(-)-Litcubine

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  • Identifiers

    CAS number
    172924-22-0

    Molecular formula
    C19H22NO4+

    SMILES
    C[N+]12CCC3=CC(=C(C=C3C1CC4=CC(=C(C=C24)O)OC)O)OC

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 56.13%
    Spicy 49.97%
    Vanilla 42.49%
    Sweet 42.21%
    Smoky 40.7%
    Woody 35.32%
    Balsamic 35.08%
    Powdery 34.14%
    Burnt 31.36%
    Musk 25.28%

     

    Flavor
    Bitter 85.14%
    Bland 21.25%
    Sweet-like 21.21%
    Eugenol 20.57%
    Parsley 20.36%
    Cedarleaf 20.34%
    Naphthalic 19.76%
    Very strong 19.57%
    Indole 19.54%
    Ripe apricot 19.17%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    8.5 (weak base)

    Molecular weight
    328.4 g/mol

    Flash point

    • 78.23 ˚C est.

  • Synonyms

    • (-)-Litcubine
    • 172924-22-0
    • RefChem:67881
    • Litcubine
    • CHEBI:169824
    • DTXSID201317638
    • 3,10-dimethoxy-7-methyl-5,6,12,12a-tetrahydroindolo[2,1-a]isoquinolin-7-ium-2,9-diol
    • 2,9-Dihydroxy-3,10-dimethoxy-7-methyl-5,6,12,12a-tetrahydroindolo[2,1-a]isoquinolin-7-ium
    • 172924-22-0

  • Applications

    (-)-Litcubine (CAS 172924-22-0) is primarily used as a chiral intermediate and building block in pharmaceutical and fine-chemical synthesis, where its stereochemistry enables enantioselective routes. It is commonly evaluated for use in asymmetric catalysis and as a precursor to more complex intermediates for biologically active compounds. In polymer and materials chemistry, it may serve as a functional building block or precursor for specialized monomers. It can also find applications in coatings and inks as a reactive intermediate in formulation chemistries. In research and development, it is employed as a reference material for chiral separations and method development in analytical chemistry. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.15
    methanol 4.46
    isopropanol 1.85
    water 0.09
    ethyl acetate 6.4
    n-propanol 1.92
    acetone 4.97
    n-butanol 2.17
    acetonitrile 2.97
    DMF 13.7
    toluene 1.08
    isobutanol 1.51
    1,4-dioxane 9.49
    methyl acetate 4.16
    THF 13.85
    2-butanone 3.62
    n-pentanol 1.32
    sec-butanol 0.76
    n-hexane 0.03
    ethylene glycol 3.49
    NMP 6.74
    cyclohexane 0.11
    DMSO 22.35
    n-butyl acetate 6.45
    n-octanol 1.68
    chloroform 18.83
    n-propyl acetate 4.64
    acetic acid 16.07
    dichloromethane 14.42
    cyclohexanone 8.66
    propylene glycol 0.74
    isopropyl acetate 6.07
    DMAc 19.0
    2-ethoxyethanol 11.28
    isopentanol 2.91
    n-heptane 0.12
    ethyl formate 5.88
    1,2-dichloroethane 8.43
    n-hexanol 2.79
    2-methoxyethanol 22.01
    isobutyl acetate 4.29
    tetrachloromethane 2.99
    n-pentyl acetate 7.04
    transcutol 24.62
    n-heptanol 3.34
    ethylbenzene 0.71
    MIBK 5.1
    2-propoxyethanol 20.4
    tert-butanol 3.11
    MTBE 1.5
    2-butoxyethanol 15.35
    propionic acid 3.47
    o-xylene 1.03
    formic acid 14.72
    diethyl ether 2.06
    m-xylene 1.12
    p-xylene 1.09
    chlorobenzene 2.76
    dimethyl carbonate 10.0
    n-octane 0.1
    formamide 22.14
    cyclopentanone 9.05
    2-pentanone 4.26
    anisole 2.99
    cyclopentyl methyl ether 3.27
    gamma-butyrolactone 13.95
    1-methoxy-2-propanol 12.31
    pyridine 6.79
    3-pentanone 3.45
    furfural 21.69
    n-dodecane 0.1
    diethylene glycol 28.56
    diisopropyl ether 0.92
    tert-amyl alcohol 1.46
    acetylacetone 12.15
    n-hexadecane 0.13
    acetophenone 5.75
    methyl propionate 5.28
    isopentyl acetate 7.89
    trichloroethylene 22.25
    n-nonanol 2.26
    cyclohexanol 1.71
    benzyl alcohol 3.92
    2-ethylhexanol 2.17
    isooctanol 3.29
    dipropyl ether 2.45
    1,2-dichlorobenzene 4.64
    ethyl lactate 5.78
    propylene carbonate 9.97
    n-methylformamide 8.6
    2-pentanol 1.01
    n-pentane 0.05
    1-propoxy-2-propanol 10.58
    1-methoxy-2-propyl acetate 15.21
    2-(2-methoxypropoxy) propanol 11.04
    mesitylene 0.83
    ε-caprolactone 8.64
    p-cymene 1.65
    epichlorohydrin 19.44
    1,1,1-trichloroethane 7.03
    2-aminoethanol 3.12
    morpholine-4-carbaldehyde 21.1
    sulfolane 18.72
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 3.11
    n-hexyl acetate 5.23
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 13.66
    sec-butyl acetate 3.6
    tert-butyl acetate 7.66
    decalin 0.12
    glycerin 6.78
    diglyme 33.45
    acrylic acid 6.03
    isopropyl myristate 2.88
    n-butyric acid 8.1
    acetyl acetate 10.04
    di(2-ethylhexyl) phthalate 4.95
    ethyl propionate 4.67
    nitromethane 29.16
    1,2-diethoxyethane 7.71
    benzonitrile 5.4
    trioctyl phosphate 3.64
    1-bromopropane 1.77
    gamma-valerolactone 25.25
    n-decanol 1.62
    triethyl phosphate 6.13
    4-methyl-2-pentanol 1.59
    propionitrile 3.45
    vinylene carbonate 13.81
    1,1,2-trichlorotrifluoroethane 32.07
    DMS 8.88
    cumene 0.74
    2-octanol 1.6
    2-hexanone 3.06
    octyl acetate 3.49
    limonene 1.61
    1,2-dimethoxyethane 17.27
    ethyl orthosilicate 5.36
    tributyl phosphate 3.85
    diacetone alcohol 10.65
    N,N-dimethylaniline 2.5
    acrylonitrile 6.28
    aniline 2.78
    1,3-propanediol 8.81
    bromobenzene 2.59
    dibromomethane 6.2
    1,1,2,2-tetrachloroethane 15.35
    2-methyl-cyclohexyl acetate 6.79
    tetrabutyl urea 5.18
    diisobutyl methanol 1.86
    2-phenylethanol 7.36
    styrene 0.79
    dioctyl adipate 5.22
    dimethyl sulfate 17.97
    ethyl butyrate 5.75
    methyl lactate 7.89
    butyl lactate 7.59
    diethyl carbonate 6.29
    propanediol butyl ether 6.6
    triethyl orthoformate 6.55
    p-tert-butyltoluene 1.59
    methyl 4-tert-butylbenzoate 11.53
    morpholine 8.34
    tert-butylamine 1.03
    n-dodecanol 1.18
    dimethoxymethane 19.22
    ethylene carbonate 11.93
    cyrene 13.02
    2-ethoxyethyl acetate 14.93
    2-ethylhexyl acetate 5.63
    1,2,4-trichlorobenzene 6.19
    4-methylpyridine 4.4
    dibutyl ether 1.78
    2,6-dimethyl-4-heptanol 1.86
    DEF 6.61
    dimethyl isosorbide 22.26
    tetrachloroethylene 14.06
    eugenol 12.5
    triacetin 10.58
    span 80 7.31
    1,4-butanediol 2.42
    1,1-dichloroethane 4.2
    2-methyl-1-pentanol 1.68
    methyl formate 9.0
    2-methyl-1-butanol 1.53
    n-decane 0.18
    butyronitrile 2.72
    3,7-dimethyl-1-octanol 2.11
    1-chlorooctane 0.89
    1-chlorotetradecane 0.43
    n-nonane 0.13
    undecane 0.13
    tert-butylcyclohexane 0.1
    cyclooctane 0.06
    cyclopentanol 1.6
    tetrahydropyran 3.46
    tert-amyl methyl ether 1.23
    2,5,8-trioxanonane 22.7
    1-hexene 0.16
    2-isopropoxyethanol 7.59
    2,2,2-trifluoroethanol 14.27
    methyl butyrate 5.45

    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