Senecionine N-Oxide

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  • Identifiers

    CAS number
    13268-67-2

    Molecular formula
    C18H25NO6

    SMILES
    C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)O)C

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 49.55%
    Caramellic 44.15%
    Odorless 33.15%
    Burnt 32.63%
    Nutty 28.91%
    Roasted 28.52%
    Spicy 26.49%
    Coumarinic 23.96%
    Lactonic 23.71%
    Vanilla 23.07%

     

    Flavor
    Bitter 78.62%
    Cedarleaf 20.82%
    Fenugreek 20.11%
    Leaves 20.09%
    Lovage 19.95%
    Seedy 19.87%
    Cotton candy 19.79%
    Ripe apricot 19.76%
    Extremely sweet 19.76%
    Sweet-like 19.56%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    6.55 (neutral)

    Molecular weight
    351.4 g/mol

    Flash point

    • -328.16 ˚C est.

  • Synonyms

    • Senecionine N-oxide
    • 13268-67-2
    • 12-Hydroxysenecionan-11,16-dione 4-oxide
    • CHEBI:52070
    • DTXSID901016615
    • (1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • (1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-14-oxido-2,9-dioxa-14-azoniatricyclo(9.5.1.014,17)heptadec-11-ene-3,8-dione
    • RefChem:182375
    • DTXCID501474807
    • Senecionine oxide
    • NSC106677
    • (5R,6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-5,6-dimethyl-2,7-dioxo-2,3,4,5,6,7,9,9a1,11,13,14,14a-dodecahydro-12H-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide
    • senecionin-N-oxid
    • Senecionine-N-oxide
    • Senecionine, N-oxide
    • NSC 106677
    • Senecionine Impurity 2
    • CHEMBL471683
    • orb1684223
    • SCHEMBL27241391
    • HY-N6637
    • MSK14176
    • AKOS037515349
    • NSC-106677
    • DA-77792
    • FS161594
    • CS-0062870
    • NS00066969
    • Senecionine-N-oxide 100 microg/mL in Water
    • E80698
    • Senecionan-11,16-dione, 12-hydroxy-, 4-oxide
    • Q27104786
    • (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-3,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, 12-oxide, (3Z,5R,6R,14aR,14bR)-
    • (5R,6R,14aR,14bR)-3-Ethylidene-6-hydroxy-5,6-dimethyl-12-oxo-3,4,5,6,11,12,13,14,14a,14b-decahydro-9H-12lambda~5~-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
    • 13268-67-2

  • Applications

    Senecionine N-Oxide (CAS 13268-67-2) is primarily encountered in research and development as a synthetic intermediate and reference compound within pyrrolizidine alkaloid chemistry. In practice, it is used as a tool in organic synthesis to access related PA compounds and derivatives, and as an analytical reference material for methods that detect and quantify pyrrolizidine alkaloids in botanical materials, foods, and feed. It also features in natural products and phytochemistry research for isolation, characterization, and structure-activity relationship studies of the PA scaffold. Given the toxicity associated with pyrrolizidine alkaloids, it is handled in specialized laboratories and used under appropriate safety protocols; some studies employ Senecionine N-Oxide in toxicology or mechanistic research to understand oxidation states and metabolic pathways of PA N-oxides.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 320.02
    methanol 580.97
    isopropanol 181.09
    water 5.6
    ethyl acetate 294.44
    n-propanol 221.6
    acetone 465.48
    n-butanol 176.16
    acetonitrile 240.31
    DMF 957.01
    toluene 96.21
    isobutanol 135.91
    1,4-dioxane 397.19
    methyl acetate 250.37
    THF 558.53
    2-butanone 253.76
    n-pentanol 119.33
    sec-butanol 136.4
    n-hexane 2.76
    ethylene glycol 136.04
    NMP 625.15
    cyclohexane 6.99
    DMSO 848.59
    n-butyl acetate 108.31
    n-octanol 45.35
    chloroform 611.05
    n-propyl acetate 142.19
    acetic acid 1334.72
    dichloromethane 504.52
    cyclohexanone 367.73
    propylene glycol 120.71
    isopropyl acetate 168.1
    DMAc 666.99
    2-ethoxyethanol 373.75
    isopentanol 131.82
    n-heptane 2.47
    ethyl formate 256.78
    1,2-dichloroethane 268.58
    n-hexanol 92.62
    2-methoxyethanol 695.27
    isobutyl acetate 82.42
    tetrachloromethane 62.25
    n-pentyl acetate 92.16
    transcutol 604.74
    n-heptanol 59.09
    ethylbenzene 40.62
    MIBK 134.52
    2-propoxyethanol 330.2
    tert-butanol 135.92
    MTBE 64.08
    2-butoxyethanol 187.94
    propionic acid 324.36
    o-xylene 57.03
    formic acid 1037.54
    diethyl ether 125.74
    m-xylene 60.66
    p-xylene 50.8
    chlorobenzene 125.21
    dimethyl carbonate 261.43
    n-octane 1.66
    formamide 1200.91
    cyclopentanone 468.53
    2-pentanone 245.21
    anisole 112.99
    cyclopentyl methyl ether 166.71
    gamma-butyrolactone 638.42
    1-methoxy-2-propanol 446.14
    pyridine 373.22
    3-pentanone 165.01
    furfural 557.57
    n-dodecane 1.91
    diethylene glycol 342.64
    diisopropyl ether 27.03
    tert-amyl alcohol 109.43
    acetylacetone 385.13
    n-hexadecane 2.21
    acetophenone 168.38
    methyl propionate 274.09
    isopentyl acetate 89.07
    trichloroethylene 720.24
    n-nonanol 47.48
    cyclohexanol 137.99
    benzyl alcohol 168.36
    2-ethylhexanol 42.31
    isooctanol 45.13
    dipropyl ether 41.7
    1,2-dichlorobenzene 121.63
    ethyl lactate 124.59
    propylene carbonate 338.26
    n-methylformamide 643.47
    2-pentanol 94.5
    n-pentane 4.08
    1-propoxy-2-propanol 159.3
    1-methoxy-2-propyl acetate 187.49
    2-(2-methoxypropoxy) propanol 154.32
    mesitylene 29.45
    ε-caprolactone 369.26
    p-cymene 22.34
    epichlorohydrin 610.67
    1,1,1-trichloroethane 201.33
    2-aminoethanol 220.6
    morpholine-4-carbaldehyde 745.18
    sulfolane 610.91
    2,2,4-trimethylpentane 2.8
    2-methyltetrahydrofuran 245.29
    n-hexyl acetate 111.65
    isooctane 2.11
    2-(2-butoxyethoxy)ethanol 218.37
    sec-butyl acetate 89.28
    tert-butyl acetate 127.29
    decalin 4.59
    glycerin 291.83
    diglyme 401.09
    acrylic acid 402.75
    isopropyl myristate 38.24
    n-butyric acid 407.68
    acetyl acetate 260.28
    di(2-ethylhexyl) phthalate 65.42
    ethyl propionate 130.79
    nitromethane 1365.04
    1,2-diethoxyethane 119.28
    benzonitrile 169.06
    trioctyl phosphate 43.16
    1-bromopropane 101.88
    gamma-valerolactone 824.05
    n-decanol 32.42
    triethyl phosphate 56.51
    4-methyl-2-pentanol 57.47
    propionitrile 164.61
    vinylene carbonate 397.96
    1,1,2-trichlorotrifluoroethane 577.4
    DMS 151.23
    cumene 25.58
    2-octanol 34.79
    2-hexanone 127.87
    octyl acetate 57.07
    limonene 28.23
    1,2-dimethoxyethane 378.63
    ethyl orthosilicate 48.92
    tributyl phosphate 51.33
    diacetone alcohol 204.73
    N,N-dimethylaniline 79.97
    acrylonitrile 263.6
    aniline 180.74
    1,3-propanediol 315.8
    bromobenzene 111.62
    dibromomethane 269.99
    1,1,2,2-tetrachloroethane 419.76
    2-methyl-cyclohexyl acetate 75.71
    tetrabutyl urea 68.96
    diisobutyl methanol 24.41
    2-phenylethanol 132.43
    styrene 53.11
    dioctyl adipate 70.7
    dimethyl sulfate 412.1
    ethyl butyrate 83.68
    methyl lactate 260.35
    butyl lactate 102.02
    diethyl carbonate 66.5
    propanediol butyl ether 155.58
    triethyl orthoformate 62.63
    p-tert-butyltoluene 19.64
    methyl 4-tert-butylbenzoate 122.43
    morpholine 474.91
    tert-butylamine 49.38
    n-dodecanol 23.03
    dimethoxymethane 579.93
    ethylene carbonate 316.76
    cyrene 222.82
    2-ethoxyethyl acetate 173.72
    2-ethylhexyl acetate 66.98
    1,2,4-trichlorobenzene 165.55
    4-methylpyridine 312.14
    dibutyl ether 34.24
    2,6-dimethyl-4-heptanol 24.41
    DEF 311.91
    dimethyl isosorbide 233.13
    tetrachloroethylene 307.72
    eugenol 140.82
    triacetin 167.23
    span 80 125.75
    1,4-butanediol 127.93
    1,1-dichloroethane 240.91
    2-methyl-1-pentanol 93.24
    methyl formate 555.49
    2-methyl-1-butanol 121.5
    n-decane 3.3
    butyronitrile 151.3
    3,7-dimethyl-1-octanol 44.47
    1-chlorooctane 18.28
    1-chlorotetradecane 8.21
    n-nonane 2.5
    undecane 2.42
    tert-butylcyclohexane 3.08
    cyclooctane 2.55
    cyclopentanol 174.52
    tetrahydropyran 227.02
    tert-amyl methyl ether 59.64
    2,5,8-trioxanonane 264.1
    1-hexene 15.69
    2-isopropoxyethanol 204.37
    2,2,2-trifluoroethanol 501.78
    methyl butyrate 169.32

    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