Nivalenol

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  • Identifiers

    CAS number
    23282-20-4

    Molecular formula
    C15H20O7

    SMILES
    CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]3([C@@H]([C@H]([C@H]([C@@]34CO4)O2)O)O)C)CO

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 60.98%
    Sweet 40.17%
    Caramellic 29.5%
    Burnt 23.18%
    Woody 21.19%
    Vanilla 20.86%
    Savory 20.36%
    Milky 19.29%
    Spicy 16.52%
    Creamy 16.2%

     

    Flavor
    Bitter 79.91%
    Sweet-like 25.83%
    Odorless 25.27%
    Sweet 22.56%
    Fatty 22.43%
    Bland 21.67%
    Fenugreek 20.47%
    Cedarleaf 20.29%
    Cauliflower 19.87%
    Naphthalic 19.78%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.7

    pKa est.
    4.99 (weak acid)

    Molecular weight
    312.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    967°C

    Melting point expt.

    • 222-223 °C, decomposes

    Flash point

    • 242.3 ˚C est.

    Solubility expt.

    • Soluble in polar organic solvents

  • Synonyms

    • NIVALENOL
    • 23282-20-4
    • 5WOP02RM1U
    • DTXSID3021067
    • 12,13-Epoxy-3,4,7,15-tetrahydroxytrichothec-9-en-8-one
    • 3-alpha,4-beta,7-alpha,15-Tetrahydroxyscirp-9-en-8-one
    • 3-alpha,4-beta,7-alpha,15-Tetrahydroxy-12,13-epoxytrichothec-9-en-8-one
    • Trichothec-9-en-8-one, 12,13-epoxy-3alpha,4beta,7alpha,15-tetrahydroxy-
    • Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-, (3alpha,4beta,7alpha)-
    • NSC-269143
    • Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-, (3-alpha,4-beta,7-alpha)-
    • (1S,2R,3S,7R,9R,10R,11S,12S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one
    • (1S,2R,3S,7R,9R,10R,11S,12S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-4-one
    • RefChem:166166
    • DTXCID701067
    • (1'S,2R,2'R,3'S,7'R,9'R,10'R,11'S)-3',10',11'-trihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro(oxirane-2,12'-tricyclo(7.2.1.0^(2,7))dodecan)-5'-en-4'-one
    • 3',10',11'-trihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro(oxirane-2,12'-tricyclo(7.2.1.02,7)dodecan)-5'-en-4'-one
    • 621-749-5
    • CCRIS 4141
    • HSDB 3517
    • Nivalenol from Fusarium nivale
    • UNII-5WOP02RM1U
    • NSC 269143
    • BRN 3625724
    • Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-, (3.alpha.,4.beta.,7.alpha.)-
    • UKOTXHQERFPCBU-XBXCNEFVSA-N
    • Nivalenol 100 microg/mL in Acetonitrile
    • NIVALENOL [MI]
    • NIVALENOL [HSDB]
    • 3-.alpha.,4-.beta.,7-.alpha.,15-Tetrahydroxyscirp-9-en-8-one
    • CHEMBL509655
    • 3alpha,4beta,7alpha,15-tetrahydroxy-12,13-epoxytrichothec-9-en-8-one
    • SCHEMBL29453863
    • MSK7230
    • AKOS040740860
    • BN162740
    • DA-66116
    • Q63395242
    • D71DF4BF-1A4B-492C-B185-9E8A20E9DA10
    • Nivalenol in acetonitrile, IRMM(R) certified Reference Material
    • 3.ALPHA.,4.BETA.,7.ALPHA.,15-TETRAHYDROXYSCRIP-9-EN-8-ONE
    • (3alpha,4beta,7alpha)-3,4,7,15-tetrahydroxy-12,13-epoxytrichothec-9-en-8-one\
    • 12,13-EPOXY-3.ALPHA.,4.BETA.,7.ALPHA.,15-TETRAHYDROXYTRICHOTHEC-9-EN-8-ONE
    • 3-.ALPHA.,4-.BETA.,7-.ALPHA.,15-TETRAHYDROXY-12,13- EPOXYTRICHOTHEC-9-EN-8-ONE
    • TRICHOTHEC-9-EN-8-ONE, 12,13-EPOXY-3.ALPHA.,4.BETA.,7.ALPHA.,15- TETRAHYDROXY-
    • (2R,2'S,3R,4S,5S,5aR,6S,9aR)-3,4,6-trihydroxy-5a-(hydroxymethyl)-5,8-dimethyl-2,3,4,5,5a,6-hexahydrospiro[2,5-methanobenzo[b]oxepine-10,2'-oxiran]-7(9aH)-one
    • TRICHOTHEC-9-EN-8-ONE, 12,13-EPOXY-3,4,7,15-TETRAHYDROXY-, (3-.ALPHA.,4-.BETA.,7-.ALPHA.)-
    • 23282-20-4

  • Applications

    Nivalenol, a type B trichothecene mycotoxin, is primarily encountered in analytical chemistry and food safety contexts. Real-world applications include: serving as a reference standard for developing and validating LC-MS/MS and immunoassay methods to detect nivalenol in cereals and processed foods; supporting routine mycotoxin monitoring programs by quantifying contamination levels in grains such as wheat, barley, and oats; enabling toxicology research to study mechanism of action and toxic effects in in vitro and in vivo systems; informing risk assessment and regulatory discussions by providing data used in exposure assessment and limit setting; and assisting training and method transfer in specialized mycotoxin laboratories.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.44
    methanol 42.55
    isopropanol 2.01
    water 2.18
    ethyl acetate 5.93
    n-propanol 2.58
    acetone 13.48
    n-butanol 1.84
    acetonitrile 6.47
    DMF 82.51
    toluene 0.78
    isobutanol 1.11
    1,4-dioxane 17.25
    methyl acetate 4.89
    THF 27.13
    2-butanone 4.93
    n-pentanol 1.1
    sec-butanol 0.77
    n-hexane 0.06
    ethylene glycol 19.3
    NMP 47.68
    cyclohexane 0.2
    DMSO 116.92
    n-butyl acetate 2.98
    n-octanol 1.41
    chloroform 2.49
    n-propyl acetate 2.67
    acetic acid 19.86
    dichloromethane 3.8
    cyclohexanone 10.86
    propylene glycol 4.11
    isopropyl acetate 4.06
    DMAc 39.66
    2-ethoxyethanol 15.61
    isopentanol 1.44
    n-heptane 0.15
    ethyl formate 7.36
    1,2-dichloroethane 3.04
    n-hexanol 2.01
    2-methoxyethanol 49.24
    isobutyl acetate 1.35
    tetrachloromethane 0.75
    n-pentyl acetate 3.03
    transcutol 14.86
    n-heptanol 2.25
    ethylbenzene 0.53
    MIBK 3.78
    2-propoxyethanol 19.63
    tert-butanol 2.0
    MTBE 0.9
    2-butoxyethanol 10.81
    propionic acid 4.57
    o-xylene 0.81
    formic acid 70.75
    diethyl ether 2.45
    m-xylene 0.81
    p-xylene 0.67
    chlorobenzene 0.92
    dimethyl carbonate 12.92
    n-octane 0.08
    formamide 93.42
    cyclopentanone 19.6
    2-pentanone 5.63
    anisole 1.95
    cyclopentyl methyl ether 4.98
    gamma-butyrolactone 25.77
    1-methoxy-2-propanol 21.58
    pyridine 6.95
    3-pentanone 4.01
    furfural 26.41
    n-dodecane 0.06
    diethylene glycol 40.18
    diisopropyl ether 0.69
    tert-amyl alcohol 1.03
    acetylacetone 16.0
    n-hexadecane 0.07
    acetophenone 3.9
    methyl propionate 7.57
    isopentyl acetate 2.41
    trichloroethylene 5.65
    n-nonanol 1.6
    cyclohexanol 1.69
    benzyl alcohol 2.85
    2-ethylhexanol 1.17
    isooctanol 1.62
    dipropyl ether 1.87
    1,2-dichlorobenzene 1.26
    ethyl lactate 4.54
    propylene carbonate 9.42
    n-methylformamide 45.07
    2-pentanol 0.82
    n-pentane 0.08
    1-propoxy-2-propanol 8.29
    1-methoxy-2-propyl acetate 9.21
    2-(2-methoxypropoxy) propanol 7.47
    mesitylene 0.64
    ε-caprolactone 8.99
    p-cymene 0.76
    epichlorohydrin 17.6
    1,1,1-trichloroethane 1.1
    2-aminoethanol 11.86
    morpholine-4-carbaldehyde 55.12
    sulfolane 44.93
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 5.06
    n-hexyl acetate 3.02
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 9.95
    sec-butyl acetate 1.49
    tert-butyl acetate 4.25
    decalin 0.1
    glycerin 25.44
    diglyme 23.11
    acrylic acid 9.34
    isopropyl myristate 1.25
    n-butyric acid 5.32
    acetyl acetate 7.47
    di(2-ethylhexyl) phthalate 2.2
    ethyl propionate 3.16
    nitromethane 57.1
    1,2-diethoxyethane 3.87
    benzonitrile 2.79
    trioctyl phosphate 1.87
    1-bromopropane 0.61
    gamma-valerolactone 43.87
    n-decanol 1.04
    triethyl phosphate 2.46
    4-methyl-2-pentanol 0.87
    propionitrile 2.71
    vinylene carbonate 11.59
    1,1,2-trichlorotrifluoroethane 26.64
    DMS 4.77
    cumene 0.43
    2-octanol 0.98
    2-hexanone 2.51
    octyl acetate 1.82
    limonene 1.01
    1,2-dimethoxyethane 21.65
    ethyl orthosilicate 1.95
    tributyl phosphate 1.54
    diacetone alcohol 8.5
    N,N-dimethylaniline 1.97
    acrylonitrile 7.0
    aniline 1.96
    1,3-propanediol 13.32
    bromobenzene 0.72
    dibromomethane 1.57
    1,1,2,2-tetrachloroethane 3.56
    2-methyl-cyclohexyl acetate 2.7
    tetrabutyl urea 2.97
    diisobutyl methanol 0.89
    2-phenylethanol 4.13
    styrene 0.51
    dioctyl adipate 2.32
    dimethyl sulfate 25.03
    ethyl butyrate 2.81
    methyl lactate 14.1
    butyl lactate 3.84
    diethyl carbonate 2.42
    propanediol butyl ether 6.5
    triethyl orthoformate 2.66
    p-tert-butyltoluene 0.74
    methyl 4-tert-butylbenzoate 6.18
    morpholine 16.25
    tert-butylamine 0.64
    n-dodecanol 0.68
    dimethoxymethane 45.03
    ethylene carbonate 8.93
    cyrene 13.98
    2-ethoxyethyl acetate 6.5
    2-ethylhexyl acetate 1.77
    1,2,4-trichlorobenzene 1.66
    4-methylpyridine 3.78
    dibutyl ether 0.86
    2,6-dimethyl-4-heptanol 0.89
    DEF 11.31
    dimethyl isosorbide 14.31
    tetrachloroethylene 4.31
    eugenol 7.01
    triacetin 5.56
    span 80 5.29
    1,4-butanediol 4.27
    1,1-dichloroethane 0.97
    2-methyl-1-pentanol 0.89
    methyl formate 36.29
    2-methyl-1-butanol 0.97
    n-decane 0.11
    butyronitrile 2.21
    3,7-dimethyl-1-octanol 1.07
    1-chlorooctane 0.46
    1-chlorotetradecane 0.19
    n-nonane 0.09
    undecane 0.08
    tert-butylcyclohexane 0.07
    cyclooctane 0.12
    cyclopentanol 2.9
    tetrahydropyran 4.1
    tert-amyl methyl ether 1.0
    2,5,8-trioxanonane 15.02
    1-hexene 0.21
    2-isopropoxyethanol 6.64
    2,2,2-trifluoroethanol 16.71
    methyl butyrate 4.02

    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