(-)-Nuciferine

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  • Identifiers

    CAS number
    475-83-2

    Molecular formula
    C19H21NO2

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

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Animal 34.89%
    Sweet 34.7%
    Phenolic 30.26%
    Musk 29.28%
    Vanilla 27.98%
    Floral 27.38%
    Powdery 26.91%
    Spicy 25.99%
    Odorless 24.57%
    Smoky 21.84%

     

    Flavor
    Bitter 91.84%
    Cedarleaf 20.81%
    Sweet-like 19.98%
    Parsley 19.94%
    Very strong 19.77%
    Bland 19.72%
    Indole 19.61%
    Cereal 19.24%
    Lovage 18.84%
    Ripe apricot 18.73%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    7.25 (neutral)

    Molecular weight
    295.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    539°C

    Flash point

    • 191.59 ˚C est.

  • Synonyms

    • Nuciferine
    • 475-83-2
    • l-Nuciferine
    • Sanjoinine E
    • (-)-nuciferine
    • (R)-1,2-Dimethoxyaporphine
    • l-5,6-Dimethoxyaporphine
    • 1,2-Dimethoxy-6abeta-aporphine
    • (6ar)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline
    • W26UEB90B7
    • DTXSID40963862
    • (6aR)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline
    • RefChem:166941
    • DTXCID701391590
    • 842-235-9
    • Nuciferin
    • (-)-Nucipherine
    • (R)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
    • MFCD01664592
    • 4H-Dibenzo(de,g)quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-, (R)-
    • 1-5, 6-Dimethoxyaporphine
    • (R)-NUCIFERINE
    • UNII-W26UEB90B7
    • 6a-.beta.-Aporphine, 1,2-dimethoxy-
    • ORJVQPIHKOARKV-OAHLLOKOSA-N
    • Nuciferine (Standard)
    • 6a-beta-APORPHINE, 1,2-DIMETHOXY-
    • CHEMBL464529
    • Nuciferine - Bio-X trade mark
    • orb1304271
    • SCHEMBL20544868
    • SCHEMBL29521272
    • HY-N0049R
    • VLT-049
    • HMS3887A19
    • HY-N0049
    • MSK40326
    • BDBM50637409
    • NSC785145
    • s3821
    • AKOS015903258
    • AC-7998
    • CCG-267422
    • CS-4270
    • FN65106
    • NSC-785145
    • BN300106
    • BS-42200
    • SY068873
    • 1,2-DIMETHOXY-6A.BETA.-APORPHINE
    • N1170
    • NS00067009
    • 475N832
    • AG-690/36921306
    • Q7067904
    • 4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-, (6aR)-
    • 475-83-2

  • Applications

    (-)-Nuciferine (CAS 475-83-2) is an aporphine alkaloid found in Nelumbo nucifera (lotus) leaves and is mainly encountered in research contexts. In pharmaceutical and biomedical research, it is studied as a lead compound and tool for investigating dopaminergic signaling, receptor interactions, and related neuropharmacological activity, supporting basic research and the development of new derivatives. In analytical chemistry, nuciferine is used as a reference or marker compound for quality control and profiling of lotus leaf alkaloids in extracts by LC-MS/HPLC methods. In natural product chemistry and synthetic chemistry, it serves as a scaffold for exploring and synthesizing related aporphine derivatives. It may also occur in lotus leaf-based nutraceutical formulations and is commonly evaluated for inclusion in quality-control workflows of such products. These applications depend on local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 25.67
    methanol 27.04
    isopropanol 13.45
    water 0.27
    ethyl acetate 36.43
    n-propanol 25.64
    acetone 35.11
    n-butanol 27.22
    acetonitrile 13.88
    DMF 94.18
    toluene 18.98
    isobutanol 22.34
    1,4-dioxane 77.37
    methyl acetate 36.74
    THF 63.83
    2-butanone 36.11
    n-pentanol 23.31
    sec-butanol 10.15
    n-hexane 0.77
    ethylene glycol 21.62
    NMP 79.35
    cyclohexane 4.04
    DMSO 65.23
    n-butyl acetate 40.3
    n-octanol 10.81
    chloroform 264.14
    n-propyl acetate 39.93
    acetic acid 66.91
    dichloromethane 241.65
    cyclohexanone 94.01
    propylene glycol 8.31
    isopropyl acetate 25.73
    DMAc 75.66
    2-ethoxyethanol 61.1
    isopentanol 27.29
    n-heptane 1.41
    ethyl formate 68.04
    1,2-dichloroethane 140.87
    n-hexanol 28.05
    2-methoxyethanol 85.61
    isobutyl acetate 35.34
    tetrachloromethane 41.07
    n-pentyl acetate 37.15
    transcutol 93.69
    n-heptanol 22.16
    ethylbenzene 13.82
    MIBK 25.43
    2-propoxyethanol 77.12
    tert-butanol 13.99
    MTBE 8.72
    2-butoxyethanol 58.36
    propionic acid 37.28
    o-xylene 17.22
    formic acid 39.58
    diethyl ether 13.79
    m-xylene 16.36
    p-xylene 20.0
    chlorobenzene 59.71
    dimethyl carbonate 39.24
    n-octane 1.02
    formamide 57.94
    cyclopentanone 89.69
    2-pentanone 32.89
    anisole 26.64
    cyclopentyl methyl ether 29.34
    gamma-butyrolactone 115.83
    1-methoxy-2-propanol 42.27
    pyridine 90.84
    3-pentanone 27.81
    furfural 163.59
    n-dodecane 1.04
    diethylene glycol 88.9
    diisopropyl ether 5.49
    tert-amyl alcohol 10.64
    acetylacetone 47.41
    n-hexadecane 1.24
    acetophenone 47.5
    methyl propionate 36.54
    isopentyl acetate 42.02
    trichloroethylene 305.27
    n-nonanol 12.07
    cyclohexanol 27.92
    benzyl alcohol 49.57
    2-ethylhexanol 20.98
    isooctanol 19.77
    dipropyl ether 12.89
    1,2-dichlorobenzene 71.58
    ethyl lactate 29.65
    propylene carbonate 82.06
    n-methylformamide 65.36
    2-pentanol 10.71
    n-pentane 1.04
    1-propoxy-2-propanol 35.39
    1-methoxy-2-propyl acetate 46.87
    2-(2-methoxypropoxy) propanol 36.45
    mesitylene 11.67
    ε-caprolactone 87.16
    p-cymene 15.01
    epichlorohydrin 161.12
    1,1,1-trichloroethane 82.27
    2-aminoethanol 26.22
    morpholine-4-carbaldehyde 115.33
    sulfolane 115.06
    2,2,4-trimethylpentane 1.1
    2-methyltetrahydrofuran 35.83
    n-hexyl acetate 29.67
    isooctane 0.92
    2-(2-butoxyethoxy)ethanol 51.42
    sec-butyl acetate 24.61
    tert-butyl acetate 24.58
    decalin 2.93
    glycerin 29.17
    diglyme 99.42
    acrylic acid 56.95
    isopropyl myristate 13.29
    n-butyric acid 61.21
    acetyl acetate 39.16
    di(2-ethylhexyl) phthalate 26.26
    ethyl propionate 28.27
    nitromethane 91.48
    1,2-diethoxyethane 33.41
    benzonitrile 55.64
    trioctyl phosphate 17.8
    1-bromopropane 33.08
    gamma-valerolactone 155.24
    n-decanol 9.46
    triethyl phosphate 27.95
    4-methyl-2-pentanol 11.23
    propionitrile 23.93
    vinylene carbonate 111.53
    1,1,2-trichlorotrifluoroethane 167.53
    DMS 41.4
    cumene 13.33
    2-octanol 10.1
    2-hexanone 31.32
    octyl acetate 17.94
    limonene 15.56
    1,2-dimethoxyethane 73.28
    ethyl orthosilicate 26.8
    tributyl phosphate 19.74
    diacetone alcohol 33.59
    N,N-dimethylaniline 22.18
    acrylonitrile 41.83
    aniline 40.47
    1,3-propanediol 46.62
    bromobenzene 56.06
    dibromomethane 117.88
    1,1,2,2-tetrachloroethane 203.52
    2-methyl-cyclohexyl acetate 40.19
    tetrabutyl urea 24.49
    diisobutyl methanol 11.46
    2-phenylethanol 54.66
    styrene 16.88
    dioctyl adipate 25.91
    dimethyl sulfate 59.54
    ethyl butyrate 32.2
    methyl lactate 32.24
    butyl lactate 33.18
    diethyl carbonate 31.4
    propanediol butyl ether 28.07
    triethyl orthoformate 29.08
    p-tert-butyltoluene 12.24
    methyl 4-tert-butylbenzoate 42.31
    morpholine 78.38
    tert-butylamine 7.4
    n-dodecanol 7.48
    dimethoxymethane 67.66
    ethylene carbonate 87.33
    cyrene 60.69
    2-ethoxyethyl acetate 57.26
    2-ethylhexyl acetate 36.3
    1,2,4-trichlorobenzene 84.38
    4-methylpyridine 61.75
    dibutyl ether 10.14
    2,6-dimethyl-4-heptanol 11.46
    DEF 50.12
    dimethyl isosorbide 71.7
    tetrachloroethylene 183.31
    eugenol 49.96
    triacetin 39.62
    span 80 31.59
    1,4-butanediol 22.98
    1,1-dichloroethane 62.2
    2-methyl-1-pentanol 24.66
    methyl formate 73.02
    2-methyl-1-butanol 22.47
    n-decane 1.47
    butyronitrile 26.14
    3,7-dimethyl-1-octanol 11.95
    1-chlorooctane 7.47
    1-chlorotetradecane 3.95
    n-nonane 1.15
    undecane 1.19
    tert-butylcyclohexane 2.18
    cyclooctane 1.48
    cyclopentanol 25.62
    tetrahydropyran 45.38
    tert-amyl methyl ether 8.52
    2,5,8-trioxanonane 68.75
    1-hexene 4.13
    2-isopropoxyethanol 40.26
    2,2,2-trifluoroethanol 48.34
    methyl butyrate 43.72

    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