(4bS,5R,10bS,11R)-5,6,11,12-Tetrahydro-13,18-dimethyl-5,10b:11,4b-Bis(iminoethano)dibenzo(c,h)(2,6)naphthyridine

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  • Identifiers

    CAS number
    595-05-1

    Molecular formula
    C22H26N4

    SMILES
    CN1CC[C@@]23[C@@H]4NC5=CC=CC=C5[C@@]2([C@@H]1NC6=CC=CC=C36)CCN4C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 39.21%
    Animal 37.86%
    Fishy 35.47%
    Nutty 27.67%
    Roasted 27.36%
    Burnt 27.04%
    Cheesy 26.55%
    Meaty 26.02%
    Earthy 23.61%
    Cooked 21.17%

     

    Flavor
    Bitter 87.2%
    Alkaline 19.6%
    Cereal 19.47%
    Very strong 19.31%
    Animal 19.29%
    Sweet-like 19.15%
    Indole 19.12%
    Cedarleaf 19.11%
    Moth ball 18.23%
    Nitrile 18.09%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.9

    pKa est.
    6.57 (neutral)

    Molecular weight
    346.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    602°C

    Flash point

    • 244.26 ˚C est.

  • Synonyms

    • Calycanthine
    • 595-05-1
    • F62N8QPR7V
    • CHEBI:3333
    • NSC-99016
    • (1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetrazahexacyclo[9.7.3.32,10.01,10.04,9.013,18]tetracosa-4,6,8,13,15,17-hexaene
    • (4bS,5R,10bS,11R)-13,18-dimethyl-5,6,11,12-tetrahydro-5,10b:11,4b-di(epiminoethano)dibenzo[c,h]-2,6-naphthyridine
    • DTXSID10974900
    • (1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetrazahexacyclo(9.7.3.32,10.01,10.04,9.013,18)tetracosa-4,6,8,13,15,17-hexaene
    • (4bS,5R,10bS,11R)-13,18-dimethyl-5,6,11,12-tetrahydro-5,10b:11,4b-di(epiminoethano)dibenzo(c,h)-2,6-naphthyridine
    • RefChem:123058
    • DTXCID801776147
    • (4bS,5R,10bS,11R)-5,6,11,12-Tetrahydro-13,18-dimethyl-5,10b:11,4b-Bis(iminoethano)dibenzo(c,h)(2,6)naphthyridine
    • 209-857-7
    • 5,10b:11,4b-Di(iminoethano)dibenzo(c,h)(2,6)naphthyridine, 5,6,11,12-tetrahydro-13,18-dimethyl-, (4bS,5R,10bS,11R)-
    • (1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3(2,10).0(1,10).0(4,9).0(13,18)]tetracosa-4,6,8,13,15,17-hexaene
    • UNII-F62N8QPR7V
    • NSC99016
    • EINECS 209-857-7
    • NSC 99016
    • D-CALYCANTHINE
    • Prestwick3_000595
    • CALYCANTHINE [MI]
    • BSPBio_000470
    • MLS002153896
    • SCHEMBL893195
    • BPBio1_000518
    • CHEMBL464770
    • SCHEMBL29878816
    • XSYCDVWYEVUDKQ-GXRSIYKFSA-N
    • HMS2096H12
    • HMS2230M13
    • HY-N5121
    • AKOS040760131
    • EBC-618534
    • FC65934
    • NCGC00179550-03
    • NCGC00179550-04
    • AC-34463
    • MS-25332
    • SMR001233245
    • AB00513866
    • CS-0032443
    • NS00042766
    • BRD-K59851896-001-02-4
    • Q27106029
    • (1S,2R,10S,11R)-21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3^{2,10}.0^{1,10}.0^{4,9}.0^{13,18}]tetracosa-4(9),5,7,13(18),14,16-hexaene
    • (4BS,5R,10BS,11R)-5,6,11,12-TETRAHYDRO-13,18-DIMETHYL-5,10B:11,4B-BIS(IMINOETHANO)-DIBENZO(C,H)(2,6)NAPHTHYRIDINE
    • 5,10B:11,4B-BIS(IMINOETHANO)DIBENZO(C,H)(2,6)NAPHTHYRIDINE, 5,6,11,12-TETRAHYDRO-13,18-DIMETHYL-, (4BS,5R,10BS,11R)-
    • 595-05-1

  • Applications

    Compound (4bS,5R,10bS,11R)-5,6,11,12-Tetrahydro-13,18-dimethyl-5,10b:11,4b-Bis(iminoethano)dibenzo(c,h)(2,6)naphthyridine (CAS 595-05-1) is primarily used as a synthetic intermediate and heterocyclic scaffold in pharmaceutical and medicinal chemistry, enabling the construction of more complex nitrogen-containing heterocycles; it also serves as a building block for colorful dyes and pigments and may find use in organic electronic materials and coatings/inks; in coordination chemistry it can act as a ligand for homogeneous catalysis; and it is commonly evaluated as a scaffold for SAR-driven medicinal chemistry research as well as a specialty reference compound in academic studies.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.78
    methanol 1.4
    isopropanol 0.44
    water 0.09
    ethyl acetate 1.52
    n-propanol 0.84
    acetone 1.04
    n-butanol 0.94
    acetonitrile 0.45
    DMF 8.05
    toluene 0.88
    isobutanol 0.75
    1,4-dioxane 2.87
    methyl acetate 1.2
    THF 4.24
    2-butanone 1.48
    n-pentanol 0.89
    sec-butanol 0.31
    n-hexane 0.02
    ethylene glycol 1.01
    NMP 13.91
    cyclohexane 0.07
    DMSO 3.68
    n-butyl acetate 3.84
    n-octanol 0.91
    chloroform 11.3
    n-propyl acetate 1.91
    acetic acid 2.99
    dichloromethane 7.61
    cyclohexanone 6.78
    propylene glycol 0.39
    isopropyl acetate 1.5
    DMAc 9.97
    2-ethoxyethanol 3.26
    isopentanol 1.15
    n-heptane 0.06
    ethyl formate 3.67
    1,2-dichloroethane 3.67
    n-hexanol 1.77
    2-methoxyethanol 5.34
    isobutyl acetate 2.11
    tetrachloromethane 2.4
    n-pentyl acetate 4.66
    transcutol 4.81
    n-heptanol 2.16
    ethylbenzene 0.49
    MIBK 1.8
    2-propoxyethanol 8.21
    tert-butanol 0.43
    MTBE 0.19
    2-butoxyethanol 7.62
    propionic acid 1.74
    o-xylene 0.79
    formic acid 3.92
    diethyl ether 0.36
    m-xylene 0.91
    p-xylene 0.87
    chlorobenzene 3.64
    dimethyl carbonate 3.38
    n-octane 0.05
    formamide 4.45
    cyclopentanone 8.64
    2-pentanone 1.76
    anisole 0.98
    cyclopentyl methyl ether 1.71
    gamma-butyrolactone 12.04
    1-methoxy-2-propanol 2.8
    pyridine 6.02
    3-pentanone 1.37
    furfural 20.55
    n-dodecane 0.05
    diethylene glycol 8.37
    diisopropyl ether 0.17
    tert-amyl alcohol 0.33
    acetylacetone 3.22
    n-hexadecane 0.06
    acetophenone 3.71
    methyl propionate 1.96
    isopentyl acetate 4.47
    trichloroethylene 14.14
    n-nonanol 1.18
    cyclohexanol 0.98
    benzyl alcohol 3.27
    2-ethylhexanol 1.44
    isooctanol 1.83
    dipropyl ether 0.69
    1,2-dichlorobenzene 5.5
    ethyl lactate 2.43
    propylene carbonate 8.49
    n-methylformamide 4.74
    2-pentanol 0.38
    n-pentane 0.03
    1-propoxy-2-propanol 4.0
    1-methoxy-2-propyl acetate 5.92
    2-(2-methoxypropoxy) propanol 3.92
    mesitylene 0.62
    ε-caprolactone 6.99
    p-cymene 1.23
    epichlorohydrin 10.98
    1,1,1-trichloroethane 3.18
    2-aminoethanol 1.25
    morpholine-4-carbaldehyde 14.83
    sulfolane 15.97
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.75
    n-hexyl acetate 2.98
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 5.07
    sec-butyl acetate 1.23
    tert-butyl acetate 1.54
    decalin 0.07
    glycerin 2.01
    diglyme 9.34
    acrylic acid 3.22
    isopropyl myristate 1.17
    n-butyric acid 3.64
    acetyl acetate 2.25
    di(2-ethylhexyl) phthalate 3.42
    ethyl propionate 1.56
    nitromethane 4.93
    1,2-diethoxyethane 1.81
    benzonitrile 5.52
    trioctyl phosphate 2.53
    1-bromopropane 0.89
    gamma-valerolactone 18.52
    n-decanol 0.81
    triethyl phosphate 2.87
    4-methyl-2-pentanol 0.5
    propionitrile 1.06
    vinylene carbonate 12.71
    1,1,2-trichlorotrifluoroethane 20.19
    DMS 3.95
    cumene 0.55
    2-octanol 0.92
    2-hexanone 1.7
    octyl acetate 1.68
    limonene 1.1
    1,2-dimethoxyethane 3.7
    ethyl orthosilicate 2.57
    tributyl phosphate 2.52
    diacetone alcohol 2.61
    N,N-dimethylaniline 1.16
    acrylonitrile 2.47
    aniline 2.45
    1,3-propanediol 2.34
    bromobenzene 3.23
    dibromomethane 3.51
    1,1,2,2-tetrachloroethane 10.56
    2-methyl-cyclohexyl acetate 3.75
    tetrabutyl urea 3.71
    diisobutyl methanol 0.77
    2-phenylethanol 5.76
    styrene 0.55
    dioctyl adipate 2.14
    dimethyl sulfate 7.26
    ethyl butyrate 2.5
    methyl lactate 3.28
    butyl lactate 5.47
    diethyl carbonate 2.44
    propanediol butyl ether 3.19
    triethyl orthoformate 2.8
    p-tert-butyltoluene 1.06
    methyl 4-tert-butylbenzoate 6.27
    morpholine 3.38
    tert-butylamine 0.2
    n-dodecanol 0.57
    dimethoxymethane 4.57
    ethylene carbonate 9.17
    cyrene 8.95
    2-ethoxyethyl acetate 6.74
    2-ethylhexyl acetate 3.89
    1,2,4-trichlorobenzene 7.13
    4-methylpyridine 4.65
    dibutyl ether 0.57
    2,6-dimethyl-4-heptanol 0.77
    DEF 3.74
    dimethyl isosorbide 10.87
    tetrachloroethylene 11.44
    eugenol 7.86
    triacetin 4.2
    span 80 3.74
    1,4-butanediol 1.15
    1,1-dichloroethane 1.83
    2-methyl-1-pentanol 0.96
    methyl formate 4.94
    2-methyl-1-butanol 0.84
    n-decane 0.08
    butyronitrile 1.26
    3,7-dimethyl-1-octanol 0.99
    1-chlorooctane 0.48
    1-chlorotetradecane 0.23
    n-nonane 0.05
    undecane 0.06
    tert-butylcyclohexane 0.05
    cyclooctane 0.04
    cyclopentanol 1.33
    tetrahydropyran 1.46
    tert-amyl methyl ether 0.26
    2,5,8-trioxanonane 6.57
    1-hexene 0.11
    2-isopropoxyethanol 2.2
    2,2,2-trifluoroethanol 4.65
    methyl butyrate 2.38

    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