(-)-Nornuciferine

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  • Identifiers

    CAS number
    3153-55-7

    Molecular formula
    C18H19NO2

    SMILES
    CN1CCC2=CC(=C(C3=C2[C@H]1CC4=CC=CC=C43)OC)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 37.69%
    Phenolic 35.46%
    Animal 31.58%
    Sweet 29.13%
    Spicy 27.15%
    Smoky 25.2%
    Vanilla 25.19%
    Burnt 24.06%
    Musk 21.99%
    Powdery 20.79%

     

    Flavor
    Bitter 92.81%
    Cedarleaf 20.73%
    Sweet-like 20.57%
    Very strong 20.09%
    Indole 19.8%
    Bland 19.49%
    Parsley 19.17%
    Cereal 19.16%
    Alkaline 19.03%
    Nitrile 18.84%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    8.18 (weak base)

    Molecular weight
    281.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    607°C

    Flash point

    • 210.28 ˚C est.

  • Synonyms

    • 3153-55-7
    • (-)-Nornuciferine
    • 2D75P3S5Q6
    • Nornuciferine, (-)-
    • RefChem:1049126
    • O-Nornuciferine
    • N-Methylasimilobine
    • Asimilobine, N-methyl-
    • Methylasimilobine
    • ORTHO-NORNUCIFERINE
    • (6aR)-1-methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
    • (6aR)-5,6,6a,7-Tetrahydro-1-methoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol
    • 4H-Dibenzo(de,g)quinolin-2-ol, 5,6,6a,7-tetrahydro-1-methoxy-6-methyl-, (R)-
    • 4H-Dibenzo[de,g]quinolin-2-ol, 5,6,6a,7-tetrahydro-1-methoxy-6-methyl-, (6aR)-
    • CCRIS 3808
    • O-demethyl nuciferine
    • 6a-beta-Aporphin-2-ol, 1-methoxy-
    • 6a.beta.-Aporphin-2-ol, 1-methoxy-
    • 4H-Dibenzo[de,g]quinolin-2-ol, 5,6,6a,7-tetrahydro-1-methoxy-6-methyl-, (R)-
    • (-)-O-Nornuciferine
    • O-Nornuciferine, (-)-
    • orb1297558
    • (R)-1-Methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
    • CHEMBL2316499
    • SCHEMBL29689806
    • DTXSID10953513
    • AKXOIHNFHOEPHN-CQSZACIVSA-N
    • HY-N7511
    • AKOS040760144
    • EBC-615867
    • DA-66344
    • MS-23997
    • CS-0131116
    • NS00094128
    • D85014
    • (9R)-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,13(17),14-hexaen-15-ol
    • 3153-55-7

  • Applications

    (-)-Nornuciferine is an aporphine alkaloid of plant origin that is primarily used as a building block and scaffold for the enantioselective synthesis of related alkaloids and as reference material for chemical analysis and phytochemistry work. In pharmaceutical and medicinal chemistry contexts, it is treated as a core substrate for the synthesis of alkaloid-derived compounds and as a valuable chiral building block for asymmetric reactions. In molecular biology and pharmacology research, it is employed as a test compound to evaluate receptor-binding characteristics and neuropharmacology in laboratory studies. Additionally, it serves as a scaffold for the preparation of related aporphine structures and a potential precursor in synthetic routes toward related compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.77
    methanol 16.54
    isopropanol 7.19
    water 0.12
    ethyl acetate 10.61
    n-propanol 12.01
    acetone 15.22
    n-butanol 11.66
    acetonitrile 4.17
    DMF 63.63
    toluene 7.71
    isobutanol 9.31
    1,4-dioxane 31.58
    methyl acetate 11.71
    THF 32.06
    2-butanone 14.28
    n-pentanol 9.71
    sec-butanol 3.96
    n-hexane 0.12
    ethylene glycol 12.12
    NMP 36.13
    cyclohexane 0.68
    DMSO 37.45
    n-butyl acetate 16.68
    n-octanol 5.67
    chloroform 61.6
    n-propyl acetate 15.03
    acetic acid 31.1
    dichloromethane 54.59
    cyclohexanone 44.16
    propylene glycol 4.73
    isopropyl acetate 10.23
    DMAc 46.82
    2-ethoxyethanol 28.58
    isopentanol 13.05
    n-heptane 0.35
    ethyl formate 24.63
    1,2-dichloroethane 36.49
    n-hexanol 13.21
    2-methoxyethanol 50.42
    isobutyl acetate 15.93
    tetrachloromethane 8.29
    n-pentyl acetate 18.1
    transcutol 56.33
    n-heptanol 12.0
    ethylbenzene 4.88
    MIBK 12.13
    2-propoxyethanol 44.22
    tert-butanol 8.13
    MTBE 2.96
    2-butoxyethanol 35.17
    propionic acid 15.03
    o-xylene 6.87
    formic acid 21.69
    diethyl ether 3.75
    m-xylene 7.44
    p-xylene 7.35
    chlorobenzene 18.11
    dimethyl carbonate 16.8
    n-octane 0.28
    formamide 32.3
    cyclopentanone 42.96
    2-pentanone 12.43
    anisole 10.97
    cyclopentyl methyl ether 11.16
    gamma-butyrolactone 47.07
    1-methoxy-2-propanol 25.41
    pyridine 40.03
    3-pentanone 8.71
    furfural 78.75
    n-dodecane 0.35
    diethylene glycol 55.08
    diisopropyl ether 1.8
    tert-amyl alcohol 4.41
    acetylacetone 21.07
    n-hexadecane 0.43
    acetophenone 22.02
    methyl propionate 11.55
    isopentyl acetate 20.53
    trichloroethylene 85.33
    n-nonanol 6.63
    cyclohexanol 10.77
    benzyl alcohol 23.68
    2-ethylhexanol 9.41
    isooctanol 10.78
    dipropyl ether 5.04
    1,2-dichlorobenzene 23.34
    ethyl lactate 14.41
    propylene carbonate 33.63
    n-methylformamide 33.34
    2-pentanol 4.08
    n-pentane 0.18
    1-propoxy-2-propanol 20.27
    1-methoxy-2-propyl acetate 23.89
    2-(2-methoxypropoxy) propanol 22.22
    mesitylene 4.9
    ε-caprolactone 35.32
    p-cymene 6.6
    epichlorohydrin 63.23
    1,1,1-trichloroethane 19.21
    2-aminoethanol 14.94
    morpholine-4-carbaldehyde 62.16
    sulfolane 58.51
    2,2,4-trimethylpentane 0.24
    2-methyltetrahydrofuran 12.44
    n-hexyl acetate 14.27
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 31.23
    sec-butyl acetate 9.74
    tert-butyl acetate 11.58
    decalin 0.69
    glycerin 20.12
    diglyme 55.28
    acrylic acid 22.85
    isopropyl myristate 6.86
    n-butyric acid 26.62
    acetyl acetate 13.7
    di(2-ethylhexyl) phthalate 14.27
    ethyl propionate 10.26
    nitromethane 38.49
    1,2-diethoxyethane 16.13
    benzonitrile 26.13
    trioctyl phosphate 9.94
    1-bromopropane 7.49
    gamma-valerolactone 80.01
    n-decanol 5.1
    triethyl phosphate 12.74
    4-methyl-2-pentanol 5.29
    propionitrile 8.48
    vinylene carbonate 47.93
    1,1,2-trichlorotrifluoroethane 76.52
    DMS 18.32
    cumene 4.88
    2-octanol 5.33
    2-hexanone 13.14
    octyl acetate 9.08
    limonene 6.49
    1,2-dimethoxyethane 37.77
    ethyl orthosilicate 12.08
    tributyl phosphate 9.94
    diacetone alcohol 19.18
    N,N-dimethylaniline 9.98
    acrylonitrile 17.4
    aniline 17.8
    1,3-propanediol 26.86
    bromobenzene 16.06
    dibromomethane 24.66
    1,1,2,2-tetrachloroethane 59.63
    2-methyl-cyclohexyl acetate 19.17
    tetrabutyl urea 13.59
    diisobutyl methanol 5.61
    2-phenylethanol 27.57
    styrene 5.61
    dioctyl adipate 13.19
    dimethyl sulfate 26.72
    ethyl butyrate 13.07
    methyl lactate 16.89
    butyl lactate 19.25
    diethyl carbonate 13.19
    propanediol butyl ether 18.64
    triethyl orthoformate 13.53
    p-tert-butyltoluene 5.64
    methyl 4-tert-butylbenzoate 23.94
    morpholine 34.72
    tert-butylamine 3.41
    n-dodecanol 3.93
    dimethoxymethane 35.68
    ethylene carbonate 36.23
    cyrene 34.54
    2-ethoxyethyl acetate 28.54
    2-ethylhexyl acetate 15.94
    1,2,4-trichlorobenzene 29.39
    4-methylpyridine 27.78
    dibutyl ether 4.34
    2,6-dimethyl-4-heptanol 5.61
    DEF 20.02
    dimethyl isosorbide 39.74
    tetrachloroethylene 53.6
    eugenol 29.77
    triacetin 19.78
    span 80 19.08
    1,4-butanediol 10.99
    1,1-dichloroethane 14.34
    2-methyl-1-pentanol 10.31
    methyl formate 33.36
    2-methyl-1-butanol 8.9
    n-decane 0.5
    butyronitrile 9.15
    3,7-dimethyl-1-octanol 6.41
    1-chlorooctane 2.73
    1-chlorotetradecane 1.49
    n-nonane 0.34
    undecane 0.41
    tert-butylcyclohexane 0.54
    cyclooctane 0.3
    cyclopentanol 10.12
    tetrahydropyran 16.78
    tert-amyl methyl ether 2.8
    2,5,8-trioxanonane 41.08
    1-hexene 0.88
    2-isopropoxyethanol 19.42
    2,2,2-trifluoroethanol 19.09
    methyl butyrate 16.65

    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