Cyclanoline

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  • Identifiers

    CAS number
    18556-27-9

    Molecular formula
    C20H24NO4+

    SMILES
    C[N@@+]12CCC3=CC(=C(C=C3[C@@H]1CC4=C(C2)C(=C(C=C4)OC)O)O)OC

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 59.46%
    Spicy 53.89%
    Sweet 45.81%
    Vanilla 44.14%
    Smoky 44.13%
    Woody 37.76%
    Balsamic 36.61%
    Powdery 34.28%
    Burnt 31.74%
    Medicinal 27.1%

     

    Flavor
    Bitter 80.58%
    Sweet 26.17%
    Eugenol 21.3%
    Sweet-like 20.79%
    Naphthalic 20.68%
    Parsley 20.66%
    Cedarleaf 20.26%
    Flat 19.79%
    Very strong 19.72%
    Indole 19.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    8.4 (weak base)

    Molecular weight
    342.4 g/mol

    Flash point

    • 89.97 ˚C est.

  • Synonyms

    • Cyclanoline
    • Cissamine
    • 18556-27-9
    • 77QC59KBD2
    • (7S,13aS)-3,10-dimethoxy-7-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium-2,9-diol
    • CHEBI:76923
    • DTXSID00171789
    • 6H-Dibenzo(a,g)quinolizinium, 5,8,13,13a-tetrahydro-2,9-dihydroxy-3,10-dimethoxy-7-methyl-, (7S-cis)-
    • (7S,13aS)-3,10-dimethoxy-7-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino(2,1-b)isoquinolin-7-ium-2,9-diol
    • 6H-Dibenzo[a,g]quinolizinium, 5,8,13,13a-tetrahydro-2,9-dihydroxy-3,10-dimethoxy-7-methyl-, (7S-cis)-
    • RefChem:129178
    • DTXCID5094280
    • UNII-77QC59KBD2
    • cyclanolin
    • alpha-Cyclanoline
    • (-)-Cyclanoline
    • (-)-Cissamine
    • (S,S)-N-methylscoulerine
    • (S)-cis-N-methylscoulerine
    • orb1739363
    • SCHEMBL29556643
    • Q15410909
    • (7S,13aS)-2,9-Dihydroxy-3,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-7-ium
    • (7S,13aS)-2,9-dihydroxy-3,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolinium
    • (7S,13aS)-5,8,13,13a-Tetrahydro-2,9-dihydroxy-3,10-dimethoxy-7-methyl-6H-dibenzo[a,g]quinolizinium
    • 6H-Dibenzo[a,g]quinolizinium, 5,8,13,13a-tetrahydro-2,9-dihydroxy-3,10-dimethoxy-7-methyl-, (7S,13aS)-
    • 6H-Dibenzo[a,g]quinolizinium,5,8,13,13a-tetrahydro-2,9-dihydroxy-3,10-dimethoxy-7-methyl-,(7s,13as)-
    • 18556-27-9

  • Applications

    Cyclanoline (CAS 18556-27-9) is an industrially relevant chemical used as a synthetic intermediate and may function as a solvent or reaction partner in large-scale manufacturing; it serves as a precursor for pharmaceutical and agrochemical syntheses; it may be evaluated for fragrance and cosmetic applications as an odorant ingredient or fixative; it can be employed as an additive or processing aid in coatings and inks; and it may act as a precursor or functional component in polymer or plastics formulations; usage is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.07
    methanol 6.89
    isopropanol 3.06
    water 0.05
    ethyl acetate 8.23
    n-propanol 3.92
    acetone 7.44
    n-butanol 4.01
    acetonitrile 3.12
    DMF 13.09
    toluene 3.22
    isobutanol 2.7
    1,4-dioxane 16.04
    methyl acetate 5.44
    THF 24.85
    2-butanone 5.81
    n-pentanol 2.82
    sec-butanol 1.38
    n-hexane 0.06
    ethylene glycol 3.93
    NMP 6.14
    cyclohexane 0.26
    DMSO 27.63
    n-butyl acetate 6.68
    n-octanol 2.63
    chloroform 25.96
    n-propyl acetate 5.74
    acetic acid 19.94
    dichloromethane 19.06
    cyclohexanone 13.14
    propylene glycol 1.34
    isopropyl acetate 7.62
    DMAc 17.78
    2-ethoxyethanol 18.51
    isopentanol 4.79
    n-heptane 0.23
    ethyl formate 8.14
    1,2-dichloroethane 11.83
    n-hexanol 4.51
    2-methoxyethanol 32.93
    isobutyl acetate 5.62
    tetrachloromethane 3.68
    n-pentyl acetate 9.3
    transcutol 45.7
    n-heptanol 5.04
    ethylbenzene 1.52
    MIBK 7.33
    2-propoxyethanol 27.34
    tert-butanol 4.7
    MTBE 2.12
    2-butoxyethanol 20.33
    propionic acid 4.88
    o-xylene 2.28
    formic acid 14.71
    diethyl ether 3.32
    m-xylene 2.68
    p-xylene 2.09
    chlorobenzene 5.04
    dimethyl carbonate 10.91
    n-octane 0.17
    formamide 22.25
    cyclopentanone 12.99
    2-pentanone 6.64
    anisole 4.86
    cyclopentyl methyl ether 5.97
    gamma-butyrolactone 16.04
    1-methoxy-2-propanol 17.8
    pyridine 13.28
    3-pentanone 4.95
    furfural 28.79
    n-dodecane 0.17
    diethylene glycol 33.96
    diisopropyl ether 1.45
    tert-amyl alcohol 2.19
    acetylacetone 15.19
    n-hexadecane 0.21
    acetophenone 8.2
    methyl propionate 6.75
    isopentyl acetate 8.71
    trichloroethylene 29.79
    n-nonanol 3.41
    cyclohexanol 3.07
    benzyl alcohol 6.96
    2-ethylhexanol 3.17
    isooctanol 4.79
    dipropyl ether 3.77
    1,2-dichlorobenzene 6.82
    ethyl lactate 6.54
    propylene carbonate 11.08
    n-methylformamide 9.54
    2-pentanol 1.71
    n-pentane 0.1
    1-propoxy-2-propanol 12.44
    1-methoxy-2-propyl acetate 16.75
    2-(2-methoxypropoxy) propanol 13.9
    mesitylene 1.76
    ε-caprolactone 11.13
    p-cymene 2.65
    epichlorohydrin 27.94
    1,1,1-trichloroethane 9.08
    2-aminoethanol 4.77
    morpholine-4-carbaldehyde 23.28
    sulfolane 20.91
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 5.17
    n-hexyl acetate 7.29
    isooctane 0.11
    2-(2-butoxyethoxy)ethanol 19.98
    sec-butyl acetate 4.44
    tert-butyl acetate 9.69
    decalin 0.24
    glycerin 8.79
    diglyme 45.18
    acrylic acid 7.86
    isopropyl myristate 3.79
    n-butyric acid 11.45
    acetyl acetate 11.55
    di(2-ethylhexyl) phthalate 6.45
    ethyl propionate 5.48
    nitromethane 28.38
    1,2-diethoxyethane 11.92
    benzonitrile 7.82
    trioctyl phosphate 4.58
    1-bromopropane 2.83
    gamma-valerolactone 32.62
    n-decanol 2.43
    triethyl phosphate 6.52
    4-methyl-2-pentanol 2.47
    propionitrile 4.36
    vinylene carbonate 16.6
    1,1,2-trichlorotrifluoroethane 38.73
    DMS 9.99
    cumene 1.42
    2-octanol 2.29
    2-hexanone 4.5
    octyl acetate 4.72
    limonene 2.57
    1,2-dimethoxyethane 23.77
    ethyl orthosilicate 6.14
    tributyl phosphate 4.63
    diacetone alcohol 13.27
    N,N-dimethylaniline 4.04
    acrylonitrile 7.57
    aniline 5.58
    1,3-propanediol 13.81
    bromobenzene 4.79
    dibromomethane 8.6
    1,1,2,2-tetrachloroethane 21.54
    2-methyl-cyclohexyl acetate 8.13
    tetrabutyl urea 6.28
    diisobutyl methanol 2.62
    2-phenylethanol 10.41
    styrene 1.72
    dioctyl adipate 6.8
    dimethyl sulfate 17.03
    ethyl butyrate 6.27
    methyl lactate 8.96
    butyl lactate 8.91
    diethyl carbonate 6.31
    propanediol butyl ether 9.74
    triethyl orthoformate 7.39
    p-tert-butyltoluene 2.49
    methyl 4-tert-butylbenzoate 15.01
    morpholine 14.47
    tert-butylamine 1.68
    n-dodecanol 1.77
    dimethoxymethane 25.6
    ethylene carbonate 13.94
    cyrene 15.19
    2-ethoxyethyl acetate 19.56
    2-ethylhexyl acetate 6.18
    1,2,4-trichlorobenzene 9.03
    4-methylpyridine 7.91
    dibutyl ether 2.64
    2,6-dimethyl-4-heptanol 2.62
    DEF 7.64
    dimethyl isosorbide 28.18
    tetrachloroethylene 19.16
    eugenol 15.86
    triacetin 13.15
    span 80 10.15
    1,4-butanediol 3.7
    1,1-dichloroethane 5.74
    2-methyl-1-pentanol 3.13
    methyl formate 10.27
    2-methyl-1-butanol 2.6
    n-decane 0.29
    butyronitrile 3.68
    3,7-dimethyl-1-octanol 3.14
    1-chlorooctane 1.33
    1-chlorotetradecane 0.64
    n-nonane 0.21
    undecane 0.21
    tert-butylcyclohexane 0.19
    cyclooctane 0.15
    cyclopentanol 2.65
    tetrahydropyran 6.9
    tert-amyl methyl ether 1.77
    2,5,8-trioxanonane 30.03
    1-hexene 0.33
    2-isopropoxyethanol 11.29
    2,2,2-trifluoroethanol 12.03
    methyl butyrate 6.43

    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