Gelsemine

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  • Identifiers

    CAS number
    509-15-9

    Molecular formula
    C20H22N2O2

    SMILES
    CN1C[C@]2([C@@H]3C[C@@H]4[C@]5([C@H]2[C@H]1[C@H]3CO4)C6=CC=CC=C6NC5=O)C=C

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 50.97%
    Nutty 26.27%
    Spicy 23.4%
    Popcorn 20.35%
    Roasted 20.08%
    Burnt 19.09%
    Bitter 19.03%
    Green 18.1%
    Earthy 18.02%
    Cooling 16.87%

     

    Flavor
    Bitter 93.36%
    Cedarleaf 19.67%
    Sweet-like 18.75%
    Nitrile 18.23%
    Alkaline 17.91%
    Cereal 17.7%
    Very strong 17.66%
    Indole 17.64%
    Oriental 17.25%
    Lovage 17.17%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    6.3 (neutral)

    Molecular weight
    322.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    519°C

    Melting point expt.

    • 178 °C

    Flash point

    • 231.95 ˚C est.

    Solubility expt.

    • SLIGHTLY SOL IN WATER; SOL IN ALCOHOL, BENZENE, CHLOROFORM, ETHER, ACETONE, DILUTE ACIDS

  • Synonyms

    • GELSEMINE
    • 509-15-9
    • Gelsemin
    • 5Y13A78Z72
    • DTXSID40878487
    • NSC-21729
    • (3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methylspiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1',H)-one
    • Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R,3'S,4aR,5S,8S,8aS,9S)-
    • (1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methylspiro(1H-indole-3,7'-9-oxa-4-azatetracyclo(6.3.1.02,6.05,11)dodecane)-2-one
    • (1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-one
    • RefChem:639803
    • DTXCID501782911
    • 2'-ethenyl-4'-methylspiro(1H-indole-3,7'-9-oxa-4-azatetracyclo(6.3.1.02,6.05,11)dodecane)-2-one
    • (2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro(indole-3,7'-tetracyclo(6.3.1.02,6.05,11)dodecane)-2-ol
    • 208-095-2
    • MFCD00082347
    • (3S,3aS,3'S,5R,8aS,9R)-1-Methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-(epiethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indolin]-2'-one
    • NSC21729
    • UNII-5Y13A78Z72
    • HSDB 3488
    • gelsemine free base
    • (+)-Gelsemine
    • EINECS 208-095-2
    • NSC 21729
    • Gelsemine (Standard)
    • BRN 5406576
    • GELSEMIN [HSDB]
    • GELSEMINE [MI]
    • GELSEMINE [WHO-DD]
    • GELSEMINE, (+)-
    • 4-27-00-07526 (Beilstein Handbook Reference)
    • CHEMBL521561
    • HY-N0388R
    • NFYYATWFXNPTRM-QJICHLCESA-N
    • MSK40269
    • BDBM50459893
    • s9294
    • CCG-267730
    • AC-34231
    • DA-53535
    • Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-
    • 509G159
    • (3S)-methyl(vinyl)spiro[[?]-3,3'-indoline]-2'-one
    • (1R,2S,5S,6S,7S,8R,11S)-4-methyl-2-vinyl-spiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indoline]-2'-one
    • (3R-(3.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8A.BETA.,9S*,10S*))-5-ETHENYL-3,4,4A,5,6,7,8,8A-OCTAHYDRO-7-METHYLSPIRO(3,5,8-ETHANYLYLIDENE-1H-PYRANO(3,4-C)PYRIDINE-10,3'-(3H)INDOL)-2'(1'H)-ONE
    • (3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-5-ethenyl-3,4,- 4a,5,6,7,8,8a-octahydro-7-methylspiro(3,5,8-ethanylylidene-1H-pyr- ano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1',H)-one
    • (3S,3'S,3aS,5R,8S,8aS,9R)-3-Ethenyl-1-methyl-2,3,3a,7,8,8a-hexahydro-1H,5H-spiro[3,8,5-(ethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indol]-2'(1'H)-one
    • (3S,3aS,3'S,8S,8aS)-1-methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-(epiethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indolin]-2'-one
    • SPIRO(3,5,8-ETHANYLYLIDENE-1H-PYRANO(3,4-C)PYRIDINE-10,3'-(3H)INDOL)-2'(1'H)-ONE, 5-ETHENYL-3,4,4A,5,6,7,8,8A-OCTAHYDRO-7-METHYL-, (3R-(3.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8.ABETA.,9S*,10S*))-
    • 509-15-9

  • Applications

    Gelsemine (CAS 509-15-9) is a highly toxic alkaloid of the indole class primarily used in research settings rather than consumer products; in pharmaceutical and toxicology studies it serves as a tool to explore neuropharmacology and mechanisms of analgesic or antispasmodic activity, analytical chemists employ it as a reference standard for plant alkaloids and to develop LC-MS/GC methods for alkaloid profiling, and in academic laboratories it supports method development, isolation, and structural characterization of natural products; due to its toxicity, handling is restricted to controlled laboratory environments under applicable regulations, limiting broader industrial use.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.57
    methanol 4.92
    isopropanol 2.72
    water 0.32
    ethyl acetate 4.22
    n-propanol 2.27
    acetone 6.37
    n-butanol 4.05
    acetonitrile 3.16
    DMF 23.71
    toluene 1.94
    isobutanol 2.85
    1,4-dioxane 8.96
    methyl acetate 4.23
    THF 10.38
    2-butanone 5.49
    n-pentanol 2.66
    sec-butanol 1.35
    n-hexane 0.03
    ethylene glycol 4.91
    NMP 19.2
    cyclohexane 0.14
    DMSO 11.6
    n-butyl acetate 6.88
    n-octanol 3.36
    chloroform 16.91
    n-propyl acetate 4.13
    acetic acid 9.06
    dichloromethane 8.93
    cyclohexanone 18.85
    propylene glycol 2.14
    isopropyl acetate 5.17
    DMAc 23.68
    2-ethoxyethanol 8.3
    isopentanol 6.11
    n-heptane 0.1
    ethyl formate 7.43
    1,2-dichloroethane 5.8
    n-hexanol 4.71
    2-methoxyethanol 17.32
    isobutyl acetate 5.62
    tetrachloromethane 2.97
    n-pentyl acetate 9.59
    transcutol 20.61
    n-heptanol 6.03
    ethylbenzene 0.95
    MIBK 7.42
    2-propoxyethanol 19.07
    tert-butanol 3.07
    MTBE 0.66
    2-butoxyethanol 19.93
    propionic acid 4.56
    o-xylene 1.8
    formic acid 12.12
    diethyl ether 0.9
    m-xylene 2.26
    p-xylene 1.86
    chlorobenzene 5.17
    dimethyl carbonate 8.41
    n-octane 0.08
    formamide 14.15
    cyclopentanone 18.7
    2-pentanone 6.91
    anisole 2.55
    cyclopentyl methyl ether 3.36
    gamma-butyrolactone 19.18
    1-methoxy-2-propanol 14.78
    pyridine 9.51
    3-pentanone 4.47
    furfural 29.61
    n-dodecane 0.15
    diethylene glycol 28.32
    diisopropyl ether 0.63
    tert-amyl alcohol 1.55
    acetylacetone 12.21
    n-hexadecane 0.18
    acetophenone 7.26
    methyl propionate 5.15
    isopentyl acetate 9.79
    trichloroethylene 17.57
    n-nonanol 4.02
    cyclohexanol 4.39
    benzyl alcohol 6.79
    2-ethylhexanol 3.66
    isooctanol 5.7
    dipropyl ether 1.35
    1,2-dichlorobenzene 7.44
    ethyl lactate 8.17
    propylene carbonate 13.74
    n-methylformamide 12.47
    2-pentanol 2.08
    n-pentane 0.05
    1-propoxy-2-propanol 12.99
    1-methoxy-2-propyl acetate 13.21
    2-(2-methoxypropoxy) propanol 15.09
    mesitylene 1.62
    ε-caprolactone 13.62
    p-cymene 2.33
    epichlorohydrin 17.42
    1,1,1-trichloroethane 6.19
    2-aminoethanol 4.56
    morpholine-4-carbaldehyde 27.97
    sulfolane 23.1
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 3.47
    n-hexyl acetate 8.86
    isooctane 0.1
    2-(2-butoxyethoxy)ethanol 18.83
    sec-butyl acetate 3.25
    tert-butyl acetate 5.02
    decalin 0.17
    glycerin 12.78
    diglyme 29.08
    acrylic acid 7.59
    isopropyl myristate 4.35
    n-butyric acid 10.63
    acetyl acetate 6.85
    di(2-ethylhexyl) phthalate 8.94
    ethyl propionate 3.9
    nitromethane 18.16
    1,2-diethoxyethane 5.14
    benzonitrile 11.33
    trioctyl phosphate 7.06
    1-bromopropane 1.46
    gamma-valerolactone 35.9
    n-decanol 2.97
    triethyl phosphate 5.72
    4-methyl-2-pentanol 3.08
    propionitrile 4.66
    vinylene carbonate 20.7
    1,1,2-trichlorotrifluoroethane 31.38
    DMS 8.99
    cumene 1.21
    2-octanol 3.05
    2-hexanone 4.87
    octyl acetate 5.76
    limonene 2.13
    1,2-dimethoxyethane 11.18
    ethyl orthosilicate 4.91
    tributyl phosphate 6.79
    diacetone alcohol 10.83
    N,N-dimethylaniline 2.63
    acrylonitrile 8.82
    aniline 5.08
    1,3-propanediol 10.39
    bromobenzene 4.27
    dibromomethane 4.13
    1,1,2,2-tetrachloroethane 14.93
    2-methyl-cyclohexyl acetate 7.41
    tetrabutyl urea 10.39
    diisobutyl methanol 2.63
    2-phenylethanol 11.07
    styrene 0.99
    dioctyl adipate 7.03
    dimethyl sulfate 13.44
    ethyl butyrate 4.93
    methyl lactate 12.24
    butyl lactate 13.66
    diethyl carbonate 4.89
    propanediol butyl ether 12.98
    triethyl orthoformate 5.49
    p-tert-butyltoluene 1.92
    methyl 4-tert-butylbenzoate 12.59
    morpholine 8.92
    tert-butylamine 1.05
    n-dodecanol 2.2
    dimethoxymethane 14.15
    ethylene carbonate 16.7
    cyrene 18.93
    2-ethoxyethyl acetate 12.74
    2-ethylhexyl acetate 7.3
    1,2,4-trichlorobenzene 9.38
    4-methylpyridine 9.22
    dibutyl ether 1.71
    2,6-dimethyl-4-heptanol 2.63
    DEF 7.74
    dimethyl isosorbide 23.6
    tetrachloroethylene 12.58
    eugenol 17.21
    triacetin 10.9
    span 80 12.6
    1,4-butanediol 4.84
    1,1-dichloroethane 4.41
    2-methyl-1-pentanol 3.2
    methyl formate 11.6
    2-methyl-1-butanol 3.36
    n-decane 0.2
    butyronitrile 5.15
    3,7-dimethyl-1-octanol 4.01
    1-chlorooctane 1.16
    1-chlorotetradecane 0.71
    n-nonane 0.13
    undecane 0.17
    tert-butylcyclohexane 0.13
    cyclooctane 0.08
    cyclopentanol 4.22
    tetrahydropyran 3.94
    tert-amyl methyl ether 0.74
    2,5,8-trioxanonane 23.15
    1-hexene 0.18
    2-isopropoxyethanol 6.49
    2,2,2-trifluoroethanol 12.52
    methyl butyrate 5.93

    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