Norsanguinarine

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  • Identifiers

    CAS number
    522-30-5

    Molecular formula
    C19H11NO4

    SMILES
    C1OC2=C(O1)C3=CN=C4C(=C3C=C2)C=CC5=CC6=C(C=C54)OCO6

    Safety labels

  • Odor profile

    Fragrance
    Floral 55.32%
    Animal 32.43%
    Sweet 30.64%
    Fruity 28.26%
    Powdery 27.74%
    Phenolic 27.51%
    Spicy 25.63%
    Aromatic 19.83%
    Neroli 19.38%
    Musk 18.6%

     

    Flavor
    Bitter 98.2%
    Very strong 16.22%
    Indole 15.92%
    Cedarleaf 15.6%
    Cereal 15.43%
    Sweet-like 15.31%
    Rotten 15.03%
    Alkaline 14.9%
    Parsley 14.89%
    Moth ball 14.84%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.3

    pKa est.
    3.67 (weak acid)

    Molecular weight
    317.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    557°C

    Melting point expt.

    • 285 - 287 °C

    Flash point

    • 252.14 ˚C est.

  • Synonyms

    • Norsanguinarine
    • 522-30-5
    • 5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
    • 5,7,18,20-tetraoxa-24-azahexacyclo(11.11.0.0^(2,10).0^(4,8).0^(14,22).0^(17,21))tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene
    • 5,7,18,20-tetraoxa-24-azahexacyclo(11.11.0.02,10.04,8.014,22.017,21)tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
    • 5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene
    • RefChem:166688
    • Sanguinarine, 13-demethyl-
    • (1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridine
    • [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine
    • 1,3-Dioxolo[i][1,3]dioxolo[4,5]benzo[1,2-c]phenanthridine
    • [1,3]Dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine
    • 1,3-Dioxolo(i)(1,3)dioxolo(4,5)benzo(1,2-c)phenanthridine
    • 5157-23-3
    • demethylsanguinarine
    • NSC 143762
    • 13-Demethyl-Sanguinarine
    • orb1684372
    • CHEMBL4751586
    • SCHEMBL16125304
    • SCHEMBL30425829
    • SCHEMBL30878399
    • DTXSID90965891
    • CHEBI:179641
    • CNXVDVMAYXLWPD-UHFFFAOYSA-N
    • MFCD30546981
    • NSC143762
    • AKOS030535106
    • FS-8003
    • NSC-143762
    • HY-123077
    • NS00093944
    • [1,6-c]-1,3-dioxolo[4,5-i]phenanthridine
    • 7,8-Bis(methylenedioxy)benzo[c]phenanthridine
    • 1,3]dioxolo[4,5]benzo[1,2-c]phenanthridine
    • 2H,10H-[1,3]Benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine
    • 522-30-5

  • Applications

    Norsanguinarine, CAS 522-30-5, is a benzophenanthridine alkaloid that is primarily encountered as an intermediate in the synthesis of related alkaloids and is studied in pharmaceutical chemistry and biochemistry as a scaffold for derivatives and to explore bioactivity. In practical terms, its applications are mainly as an analytical reference standard for alkaloid assays and related analytical methods; it is also evaluated in agricultural and applied chemistry research to explore its bioactive properties, while use in consumer products is limited by safety and regulatory concerns and must be subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.21
    methanol 0.17
    isopropanol 0.21
    water 0.0
    ethyl acetate 1.56
    n-propanol 0.24
    acetone 0.82
    n-butanol 0.33
    acetonitrile 0.67
    DMF 1.52
    toluene 0.81
    isobutanol 0.23
    1,4-dioxane 3.13
    methyl acetate 1.08
    THF 4.72
    2-butanone 1.15
    n-pentanol 0.37
    sec-butanol 0.2
    n-hexane 0.03
    ethylene glycol 0.31
    NMP 1.37
    cyclohexane 0.05
    DMSO 3.05
    n-butyl acetate 1.58
    n-octanol 0.56
    chloroform 2.18
    n-propyl acetate 1.53
    acetic acid 1.52
    dichloromethane 2.88
    cyclohexanone 1.9
    propylene glycol 0.12
    isopropyl acetate 2.1
    DMAc 3.85
    2-ethoxyethanol 2.3
    isopentanol 0.56
    n-heptane 0.11
    ethyl formate 0.81
    1,2-dichloroethane 1.85
    n-hexanol 0.47
    2-methoxyethanol 2.3
    isobutyl acetate 1.51
    tetrachloromethane 0.37
    n-pentyl acetate 2.11
    transcutol 11.26
    n-heptanol 0.73
    ethylbenzene 0.72
    MIBK 1.69
    2-propoxyethanol 3.46
    tert-butanol 0.36
    MTBE 0.53
    2-butoxyethanol 3.19
    propionic acid 0.64
    o-xylene 0.77
    formic acid 1.03
    diethyl ether 0.87
    m-xylene 0.79
    p-xylene 0.81
    chlorobenzene 0.74
    dimethyl carbonate 2.15
    n-octane 0.08
    formamide 2.03
    cyclopentanone 2.16
    2-pentanone 1.22
    anisole 1.88
    cyclopentyl methyl ether 1.61
    gamma-butyrolactone 2.91
    1-methoxy-2-propanol 1.83
    pyridine 2.88
    3-pentanone 1.26
    furfural 3.97
    n-dodecane 0.11
    diethylene glycol 3.84
    diisopropyl ether 0.69
    tert-amyl alcohol 0.35
    acetylacetone 3.46
    n-hexadecane 0.13
    acetophenone 2.53
    methyl propionate 1.38
    isopentyl acetate 2.46
    trichloroethylene 4.41
    n-nonanol 0.85
    cyclohexanol 0.5
    benzyl alcohol 1.5
    2-ethylhexanol 0.76
    isooctanol 0.94
    dipropyl ether 1.66
    1,2-dichlorobenzene 1.31
    ethyl lactate 1.48
    propylene carbonate 1.79
    n-methylformamide 0.87
    2-pentanol 0.31
    n-pentane 0.03
    1-propoxy-2-propanol 2.52
    1-methoxy-2-propyl acetate 4.23
    2-(2-methoxypropoxy) propanol 5.16
    mesitylene 0.66
    ε-caprolactone 2.43
    p-cymene 1.14
    epichlorohydrin 4.94
    1,1,1-trichloroethane 1.29
    2-aminoethanol 0.33
    morpholine-4-carbaldehyde 4.28
    sulfolane 3.35
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 1.56
    n-hexyl acetate 2.06
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 5.33
    sec-butyl acetate 1.78
    tert-butyl acetate 2.84
    decalin 0.12
    glycerin 0.88
    diglyme 12.02
    acrylic acid 0.98
    isopropyl myristate 2.04
    n-butyric acid 1.26
    acetyl acetate 2.42
    di(2-ethylhexyl) phthalate 2.15
    ethyl propionate 1.99
    nitromethane 3.17
    1,2-diethoxyethane 4.49
    benzonitrile 1.64
    trioctyl phosphate 1.39
    1-bromopropane 0.61
    gamma-valerolactone 4.92
    n-decanol 0.71
    triethyl phosphate 2.63
    4-methyl-2-pentanol 0.48
    propionitrile 0.83
    vinylene carbonate 2.3
    1,1,2-trichlorotrifluoroethane 5.19
    DMS 3.25
    cumene 0.71
    2-octanol 0.51
    2-hexanone 1.32
    octyl acetate 1.8
    limonene 0.9
    1,2-dimethoxyethane 4.9
    ethyl orthosilicate 2.69
    tributyl phosphate 1.69
    diacetone alcohol 2.83
    N,N-dimethylaniline 1.79
    acrylonitrile 1.46
    aniline 1.13
    1,3-propanediol 0.9
    bromobenzene 0.91
    dibromomethane 1.39
    1,1,2,2-tetrachloroethane 3.09
    2-methyl-cyclohexyl acetate 2.84
    tetrabutyl urea 2.63
    diisobutyl methanol 0.96
    2-phenylethanol 2.1
    styrene 0.65
    dioctyl adipate 3.09
    dimethyl sulfate 3.4
    ethyl butyrate 2.32
    methyl lactate 1.55
    butyl lactate 1.86
    diethyl carbonate 2.33
    propanediol butyl ether 1.57
    triethyl orthoformate 3.11
    p-tert-butyltoluene 1.0
    methyl 4-tert-butylbenzoate 4.74
    morpholine 2.38
    tert-butylamine 0.19
    n-dodecanol 0.63
    dimethoxymethane 3.26
    ethylene carbonate 1.87
    cyrene 3.81
    2-ethoxyethyl acetate 4.61
    2-ethylhexyl acetate 2.06
    1,2,4-trichlorobenzene 1.8
    4-methylpyridine 1.49
    dibutyl ether 1.5
    2,6-dimethyl-4-heptanol 0.96
    DEF 1.94
    dimethyl isosorbide 9.6
    tetrachloroethylene 2.61
    eugenol 4.65
    triacetin 4.49
    span 80 2.74
    1,4-butanediol 0.43
    1,1-dichloroethane 0.73
    2-methyl-1-pentanol 0.62
    methyl formate 0.84
    2-methyl-1-butanol 0.4
    n-decane 0.16
    butyronitrile 0.68
    3,7-dimethyl-1-octanol 0.97
    1-chlorooctane 0.54
    1-chlorotetradecane 0.38
    n-nonane 0.11
    undecane 0.13
    tert-butylcyclohexane 0.1
    cyclooctane 0.05
    cyclopentanol 0.38
    tetrahydropyran 1.36
    tert-amyl methyl ether 0.7
    2,5,8-trioxanonane 10.47
    1-hexene 0.12
    2-isopropoxyethanol 2.06
    2,2,2-trifluoroethanol 1.31
    methyl butyrate 1.68

    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