Sanguinarine

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  • Identifiers

    CAS number
    2447-54-3

    Molecular formula
    C20H14NO4+

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

    Safety labels

  • 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

    XLogP3-AA
    4.4

    pKa est.
    4.51 (weak acid)

    Molecular weight
    332.3 g/mol

    Melting point expt.

    • 266 °C

    Flash point

    • 247.2 ˚C est.

  • Synonyms

    • SANGUINARINE
    • 2447-54-3
    • Pseudochelerythrine
    • Sanguinarin
    • SANGUINARIUM
    • sangvinarin
    • Sanguiritrin
    • Dimethylenedioxy benzphenanthridine
    • AV9VK043SS
    • DTXSID0045204
    • 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
    • DTXCID8025204
    • CHEBI:17183
    • pseudo-chelerythrine
    • 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(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium
    • 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(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium
    • 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
    • RefChem:48744
    • 219-503-3
    • 24-methyl-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-nonaen-24-ium
    • Sangrovit
    • Veadent
    • [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-
    • Pseudochelerythrine;Sanguinarin
    • Benzophenanthridine alkaloid
    • NCGC00015959-03
    • CAS-2447-54-3
    • 13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium
    • 13-Methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium
    • 13-Methyl[1,3]benzodioxolo[5,6-C][1,3]dioxolo[4,5-I]phenanthridin-13-Ium
    • EINECS 219-503-3
    • UNII-AV9VK043SS
    • BRN 3915507
    • y-Chelerythrine
    • SR-01000075650
    • (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDINIUM, 13-METHYL-
    • UI5
    • sanguinarium-chloride
    • Spectrum_000259
    • Prestwick0_000987
    • Prestwick1_000987
    • Prestwick2_000987
    • Prestwick3_000987
    • Spectrum2_000724
    • Spectrum3_001148
    • Spectrum4_001838
    • Spectrum5_000635
    • Lopac-S-5890
    • SANGUINARINE [MI]
    • (1,3)-Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl-
    • cid_5154
    • Lopac0_001108
    • BSPBio_001053
    • BSPBio_002675
    • KBioGR_002542
    • KBioSS_000739
    • MLS002154085
    • DivK1c_000495
    • SANGUINARINE [WHO-DD]
    • SCHEMBL123241
    • SPBio_000648
    • SPBio_002954
    • BPBio1_001159
    • CHEMBL417799
    • orb1305027
    • SCHEMBL29385229
    • SCHEMBL30129850
    • SCHEMBL30153784
    • BDBM25525
    • GTPL11563
    • KBio1_000495
    • KBio2_000739
    • KBio2_003307
    • KBio2_005875
    • KBio3_002175
    • NINDS_000495
    • C20H14NO4+
    • HMS1571E15
    • HMS2098E15
    • HMS5086G15
    • EX-A5014
    • HY-N0052
    • Tox21_110268
    • MFCD00064925
    • NSC765394
    • s9032
    • AKOS025311557
    • Tox21_110268_1
    • CCG-205184
    • compound 1 [PMID: 28621943]
    • CS-3818
    • FS40153
    • NSC-765394
    • SDCCGMLS-0066612.P001
    • IDI1_000495
    • NCGC00015959-01
    • NCGC00015959-02
    • NCGC00015959-04
    • NCGC00015959-05
    • NCGC00015959-09
    • NCGC00015959-16
    • NCGC00015959-22
    • NCGC00160289-01
    • NCGC00160289-02
    • AC-34836
    • SMR001233394
    • SBI-0051077.P003
    • DB-046461
    • AB00053789
    • NS00018310
    • C06162
    • E80766
    • AB00053789_04
    • 447S543
    • Q347392
    • SR-01000075650-7
    • BRD-K66898851-001-03-7
    • BRD-K66898851-003-02-5
    • BRD-K66898851-003-03-3
    • 5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+)
    • 13-Methyl-2H,10H-[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium
    • 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium nitrate
    • 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9CI
    • 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium
    • 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(13),2,4(8),9,11,14(22),15,17(21),23-nonaen-24-ium
    • 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
    • 2447-54-3

  • Applications

    Sanguinarine (CAS 2447-54-3) is a benzophenanthridine alkaloid with antimicrobial and antifungal activity, and is used as a starting material for the synthesis of related benzophenanthridine alkaloids in pharmaceutical research; it is evaluated for cosmetics and personal care applications as an antimicrobial active ingredient; it is studied for cleaning and disinfection formulations in household products; it is investigated as a bioactive agent in agriculture for pest management; and it is considered as a bioactive additive for coatings, inks, and other industrial materials formulations; subject to local regulations and formulation limits.

    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