Aspidospermine

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  • Identifiers

    CAS number
    466-49-9

    Molecular formula
    C22H30N2O2

    SMILES
    CC[C@]12CCCN3[C@H]1[C@@]4(CC3)[C@@H](CC2)N(C5=C4C=CC=C5OC)C(=O)C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 38.67%
    Animal 30.84%
    Nutty 23.36%
    Roasted 23.14%
    Popcorn 21.91%
    Cooling 21.63%
    Earthy 20.82%
    Woody 20.81%
    Fresh 18.95%
    Mint 17.11%

     

    Flavor
    Bitter 83.47%
    Cedarleaf 22.15%
    Bland 20.62%
    Sweet-like 20.47%
    Cereal 20.2%
    Very strong 19.56%
    Odorless 19.43%
    Alkaline 19.41%
    Nitrile 19.36%
    Lovage 19.31%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    7.65 (neutral)

    Molecular weight
    354.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    532°C

    Melting point expt.

    • 208 - 209 °C

    Flash point

    • 224.22 ˚C est.

  • Synonyms

    • ASPIDOSPERMINE
    • Aspidospermin
    • (-)-Aspidospermine
    • 466-49-9
    • NSC-19508
    • NSC-61811
    • U1475W62Q5
    • CHEBI:28463
    • DTXSID70196883
    • 1-(17-methoxyaspidospermidin-1-yl)ethanone
    • 1-((1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo(10.6.1.0^(1,9).0^(2,7).0^(16,19))nonadeca-2(7),3,5-trien-8-yl)ethan-1-one
    • 1-((1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2(7),3,5-trien-8-yl)ethanone
    • 1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5-trien-8-yl]ethan-1-one
    • 1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5-trien-8-yl]ethanone
    • RefChem:916386
    • DTXCID10119374
    • 207-376-7
    • 1-Acetyl-17-methoxyaspidospermidine
    • CHEMBL519457
    • NSC61811
    • Aspidospermidine, 1-acetyl-17-methoxy-
    • Vincaminorine
    • WLN: T C6 B5665 2AB S BX IN QN JH&&TTTJ GO1 IV1 M2
    • UNII-U1475W62Q5
    • EINECS 207-376-7
    • NSC 19508
    • BRN 0048882
    • ASPIDOSPERMINE [MI]
    • TimTec1_000915
    • 5-23-12-00210 (Beilstein Handbook Reference)
    • SCHEMBL918176
    • Vincaminorein (Aspidospermine)
    • SCHEMBL30137188
    • ARQOGCYMPUOVHK-ZHHKINOHSA-N
    • 1-[ethyl(methoxy)[?]yl]ethanone
    • HMS1536J13
    • NSC19508
    • BDBM50252054
    • CCG-35302
    • CCG-36039
    • NCGC00174986-01
    • NCI60_005440
    • ST012029
    • 1-Acetyl-17-methoxyaspidospermidine, 9CI
    • NS00031621
    • 1-(17-Methoxyaspidospermidin-1-yl)-ethanone
    • C09042
    • 1-(17-Methoxyaspidospermidin-1-yl)ethan-1-one
    • BRD-K06579228-001-01-6
    • Q27103707
    • ETHANONE, 1-(17-METHOXYASPIDOSPERMIDIN-1-YL)-
    • (1S,9R,12R,19R)-8-acetyl-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.0<1,9> .0<2,7>.0<16,19>]nonadeca-2,4,6-triene
    • 1-((3aR,5aR,10bR,12bR)-3a-Ethyl-7-methoxy-2,3,3a,5,5a,11,12,12b-octahydro-1H,4H-6,12a-diaza-indeno[7,1-cd]fluoren-6-yl)-ethanone
    • 1935-07-5
    • 2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-10-methyl-, methyl ester, (7S-(7R*,9R*))-
    • 466-49-9

  • Applications

    Aspidospermine is a natural monoterpene indole alkaloid isolated from Aspidosperma species; typical applications are in chemical research and synthesis, including use as a synthetic intermediate and building block for aspidosperma-type alkaloids, as a scaffold for stereochemical libraries in asymmetric synthesis, and as an analytical reference material to support structure elucidation and analytical method development; it is studied in pharmaceutical research for potential bioactivity and as a lead in natural product discovery, but it is not presented as a therapeutic agent, and its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.94
    methanol 14.6
    isopropanol 8.65
    water 0.6
    ethyl acetate 47.37
    n-propanol 12.64
    acetone 48.69
    n-butanol 17.17
    acetonitrile 22.84
    DMF 83.99
    toluene 28.11
    isobutanol 12.87
    1,4-dioxane 53.31
    methyl acetate 44.22
    THF 64.93
    2-butanone 52.07
    n-pentanol 10.89
    sec-butanol 6.02
    n-hexane 0.17
    ethylene glycol 10.23
    NMP 131.05
    cyclohexane 1.23
    DMSO 39.46
    n-butyl acetate 43.58
    n-octanol 5.58
    chloroform 272.81
    n-propyl acetate 31.95
    acetic acid 69.6
    dichloromethane 207.21
    cyclohexanone 133.92
    propylene glycol 5.92
    isopropyl acetate 40.77
    DMAc 111.21
    2-ethoxyethanol 29.1
    isopentanol 22.85
    n-heptane 0.21
    ethyl formate 43.86
    1,2-dichloroethane 97.82
    n-hexanol 13.5
    2-methoxyethanol 48.61
    isobutyl acetate 33.8
    tetrachloromethane 27.66
    n-pentyl acetate 41.36
    transcutol 65.95
    n-heptanol 10.94
    ethylbenzene 8.59
    MIBK 37.78
    2-propoxyethanol 55.21
    tert-butanol 9.4
    MTBE 6.25
    2-butoxyethanol 46.81
    propionic acid 35.65
    o-xylene 15.87
    formic acid 42.89
    diethyl ether 8.29
    m-xylene 18.98
    p-xylene 14.5
    chlorobenzene 80.93
    dimethyl carbonate 48.37
    n-octane 0.15
    formamide 48.04
    cyclopentanone 139.25
    2-pentanone 48.28
    anisole 21.83
    cyclopentyl methyl ether 25.61
    gamma-butyrolactone 163.46
    1-methoxy-2-propanol 38.86
    pyridine 93.46
    3-pentanone 39.07
    furfural 184.9
    n-dodecane 0.25
    diethylene glycol 57.13
    diisopropyl ether 3.72
    tert-amyl alcohol 6.67
    acetylacetone 77.22
    n-hexadecane 0.32
    acetophenone 47.77
    methyl propionate 45.37
    isopentyl acetate 49.22
    trichloroethylene 329.59
    n-nonanol 6.92
    cyclohexanol 22.75
    benzyl alcohol 40.62
    2-ethylhexanol 10.39
    isooctanol 10.71
    dipropyl ether 5.37
    1,2-dichlorobenzene 90.72
    ethyl lactate 32.05
    propylene carbonate 115.63
    n-methylformamide 53.81
    2-pentanol 7.68
    n-pentane 0.3
    1-propoxy-2-propanol 31.12
    1-methoxy-2-propyl acetate 66.29
    2-(2-methoxypropoxy) propanol 37.58
    mesitylene 10.11
    ε-caprolactone 114.57
    p-cymene 9.76
    epichlorohydrin 156.0
    1,1,1-trichloroethane 86.23
    2-aminoethanol 12.74
    morpholine-4-carbaldehyde 134.55
    sulfolane 146.27
    2,2,4-trimethylpentane 0.39
    2-methyltetrahydrofuran 32.45
    n-hexyl acetate 34.54
    isooctane 0.34
    2-(2-butoxyethoxy)ethanol 41.9
    sec-butyl acetate 25.6
    tert-butyl acetate 34.0
    decalin 0.86
    glycerin 25.48
    diglyme 79.43
    acrylic acid 56.08
    isopropyl myristate 13.31
    n-butyric acid 65.51
    acetyl acetate 74.01
    di(2-ethylhexyl) phthalate 30.87
    ethyl propionate 29.09
    nitromethane 127.46
    1,2-diethoxyethane 19.55
    benzonitrile 77.45
    trioctyl phosphate 18.87
    1-bromopropane 20.84
    gamma-valerolactone 214.13
    n-decanol 4.9
    triethyl phosphate 25.54
    4-methyl-2-pentanol 9.83
    propionitrile 34.16
    vinylene carbonate 153.04
    1,1,2-trichlorotrifluoroethane 171.98
    DMS 55.73
    cumene 7.37
    2-octanol 5.3
    2-hexanone 28.12
    octyl acetate 18.55
    limonene 9.7
    1,2-dimethoxyethane 41.99
    ethyl orthosilicate 20.95
    tributyl phosphate 22.75
    diacetone alcohol 39.77
    N,N-dimethylaniline 15.59
    acrylonitrile 62.48
    aniline 44.74
    1,3-propanediol 28.53
    bromobenzene 79.05
    dibromomethane 90.07
    1,1,2,2-tetrachloroethane 182.5
    2-methyl-cyclohexyl acetate 36.67
    tetrabutyl urea 27.96
    diisobutyl methanol 6.3
    2-phenylethanol 48.68
    styrene 11.03
    dioctyl adipate 25.94
    dimethyl sulfate 80.7
    ethyl butyrate 29.97
    methyl lactate 41.95
    butyl lactate 41.07
    diethyl carbonate 30.29
    propanediol butyl ether 26.81
    triethyl orthoformate 25.53
    p-tert-butyltoluene 7.92
    methyl 4-tert-butylbenzoate 49.28
    morpholine 50.27
    tert-butylamine 3.67
    n-dodecanol 3.57
    dimethoxymethane 50.95
    ethylene carbonate 117.38
    cyrene 65.79
    2-ethoxyethyl acetate 68.4
    2-ethylhexyl acetate 39.39
    1,2,4-trichlorobenzene 109.64
    4-methylpyridine 86.59
    dibutyl ether 4.69
    2,6-dimethyl-4-heptanol 6.3
    DEF 51.34
    dimethyl isosorbide 72.78
    tetrachloroethylene 134.46
    eugenol 55.31
    triacetin 54.31
    span 80 31.28
    1,4-butanediol 13.36
    1,1-dichloroethane 67.03
    2-methyl-1-pentanol 14.19
    methyl formate 54.77
    2-methyl-1-butanol 15.84
    n-decane 0.36
    butyronitrile 30.07
    3,7-dimethyl-1-octanol 8.76
    1-chlorooctane 3.28
    1-chlorotetradecane 1.62
    n-nonane 0.23
    undecane 0.29
    tert-butylcyclohexane 0.57
    cyclooctane 0.39
    cyclopentanol 20.38
    tetrahydropyran 31.95
    tert-amyl methyl ether 5.91
    2,5,8-trioxanonane 56.43
    1-hexene 1.23
    2-isopropoxyethanol 24.28
    2,2,2-trifluoroethanol 64.62
    methyl butyrate 39.78

    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