Seneciphylline

Overview IFRA Request a quote

  • Identifiers

    CAS number
    480-81-9

    Molecular formula
    C18H23NO5

    SMILES
    C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Sweet 55.71%
    Caramellic 52.0%
    Burnt 38.92%
    Nutty 38.81%
    Roasted 33.77%
    Coumarinic 28.04%
    Spicy 27.87%
    Coconut 24.9%
    Odorless 24.75%
    Popcorn 24.35%

     

    Flavor
    Bitter 81.95%
    Lovage 20.11%
    Cedarleaf 19.9%
    Fenugreek 19.84%
    Seedy 19.59%
    Extremely sweet 19.52%
    Cotton candy 19.45%
    Leaves 19.28%
    Ripe apricot 19.21%
    Basil 19.11%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    7.72 (neutral)

    Molecular weight
    333.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    678°C

    Melting point expt.

    • 423 °F (NTP, 1992)
    • 217--218 °C

    Flash point

    • 208.8 ˚C est.

    Solubility expt.

    • less than 0.1 mg/mL at 64 °F (NTP, 1992)
    • Sol in water /Hydrochloride/
    • Sol in chloroform; sparingly sol in ethanol, acetone; slightly sol in water
    • Difficult solubility in ether and ligroin.
    • In water, 1X10+6 mg/L @ 25 °C /Estimated/

  • Synonyms

    • SENECIPHYLLINE
    • 480-81-9
    • Seneciphyllin
    • Jacodine
    • 13,19-Didehydro-12-hydroxysenecionan-11,16-dione
    • ALPHA-LONGILOBINE
    • NSC 30622
    • NSC-30622
    • DTXSID8026016
    • 0ZYZ9L5454
    • NCI-C61165
    • (1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • Senecionan-11,16-dione, 13,19-didehydro-12-hydroxy-
    • trans-15-Ethylidene-12beta-hydroxy-12alpha-methyl-13-methylenesenec-1-enine
    • (1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo(9.5.1.014,17)heptadec-11-ene-3,8-dione
    • RefChem:182378
    • DTXCID306016
    • C18H23NO5
    • NSC30622
    • [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-
    • MLS000737616
    • CHEBI:9108
    • MFCD00221722
    • Seniciphylline
    • Seneciphylline, analytical standard
    • (1R,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylene-2,9-dioxa-14-azatricyc lo[9.5.1.0<14,17>]heptadec-11-ene-3,8-dione
    • (6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
    • SMR000393787
    • senenciphylline
    • Seneciophylline
    • Seneciphynine
    • UNII-0ZYZ9L5454
    • CCRIS 4336
    • HSDB 5188
    • FCEVNJIUIMLVML-QPSVUOIXSA-N
    • (3Z,6R,14AR,14BR)-3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-6-METHYL-5-METHYLENE(1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE
    • (3Z,6R,14aR,14bR)-3-Ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
    • Prestwick_446
    • Prestwick2_000599
    • Prestwick3_000599
    • Seneciphylline (Standard)
    • Seneciphylline Impurity 1
    • .ALPHA.-LONGILOBINE
    • SENECIPHYLLINE [MI]
    • BSPBio_000478
    • SENECIPHYLLINE [HSDB]
    • SENECIPHYLLINE [IARC]
    • MLS002222214
    • SCHEMBL177867
    • BPBio1_000526
    • CHEMBL523911
    • orb1297567
    • CHEBI:92677
    • HY-N1282R
    • HMS1569H20
    • HMS2096H20
    • HMS2763J21
    • (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-
    • HY-N1282
    • MSK14177
    • BDBM50480273
    • EX-A11101
    • AKOS024282719
    • EBC-616357
    • Seneciphylline 100 microg/mL in Water
    • NCGC00017384-04
    • NCGC00142562-03
    • AC-34599
    • DA-57794
    • FS161595
    • MS-25026
    • Seneciphylline 100 microg/mL in Methanol
    • ST057705
    • CS-0016686
    • Senecionan-11, 13,19-didehydro-12-hydroxy-
    • (Z)-ethylidene-hydroxy-methyl-methylene-[?]dione
    • BRD-K38449220-001-03-8
    • Q27108272
    • (15Z)-12-Hydroxy-13,19-didehydrosenecionan-11,16-dione
    • 2H-Pyran-2-carboxylicacid,5-ethyltetrahydro-2,3-dimethyl-6-oxo-(9ci)
    • (1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • (1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0,14,17]heptadec-11-ene-3,8-dione
    • Pyrrolizine-2, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene(1,6)dioxacyclododecino[2,3,4-gh]-
    • 480-81-9

  • Applications

    Seneciphylline (CAS 480-81-9) is a pyrrolizidine alkaloid found in certain Senecio species. In practical terms, it is mainly used in research settings: as a reference or standard compound for analytical method development and quantification of pyrrolizidine alkaloids in plant materials; as a tool in toxicology and pharmacology studies to understand structure-activity relationships and hepatotoxicity mechanisms; in natural product chemistry for isolation, structure elucidation, and biosynthesis investigations; and as a model for spectroscopic and chemotaxonomic analyses.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 139.59
    methanol 249.96
    isopropanol 103.91
    water 0.59
    ethyl acetate 161.32
    n-propanol 127.65
    acetone 196.45
    n-butanol 133.87
    acetonitrile 77.42
    DMF 487.81
    toluene 72.96
    isobutanol 92.28
    1,4-dioxane 216.08
    methyl acetate 136.35
    THF 330.06
    2-butanone 152.36
    n-pentanol 78.57
    sec-butanol 97.07
    n-hexane 1.49
    ethylene glycol 42.27
    NMP 321.42
    cyclohexane 3.71
    DMSO 315.99
    n-butyl acetate 79.8
    n-octanol 27.85
    chloroform 422.86
    n-propyl acetate 85.46
    acetic acid 484.13
    dichloromethane 315.54
    cyclohexanone 230.51
    propylene glycol 49.87
    isopropyl acetate 112.53
    DMAc 417.65
    2-ethoxyethanol 205.82
    isopentanol 115.23
    n-heptane 1.43
    ethyl formate 122.36
    1,2-dichloroethane 164.21
    n-hexanol 66.83
    2-methoxyethanol 375.58
    isobutyl acetate 55.73
    tetrachloromethane 36.39
    n-pentyl acetate 69.43
    transcutol 431.51
    n-heptanol 43.11
    ethylbenzene 27.07
    MIBK 102.06
    2-propoxyethanol 209.23
    tert-butanol 90.76
    MTBE 46.81
    2-butoxyethanol 130.26
    propionic acid 156.5
    o-xylene 43.12
    formic acid 315.96
    diethyl ether 75.29
    m-xylene 47.31
    p-xylene 35.03
    chlorobenzene 81.36
    dimethyl carbonate 130.37
    n-octane 0.9
    formamide 425.85
    cyclopentanone 255.03
    2-pentanone 158.8
    anisole 68.27
    cyclopentyl methyl ether 114.27
    gamma-butyrolactone 312.64
    1-methoxy-2-propanol 273.32
    pyridine 225.27
    3-pentanone 102.23
    furfural 292.22
    n-dodecane 1.06
    diethylene glycol 194.36
    diisopropyl ether 18.62
    tert-amyl alcohol 86.24
    acetylacetone 208.05
    n-hexadecane 1.25
    acetophenone 106.03
    methyl propionate 147.88
    isopentyl acetate 77.0
    trichloroethylene 446.48
    n-nonanol 31.1
    cyclohexanol 106.57
    benzyl alcohol 117.2
    2-ethylhexanol 34.63
    isooctanol 37.06
    dipropyl ether 25.32
    1,2-dichlorobenzene 81.26
    ethyl lactate 73.02
    propylene carbonate 176.36
    n-methylformamide 263.67
    2-pentanol 81.72
    n-pentane 2.58
    1-propoxy-2-propanol 114.07
    1-methoxy-2-propyl acetate 130.97
    2-(2-methoxypropoxy) propanol 113.16
    mesitylene 23.46
    ε-caprolactone 221.14
    p-cymene 17.38
    epichlorohydrin 348.44
    1,1,1-trichloroethane 122.35
    2-aminoethanol 92.69
    morpholine-4-carbaldehyde 416.58
    sulfolane 312.89
    2,2,4-trimethylpentane 2.24
    2-methyltetrahydrofuran 159.68
    n-hexyl acetate 77.21
    isooctane 1.72
    2-(2-butoxyethoxy)ethanol 161.08
    sec-butyl acetate 64.41
    tert-butyl acetate 94.92
    decalin 2.94
    glycerin 128.46
    diglyme 275.99
    acrylic acid 175.51
    isopropyl myristate 28.25
    n-butyric acid 242.29
    acetyl acetate 139.39
    di(2-ethylhexyl) phthalate 47.79
    ethyl propionate 76.87
    nitromethane 509.28
    1,2-diethoxyethane 92.2
    benzonitrile 103.73
    trioctyl phosphate 31.62
    1-bromopropane 65.64
    gamma-valerolactone 452.16
    n-decanol 21.92
    triethyl phosphate 40.44
    4-methyl-2-pentanol 52.55
    propionitrile 82.06
    vinylene carbonate 206.3
    1,1,2-trichlorotrifluoroethane 347.35
    DMS 95.78
    cumene 18.51
    2-octanol 24.95
    2-hexanone 83.49
    octyl acetate 40.11
    limonene 21.2
    1,2-dimethoxyethane 225.43
    ethyl orthosilicate 36.14
    tributyl phosphate 38.08
    diacetone alcohol 149.22
    N,N-dimethylaniline 53.5
    acrylonitrile 129.38
    aniline 122.95
    1,3-propanediol 169.81
    bromobenzene 71.86
    dibromomethane 166.58
    1,1,2,2-tetrachloroethane 291.13
    2-methyl-cyclohexyl acetate 55.57
    tetrabutyl urea 50.94
    diisobutyl methanol 21.45
    2-phenylethanol 98.05
    styrene 33.72
    dioctyl adipate 48.35
    dimethyl sulfate 198.59
    ethyl butyrate 56.32
    methyl lactate 144.25
    butyl lactate 75.01
    diethyl carbonate 45.23
    propanediol butyl ether 107.49
    triethyl orthoformate 47.13
    p-tert-butyltoluene 15.73
    methyl 4-tert-butylbenzoate 88.39
    morpholine 282.17
    tert-butylamine 34.26
    n-dodecanol 15.44
    dimethoxymethane 299.95
    ethylene carbonate 172.05
    cyrene 149.16
    2-ethoxyethyl acetate 121.83
    2-ethylhexyl acetate 56.0
    1,2,4-trichlorobenzene 108.64
    4-methylpyridine 210.82
    dibutyl ether 23.11
    2,6-dimethyl-4-heptanol 21.45
    DEF 186.18
    dimethyl isosorbide 171.0
    tetrachloroethylene 204.66
    eugenol 99.0
    triacetin 102.11
    span 80 90.56
    1,4-butanediol 61.36
    1,1-dichloroethane 146.82
    2-methyl-1-pentanol 79.49
    methyl formate 216.18
    2-methyl-1-butanol 106.62
    n-decane 1.69
    butyronitrile 85.52
    3,7-dimethyl-1-octanol 34.73
    1-chlorooctane 11.13
    1-chlorotetradecane 5.03
    n-nonane 1.21
    undecane 1.3
    tert-butylcyclohexane 2.18
    cyclooctane 1.53
    cyclopentanol 106.46
    tetrahydropyran 144.28
    tert-amyl methyl ether 48.35
    2,5,8-trioxanonane 178.83
    1-hexene 10.26
    2-isopropoxyethanol 127.24
    2,2,2-trifluoroethanol 187.8
    methyl butyrate 101.74

    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