Bis(1,3)benzodioxolo(4,5-c:5',6'-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-, hydrochloride (1:1)

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  • Identifiers

    CAS number
    6164-47-2

    Molecular formula
    C20H20ClNO5

    SMILES
    CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3.Cl

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Sweet 38.66%
    Spicy 32.05%
    Vanilla 31.17%
    Phenolic 30.13%
    Animal 30.02%
    Floral 29.06%
    Odorless 28.4%
    Powdery 28.25%
    Creamy 22.08%
    Coconut 21.58%

     

    Flavor
    Bitter 94.3%
    Cedarleaf 19.37%
    Sweet-like 18.84%
    Parsley 18.75%
    Cereal 18.7%
    Naphthalic 18.61%
    Alkaline 18.3%
    Lovage 18.3%
    Indole 18.26%
    Very strong 18.17%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    6.72 (neutral)

    Molecular weight
    389.8 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    558°C

    Flash point

    • 240.24 ˚C est.

    Solubility expt.

    • SOL IN 143 PARTS WATER @ 13 °C, SOL IN ALC

  • Synonyms

    • PROTOPINE HYDROCHLORIDE
    • 6164-47-2
    • Protopine HCl
    • NSC-11440
    • 96481YJ70G
    • 7,13a-Secoberbin-13a-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-, hydrochloride
    • Bis(1,3)benzodioxolo(4,5-C:5',6'-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-, hydrochloride
    • DTXSID70210654
    • BIS(1,3)BENZODIOXOLO(4,5-C:5',6'-G)AZECIN-13(5H)-ONE, 4,6,7,14-TETRAHYDRO-5-METHYL-, HYDROCHLORIDE (1:1)
    • RefChem:176687
    • DTXCID00133145
    • 228-196-5
    • Protopine (hydrochloride)
    • 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one;hydrochloride
    • NSC11440
    • HSDB 3556
    • EINECS 228-196-5
    • NSC 11440
    • UNII-96481YJ70G
    • ARGEMONINE (PROTOPINE
    • orb1685014
    • SCHEMBL4456077
    • CHEMBL2165579
    • SCHEMBL29389905
    • HY-N0793A
    • NWNVDSJZGYDVQW-UHFFFAOYSA-N
    • PROTOPINE HYDROCHLORIDE [MI]
    • MFCD00236406
    • AKOS040760082
    • FS-9817
    • Protopine hydrochloride, >=98%, solid
    • DA-77171
    • CS-0084037
    • NS00080865
    • Q27271857
    • 7, 7-methyl-2,3:9,10-bis(methylenedioxy)-, hydrochloride
    • Bis[1,5-c:5',6'-g]azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-, hydrochloride
    • 7-Methyl-6,8,9,16-tetrahydro-4H,12H-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one--hydrogen chloride (1/1)
    • 6164-47-2

  • Applications

    Bis(1,3)benzodioxolo(4,5-c:5',6'-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-, hydrochloride (1:1), CAS 6164-47-2 is primarily used as an intermediate in pharmaceutical synthesis and as a versatile building block in organic chemistry for constructing polycyclic heterocycles. Its benzodioxole-containing scaffold may be evaluated for fragrance-related chemistry, and the compound can serve as a precursor or scaffold in cosmetic/personal care formulation development. In addition, it is encountered in specialty chemical research for potential use in advanced polymer or coating applications where rigid, fused-ring systems are advantageous, subject to local regulatory and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.21
    methanol 5.5
    isopropanol 2.29
    water 0.2
    ethyl acetate 15.12
    n-propanol 2.52
    acetone 20.04
    n-butanol 2.84
    acetonitrile 18.88
    DMF 37.76
    toluene 3.34
    isobutanol 2.32
    1,4-dioxane 16.74
    methyl acetate 16.22
    THF 20.63
    2-butanone 15.08
    n-pentanol 2.98
    sec-butanol 1.42
    n-hexane 0.04
    ethylene glycol 5.3
    NMP 31.54
    cyclohexane 0.18
    DMSO 59.37
    n-butyl acetate 11.42
    n-octanol 3.21
    chloroform 62.22
    n-propyl acetate 14.45
    acetic acid 45.02
    dichloromethane 56.97
    cyclohexanone 29.25
    propylene glycol 1.87
    isopropyl acetate 10.73
    DMAc 68.9
    2-ethoxyethanol 21.01
    isopentanol 4.41
    n-heptane 0.12
    ethyl formate 20.14
    1,2-dichloroethane 25.01
    n-hexanol 3.62
    2-methoxyethanol 25.92
    isobutyl acetate 10.75
    tetrachloromethane 4.96
    n-pentyl acetate 11.1
    transcutol 36.0
    n-heptanol 4.39
    ethylbenzene 1.81
    MIBK 9.41
    2-propoxyethanol 26.92
    tert-butanol 3.05
    MTBE 1.5
    2-butoxyethanol 20.07
    propionic acid 10.86
    o-xylene 2.42
    formic acid 33.01
    diethyl ether 2.4
    m-xylene 2.49
    p-xylene 3.23
    chlorobenzene 10.08
    dimethyl carbonate 19.59
    n-octane 0.11
    formamide 47.19
    cyclopentanone 30.76
    2-pentanone 11.73
    anisole 6.83
    cyclopentyl methyl ether 5.4
    gamma-butyrolactone 39.61
    1-methoxy-2-propanol 14.65
    pyridine 24.87
    3-pentanone 9.57
    furfural 58.1
    n-dodecane 0.17
    diethylene glycol 33.06
    diisopropyl ether 0.99
    tert-amyl alcohol 2.11
    acetylacetone 26.6
    n-hexadecane 0.21
    acetophenone 16.07
    methyl propionate 14.34
    isopentyl acetate 12.06
    trichloroethylene 74.68
    n-nonanol 3.99
    cyclohexanol 3.54
    benzyl alcohol 12.53
    2-ethylhexanol 3.38
    isooctanol 4.42
    dipropyl ether 2.75
    1,2-dichlorobenzene 12.12
    ethyl lactate 14.04
    propylene carbonate 27.97
    n-methylformamide 22.8
    2-pentanol 1.45
    n-pentane 0.05
    1-propoxy-2-propanol 13.96
    1-methoxy-2-propyl acetate 19.83
    2-(2-methoxypropoxy) propanol 20.28
    mesitylene 1.54
    ε-caprolactone 26.14
    p-cymene 2.45
    epichlorohydrin 49.56
    1,1,1-trichloroethane 17.05
    2-aminoethanol 4.78
    morpholine-4-carbaldehyde 47.88
    sulfolane 47.44
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 7.11
    n-hexyl acetate 10.26
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 21.59
    sec-butyl acetate 8.47
    tert-butyl acetate 9.04
    decalin 0.18
    glycerin 11.17
    diglyme 43.55
    acrylic acid 19.51
    isopropyl myristate 5.11
    n-butyric acid 17.43
    acetyl acetate 20.8
    di(2-ethylhexyl) phthalate 9.42
    ethyl propionate 11.84
    nitromethane 85.87
    1,2-diethoxyethane 10.14
    benzonitrile 20.83
    trioctyl phosphate 6.18
    1-bromopropane 4.54
    gamma-valerolactone 59.85
    n-decanol 2.93
    triethyl phosphate 10.33
    4-methyl-2-pentanol 2.01
    propionitrile 12.78
    vinylene carbonate 38.72
    1,1,2-trichlorotrifluoroethane 63.86
    DMS 15.06
    cumene 1.59
    2-octanol 2.28
    2-hexanone 11.95
    octyl acetate 6.8
    limonene 2.32
    1,2-dimethoxyethane 30.8
    ethyl orthosilicate 8.21
    tributyl phosphate 7.27
    diacetone alcohol 14.51
    N,N-dimethylaniline 5.19
    acrylonitrile 26.97
    aniline 8.25
    1,3-propanediol 10.27
    bromobenzene 9.28
    dibromomethane 23.09
    1,1,2,2-tetrachloroethane 44.9
    2-methyl-cyclohexyl acetate 12.04
    tetrabutyl urea 10.23
    diisobutyl methanol 2.01
    2-phenylethanol 13.76
    styrene 2.31
    dioctyl adipate 10.29
    dimethyl sulfate 32.24
    ethyl butyrate 11.22
    methyl lactate 15.25
    butyl lactate 12.42
    diethyl carbonate 11.98
    propanediol butyl ether 10.95
    triethyl orthoformate 9.74
    p-tert-butyltoluene 1.94
    methyl 4-tert-butylbenzoate 16.64
    morpholine 16.21
    tert-butylamine 1.01
    n-dodecanol 2.23
    dimethoxymethane 24.76
    ethylene carbonate 30.31
    cyrene 26.44
    2-ethoxyethyl acetate 20.01
    2-ethylhexyl acetate 9.4
    1,2,4-trichlorobenzene 16.05
    4-methylpyridine 18.6
    dibutyl ether 2.99
    2,6-dimethyl-4-heptanol 2.01
    DEF 18.22
    dimethyl isosorbide 31.32
    tetrachloroethylene 29.81
    eugenol 20.45
    triacetin 18.69
    span 80 12.48
    1,4-butanediol 5.64
    1,1-dichloroethane 14.96
    2-methyl-1-pentanol 3.92
    methyl formate 25.13
    2-methyl-1-butanol 2.85
    n-decane 0.26
    butyronitrile 10.13
    3,7-dimethyl-1-octanol 3.68
    1-chlorooctane 1.69
    1-chlorotetradecane 0.82
    n-nonane 0.19
    undecane 0.21
    tert-butylcyclohexane 0.13
    cyclooctane 0.09
    cyclopentanol 3.75
    tetrahydropyran 6.3
    tert-amyl methyl ether 1.62
    2,5,8-trioxanonane 33.56
    1-hexene 0.31
    2-isopropoxyethanol 14.22
    2,2,2-trifluoroethanol 31.52
    methyl butyrate 16.35

    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