Calycanthidine

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  • Identifiers

    CAS number
    5516-85-8

    Molecular formula
    C23H28N4

    SMILES
    CN1CCC2(C1NC3=CC=CC=C32)C45CCN(C4N(C6=CC=CC=C56)C)C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 40.49%
    Animal 35.35%
    Fishy 32.51%
    Burnt 25.2%
    Roasted 24.12%
    Cheesy 23.68%
    Nutty 23.55%
    Meaty 23.46%
    Earthy 23.32%
    Ripe 21.05%

     

    Flavor
    Bitter 87.78%
    Sweet-like 19.33%
    Cedarleaf 19.28%
    Very strong 18.89%
    Cereal 18.71%
    Alkaline 18.65%
    Indole 18.57%
    Nitrile 18.16%
    Moth ball 17.81%
    Rotten 17.59%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.1

    pKa est.
    4.11 (weak acid)

    Molecular weight
    360.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    566°C

    Melting point expt.

    • 142 °C

    Flash point

    • 349.29 ˚C est.

  • Synonyms

    • Calycanthidine
    • CHEBI:38970
    • 1,1',8-trimethyl-2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo[2,3-b]indole
    • 3a,3'a(1H,1'H)-Bipyrrolo[2,3-b]indole, 2,2',3,3',8,8',8a,8'a-octahydro-1,1',8-trimethyl-
    • 1,1',8-trimethyl-2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo(2,3-b)indole
    • 3a,3'a(1H,1'H)-Bipyrrolo(2,3-b)indole, 2,2',3,3',8,8',8a,8'a-octahydro-1,1',8-trimethyl-
    • RefChem:123057
    • 5516-85-8
    • GSQUXSFTXJRLQJ-UHFFFAOYSA-N
    • (3aR,3'aR,8aS,8'aS)-2,2',3,3',8,8',8a,8'a-Octahydro-1,1',8-trimethyl-3a,3'a(1H,1'H)-bipyrrolo[2,3-b]indole
    • 3,4-dimethyl-8b-(3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole
    • Q27118067
    • 5516-85-8

  • Applications

    Calycanthidine (CAS 5516-85-8) is a natural alkaloid isolated from Calycanthus species. In practical settings, it is commonly viewed as a chemical intermediate for organic synthesis and as a reference component in structure–activity studies of alkaloids. Additionally, it is evaluated as a research material for medicinal chemistry and natural product research, and can be used as an analytical reference standard in analytical methods; some studies also explore its potential as a scaffold for the development of heterocyclic compounds. These applications are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.83
    methanol 5.67
    isopropanol 1.86
    water 0.43
    ethyl acetate 6.42
    n-propanol 3.22
    acetone 6.28
    n-butanol 3.82
    acetonitrile 3.38
    DMF 30.47
    toluene 3.7
    isobutanol 3.14
    1,4-dioxane 12.37
    methyl acetate 6.26
    THF 15.99
    2-butanone 7.53
    n-pentanol 3.92
    sec-butanol 1.33
    n-hexane 0.07
    ethylene glycol 3.89
    NMP 47.57
    cyclohexane 0.21
    DMSO 10.44
    n-butyl acetate 12.26
    n-octanol 3.73
    chloroform 48.38
    n-propyl acetate 8.66
    acetic acid 14.74
    dichloromethane 31.73
    cyclohexanone 25.64
    propylene glycol 1.91
    isopropyl acetate 6.81
    DMAc 34.03
    2-ethoxyethanol 12.57
    isopentanol 4.71
    n-heptane 0.18
    ethyl formate 11.67
    1,2-dichloroethane 13.91
    n-hexanol 6.0
    2-methoxyethanol 16.21
    isobutyl acetate 11.39
    tetrachloromethane 6.8
    n-pentyl acetate 15.62
    transcutol 15.53
    n-heptanol 7.41
    ethylbenzene 1.96
    MIBK 8.1
    2-propoxyethanol 23.69
    tert-butanol 1.99
    MTBE 1.21
    2-butoxyethanol 23.36
    propionic acid 7.33
    o-xylene 2.87
    formic acid 14.97
    diethyl ether 1.58
    m-xylene 3.53
    p-xylene 3.48
    chlorobenzene 13.88
    dimethyl carbonate 13.62
    n-octane 0.13
    formamide 16.54
    cyclopentanone 30.24
    2-pentanone 7.74
    anisole 5.54
    cyclopentyl methyl ether 6.9
    gamma-butyrolactone 40.61
    1-methoxy-2-propanol 10.75
    pyridine 20.28
    3-pentanone 6.08
    furfural 62.04
    n-dodecane 0.17
    diethylene glycol 23.06
    diisopropyl ether 0.84
    tert-amyl alcohol 1.53
    acetylacetone 14.89
    n-hexadecane 0.21
    acetophenone 14.73
    methyl propionate 8.4
    isopentyl acetate 15.59
    trichloroethylene 51.08
    n-nonanol 4.55
    cyclohexanol 4.18
    benzyl alcohol 12.85
    2-ethylhexanol 5.32
    isooctanol 7.04
    dipropyl ether 2.46
    1,2-dichlorobenzene 19.38
    ethyl lactate 10.82
    propylene carbonate 29.0
    n-methylformamide 17.79
    2-pentanol 1.64
    n-pentane 0.09
    1-propoxy-2-propanol 13.66
    1-methoxy-2-propyl acetate 20.78
    2-(2-methoxypropoxy) propanol 13.24
    mesitylene 2.14
    ε-caprolactone 24.78
    p-cymene 3.88
    epichlorohydrin 39.56
    1,1,1-trichloroethane 13.38
    2-aminoethanol 4.89
    morpholine-4-carbaldehyde 51.07
    sulfolane 44.61
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 7.21
    n-hexyl acetate 11.85
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 15.61
    sec-butyl acetate 5.96
    tert-butyl acetate 6.86
    decalin 0.28
    glycerin 8.25
    diglyme 30.48
    acrylic acid 12.91
    isopropyl myristate 4.37
    n-butyric acid 13.67
    acetyl acetate 10.72
    di(2-ethylhexyl) phthalate 11.45
    ethyl propionate 6.67
    nitromethane 25.5
    1,2-diethoxyethane 6.48
    benzonitrile 18.33
    trioctyl phosphate 8.17
    1-bromopropane 3.34
    gamma-valerolactone 66.48
    n-decanol 3.03
    triethyl phosphate 9.21
    4-methyl-2-pentanol 2.31
    propionitrile 5.17
    vinylene carbonate 41.49
    1,1,2-trichlorotrifluoroethane 56.83
    DMS 13.96
    cumene 2.26
    2-octanol 3.62
    2-hexanone 7.87
    octyl acetate 6.48
    limonene 3.47
    1,2-dimethoxyethane 15.07
    ethyl orthosilicate 8.03
    tributyl phosphate 7.81
    diacetone alcohol 10.57
    N,N-dimethylaniline 5.42
    acrylonitrile 11.4
    aniline 8.9
    1,3-propanediol 7.46
    bromobenzene 12.96
    dibromomethane 13.67
    1,1,2,2-tetrachloroethane 34.92
    2-methyl-cyclohexyl acetate 13.99
    tetrabutyl urea 10.6
    diisobutyl methanol 2.57
    2-phenylethanol 18.52
    styrene 2.36
    dioctyl adipate 8.4
    dimethyl sulfate 23.52
    ethyl butyrate 9.17
    methyl lactate 12.93
    butyl lactate 17.5
    diethyl carbonate 8.57
    propanediol butyl ether 11.71
    triethyl orthoformate 9.52
    p-tert-butyltoluene 3.16
    methyl 4-tert-butylbenzoate 19.15
    morpholine 13.54
    tert-butylamine 0.88
    n-dodecanol 2.05
    dimethoxymethane 17.34
    ethylene carbonate 30.06
    cyrene 29.86
    2-ethoxyethyl acetate 21.52
    2-ethylhexyl acetate 13.09
    1,2,4-trichlorobenzene 25.23
    4-methylpyridine 17.44
    dibutyl ether 2.05
    2,6-dimethyl-4-heptanol 2.57
    DEF 13.34
    dimethyl isosorbide 30.71
    tetrachloroethylene 30.76
    eugenol 23.52
    triacetin 16.45
    span 80 12.47
    1,4-butanediol 5.14
    1,1-dichloroethane 8.99
    2-methyl-1-pentanol 4.64
    methyl formate 18.12
    2-methyl-1-butanol 3.68
    n-decane 0.27
    butyronitrile 5.68
    3,7-dimethyl-1-octanol 3.92
    1-chlorooctane 1.72
    1-chlorotetradecane 0.8
    n-nonane 0.18
    undecane 0.21
    tert-butylcyclohexane 0.22
    cyclooctane 0.12
    cyclopentanol 5.25
    tetrahydropyran 5.81
    tert-amyl methyl ether 1.43
    2,5,8-trioxanonane 20.61
    1-hexene 0.41
    2-isopropoxyethanol 9.89
    2,2,2-trifluoroethanol 17.71
    methyl butyrate 10.2

    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