Monocrotaline N-Oxide

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  • Identifiers

    CAS number
    35337-98-5

    Molecular formula
    C16H23NO7

    SMILES
    C[C@H]1C(=O)O[C@@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O)[O-]

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Sweet 49.74%
    Odorless 47.59%
    Caramellic 33.93%
    Burnt 25.89%
    Spicy 23.33%
    Nutty 22.5%
    Vanilla 22.48%
    Woody 21.75%
    Creamy 21.59%
    Lactonic 20.71%

     

    Flavor
    Bitter 79.79%
    Sweet-like 22.69%
    Odorless 21.75%
    Cedarleaf 21.38%
    Fatty 20.53%
    Fenugreek 20.32%
    Seedy 20.17%
    Cotton candy 20.16%
    Extremely sweet 20.08%
    Naphthalic 19.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.3

    pKa est.
    4.07 (weak acid)

    Molecular weight
    341.36 g/mol

    Flash point

    • -324.86 ˚C est.

  • Synonyms

    • Monocrotaline N-oxide
    • Monocrotaline oxide
    • 35337-98-5
    • 2LCP0RBK6G
    • UNII-2LCP0RBK6G
    • 14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione 4-oxide (13-alpha,14-alpha)-
    • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, 4-oxide, (13-alpha,14-alpha)-
    • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, 4-oxide, (13.alpha.,14.alpha.)-
    • 2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13A,13B-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-, 11-OXIDE, (3R,4S,5S,13AR,13BR)-
    • RefChem:159549
    • 20-NORCROTALANAN-11,15-DIONE, 14,19-DIHYDRO-12,13-DIHYDROXY-, 4-OXIDE, (13ALPHA,14ALPHA)-
    • (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-13-oxido-2,8-dioxa-13-azoniatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
    • Monocrotaline, N-oxide
    • CHEMBL469442
    • DTXSID70956767
    • NS00066966
    • Q27896174
    • (3R,4R,5R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-11-oxo-4,5,8,10,12,13,13a,13b-octahydro-2H,11H-11lambda~5~-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
    • 35337-98-5

  • Applications

    Monocrotaline N-Oxide is used primarily in research and analytical settings as a toxic pyrrolizidine alkaloid reference compound. It supports toxicology studies modeling PA-induced hepatotoxicity and pulmonary vascular effects; it serves as a reference standard in analytical methods for detecting and quantifying pyrrolizidine alkaloids in botanicals, foods, and herbal products; it can act as an intermediate in the synthesis of related pyrrolizidine alkaloids; it is used in metabolism and mechanism studies of PA; and it's used as an educational/research reference material under appropriate safety and regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 274.1
    methanol 756.71
    isopropanol 103.35
    water 28.5
    ethyl acetate 125.05
    n-propanol 131.25
    acetone 417.12
    n-butanol 82.81
    acetonitrile 133.7
    DMF 1271.25
    toluene 34.51
    isobutanol 62.15
    1,4-dioxane 346.19
    methyl acetate 128.84
    THF 587.39
    2-butanone 136.44
    n-pentanol 55.55
    sec-butanol 53.47
    n-hexane 1.49
    ethylene glycol 194.6
    NMP 712.26
    cyclohexane 4.57
    DMSO 1342.24
    n-butyl acetate 35.76
    n-octanol 22.44
    chloroform 258.23
    n-propyl acetate 65.61
    acetic acid 913.86
    dichloromethane 284.32
    cyclohexanone 250.5
    propylene glycol 115.02
    isopropyl acetate 62.04
    DMAc 598.97
    2-ethoxyethanol 338.51
    isopentanol 53.31
    n-heptane 1.27
    ethyl formate 181.91
    1,2-dichloroethane 154.14
    n-hexanol 35.53
    2-methoxyethanol 770.75
    isobutyl acetate 32.53
    tetrachloromethane 26.67
    n-pentyl acetate 31.55
    transcutol 304.63
    n-heptanol 26.06
    ethylbenzene 16.53
    MIBK 69.69
    2-propoxyethanol 241.65
    tert-butanol 80.94
    MTBE 23.74
    2-butoxyethanol 118.71
    propionic acid 175.2
    o-xylene 22.77
    formic acid 1495.17
    diethyl ether 63.34
    m-xylene 24.24
    p-xylene 23.1
    chlorobenzene 45.44
    dimethyl carbonate 184.91
    n-octane 0.86
    formamide 1771.03
    cyclopentanone 418.09
    2-pentanone 138.78
    anisole 67.57
    cyclopentyl methyl ether 111.33
    gamma-butyrolactone 559.56
    1-methoxy-2-propanol 411.39
    pyridine 221.04
    3-pentanone 80.12
    furfural 497.93
    n-dodecane 0.84
    diethylene glycol 348.45
    diisopropyl ether 10.55
    tert-amyl alcohol 48.34
    acetylacetone 258.57
    n-hexadecane 0.98
    acetophenone 100.12
    methyl propionate 146.39
    isopentyl acetate 30.14
    trichloroethylene 348.42
    n-nonanol 22.56
    cyclohexanol 66.4
    benzyl alcohol 109.27
    2-ethylhexanol 15.16
    isooctanol 18.69
    dipropyl ether 20.53
    1,2-dichlorobenzene 45.91
    ethyl lactate 76.45
    propylene carbonate 213.75
    n-methylformamide 816.04
    2-pentanol 34.66
    n-pentane 1.78
    1-propoxy-2-propanol 100.23
    1-methoxy-2-propyl acetate 77.16
    2-(2-methoxypropoxy) propanol 90.59
    mesitylene 13.1
    ε-caprolactone 224.04
    p-cymene 8.23
    epichlorohydrin 463.9
    1,1,1-trichloroethane 71.34
    2-aminoethanol 245.26
    morpholine-4-carbaldehyde 729.42
    sulfolane 668.69
    2,2,4-trimethylpentane 0.88
    2-methyltetrahydrofuran 156.64
    n-hexyl acetate 41.94
    isooctane 0.72
    2-(2-butoxyethoxy)ethanol 130.54
    sec-butyl acetate 31.58
    tert-butyl acetate 53.0
    decalin 2.14
    glycerin 327.41
    diglyme 264.08
    acrylic acid 259.09
    isopropyl myristate 15.2
    n-butyric acid 193.23
    acetyl acetate 114.37
    di(2-ethylhexyl) phthalate 28.51
    ethyl propionate 61.45
    nitromethane 1193.33
    1,2-diethoxyethane 53.58
    benzonitrile 77.34
    trioctyl phosphate 19.36
    1-bromopropane 36.63
    gamma-valerolactone 748.92
    n-decanol 15.03
    triethyl phosphate 24.53
    4-methyl-2-pentanol 22.98
    propionitrile 70.29
    vinylene carbonate 246.08
    1,1,2-trichlorotrifluoroethane 475.16
    DMS 59.24
    cumene 9.78
    2-octanol 14.49
    2-hexanone 65.15
    octyl acetate 23.02
    limonene 11.29
    1,2-dimethoxyethane 386.6
    ethyl orthosilicate 21.04
    tributyl phosphate 21.05
    diacetone alcohol 131.57
    N,N-dimethylaniline 49.4
    acrylonitrile 141.47
    aniline 92.45
    1,3-propanediol 282.9
    bromobenzene 37.48
    dibromomethane 128.81
    1,1,2,2-tetrachloroethane 225.35
    2-methyl-cyclohexyl acetate 34.34
    tetrabutyl urea 37.22
    diisobutyl methanol 9.5
    2-phenylethanol 63.84
    styrene 20.91
    dioctyl adipate 31.83
    dimethyl sulfate 332.81
    ethyl butyrate 33.92
    methyl lactate 194.72
    butyl lactate 44.89
    diethyl carbonate 25.68
    propanediol butyl ether 98.45
    triethyl orthoformate 27.14
    p-tert-butyltoluene 7.77
    methyl 4-tert-butylbenzoate 60.94
    morpholine 412.48
    tert-butylamine 23.48
    n-dodecanol 10.34
    dimethoxymethane 624.73
    ethylene carbonate 184.51
    cyrene 178.37
    2-ethoxyethyl acetate 67.13
    2-ethylhexyl acetate 21.69
    1,2,4-trichlorobenzene 64.22
    4-methylpyridine 171.34
    dibutyl ether 14.33
    2,6-dimethyl-4-heptanol 9.5
    DEF 201.72
    dimethyl isosorbide 148.46
    tetrachloroethylene 159.7
    eugenol 80.34
    triacetin 68.08
    span 80 68.01
    1,4-butanediol 117.68
    1,1-dichloroethane 90.57
    2-methyl-1-pentanol 36.26
    methyl formate 702.54
    2-methyl-1-butanol 42.15
    n-decane 1.59
    butyronitrile 66.3
    3,7-dimethyl-1-octanol 17.78
    1-chlorooctane 7.14
    1-chlorotetradecane 2.96
    n-nonane 1.29
    undecane 1.09
    tert-butylcyclohexane 1.23
    cyclooctane 1.56
    cyclopentanol 118.68
    tetrahydropyran 143.81
    tert-amyl methyl ether 23.81
    2,5,8-trioxanonane 175.83
    1-hexene 7.32
    2-isopropoxyethanol 147.37
    2,2,2-trifluoroethanol 417.99
    methyl butyrate 92.75

    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