Sanguinarine chloride

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  • Identifiers

    CAS number
    5578-73-4

    Molecular formula
    C20H14ClNO4

    SMILES
    C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6.[Cl-]

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Floral 54.28%
    Powdery 33.94%
    Fruity 33.73%
    Animal 32.26%
    Sweet 32.22%
    Phenolic 31.54%
    Musk 29.46%
    Spicy 27.35%
    Neroli 22.0%
    Aromatic 18.74%

     

    Flavor
    Bitter 97.45%
    Very strong 17.17%
    Indole 16.78%
    Cedarleaf 16.42%
    Sweet-like 16.27%
    Parsley 16.07%
    Cereal 15.95%
    Rotten 15.79%
    Eugenol 15.51%
    Moth ball 15.46%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    4.51 (weak acid)

    Molecular weight
    367.8 g/mol

    Flash point

    • 247.2 ˚C est.

  • Synonyms

    • SANGUINARINE CHLORIDE
    • RefChem:884540
    • 621-641-8
    • 5578-73-4
    • Sanguinarium Chloride
    • Viadent
    • Sanguinarine hydrochloride
    • Sanguinarine chloride hydrate
    • Sanguinarine (chloride)
    • [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium,13-methyl-, chloride (1:1)
    • MFCD00012126
    • 13-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium chloride
    • CHEMBL490129
    • 5578-73-4 (chloride)
    • B8Z8J4400H
    • Pseudochelerythrine chloride;Sanguinarium chloride
    • 13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride
    • (1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl-, chloride
    • 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[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;chloride
    • Sanguinarine, chloride
    • Sanguinarium chloride [USAN:INN]
    • UNII-B8Z8J4400H
    • SR-01000075650
    • Cloruro de sanguinario
    • Chlorure de sanguinarium
    • SCHEMBL43290
    • HY-N0052AR
    • orb1310909
    • SCHEMBL30668087
    • HY-N0052A
    • DTXSID30971158
    • GIZKAXHWLRYMLE-UHFFFAOYSA-M
    • HMS3263M18
    • HMS5084F04
    • SANGUINARINE CHLORIDE [MI]
    • Sanguinarium chloride (USAN/INN)
    • SANGUINARIUM CHLORIDE [INN]
    • MSK40313
    • Sanguinarine (chloride) (Standard)
    • SANGUINARIUM CHLORIDE [USAN]
    • Tox21_501108
    • AKOS024457036
    • CCG-212462
    • CS-4784
    • EBC-531079
    • FD10130
    • FS27791
    • LP01108
    • 13-Methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i] phenanthridinium chloride
    • NCGC00094379-01
    • NCGC00094379-02
    • NCGC00261793-01
    • AC-34926
    • LS-14752
    • DB-052796
    • A3229
    • EU-0101108
    • D05799
    • S 5890
    • Sanguinarine chloride hydrate, >=98% (HPLC)
    • SR-01000075650-2
    • Q27274521
    • 13-Methyl-2H,10H-[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium chloride
    • 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride
    • 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaen-24-ium chloride
    • 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.0^{2,10.0^{4,8.0^{14,22.0^{17,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene;chloride
    • 5578-73-4

  • Applications

    Sanguinarine chloride (CAS 5578-73-4) is an alkaloid used primarily as an intermediate in the organic synthesis of benzophenanthridine alkaloids and as a building block for related compounds. In scientific research it is used as a tool to evaluate enzyme inhibition and antimicrobial activity of analogs. It is also considered a potential antimicrobial additive in coatings, inks and cleaning formulations when regulated and formulated appropriately. In addition, sanguinarine chloride can serve as a precursor for the synthesis of dyes and specialty pigments for labeling and testing in the laboratory. In pharmaceutical research, it is commonly viewed as a lead scaffold for designing related alkaloids.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.48
    methanol 0.41
    isopropanol 0.33
    water 0.01
    ethyl acetate 2.93
    n-propanol 0.44
    acetone 2.29
    n-butanol 0.5
    acetonitrile 1.72
    DMF 3.63
    toluene 1.65
    isobutanol 0.38
    1,4-dioxane 6.1
    methyl acetate 2.39
    THF 8.9
    2-butanone 2.19
    n-pentanol 0.59
    sec-butanol 0.25
    n-hexane 0.04
    ethylene glycol 0.46
    NMP 4.93
    cyclohexane 0.1
    DMSO 5.23
    n-butyl acetate 3.79
    n-octanol 1.24
    chloroform 9.21
    n-propyl acetate 3.55
    acetic acid 3.24
    dichloromethane 11.54
    cyclohexanone 5.1
    propylene glycol 0.11
    isopropyl acetate 3.4
    DMAc 7.91
    2-ethoxyethanol 3.51
    isopentanol 0.85
    n-heptane 0.14
    ethyl formate 2.29
    1,2-dichloroethane 6.96
    n-hexanol 1.07
    2-methoxyethanol 3.28
    isobutyl acetate 3.71
    tetrachloromethane 1.34
    n-pentyl acetate 5.24
    transcutol 11.52
    n-heptanol 1.65
    ethylbenzene 1.28
    MIBK 2.95
    2-propoxyethanol 6.71
    tert-butanol 0.57
    MTBE 0.73
    2-butoxyethanol 6.08
    propionic acid 1.12
    o-xylene 1.39
    formic acid 2.4
    diethyl ether 1.3
    m-xylene 1.49
    p-xylene 1.88
    chlorobenzene 2.85
    dimethyl carbonate 4.22
    n-octane 0.12
    formamide 4.32
    cyclopentanone 6.37
    2-pentanone 2.24
    anisole 3.17
    cyclopentyl methyl ether 2.93
    gamma-butyrolactone 8.38
    1-methoxy-2-propanol 2.08
    pyridine 7.05
    3-pentanone 2.33
    furfural 11.7
    n-dodecane 0.16
    diethylene glycol 6.73
    diisopropyl ether 0.82
    tert-amyl alcohol 0.43
    acetylacetone 6.02
    n-hexadecane 0.2
    acetophenone 5.54
    methyl propionate 2.74
    isopentyl acetate 5.37
    trichloroethylene 15.34
    n-nonanol 1.7
    cyclohexanol 0.73
    benzyl alcohol 3.06
    2-ethylhexanol 1.47
    isooctanol 1.96
    dipropyl ether 2.45
    1,2-dichlorobenzene 4.2
    ethyl lactate 2.36
    propylene carbonate 4.62
    n-methylformamide 1.98
    2-pentanol 0.35
    n-pentane 0.05
    1-propoxy-2-propanol 3.89
    1-methoxy-2-propyl acetate 7.32
    2-(2-methoxypropoxy) propanol 6.55
    mesitylene 1.08
    ε-caprolactone 5.36
    p-cymene 2.14
    epichlorohydrin 13.41
    1,1,1-trichloroethane 3.97
    2-aminoethanol 0.47
    morpholine-4-carbaldehyde 9.84
    sulfolane 8.81
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 3.07
    n-hexyl acetate 4.47
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 6.94
    sec-butyl acetate 3.08
    tert-butyl acetate 4.3
    decalin 0.18
    glycerin 0.87
    diglyme 16.88
    acrylic acid 1.89
    isopropyl myristate 3.11
    n-butyric acid 2.18
    acetyl acetate 4.68
    di(2-ethylhexyl) phthalate 3.67
    ethyl propionate 3.62
    nitromethane 7.59
    1,2-diethoxyethane 5.75
    benzonitrile 4.73
    trioctyl phosphate 2.6
    1-bromopropane 1.67
    gamma-valerolactone 11.79
    n-decanol 1.33
    triethyl phosphate 4.5
    4-methyl-2-pentanol 0.65
    propionitrile 1.82
    vinylene carbonate 6.51
    1,1,2-trichlorotrifluoroethane 11.44
    DMS 6.22
    cumene 1.29
    2-octanol 0.99
    2-hexanone 3.03
    octyl acetate 3.24
    limonene 1.66
    1,2-dimethoxyethane 8.09
    ethyl orthosilicate 4.3
    tributyl phosphate 3.05
    diacetone alcohol 3.96
    N,N-dimethylaniline 2.88
    acrylonitrile 3.53
    aniline 2.26
    1,3-propanediol 1.23
    bromobenzene 3.19
    dibromomethane 5.37
    1,1,2,2-tetrachloroethane 9.08
    2-methyl-cyclohexyl acetate 5.82
    tetrabutyl urea 4.49
    diisobutyl methanol 1.33
    2-phenylethanol 4.87
    styrene 1.36
    dioctyl adipate 4.61
    dimethyl sulfate 7.09
    ethyl butyrate 4.33
    methyl lactate 2.16
    butyl lactate 3.63
    diethyl carbonate 4.34
    propanediol butyl ether 2.35
    triethyl orthoformate 4.82
    p-tert-butyltoluene 1.69
    methyl 4-tert-butylbenzoate 8.34
    morpholine 4.14
    tert-butylamine 0.3
    n-dodecanol 1.08
    dimethoxymethane 6.01
    ethylene carbonate 5.17
    cyrene 6.95
    2-ethoxyethyl acetate 8.97
    2-ethylhexyl acetate 4.56
    1,2,4-trichlorobenzene 5.32
    4-methylpyridine 4.13
    dibutyl ether 2.13
    2,6-dimethyl-4-heptanol 1.33
    DEF 3.74
    dimethyl isosorbide 14.04
    tetrachloroethylene 8.27
    eugenol 7.9
    triacetin 7.45
    span 80 3.84
    1,4-butanediol 0.61
    1,1-dichloroethane 2.68
    2-methyl-1-pentanol 0.94
    methyl formate 2.39
    2-methyl-1-butanol 0.53
    n-decane 0.25
    butyronitrile 1.59
    3,7-dimethyl-1-octanol 1.69
    1-chlorooctane 1.12
    1-chlorotetradecane 0.63
    n-nonane 0.18
    undecane 0.2
    tert-butylcyclohexane 0.14
    cyclooctane 0.07
    cyclopentanol 0.78
    tetrahydropyran 2.52
    tert-amyl methyl ether 0.81
    2,5,8-trioxanonane 12.95
    1-hexene 0.24
    2-isopropoxyethanol 3.19
    2,2,2-trifluoroethanol 3.1
    methyl butyrate 3.54

    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