Chelerythrine

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  • Identifiers

    CAS number
    34316-15-9

    Molecular formula
    C21H18NO4+

    SMILES
    C[N+]1=C2C(=C3C=CC(=C(C3=C1)OC)OC)C=CC4=CC5=C(C=C42)OCO5

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Floral 53.33%
    Sweet 43.49%
    Powdery 42.63%
    Phenolic 41.15%
    Spicy 38.69%
    Fruity 35.5%
    Vanilla 34.72%
    Musk 33.99%
    Animal 28.99%
    Woody 26.6%

     

    Flavor
    Bitter 95.81%
    Parsley 18.95%
    Very strong 18.58%
    Cedarleaf 18.22%
    Indole 18.19%
    Eugenol 18.17%
    Sweet-like 17.82%
    Bland 17.56%
    Lovage 17.25%
    Flat 17.17%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.6

    pKa est.
    4.99 (weak acid)

    Molecular weight
    348.4 g/mol

    Flash point

    • 235.51 ˚C est.

  • Synonyms

    • chelerythrine
    • 34316-15-9
    • Toddalin
    • cheleritrine
    • Toddaline
    • broussonpapyrine
    • [1,3]Benzodioxolo[5,6-c]phenanthridinium, 1,2-dimethoxy-12-methyl-
    • 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
    • E3B045W6X0
    • CHEBI:78373
    • 1,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium
    • DTXSID20861211
    • 1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
    • (1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDINIUM, 1,2-DIMETHOXY-12-METHYL-
    • 1,2-DIMETHOXY-12-METHYL(1,3)DIOXOLO)4',5':4,5)BENZO(1,2-C)PHENANTHRIDINIUM
    • 1,2-dimethoxy-12-methyl-(1,3)benzodioxolo(5,6-c)phenanthridin-12-ium
    • 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo(11.8.0.0^(2,10).0^(4,8).0^(14,19))henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium
    • 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium
    • RefChem:32228
    • DTXCID30208572
    • 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo(11.8.0.02,10.04,8.014,19)henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-21-ium
    • 251-930-0
    • EINECS 251-930-0
    • 1,2-Dimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium
    • 1,2-Dimethoxy-12-Methyl[1,3]benzodioxolo[5,6-C]phenanthridin-12-Ium
    • CHEMBL13045
    • 1,2-Dimethoxy-12-methyl-[1,3]dioxolo-[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium
    • NSC646662
    • 1,2-Dimethoxy-N-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium chloride
    • Chelerytherine
    • Chelerythrine?
    • UNII-E3B045W6X0
    • SR-01000075750
    • Lopac-C-2932
    • CHELERYTHRINE [MI]
    • Lopac0_000241
    • BSPBio_001558
    • SCHEMBL288915
    • CHELERYTHRINE [WHO-DD]
    • GTPL5953
    • MEGxp0_001953
    • orb1300271
    • SCHEMBL29357531
    • SCHEMBL30527167
    • SCHEMBL30527168
    • BDBM25524
    • HMS1791N20
    • HMS1989N20
    • HMS3402N20
    • HY-N2359
    • MFCD00270393
    • MSK157280
    • STL581484
    • AKOS028108433
    • CCG-204336
    • FC73805
    • NCGC00015225-01
    • NCGC00015225-02
    • NCGC00015225-03
    • NCGC00015225-04
    • NCGC00015225-05
    • NCGC00015225-06
    • NCGC00015225-07
    • NCGC00162102-01
    • NCGC00162102-02
    • NCGC00162102-03
    • NCGC00162102-04
    • NCGC00162102-05
    • NCI60_003349
    • NCI60_041672
    • DB-050176
    • CS-0022541
    • NS00089928
    • Q5089853
    • SR-01000075750-5
    • BRD-K87904882-001-02-3
    • 1,2-Dimethoxy-12-methyl-9H-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
    • 1,2-Dimethoxy-12-methyl-12lambda~5~-[1,3]benzodioxolo[5,6-c]phenanthridine hydrochloride
    • 17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14(19),15,17,20-nonaen-21-ium
    • 34316-15-9

  • Applications

    Chelerythrine (CAS 34316-15-9) is a natural benzophenanthridine alkaloid primarily used as a biochemical research tool, notably as a protein kinase C (PKC) inhibitor and in enzyme assays and cell signaling studies; it is also evaluated as a lead compound in benzophenanthridine alkaloid chemistry and phytochemical research, with reported antimicrobial activity that informs its use in basic research and the development of related derivatives; additionally, it serves as an intermediate in the synthesis of related alkaloids for pharmaceutical research, with use subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.24
    methanol 1.13
    isopropanol 0.88
    water 0.02
    ethyl acetate 6.7
    n-propanol 1.15
    acetone 5.8
    n-butanol 1.29
    acetonitrile 3.76
    DMF 7.44
    toluene 2.46
    isobutanol 1.07
    1,4-dioxane 10.96
    methyl acetate 5.78
    THF 14.23
    2-butanone 5.16
    n-pentanol 1.64
    sec-butanol 0.73
    n-hexane 0.2
    ethylene glycol 0.99
    NMP 9.98
    cyclohexane 0.44
    DMSO 10.04
    n-butyl acetate 7.61
    n-octanol 2.09
    chloroform 26.22
    n-propyl acetate 7.99
    acetic acid 7.79
    dichloromethane 34.29
    cyclohexanone 10.98
    propylene glycol 0.19
    isopropyl acetate 5.98
    DMAc 13.64
    2-ethoxyethanol 6.7
    isopentanol 2.03
    n-heptane 0.42
    ethyl formate 5.17
    1,2-dichloroethane 19.55
    n-hexanol 2.64
    2-methoxyethanol 5.98
    isobutyl acetate 7.55
    tetrachloromethane 4.7
    n-pentyl acetate 9.03
    transcutol 14.22
    n-heptanol 3.23
    ethylbenzene 2.55
    MIBK 5.38
    2-propoxyethanol 10.96
    tert-butanol 1.48
    MTBE 1.88
    2-butoxyethanol 9.63
    propionic acid 2.8
    o-xylene 2.57
    formic acid 4.88
    diethyl ether 3.62
    m-xylene 2.4
    p-xylene 3.71
    chlorobenzene 5.63
    dimethyl carbonate 7.93
    n-octane 0.37
    formamide 8.33
    cyclopentanone 12.44
    2-pentanone 4.83
    anisole 5.33
    cyclopentyl methyl ether 5.25
    gamma-butyrolactone 16.83
    1-methoxy-2-propanol 3.28
    pyridine 11.65
    3-pentanone 5.35
    furfural 21.02
    n-dodecane 0.33
    diethylene glycol 10.68
    diisopropyl ether 1.79
    tert-amyl alcohol 1.19
    acetylacetone 10.3
    n-hexadecane 0.4
    acetophenone 9.71
    methyl propionate 5.77
    isopentyl acetate 9.41
    trichloroethylene 37.53
    n-nonanol 2.75
    cyclohexanol 1.81
    benzyl alcohol 5.23
    2-ethylhexanol 3.24
    isooctanol 3.54
    dipropyl ether 4.37
    1,2-dichlorobenzene 9.21
    ethyl lactate 4.27
    propylene carbonate 9.49
    n-methylformamide 4.3
    2-pentanol 0.89
    n-pentane 0.19
    1-propoxy-2-propanol 5.98
    1-methoxy-2-propyl acetate 11.49
    2-(2-methoxypropoxy) propanol 8.22
    mesitylene 1.92
    ε-caprolactone 11.02
    p-cymene 3.68
    epichlorohydrin 26.49
    1,1,1-trichloroethane 11.84
    2-aminoethanol 0.98
    morpholine-4-carbaldehyde 17.07
    sulfolane 17.58
    2,2,4-trimethylpentane 0.2
    2-methyltetrahydrofuran 6.24
    n-hexyl acetate 7.2
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 9.12
    sec-butyl acetate 6.06
    tert-butyl acetate 7.08
    decalin 0.52
    glycerin 1.28
    diglyme 23.75
    acrylic acid 4.39
    isopropyl myristate 4.01
    n-butyric acid 4.44
    acetyl acetate 9.1
    di(2-ethylhexyl) phthalate 5.17
    ethyl propionate 7.29
    nitromethane 16.66
    1,2-diethoxyethane 8.69
    benzonitrile 7.55
    trioctyl phosphate 3.81
    1-bromopropane 5.05
    gamma-valerolactone 20.23
    n-decanol 2.12
    triethyl phosphate 7.95
    4-methyl-2-pentanol 1.35
    propionitrile 4.26
    vinylene carbonate 12.71
    1,1,2-trichlorotrifluoroethane 22.16
    DMS 10.16
    cumene 2.68
    2-octanol 2.02
    2-hexanone 6.83
    octyl acetate 4.61
    limonene 3.31
    1,2-dimethoxyethane 14.2
    ethyl orthosilicate 7.36
    tributyl phosphate 4.5
    diacetone alcohol 6.19
    N,N-dimethylaniline 4.86
    acrylonitrile 6.86
    aniline 3.42
    1,3-propanediol 2.18
    bromobenzene 6.14
    dibromomethane 17.4
    1,1,2,2-tetrachloroethane 21.67
    2-methyl-cyclohexyl acetate 10.1
    tetrabutyl urea 6.6
    diisobutyl methanol 2.51
    2-phenylethanol 8.12
    styrene 2.48
    dioctyl adipate 6.43
    dimethyl sulfate 13.11
    ethyl butyrate 7.83
    methyl lactate 3.35
    butyl lactate 5.85
    diethyl carbonate 7.89
    propanediol butyl ether 3.34
    triethyl orthoformate 7.81
    p-tert-butyltoluene 2.96
    methyl 4-tert-butylbenzoate 11.29
    morpholine 8.0
    tert-butylamine 0.88
    n-dodecanol 1.71
    dimethoxymethane 10.71
    ethylene carbonate 10.13
    cyrene 11.55
    2-ethoxyethyl acetate 14.65
    2-ethylhexyl acetate 8.16
    1,2,4-trichlorobenzene 10.66
    4-methylpyridine 7.09
    dibutyl ether 3.43
    2,6-dimethyl-4-heptanol 2.51
    DEF 7.72
    dimethyl isosorbide 19.04
    tetrachloroethylene 21.17
    eugenol 11.6
    triacetin 10.72
    span 80 5.22
    1,4-butanediol 1.22
    1,1-dichloroethane 8.24
    2-methyl-1-pentanol 2.33
    methyl formate 5.32
    2-methyl-1-butanol 1.45
    n-decane 0.56
    butyronitrile 3.39
    3,7-dimethyl-1-octanol 2.64
    1-chlorooctane 2.13
    1-chlorotetradecane 1.1
    n-nonane 0.43
    undecane 0.41
    tert-butylcyclohexane 0.4
    cyclooctane 0.23
    cyclopentanol 1.78
    tetrahydropyran 5.42
    tert-amyl methyl ether 1.97
    2,5,8-trioxanonane 16.8
    1-hexene 0.85
    2-isopropoxyethanol 6.07
    2,2,2-trifluoroethanol 7.47
    methyl butyrate 7.64

    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