Cycasin

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  • Identifiers

    CAS number
    14901-08-7

    Molecular formula
    C8H16N2O7

    SMILES
    C/[N+](=N/CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)/[O-]

    Safety labels

  • Odor profile

    Fragrance
    Odorless 66.3%
    Sweet 40.09%
    Savory 21.68%
    Alcoholic 19.84%
    Milky 17.59%
    Caramellic 16.21%
    Cooling 16.16%
    Meaty 16.1%
    Bitter 15.58%
    Fishy 13.85%

     

    Flavor
    Bitter 54.26%
    Odorless 52.48%
    Sweet-like 29.72%
    Sweet 29.06%
    Bland 26.69%
    Very mild 22.56%
    Very slight 21.06%
    Cauliflower 20.61%
    Bouillon 19.98%
    Alkaline 19.96%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.6

    pKa est.
    5.27 (weak acid)

    Molecular weight
    252.22 g/mol

    Flash point

    • 209.31 ˚C est.

    Solubility expt.

    • READILY SOL IN WATER & DILUTE ETHANOL; INSOL IN BENZENE, CHLOROFORM, ETHYL ACETATE, ACETONE; SPARINGLY SOL IN ABSOLUTE ETHANOL

  • Synonyms

    • Cykazine
    • CYCASIN
    • beta-D-Glucosyloxyazoxymethane
    • beta-D-Glucosyloxyazoxymethase
    • Cycas revoluta glucoside
    • 14901-08-7
    • (Methyl-ONN-azoxy)methyl beta-D-glucopyranoside
    • Methylazoxymethanol-beta-D-glucoside
    • 9H51HL0E1D
    • Methylazoxymethanol glucoside
    • beta-D-Glucopyranoside, (methyl-ONN-azoxy)methyl
    • DTXSID2057574
    • Methylazoxymethyl-b-D-glucopyranoside
    • NSC-15190
    • (Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium
    • CHEBI:17074
    • (Z)-methyl-oxido-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethylimino)azanium
    • (Z)-methyl-oxido-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxymethylimino)ammonium
    • (Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethylimino]ammonium
    • RefChem:129164
    • Methylazoxymethanol Glucuronate
    • DTXCID701481
    • Glucuronate, Methylazoxymethanol
    • Methylazoxymethanol beta D Glucoside
    • Methylazoxymethanol beta-D-glucoside
    • beta-D-Glucoside, Methylazoxymethanol
    • ((1Z)-2-METHYL-2-OXIDODIAZENYL)METHYL BETA-D-GLUCOPYRANOSIDE
    • CCRIS 185
    • HSDB 5096
    • Methylazoxymethanolbeta-D-glucoside
    • NSC 15190
    • BRN 0025396
    • UNII-9H51HL0E1D
    • (Methyl-ONN-azoxy)-methyl-beta-D-glucopyranoside
    • CYCASIN [HSDB]
    • CYCASIN [IARC]
    • CYCASIN [MI]
    • 4-17-00-03009 (Beilstein Handbook Reference)
    • beta-D-Glucopyranoside, (methyl-ONN-azoxy)methyl-
    • Cycasin and methylazoxymethanol acetate
    • C01418
    • [(Z)-Methyl-ONN-azoxy]methyl beta-D-glucopyranoside
    • beta-D-Glucopyranoside, ((Z)-methyl-ONN-azoxy) methyl
    • ((1Z)-2-METHYL-2-OXIDODIAZENYL)METHYL .BETA.-D-GLUCOPYRANOSIDE
    • 14901-08-7

  • Applications

    Cycasin (CAS 14901-08-7) is primarily encountered as a natural toxin in cycads and is used mainly as a research chemical in toxicology and cancer biology. In laboratory settings it serves as a model compound to study methylazoxymalonate–related DNA alkylation and the mechanisms of cycad seed toxicity, supporting mechanistic toxicology studies, metabolism investigations, and assay development. It is often used in safety assessments of foods and feeds derived from cycad plants and in risk assessment studies addressing exposure to natural plant toxins. Researchers may also employ cycasin as a reference compound in pharmacology and chemical biology to explore detoxification pathways and the effects of glycoside hydrolysis. Applications are typically limited to controlled research environments and are subject to local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.08
    methanol 19.52
    isopropanol 0.94
    water 362.75
    ethyl acetate 0.37
    n-propanol 1.26
    acetone 0.91
    n-butanol 0.97
    acetonitrile 0.81
    DMF 142.92
    toluene 0.23
    isobutanol 0.69
    1,4-dioxane 2.49
    methyl acetate 0.43
    THF 2.35
    2-butanone 0.58
    n-pentanol 0.44
    sec-butanol 0.81
    n-hexane 0.07
    ethylene glycol 56.31
    NMP 127.59
    cyclohexane 0.39
    DMSO 643.1
    n-butyl acetate 0.27
    n-octanol 0.63
    chloroform 0.37
    n-propyl acetate 0.24
    acetic acid 23.28
    dichloromethane 0.71
    cyclohexanone 3.35
    propylene glycol 18.94
    isopropyl acetate 0.27
    DMAc 76.22
    2-ethoxyethanol 9.87
    isopentanol 0.72
    n-heptane 0.23
    ethyl formate 1.17
    1,2-dichloroethane 0.74
    n-hexanol 0.6
    2-methoxyethanol 38.71
    isobutyl acetate 0.13
    tetrachloromethane 0.21
    n-pentyl acetate 0.31
    transcutol 16.5
    n-heptanol 0.73
    ethylbenzene 0.16
    MIBK 0.47
    2-propoxyethanol 5.47
    tert-butanol 1.26
    MTBE 0.24
    2-butoxyethanol 3.32
    propionic acid 3.51
    o-xylene 0.52
    formic acid 394.12
    diethyl ether 0.31
    m-xylene 0.33
    p-xylene 0.21
    chlorobenzene 0.14
    dimethyl carbonate 2.45
    n-octane 0.11
    formamide 286.62
    cyclopentanone 3.74
    2-pentanone 0.57
    anisole 0.46
    cyclopentyl methyl ether 1.44
    gamma-butyrolactone 6.93
    1-methoxy-2-propanol 14.51
    pyridine 1.53
    3-pentanone 0.78
    furfural 13.97
    n-dodecane 0.06
    diethylene glycol 23.49
    diisopropyl ether 0.14
    tert-amyl alcohol 1.14
    acetylacetone 1.67
    n-hexadecane 0.07
    acetophenone 1.23
    methyl propionate 1.31
    isopentyl acetate 0.29
    trichloroethylene 0.95
    n-nonanol 0.64
    cyclohexanol 2.1
    benzyl alcohol 1.33
    2-ethylhexanol 0.46
    isooctanol 0.56
    dipropyl ether 0.59
    1,2-dichlorobenzene 0.28
    ethyl lactate 2.1
    propylene carbonate 2.41
    n-methylformamide 42.53
    2-pentanol 0.51
    n-pentane 0.11
    1-propoxy-2-propanol 3.13
    1-methoxy-2-propyl acetate 1.43
    2-(2-methoxypropoxy) propanol 5.74
    mesitylene 0.33
    ε-caprolactone 3.47
    p-cymene 0.33
    epichlorohydrin 2.89
    1,1,1-trichloroethane 0.16
    2-aminoethanol 29.81
    morpholine-4-carbaldehyde 57.24
    sulfolane 66.73
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 1.03
    n-hexyl acetate 0.48
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 6.7
    sec-butyl acetate 0.15
    tert-butyl acetate 0.45
    decalin 0.1
    glycerin 102.76
    diglyme 12.39
    acrylic acid 9.98
    isopropyl myristate 0.26
    n-butyric acid 2.09
    acetyl acetate 0.53
    di(2-ethylhexyl) phthalate 0.77
    ethyl propionate 0.37
    nitromethane 19.12
    1,2-diethoxyethane 0.88
    benzonitrile 0.61
    trioctyl phosphate 0.63
    1-bromopropane 0.22
    gamma-valerolactone 16.16
    n-decanol 0.51
    triethyl phosphate 0.93
    4-methyl-2-pentanol 0.34
    propionitrile 0.48
    vinylene carbonate 3.09
    1,1,2-trichlorotrifluoroethane 25.46
    DMS 0.98
    cumene 0.17
    2-octanol 0.39
    2-hexanone 0.31
    octyl acetate 0.4
    limonene 0.55
    1,2-dimethoxyethane 6.36
    ethyl orthosilicate 0.76
    tributyl phosphate 0.64
    diacetone alcohol 3.33
    N,N-dimethylaniline 1.0
    acrylonitrile 1.33
    aniline 0.87
    1,3-propanediol 17.6
    bromobenzene 0.12
    dibromomethane 0.42
    1,1,2,2-tetrachloroethane 1.14
    2-methyl-cyclohexyl acetate 0.66
    tetrabutyl urea 1.58
    diisobutyl methanol 0.41
    2-phenylethanol 0.99
    styrene 0.14
    dioctyl adipate 0.72
    dimethyl sulfate 14.65
    ethyl butyrate 0.48
    methyl lactate 9.66
    butyl lactate 1.33
    diethyl carbonate 0.43
    propanediol butyl ether 5.54
    triethyl orthoformate 0.73
    p-tert-butyltoluene 0.33
    methyl 4-tert-butylbenzoate 2.38
    morpholine 5.02
    tert-butylamine 0.48
    n-dodecanol 0.41
    dimethoxymethane 10.75
    ethylene carbonate 1.91
    cyrene 14.16
    2-ethoxyethyl acetate 0.68
    2-ethylhexyl acetate 0.25
    1,2,4-trichlorobenzene 0.42
    4-methylpyridine 0.94
    dibutyl ether 0.35
    2,6-dimethyl-4-heptanol 0.41
    DEF 6.27
    dimethyl isosorbide 8.16
    tetrachloroethylene 1.24
    eugenol 3.1
    triacetin 1.63
    span 80 4.12
    1,4-butanediol 5.58
    1,1-dichloroethane 0.15
    2-methyl-1-pentanol 0.38
    methyl formate 16.06
    2-methyl-1-butanol 0.74
    n-decane 0.11
    butyronitrile 0.36
    3,7-dimethyl-1-octanol 0.48
    1-chlorooctane 0.2
    1-chlorotetradecane 0.11
    n-nonane 0.11
    undecane 0.08
    tert-butylcyclohexane 0.05
    cyclooctane 0.22
    cyclopentanol 2.26
    tetrahydropyran 0.9
    tert-amyl methyl ether 0.5
    2,5,8-trioxanonane 11.92
    1-hexene 0.1
    2-isopropoxyethanol 2.96
    2,2,2-trifluoroethanol 23.76
    methyl butyrate 0.59

    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