Senecivernine N-Oxide

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  • Identifiers

    CAS number
    101687-28-9

    Molecular formula
    C18H25NO6

    SMILES
    C[C@@H]1[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC(=O)C1=C)[O-])(C)O)C

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Sweet 49.48%
    Caramellic 42.14%
    Odorless 38.65%
    Burnt 34.22%
    Nutty 26.49%
    Spicy 24.84%
    Roasted 24.25%
    Woody 22.51%
    Tobacco 21.5%
    Phenolic 20.27%

     

    Flavor
    Bitter 87.35%
    Cedarleaf 21.25%
    Sweet-like 20.27%
    Fenugreek 19.78%
    Ripe apricot 19.54%
    Seedy 19.47%
    Cotton candy 19.45%
    Leaves 19.44%
    Lovage 19.4%
    Extremely sweet 19.3%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    6.0 (neutral)

    Molecular weight
    351.4 g/mol

    Flash point

    • -339.91 ˚C est.

  • Synonyms

    • Senecivernine N-Oxide
    • senecivernine oxide
    • CHEBI:136403
    • (14alpha)-12-hydroxy-14-methyl-21-norsenecionan-11,16-dione 4-oxide
    • (4R,5R,6R,14aR,14bR)-6-hydroxy-4,5,6-trimethyl-3-methylidene-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
    • (4R,5R,6R,14aR,14bR)-6-hydroxy-4,5,6-trimethyl-3-methylidene-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
    • RefChem:182381
    • (14a)-12-Hydroxy-14-methyl-21-norsenecionan-11,16-dione 4-oxide
    • 101687-28-9
    • (1R,5R,6R,7R,17R)-7-hydroxy-5,6,7-trimethyl-4-methylidene-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • Senecivernine Impurity 2
    • orb1990447
    • CHEMBL4639295
    • SCHEMBL31258582
    • DTXSID801347241
    • MSK14180
    • FS161628
    • (4R,5R,6R,9a1R,14aR)-6-hydroxy-4,5,6-trimethyl-3-methylene-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
    • 101687-28-9

  • Applications

    Senecivernine N-Oxide (CAS 101687-28-9) is primarily regarded as a chemical intermediate and a building block for nitrogen-containing heterocycles in organic synthesis, used in research to develop pyrrolizidine-type frameworks and related alkaloid derivatives; in analytical and toxicological contexts, it serves as a reference material and research substrate for pyrrolizidine alkaloids; in early-stage pharmaceutical chemistry and medicinal chemistry studies, it may be evaluated for generating novel alkaloid-inspired compounds; in academic teaching laboratories, it is used as an example to illustrate alkaloid structure and properties; all handling is subject to safety regulations and handling requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 402.13
    methanol 711.36
    isopropanol 268.28
    water 4.94
    ethyl acetate 317.94
    n-propanol 288.26
    acetone 554.59
    n-butanol 221.69
    acetonitrile 222.51
    DMF 1153.63
    toluene 105.96
    isobutanol 170.02
    1,4-dioxane 523.25
    methyl acetate 257.38
    THF 863.58
    2-butanone 291.49
    n-pentanol 138.64
    sec-butanol 178.69
    n-hexane 3.01
    ethylene glycol 148.81
    NMP 667.22
    cyclohexane 7.59
    DMSO 970.78
    n-butyl acetate 109.53
    n-octanol 46.8
    chloroform 555.8
    n-propyl acetate 140.0
    acetic acid 1430.55
    dichloromethane 457.97
    cyclohexanone 400.64
    propylene glycol 136.37
    isopropyl acetate 195.78
    DMAc 724.67
    2-ethoxyethanol 426.95
    isopentanol 165.64
    n-heptane 2.55
    ethyl formate 250.21
    1,2-dichloroethane 274.08
    n-hexanol 108.76
    2-methoxyethanol 862.41
    isobutyl acetate 83.74
    tetrachloromethane 59.89
    n-pentyl acetate 93.25
    transcutol 664.09
    n-heptanol 62.28
    ethylbenzene 41.17
    MIBK 157.57
    2-propoxyethanol 388.49
    tert-butanol 196.49
    MTBE 83.58
    2-butoxyethanol 199.51
    propionic acid 311.03
    o-xylene 61.56
    formic acid 1006.49
    diethyl ether 166.48
    m-xylene 69.42
    p-xylene 52.24
    chlorobenzene 120.82
    dimethyl carbonate 269.88
    n-octane 1.57
    formamide 1155.02
    cyclopentanone 568.52
    2-pentanone 298.33
    anisole 117.4
    cyclopentyl methyl ether 222.95
    gamma-butyrolactone 708.99
    1-methoxy-2-propanol 566.89
    pyridine 391.47
    3-pentanone 180.06
    furfural 533.63
    n-dodecane 1.76
    diethylene glycol 389.31
    diisopropyl ether 33.47
    tert-amyl alcohol 140.63
    acetylacetone 444.4
    n-hexadecane 2.04
    acetophenone 164.55
    methyl propionate 284.36
    isopentyl acetate 94.79
    trichloroethylene 655.32
    n-nonanol 48.98
    cyclohexanol 171.64
    benzyl alcohol 172.65
    2-ethylhexanol 44.2
    isooctanol 46.66
    dipropyl ether 47.16
    1,2-dichlorobenzene 113.24
    ethyl lactate 112.69
    propylene carbonate 331.23
    n-methylformamide 693.96
    2-pentanol 123.45
    n-pentane 4.63
    1-propoxy-2-propanol 183.8
    1-methoxy-2-propyl acetate 202.91
    2-(2-methoxypropoxy) propanol 155.97
    mesitylene 32.38
    ε-caprolactone 388.15
    p-cymene 22.52
    epichlorohydrin 695.74
    1,1,1-trichloroethane 199.96
    2-aminoethanol 254.83
    morpholine-4-carbaldehyde 815.54
    sulfolane 671.42
    2,2,4-trimethylpentane 2.79
    2-methyltetrahydrofuran 325.75
    n-hexyl acetate 113.38
    isooctane 2.33
    2-(2-butoxyethoxy)ethanol 225.84
    sec-butyl acetate 91.0
    tert-butyl acetate 152.52
    decalin 4.51
    glycerin 309.48
    diglyme 416.38
    acrylic acid 367.29
    isopropyl myristate 37.98
    n-butyric acid 418.99
    acetyl acetate 263.62
    di(2-ethylhexyl) phthalate 61.59
    ethyl propionate 133.11
    nitromethane 1388.9
    1,2-diethoxyethane 130.79
    benzonitrile 152.19
    trioctyl phosphate 40.87
    1-bromopropane 103.08
    gamma-valerolactone 920.0
    n-decanol 32.76
    triethyl phosphate 52.45
    4-methyl-2-pentanol 70.62
    propionitrile 164.94
    vinylene carbonate 368.08
    1,1,2-trichlorotrifluoroethane 557.81
    DMS 146.17
    cumene 25.65
    2-octanol 35.97
    2-hexanone 133.93
    octyl acetate 56.49
    limonene 28.92
    1,2-dimethoxyethane 451.03
    ethyl orthosilicate 47.49
    tributyl phosphate 48.18
    diacetone alcohol 248.15
    N,N-dimethylaniline 81.17
    acrylonitrile 252.24
    aniline 198.51
    1,3-propanediol 394.26
    bromobenzene 105.99
    dibromomethane 248.19
    1,1,2,2-tetrachloroethane 404.43
    2-methyl-cyclohexyl acetate 75.26
    tetrabutyl urea 67.54
    diisobutyl methanol 26.88
    2-phenylethanol 137.06
    styrene 51.96
    dioctyl adipate 67.56
    dimethyl sulfate 424.68
    ethyl butyrate 84.62
    methyl lactate 250.84
    butyl lactate 96.22
    diethyl carbonate 64.49
    propanediol butyl ether 155.46
    triethyl orthoformate 63.58
    p-tert-butyltoluene 20.7
    methyl 4-tert-butylbenzoate 121.03
    morpholine 624.9
    tert-butylamine 67.24
    n-dodecanol 22.85
    dimethoxymethane 734.43
    ethylene carbonate 304.89
    cyrene 223.47
    2-ethoxyethyl acetate 176.86
    2-ethylhexyl acetate 67.03
    1,2,4-trichlorobenzene 149.68
    4-methylpyridine 337.05
    dibutyl ether 35.8
    2,6-dimethyl-4-heptanol 26.88
    DEF 323.58
    dimethyl isosorbide 242.7
    tetrachloroethylene 286.91
    eugenol 136.26
    triacetin 148.88
    span 80 125.37
    1,4-butanediol 142.67
    1,1-dichloroethane 241.35
    2-methyl-1-pentanol 104.96
    methyl formate 577.71
    2-methyl-1-butanol 145.3
    n-decane 3.07
    butyronitrile 163.86
    3,7-dimethyl-1-octanol 46.13
    1-chlorooctane 17.51
    1-chlorotetradecane 7.64
    n-nonane 2.3
    undecane 2.26
    tert-butylcyclohexane 3.19
    cyclooctane 2.74
    cyclopentanol 228.3
    tetrahydropyran 318.41
    tert-amyl methyl ether 70.79
    2,5,8-trioxanonane 271.92
    1-hexene 17.34
    2-isopropoxyethanol 224.18
    2,2,2-trifluoroethanol 498.46
    methyl butyrate 169.76

    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