1-trichloroethane 0.66
    2-aminoethanol 61.84
    morpholine-4-carbaldehyde 101.15
    sulfolane 120.38
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 4.17
    n-hexyl acetate 2.35
    isooctane 0.07
    2-(2-butoxyethoxy)ethanol 17.3
    sec-butyl acetate 0.88
    tert-butyl acetate 2.23
    decalin 0.22
    glycerin 138.95
    diglyme 29.69
    acrylic acid 30.06
    isopropyl myristate 1.17
    n-butyric acid 8.25
    acetyl acetate 3.29
    di(2-ethylhexyl) phthalate 3.64
    ethyl propionate 1.77
    nitromethane 64.15
    1,2-diethoxyethane 2.71
    benzonitrile 2.55
    trioctyl phosphate 2.61
    1-bromopropane 0.47
    gamma-valerolactone 44.92
    n-decanol 1.65
    triethyl phosphate 3.11
    4-methyl-2-pentanol 0.87
    propionitrile 1.3
    vinylene carbonate 14.29
    1,1,2-trichlorotrifluoroethane 53.25
    DMS 4.32
    cumene 0.55
    2-octanol 1.32
    2-hexanone 1.34
    octyl acetate 1.82
    limonene 1.58
    1,2-dimethoxyethane 17.62
    ethyl orthosilicate 2.38
    tributyl phosphate 2.38
    diacetone alcohol 9.06
    N,N-dimethylaniline 3.02
    acrylonitrile 3.96
    aniline 2.51
    1,3-propanediol 35.19
    bromobenzene 0.56
    dibromomethane 1.12
    1,1,2,2-tetrachloroethane 3.75
    2-methyl-cyclohexyl acetate 2.81
    tetrabutyl urea 4.7
    diisobutyl methanol 1.26
    2-phenylethanol 4.14
    styrene 0.54
    dioctyl adipate 3.14
    dimethyl sulfate 33.11
    ethyl butyrate 2.03
    methyl lactate 23.39
    butyl lactate 5.58
    diethyl carbonate 1.96
    propanediol butyl ether 17.09
    triethyl orthoformate 2.49
    p-tert-butyltoluene 1.11
    methyl 4-tert-butylbenzoate 8.59
    morpholine 15.62
    tert-butylamine 1.05
    n-dodecanol 1.26
    dimethoxymethane 25.92
    ethylene carbonate 9.07
    cyrene 35.94
    2-ethoxyethyl acetate 3.75
    2-ethylhexyl acetate 1.25
    1,2,4-trichlorobenzene 1.93
    4-methylpyridine 3.25
    dibutyl ether 0.92
    2,6-dimethyl-4-heptanol 1.26
    DEF 12.64
    dimethyl isosorbide 23.5
    tetrachloroethylene 3.94
    eugenol 10.5
    triacetin 7.64
    span 80 12.64
    1,4-butanediol 16.49
    1,1-dichloroethane 0.54
    2-methyl-1-pentanol 1.2
    methyl formate 52.66
    2-methyl-1-butanol 1.56
    n-decane 0.26
    butyronitrile 1.12
    3,7-dimethyl-1-octanol 1.76
    1-chlorooctane 0.63
    1-chlorotetradecane 0.33
    n-nonane 0.24
    undecane 0.2
    tert-butylcyclohexane 0.13
    cyclooctane 0.36
    cyclopentanol 5.53
    tetrahydropyran 3.01
    tert-amyl methyl ether 1.09
    2,5,8-trioxanonane 26.46
    1-hexene 0.22
    2-isopropoxyethanol 9.13
    2,2,2-trifluoroethanol 59.22
    methyl butyrate 2.85

    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