Gyromitrin

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  • Identifiers

    CAS number
    16568-02-8

    Molecular formula
    C4H8N2O

    SMILES
    C/C=N/N(C)C=O

    Safety labels

  • Odor profile

    Fragrance
    Pungent 47.97%
    Green 35.7%
    Radish 34.5%
    Fishy 28.52%
    Roasted 24.93%
    Nutty 22.66%
    Metallic 21.85%
    Cooked 21.64%
    Cabbage 21.6%
    Odorless 21.35%

     

    Flavor
    Mustard 33.47%
    Nutty 30.24%
    Pungent 29.96%
    Roasted 29.89%
    Cooked 28.53%
    Onion 25.23%
    Sulfurous 22.56%
    Matches 22.0%
    Sulfur 21.78%
    Cabbage 21.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.3

    pKa est.
    5.36 (weak acid)

    Molecular weight
    100.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Melting point expt.

    • 19.5 °C (VACUUM)

    Boiling point

    • 143 °C

    Flash point

    • 68.56 ˚C est.

    Solubility expt.

    • SOL IN ACETONE, BENZENE, CARBON TETRACHLORIDE, CHLOROFORM, DIETHYL ETHER, ETHANOL, ETHYL ACETATE, METHANOL, DICHLOROMETHANE AND WATER

  • Synonyms

    • GYROMITRIN
    • 16568-02-8
    • Ethylidene gyromitrin
    • Acetaldehyde N-methyl-N-formylhydrazone
    • Acetaldehyde N-methylformylhydrazone
    • Formic acid, ethylidenemethylhydrazide
    • Hydrazinecarboxaldehyde, ethylidenemethyl-
    • N'-ethylidene-N-methylformohydrazide
    • Formic acid, 2-ethylidene-1-methylhydrazide
    • Cetaldehyde methylformylhydrazone
    • Acetaldehyde, N-formyl-N-methylhydrazone
    • Acetaldehyde-N-formyl-N-methylhydrazone
    • Acetaldehyde-N-methyl-N-formylhydrazone
    • N-Methyl-N-formylhydrazone acetaldehyde
    • Acetylaldehyde-N-methyl-N-formylhydrazone
    • Hydrazine carboxyaldehyde, ethylidenemethyl-
    • N-Methyl-N-formyl hydrazone of acetaldehyde
    • S9J72G0T46
    • NSC-240877
    • Acetaldehyde N-formyl-N-methylhydrazone
    • formic acid 2-ethylidene-1-methylhydrazide
    • Acetaldehyde formylmethylhydrazone
    • CHEBI:5583
    • N'-ethylidene-N-methylformic hydrazide
    • RefChem:144928
    • N-[(E)-ethylideneamino]-N-methylformamide
    • N-(ethylideneamino)-N-methylformamide
    • Hydrazinecarboxaldehyde, ethylidenemethyl-, (E)-
    • 61748-21-8
    • CCRIS 5705
    • HSDB 3489
    • N'-[(1E)-ethylidene]-N-methylformic hydrazide
    • NSC 240877
    • BRN 1922396
    • Hydrazine carboxaldehyde, ethylidenemethyl-
    • UNII-S9J72G0T46
    • Acetaldehyde N-formyl-N-methylhydrazone; Acetaldehyde Methylformylhydrazone; Acetaldehyde-N-methyl-N-formylhydrazone; Ethylidene Gyromitrin; Ethylidenemethyl-hydrazinecarboxaldehyde; Ethylidenemethylhydrazide Formic Acid
    • N'-[(E)-ethylidene]-N-methylformohydrazide
    • GYROMITRIN [HSDB]
    • GYROMITRIN [IARC]
    • WLN: VHN1&NU2
    • SCHEMBL31022843
    • DTXSID50872971
    • IMAGWKUTFZRWSB-HWKANZROSA-N
    • MSK157293
    • NSC240877
    • AKOS006279315
    • CCG-214846
    • Formic acid, N'-ethylidene-N-methyl-hydrazide
    • N'-[(1E)-Ethylidene]-N-methylformohydrazide
    • C08305
    • N'-[(E)-Ethylidene]-N-methylformic hydrazide #
    • Q423839
    • BRD-K13037776-001-01-2
    • 16568-02-8

  • Applications

    Gyromitrin (CAS 16568-02-8) is a toxic natural product of interest primarily to toxicology and mycology, with limited commercial applications. In practice, it is used in analytical toxicology and toxinology research to understand mushroom poisoning, exposure pathways, and hydrolysis to monomethylhydrazine; it serves as a target analyte and calibration reference for analytical method development, including detection in food safety and environmental monitoring; safety assessment and regulatory studies rely on its properties to define handling controls and risk characterization; in research settings, it may function as a precursor or surrogate for studies of hydrazine-related toxicity.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 62.98
    methanol 131.92
    isopropanol 31.58
    water 10.21
    ethyl acetate 31.78
    n-propanol 35.22
    acetone 55.04
    n-butanol 33.14
    acetonitrile 81.58
    DMF 114.39
    toluene 27.17
    isobutanol 28.17
    1,4-dioxane 59.37
    methyl acetate 43.44
    THF 74.84
    2-butanone 47.38
    n-pentanol 27.56
    sec-butanol 28.43
    n-hexane 4.88
    ethylene glycol 28.77
    NMP 149.98
    cyclohexane 7.14
    DMSO 154.87
    n-butyl acetate 26.31
    n-octanol 11.11
    chloroform 126.73
    n-propyl acetate 18.19
    acetic acid 121.79
    dichloromethane 166.52
    cyclohexanone 68.97
    propylene glycol 17.52
    isopropyl acetate 16.53
    DMAc 135.85
    2-ethoxyethanol 51.15
    isopentanol 29.65
    n-heptane 3.86
    ethyl formate 40.64
    1,2-dichloroethane 82.99
    n-hexanol 21.28
    2-methoxyethanol 89.47
    isobutyl acetate 12.32
    tetrachloromethane 27.9
    n-pentyl acetate 15.37
    transcutol 116.39
    n-heptanol 9.98
    ethylbenzene 15.12
    MIBK 18.2
    2-propoxyethanol 45.43
    tert-butanol 39.31
    MTBE 30.33
    2-butoxyethanol 23.65
    propionic acid 42.45
    o-xylene 27.2
    formic acid 117.63
    diethyl ether 28.58
    m-xylene 19.31
    p-xylene 23.57
    chlorobenzene 49.14
    dimethyl carbonate 14.25
    n-octane 1.83
    formamide 94.25
    cyclopentanone 74.09
    2-pentanone 28.78
    anisole 31.48
    cyclopentyl methyl ether 32.53
    gamma-butyrolactone 91.71
    1-methoxy-2-propanol 42.59
    pyridine 85.23
    3-pentanone 28.96
    furfural 135.98
    n-dodecane 1.73
    diethylene glycol 52.28
    diisopropyl ether 7.74
    tert-amyl alcohol 36.09
    acetylacetone 36.0
    n-hexadecane 1.91
    acetophenone 37.1
    methyl propionate 29.6
    isopentyl acetate 24.47
    trichloroethylene 153.2
    n-nonanol 9.97
    cyclohexanol 32.05
    benzyl alcohol 37.13
    2-ethylhexanol 15.95
    isooctanol 9.19
    dipropyl ether 14.88
    1,2-dichlorobenzene 52.54
    ethyl lactate 16.41
    propylene carbonate 48.73
    n-methylformamide 69.56
    2-pentanol 18.24
    n-pentane 5.21
    1-propoxy-2-propanol 27.06
    1-methoxy-2-propyl acetate 26.87
    2-(2-methoxypropoxy) propanol 35.66
    mesitylene 13.09
    ε-caprolactone 59.67
    p-cymene 14.7
    epichlorohydrin 98.96
    1,1,1-trichloroethane 64.96
    2-aminoethanol 38.34
    morpholine-4-carbaldehyde 114.16
    sulfolane 125.96
    2,2,4-trimethylpentane 4.41
    2-methyltetrahydrofuran 63.85
    n-hexyl acetate 21.7
    isooctane 2.08
    2-(2-butoxyethoxy)ethanol 37.03
    sec-butyl acetate 13.08
    tert-butyl acetate 19.49
    decalin 5.71
    glycerin 33.67
    diglyme 69.32
    acrylic acid 59.56
    isopropyl myristate 9.95
    n-butyric acid 45.89
    acetyl acetate 27.33
    di(2-ethylhexyl) phthalate 17.53
    ethyl propionate 19.99
    nitromethane 132.24
    1,2-diethoxyethane 33.06
    benzonitrile 60.15
    trioctyl phosphate 9.77
    1-bromopropane 43.15
    gamma-valerolactone 105.29
    n-decanol 7.63
    triethyl phosphate 18.51
    4-methyl-2-pentanol 11.81
    propionitrile 49.23
    vinylene carbonate 58.99
    1,1,2-trichlorotrifluoroethane 93.95
    DMS 27.78
    cumene 13.14
    2-octanol 7.42
    2-hexanone 21.82
    octyl acetate 12.65
    limonene 19.57
    1,2-dimethoxyethane 75.31
    ethyl orthosilicate 17.35
    tributyl phosphate 14.13
    diacetone alcohol 28.91
    N,N-dimethylaniline 29.8
    acrylonitrile 72.45
    aniline 44.41
    1,3-propanediol 43.63
    bromobenzene 48.76
    dibromomethane 97.76
    1,1,2,2-tetrachloroethane 101.42
    2-methyl-cyclohexyl acetate 23.82
    tetrabutyl urea 21.06
    diisobutyl methanol 10.42
    2-phenylethanol 28.94
    styrene 20.26
    dioctyl adipate 19.1
    dimethyl sulfate 34.58
    ethyl butyrate 23.24
    methyl lactate 21.79
    butyl lactate 16.97
    diethyl carbonate 19.58
    propanediol butyl ether 22.76
    triethyl orthoformate 18.71
    p-tert-butyltoluene 13.07
    methyl 4-tert-butylbenzoate 29.25
    morpholine 68.57
    tert-butylamine 26.35
    n-dodecanol 6.37
    dimethoxymethane 42.52
    ethylene carbonate 39.85
    cyrene 42.5
    2-ethoxyethyl acetate 25.28
    2-ethylhexyl acetate 20.66
    1,2,4-trichlorobenzene 65.37
    4-methylpyridine 79.93
    dibutyl ether 13.74
    2,6-dimethyl-4-heptanol 10.42
    DEF 52.46
    dimethyl isosorbide 64.64
    tetrachloroethylene 82.8
    eugenol 32.96
    triacetin 29.15
    span 80 26.93
    1,4-butanediol 23.07
    1,1-dichloroethane 64.51
    2-methyl-1-pentanol 27.84
    methyl formate 55.12
    2-methyl-1-butanol 29.4
    n-decane 2.47
    butyronitrile 49.4
    3,7-dimethyl-1-octanol 14.5
    1-chlorooctane 8.91
    1-chlorotetradecane 4.63
    n-nonane 2.41
    undecane 1.99
    tert-butylcyclohexane 5.07
    cyclooctane 2.68
    cyclopentanol 36.22
    tetrahydropyran 46.15
    tert-amyl methyl ether 28.54
    2,5,8-trioxanonane 58.01
    1-hexene 14.18
    2-isopropoxyethanol 29.33
    2,2,2-trifluoroethanol 49.48
    methyl butyrate 27.83

    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