Sinigrin

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  • Identifiers

    CAS number
    3952-98-5

    Molecular formula
    C10H17NO9S2

    SMILES
    C=CC/C(=N\OS(=O)(=O)O)/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 69.32%
    Meaty 32.27%
    Savory 32.21%
    Roasted 31.04%
    Sulfurous 29.36%
    Cooked 25.26%
    Onion 19.87%
    Beefy 14.64%
    Pungent 14.14%
    Burnt 13.62%

     

    Flavor
    Bitter 90.94%
    Odorless 26.74%
    Bland 25.75%
    Sweet-like 20.71%
    Nitrile 19.96%
    Cedarleaf 19.87%
    Gooseberry 18.74%
    Taco 18.62%
    Formyl 18.55%
    Bouillon 18.43%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.1

    pKa est.
    6.99 (neutral)

    Molecular weight
    359.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1061°C

    Melting point expt.

    • 125 - 127 °C

    Flash point

    • 227.05 ˚C est.

  • Synonyms

    • Myronate
    • [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-N-sulfooxybut-3-enimidothioate
    • CHEBI:79317
    • NSC-90774
    • NSC-407279
    • (((E)-(1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)sulfanyl)but-3-en-1-ylidene)amino)oxy)sulfonic acid
    • ((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) (1E)-N-sulfooxybut-3-enimidothioate
    • {[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid
    • DTXSID30427761
    • RefChem:886355
    • DTXCID701769161
    • Glucopyranose, 1-thio-, 1-(3-butenohydroximate) NO-(hydrogen sulfate), monopotassium salt, beta-D-
    • 223-545-8
    • 3952-98-5
    • 50UM64RMBJ
    • Sinigrin
    • 534-69-0
    • Myronic acid
    • Allyl glucosinolate
    • NSC90774
    • propenyl glucosinolate
    • SCHEMBL29639606
    • GTPL12456
    • .beta.-D-Glucopyranose, 1-thio-, 1-[N-(sulfooxy)-3-butenimidate]
    • 1-Thio-b-D-glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9CI
    • beta-D-Glucopyranose, 1-thio-, 1-(N-(sulfooxy)-3-butenimidate)
    • [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] (1E)-N-sulfooxybut-3-enimidothioate
    • Sinigrin

  • Applications

    Sinigrin (CAS 3952-98-5) is a natural glucosinolate found in mustard seeds and horseradish, and its value in industry mainly lies in its role as a precursor to allyl isothiocyanate (AITC) produced via enzymatic hydrolysis, enabling pungent mustard-style flavors in the food and seasoning sector. It is also explored as a feedstock for synthesizing isothiocyanate compounds in industrial chemistry and for research into glucosinolate pathways in agrochemical development. In agriculture and crop protection, the hydrolysis products of sinigrin (AITC) are studied for biofumigation and biopesticide applications against pests in stored products and soil ecosystems. In research and development, sinigrin serves as a model glucosinolate for studying enzymatic conversion, structure–activity relationships, and downstream chemical transformations, supporting broader glucosinolate-derived product development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.55
    methanol 15.43
    isopropanol 1.06
    water 20.72
    ethyl acetate 0.26
    n-propanol 1.57
    acetone 2.64
    n-butanol 0.84
    acetonitrile 0.59
    DMF 49.74
    toluene 0.24
    isobutanol 0.6
    1,4-dioxane 0.93
    methyl acetate 0.44
    THF 2.59
    2-butanone 0.89
    n-pentanol 0.47
    sec-butanol 0.71
    n-hexane 0.03
    ethylene glycol 21.21
    NMP 56.36
    cyclohexane 0.15
    DMSO 144.35
    n-butyl acetate 0.38
    n-octanol 0.46
    chloroform 0.09
    n-propyl acetate 0.25
    acetic acid 13.36
    dichloromethane 0.16
    cyclohexanone 2.57
    propylene glycol 12.75
    isopropyl acetate 0.23
    DMAc 34.05
    2-ethoxyethanol 7.27
    isopentanol 0.52
    n-heptane 0.11
    ethyl formate 1.16
    1,2-dichloroethane 0.25
    n-hexanol 0.72
    2-methoxyethanol 26.54
    isobutyl acetate 0.1
    tetrachloromethane 0.05
    n-pentyl acetate 0.4
    transcutol 8.58
    n-heptanol 0.78
    ethylbenzene 0.12
    MIBK 0.49
    2-propoxyethanol 5.72
    tert-butanol 0.95
    MTBE 0.15
    2-butoxyethanol 3.72
    propionic acid 2.62
    o-xylene 0.3
    formic acid 87.18
    diethyl ether 0.21
    m-xylene 0.22
    p-xylene 0.13
    chlorobenzene 0.08
    dimethyl carbonate 1.52
    n-octane 0.06
    formamide 85.76
    cyclopentanone 4.19
    2-pentanone 0.78
    anisole 0.28
    cyclopentyl methyl ether 0.83
    gamma-butyrolactone 5.01
    1-methoxy-2-propanol 11.81
    pyridine 1.38
    3-pentanone 0.61
    furfural 8.47
    n-dodecane 0.03
    diethylene glycol 16.66
    diisopropyl ether 0.08
    tert-amyl alcohol 0.73
    acetylacetone 2.08
    n-hexadecane 0.04
    acetophenone 0.89
    methyl propionate 0.82
    isopentyl acetate 0.31
    trichloroethylene 0.4
    n-nonanol 0.5
    cyclohexanol 1.12
    benzyl alcohol 1.09
    2-ethylhexanol 0.36
    isooctanol 0.44
    dipropyl ether 0.39
    1,2-dichlorobenzene 0.11
    ethyl lactate 1.62
    propylene carbonate 1.58
    n-methylformamide 21.54
    2-pentanol 0.41
    n-pentane 0.05
    1-propoxy-2-propanol 3.18
    1-methoxy-2-propyl acetate 1.3
    2-(2-methoxypropoxy) propanol 4.2
    mesitylene 0.18
    ε-caprolactone 1.88
    p-cymene 0.21
    epichlorohydrin 1.74
    1,1,1-trichloroethane 0.06
    2-aminoethanol 17.08
    morpholine-4-carbaldehyde 21.6
    sulfolane 28.37
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 0.72
    n-hexyl acetate 0.44
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 5.45
    sec-butyl acetate 0.13
    tert-butyl acetate 0.39
    decalin 0.03
    glycerin 43.78
    diglyme 7.19
    acrylic acid 6.08
    isopropyl myristate 0.22
    n-butyric acid 1.79
    acetyl acetate 0.34
    di(2-ethylhexyl) phthalate 0.62
    ethyl propionate 0.25
    nitromethane 12.17
    1,2-diethoxyethane 0.6
    benzonitrile 0.47
    trioctyl phosphate 0.54
    1-bromopropane 0.08
    gamma-valerolactone 11.07
    n-decanol 0.41
    triethyl phosphate 0.42
    4-methyl-2-pentanol 0.22
    propionitrile 0.37
    vinylene carbonate 1.73
    1,1,2-trichlorotrifluoroethane 10.57
    DMS 0.64
    cumene 0.1
    2-octanol 0.35
    2-hexanone 0.35
    octyl acetate 0.41
    limonene 0.33
    1,2-dimethoxyethane 3.62
    ethyl orthosilicate 0.34
    tributyl phosphate 0.44
    diacetone alcohol 3.08
    N,N-dimethylaniline 0.52
    acrylonitrile 1.11
    aniline 0.73
    1,3-propanediol 10.53
    bromobenzene 0.05
    dibromomethane 0.09
    1,1,2,2-tetrachloroethane 0.42
    2-methyl-cyclohexyl acetate 0.53
    tetrabutyl urea 1.33
    diisobutyl methanol 0.24
    2-phenylethanol 1.1
    styrene 0.12
    dioctyl adipate 0.57
    dimethyl sulfate 5.86
    ethyl butyrate 0.38
    methyl lactate 6.52
    butyl lactate 1.56
    diethyl carbonate 0.29
    propanediol butyl ether 5.08
    triethyl orthoformate 0.45
    p-tert-butyltoluene 0.23
    methyl 4-tert-butylbenzoate 2.11
    morpholine 2.26
    tert-butylamine 0.31
    n-dodecanol 0.3
    dimethoxymethane 7.21
    ethylene carbonate 0.98
    cyrene 9.94
    2-ethoxyethyl acetate 0.74
    2-ethylhexyl acetate 0.23
    1,2,4-trichlorobenzene 0.2
    4-methylpyridine 0.76
    dibutyl ether 0.19
    2,6-dimethyl-4-heptanol 0.24
    DEF 2.88
    dimethyl isosorbide 6.13
    tetrachloroethylene 0.48
    eugenol 3.05
    triacetin 1.25
    span 80 3.55
    1,4-butanediol 3.69
    1,1-dichloroethane 0.07
    2-methyl-1-pentanol 0.31
    methyl formate 11.2
    2-methyl-1-butanol 0.52
    n-decane 0.06
    butyronitrile 0.3
    3,7-dimethyl-1-octanol 0.32
    1-chlorooctane 0.11
    1-chlorotetradecane 0.06
    n-nonane 0.06
    undecane 0.04
    tert-butylcyclohexane 0.02
    cyclooctane 0.08
    cyclopentanol 1.6
    tetrahydropyran 0.52
    tert-amyl methyl ether 0.24
    2,5,8-trioxanonane 7.48
    1-hexene 0.06
    2-isopropoxyethanol 2.24
    2,2,2-trifluoroethanol 7.47
    methyl butyrate 0.45

    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