Nornantenine

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  • Identifiers

    CAS number
    15401-66-8

    Molecular formula
    C19H19NO4

    SMILES
    COC1=C(C2=C3C(CC4=CC5=C(C=C42)OCO5)NCCC3=C1)OC

    Safety labels

  • Odor profile

    Fragrance
    Spicy 31.65%
    Vanilla 29.81%
    Phenolic 29.56%
    Animal 29.43%
    Odorless 29.42%
    Sweet 28.51%
    Powdery 26.62%
    Floral 26.34%
    Musk 23.63%
    Smoky 20.46%

     

    Flavor
    Bitter 95.57%
    Bland 20.93%
    Cedarleaf 18.9%
    Sweet-like 18.74%
    Parsley 17.98%
    Cereal 17.72%
    Indole 17.62%
    Very strong 17.56%
    Alkaline 17.07%
    Eugenol 16.85%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    5.94 (weak acid)

    Molecular weight
    325.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    722°C

    Melting point expt.

    • 163 - 164 °C

    Flash point

    • 213.9 ˚C est.

  • Synonyms

    • Nornantenine
    • 15401-66-8
    • 4H-Benzo(de)(1,3)benzodioxolo(5,6-g)quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-, (S)-
    • 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0^{2,10}.0^{4,8}.0^{16,20}]icosa-1(20),2,4(8),9,16,18-hexaene
    • 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene
    • 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo(10.7.1.0^(2,10).0^(4,8).0^(16,20))icosa-1(20),2,4(8),9,16,18-hexaene
    • 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo(10.7.1.02,10.04,8.016,20)icosa-1(20),2,4(8),9,16,18-hexaene
    • RefChem:166656
    • N-Nornantenine
    • (+)-Nornantenine
    • SCHEMBL6689417
    • CHEMBL1254951
    • DTXSID00934896
    • CHEBI:175147
    • 1,2-Dimethoxy-9,10-methylenedioxynoraporphine
    • 1,2-Dimethoxy-5,6,6a,7-tetrahydro-4H,10H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline
    • 15401-66-8

  • Applications

    Nornantenine (CAS 15401-66-8) is primarily used as an alkaloid scaffold and research intermediate in the exploration and synthesis of related aporphine-type compounds. In practice, it serves as a building block for medicinal-chemistry programs and can function as a reference or analytical standard for alkaloid-related method development (for example LC–MS) in analytical laboratories. It is commonly evaluated in early-stage pharmacological research to probe structure–activity relationships and biological activity of related structures, and may be used to prepare derivatives to enable SAR studies. In industrial and research settings, it is treated as a specialized synthetic intermediate with usage dependent on specific project goals and regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.65
    methanol 6.51
    isopropanol 2.89
    water 0.22
    ethyl acetate 12.72
    n-propanol 3.62
    acetone 12.97
    n-butanol 4.54
    acetonitrile 7.25
    DMF 30.08
    toluene 2.03
    isobutanol 3.31
    1,4-dioxane 15.39
    methyl acetate 10.14
    THF 16.15
    2-butanone 9.85
    n-pentanol 4.87
    sec-butanol 1.76
    n-hexane 0.1
    ethylene glycol 6.61
    NMP 27.01
    cyclohexane 0.37
    DMSO 39.14
    n-butyl acetate 14.39
    n-octanol 5.17
    chloroform 35.32
    n-propyl acetate 14.44
    acetic acid 27.34
    dichloromethane 33.77
    cyclohexanone 24.98
    propylene glycol 1.68
    isopropyl acetate 10.41
    DMAc 37.61
    2-ethoxyethanol 21.04
    isopentanol 6.42
    n-heptane 0.29
    ethyl formate 18.18
    1,2-dichloroethane 21.36
    n-hexanol 6.92
    2-methoxyethanol 26.96
    isobutyl acetate 12.09
    tetrachloromethane 6.24
    n-pentyl acetate 15.96
    transcutol 31.8
    n-heptanol 7.63
    ethylbenzene 2.06
    MIBK 9.94
    2-propoxyethanol 29.52
    tert-butanol 3.88
    MTBE 1.88
    2-butoxyethanol 24.32
    propionic acid 9.05
    o-xylene 2.62
    formic acid 22.83
    diethyl ether 3.4
    m-xylene 2.53
    p-xylene 3.27
    chlorobenzene 8.65
    dimethyl carbonate 16.74
    n-octane 0.31
    formamide 30.36
    cyclopentanone 22.64
    2-pentanone 10.65
    anisole 5.94
    cyclopentyl methyl ether 6.21
    gamma-butyrolactone 33.24
    1-methoxy-2-propanol 14.39
    pyridine 15.38
    3-pentanone 8.11
    furfural 48.52
    n-dodecane 0.43
    diethylene glycol 38.66
    diisopropyl ether 1.53
    tert-amyl alcohol 2.64
    acetylacetone 20.27
    n-hexadecane 0.5
    acetophenone 14.51
    methyl propionate 11.78
    isopentyl acetate 14.72
    trichloroethylene 44.37
    n-nonanol 6.24
    cyclohexanol 5.11
    benzyl alcohol 11.77
    2-ethylhexanol 6.15
    isooctanol 7.36
    dipropyl ether 4.09
    1,2-dichlorobenzene 12.93
    ethyl lactate 13.57
    propylene carbonate 25.63
    n-methylformamide 20.08
    2-pentanol 2.23
    n-pentane 0.14
    1-propoxy-2-propanol 15.68
    1-methoxy-2-propyl acetate 21.28
    2-(2-methoxypropoxy) propanol 18.32
    mesitylene 2.16
    ε-caprolactone 23.95
    p-cymene 4.1
    epichlorohydrin 37.74
    1,1,1-trichloroethane 13.59
    2-aminoethanol 5.72
    morpholine-4-carbaldehyde 42.29
    sulfolane 42.03
    2,2,4-trimethylpentane 0.17
    2-methyltetrahydrofuran 7.62
    n-hexyl acetate 13.55
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 22.39
    sec-butyl acetate 9.05
    tert-butyl acetate 10.09
    decalin 0.43
    glycerin 11.99
    diglyme 40.85
    acrylic acid 15.57
    isopropyl myristate 6.9
    n-butyric acid 16.19
    acetyl acetate 16.31
    di(2-ethylhexyl) phthalate 11.64
    ethyl propionate 10.59
    nitromethane 41.04
    1,2-diethoxyethane 12.37
    benzonitrile 16.1
    trioctyl phosphate 8.7
    1-bromopropane 4.76
    gamma-valerolactone 47.83
    n-decanol 4.89
    triethyl phosphate 11.72
    4-methyl-2-pentanol 3.12
    propionitrile 7.68
    vinylene carbonate 32.11
    1,1,2-trichlorotrifluoroethane 56.28
    DMS 17.06
    cumene 2.4
    2-octanol 4.32
    2-hexanone 11.31
    octyl acetate 9.02
    limonene 4.38
    1,2-dimethoxyethane 25.55
    ethyl orthosilicate 10.26
    tributyl phosphate 9.56
    diacetone alcohol 15.09
    N,N-dimethylaniline 5.82
    acrylonitrile 14.55
    aniline 6.44
    1,3-propanediol 11.38
    bromobenzene 7.53
    dibromomethane 16.35
    1,1,2,2-tetrachloroethane 32.62
    2-methyl-cyclohexyl acetate 13.99
    tetrabutyl urea 12.55
    diisobutyl methanol 3.92
    2-phenylethanol 15.44
    styrene 2.36
    dioctyl adipate 11.58
    dimethyl sulfate 27.06
    ethyl butyrate 12.45
    methyl lactate 14.69
    butyl lactate 15.35
    diethyl carbonate 12.38
    propanediol butyl ether 12.46
    triethyl orthoformate 11.32
    p-tert-butyltoluene 3.31
    methyl 4-tert-butylbenzoate 19.15
    morpholine 15.39
    tert-butylamine 1.61
    n-dodecanol 3.8
    dimethoxymethane 24.8
    ethylene carbonate 27.21
    cyrene 26.98
    2-ethoxyethyl acetate 25.58
    2-ethylhexyl acetate 12.11
    1,2,4-trichlorobenzene 14.85
    4-methylpyridine 12.02
    dibutyl ether 4.63
    2,6-dimethyl-4-heptanol 3.92
    DEF 17.72
    dimethyl isosorbide 30.8
    tetrachloroethylene 28.37
    eugenol 21.54
    triacetin 18.9
    span 80 13.94
    1,4-butanediol 6.49
    1,1-dichloroethane 10.33
    2-methyl-1-pentanol 5.87
    methyl formate 22.15
    2-methyl-1-butanol 4.17
    n-decane 0.61
    butyronitrile 8.34
    3,7-dimethyl-1-octanol 5.52
    1-chlorooctane 3.1
    1-chlorotetradecane 1.7
    n-nonane 0.43
    undecane 0.5
    tert-butylcyclohexane 0.32
    cyclooctane 0.21
    cyclopentanol 4.82
    tetrahydropyran 7.04
    tert-amyl methyl ether 2.17
    2,5,8-trioxanonane 31.63
    1-hexene 0.61
    2-isopropoxyethanol 14.91
    2,2,2-trifluoroethanol 25.56
    methyl butyrate 14.66

    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