seneciphylline N-oxide

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  • Identifiers

    CAS number
    38710-26-8

    Molecular formula
    C18H23NO6

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

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 54.9%
    Caramellic 48.42%
    Burnt 36.75%
    Nutty 31.22%
    Odorless 30.12%
    Roasted 28.2%
    Spicy 27.08%
    Coumarinic 24.32%
    Tobacco 23.21%
    Hay 21.5%

     

    Flavor
    Bitter 80.74%
    Cedarleaf 20.17%
    Fenugreek 19.8%
    Lovage 19.76%
    Seedy 19.56%
    Leaves 19.53%
    Extremely sweet 19.47%
    Cotton candy 19.35%
    Ripe apricot 19.29%
    Basil 19.26%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.1

    pKa est.
    6.07 (neutral)

    Molecular weight
    349.4 g/mol

    Flash point

    • -331.6 ˚C est.

  • Synonyms

    • Seneciphylline N-oxide
    • 38710-26-8
    • Seneciphylline oxide
    • CHEBI:136404
    • DTXSID301016605
    • 13,19-didehydro-12-hydroxysenecionan-11,16-dione 4-oxide
    • (3Z,6R,14aR,14bR)-3-ethylidene-6-hydroxy-6-methyl-5-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
    • (3Z,6R,14aR,14bR)-3-ethylidene-6-hydroxy-6-methyl-5-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:884870
    • Senecionan-11,16-dione, 13,19-didehydro-12-hydroxy-, 4-oxide
    • DTXCID001783207
    • (1R,4E,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-14-oxido-2,9-dioxa-14-azoniatricyclo(9.5.1.014,17)heptadec-11-ene-3,8-dione
    • (1R,4E,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • Seneciphylline-N-oxide
    • (1R,4Z,7R,17R)-4-Ethylidene-7-hydroxy-7-methyl-6-methylidene-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • SeneciphyllineN-oxide
    • seneciphyllin N-oxide
    • speciophylline N-oxide
    • orb1684222
    • HY-N2561
    • AKOS037514835
    • AKOS040760708
    • FS-9852
    • CS-0022893
    • Seneciphylline-N-oxide 100 microg/mL in Water
    • (6R,14aR,14bR)-3-Ethylidene-6-hydroxy-6-methyl-5-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
    • 38710-26-8

  • Applications

    seneciphylline N-oxide (CAS 38710-26-8) is a natural pyrrolizidine alkaloid, and due to its toxicity and related regulatory constraints, its industrial use is limited; in practice, its applications are mainly in research and analytical contexts: it is used as a reference standard for identifying and quantifying pyrrolizidine alkaloids in plant extracts and natural products; serves as a precursor or intermediate in the organic synthesis of related pyrrolizidine derivatives; used as a tool in synthetic chemistry studies and mechanistic investigations; employed in laboratory toxicology and risk assessment studies; and regarded as material for building a natural-product library and quality-control assessments in plant research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 211.44
    methanol 432.63
    isopropanol 129.16
    water 1.65
    ethyl acetate 229.96
    n-propanol 160.51
    acetone 392.26
    n-butanol 133.47
    acetonitrile 176.84
    DMF 899.62
    toluene 66.62
    isobutanol 95.59
    1,4-dioxane 309.93
    methyl acetate 194.01
    THF 510.93
    2-butanone 213.44
    n-pentanol 88.28
    sec-butanol 102.74
    n-hexane 1.63
    ethylene glycol 88.34
    NMP 555.02
    cyclohexane 3.82
    DMSO 699.18
    n-butyl acetate 81.05
    n-octanol 31.66
    chloroform 463.37
    n-propyl acetate 110.86
    acetic acid 942.87
    dichloromethane 393.64
    cyclohexanone 301.34
    propylene glycol 82.94
    isopropyl acetate 128.75
    DMAc 630.24
    2-ethoxyethanol 305.57
    isopentanol 103.53
    n-heptane 1.51
    ethyl formate 193.14
    1,2-dichloroethane 205.2
    n-hexanol 66.01
    2-methoxyethanol 585.1
    isobutyl acetate 62.86
    tetrachloromethane 36.47
    n-pentyl acetate 66.2
    transcutol 484.14
    n-heptanol 41.36
    ethylbenzene 28.33
    MIBK 111.27
    2-propoxyethanol 261.98
    tert-butanol 103.91
    MTBE 47.81
    2-butoxyethanol 138.56
    propionic acid 230.64
    o-xylene 40.0
    formic acid 667.92
    diethyl ether 95.19
    m-xylene 41.13
    p-xylene 34.52
    chlorobenzene 83.77
    dimethyl carbonate 213.12
    n-octane 1.01
    formamide 891.95
    cyclopentanone 411.75
    2-pentanone 209.05
    anisole 93.8
    cyclopentyl methyl ether 138.95
    gamma-butyrolactone 534.09
    1-methoxy-2-propanol 375.26
    pyridine 300.67
    3-pentanone 133.07
    furfural 443.71
    n-dodecane 1.23
    diethylene glycol 272.25
    diisopropyl ether 19.07
    tert-amyl alcohol 86.28
    acetylacetone 321.64
    n-hexadecane 1.43
    acetophenone 134.25
    methyl propionate 216.71
    isopentyl acetate 68.08
    trichloroethylene 562.74
    n-nonanol 33.94
    cyclohexanol 106.88
    benzyl alcohol 138.27
    2-ethylhexanol 31.48
    isooctanol 32.92
    dipropyl ether 31.81
    1,2-dichlorobenzene 83.01
    ethyl lactate 99.2
    propylene carbonate 262.81
    n-methylformamide 527.93
    2-pentanol 72.05
    n-pentane 2.31
    1-propoxy-2-propanol 126.02
    1-methoxy-2-propyl acetate 148.12
    2-(2-methoxypropoxy) propanol 128.42
    mesitylene 19.63
    ε-caprolactone 297.79
    p-cymene 15.84
    epichlorohydrin 526.0
    1,1,1-trichloroethane 137.72
    2-aminoethanol 156.17
    morpholine-4-carbaldehyde 649.37
    sulfolane 520.92
    2,2,4-trimethylpentane 1.72
    2-methyltetrahydrofuran 206.04
    n-hexyl acetate 81.9
    isooctane 1.29
    2-(2-butoxyethoxy)ethanol 175.97
    sec-butyl acetate 69.86
    tert-butyl acetate 103.62
    decalin 2.83
    glycerin 211.45
    diglyme 327.16
    acrylic acid 289.87
    isopropyl myristate 29.76
    n-butyric acid 296.94
    acetyl acetate 190.84
    di(2-ethylhexyl) phthalate 50.37
    ethyl propionate 104.19
    nitromethane 1097.15
    1,2-diethoxyethane 95.8
    benzonitrile 126.53
    trioctyl phosphate 32.51
    1-bromopropane 72.11
    gamma-valerolactone 704.57
    n-decanol 23.61
    triethyl phosphate 44.98
    4-methyl-2-pentanol 44.74
    propionitrile 129.17
    vinylene carbonate 311.13
    1,1,2-trichlorotrifluoroethane 469.02
    DMS 113.55
    cumene 17.51
    2-octanol 24.23
    2-hexanone 107.34
    octyl acetate 44.54
    limonene 20.52
    1,2-dimethoxyethane 332.86
    ethyl orthosilicate 38.84
    tributyl phosphate 39.45
    diacetone alcohol 179.68
    N,N-dimethylaniline 65.69
    acrylonitrile 205.74
    aniline 135.68
    1,3-propanediol 229.39
    bromobenzene 75.1
    dibromomethane 197.76
    1,1,2,2-tetrachloroethane 326.72
    2-methyl-cyclohexyl acetate 59.21
    tetrabutyl urea 57.0
    diisobutyl methanol 18.45
    2-phenylethanol 102.46
    styrene 38.43
    dioctyl adipate 55.98
    dimethyl sulfate 341.58
    ethyl butyrate 65.37
    methyl lactate 205.56
    butyl lactate 76.85
    diethyl carbonate 52.54
    propanediol butyl ether 115.71
    triethyl orthoformate 49.4
    p-tert-butyltoluene 13.91
    methyl 4-tert-butylbenzoate 96.84
    morpholine 389.2
    tert-butylamine 34.88
    n-dodecanol 16.71
    dimethoxymethane 520.15
    ethylene carbonate 244.69
    cyrene 194.02
    2-ethoxyethyl acetate 129.24
    2-ethylhexyl acetate 50.74
    1,2,4-trichlorobenzene 118.09
    4-methylpyridine 252.19
    dibutyl ether 26.27
    2,6-dimethyl-4-heptanol 18.45
    DEF 264.86
    dimethyl isosorbide 198.45
    tetrachloroethylene 224.04
    eugenol 113.43
    triacetin 125.79
    span 80 99.36
    1,4-butanediol 91.31
    1,1-dichloroethane 171.31
    2-methyl-1-pentanol 72.11
    methyl formate 444.85
    2-methyl-1-butanol 95.77
    n-decane 2.1
    butyronitrile 116.59
    3,7-dimethyl-1-octanol 33.76
    1-chlorooctane 12.66
    1-chlorotetradecane 5.54
    n-nonane 1.54
    undecane 1.56
    tert-butylcyclohexane 1.95
    cyclooctane 1.44
    cyclopentanol 132.14
    tetrahydropyran 179.48
    tert-amyl methyl ether 47.43
    2,5,8-trioxanonane 217.02
    1-hexene 10.75
    2-isopropoxyethanol 161.78
    2,2,2-trifluoroethanol 320.31
    methyl butyrate 141.64

    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