Berberrubine

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  • Identifiers

    CAS number
    17388-19-1

    Molecular formula
    C19H16NO4+

    SMILES
    COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 46.94%
    Spicy 44.1%
    Sweet 40.07%
    Vanilla 35.92%
    Powdery 35.45%
    Floral 31.79%
    Smoky 29.06%
    Balsamic 28.7%
    Animal 26.31%
    Musk 25.68%

     

    Flavor
    Bitter 96.1%
    Very strong 19.0%
    Indole 18.68%
    Sweet-like 18.59%
    Cedarleaf 18.5%
    Parsley 18.28%
    Eugenol 18.0%
    Naphthalic 17.93%
    Cereal 17.78%
    Alkaline 17.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    6.44 (neutral)

    Molecular weight
    322.3 g/mol

    Flash point

    • 246.24 ˚C est.

  • Synonyms

    • Berberrubine
    • 17388-19-1
    • Berberrubin
    • Beroline
    • ZZT5GBZ8KE
    • DTXSID90169675
    • Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
    • Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
    • 9-Berberoline chloride
    • 17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol
    • 17-methoxy-5,7-dioxa-13-azoniapentacyclo(11.8.0.02,10.04,8.015,20)henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol
    • RefChem:326349
    • DTXCID0092166
    • 17-methoxy-5,7-dioxa-13-azoniapentacyclo(11.8.0.02,10.04,8.015,20)henicosa-1(21),2,4(8),9,14,17,19-heptaen-16-one
    • 9-Berberoline
    • 5,6-Dihydro-9-hydroxy-10-methoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
    • MLS002472969
    • SCHEMBL910779
    • CHEMBL203135
    • orb2893426
    • SCHEMBL30239957
    • SCHEMBL30556350
    • SCHEMBL30556352
    • AKOS037514567
    • 6847-93-4 (INNER SALT)
    • FB167753
    • NCI60_042148
    • SMR001397076
    • 10-Methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol
    • Benzo[g]benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
    • Berbinium, 7,8,13,13a-tetradehydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-
    • 9-Hydroxy-10-methoxy-5,6-dihydro-2H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
    • 17388-19-1

  • Applications

    Berberrubine (CAS 17388-19-1) is used as a colorant precursor and building block in the synthesis of dyes and pigments, with applications in coatings, inks, and related color formulations; in pharmaceutical research it provides a scaffold for isoquinoline alkaloid derivatives and is evaluated in medicinal chemistry studies; it is also employed in analytical chemistry as a reference standard and in UV-Vis/HPLC characterization of related compounds; and it may be considered for cosmetic colorant use in exploratory development, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.82
    methanol 0.79
    isopropanol 0.92
    water 0.01
    ethyl acetate 3.85
    n-propanol 0.89
    acetone 3.37
    n-butanol 1.22
    acetonitrile 1.65
    DMF 3.69
    toluene 2.15
    isobutanol 0.77
    1,4-dioxane 9.08
    methyl acetate 2.54
    THF 12.19
    2-butanone 3.2
    n-pentanol 1.06
    sec-butanol 0.57
    n-hexane 0.05
    ethylene glycol 0.98
    NMP 2.01
    cyclohexane 0.16
    DMSO 10.45
    n-butyl acetate 3.11
    n-octanol 1.24
    chloroform 8.05
    n-propyl acetate 3.02
    acetic acid 5.71
    dichloromethane 9.58
    cyclohexanone 5.6
    propylene glycol 0.32
    isopropyl acetate 4.26
    DMAc 7.38
    2-ethoxyethanol 6.72
    isopentanol 1.83
    n-heptane 0.21
    ethyl formate 2.35
    1,2-dichloroethane 6.84
    n-hexanol 1.56
    2-methoxyethanol 8.47
    isobutyl acetate 3.13
    tetrachloromethane 1.3
    n-pentyl acetate 4.56
    transcutol 24.56
    n-heptanol 1.98
    ethylbenzene 1.18
    MIBK 3.63
    2-propoxyethanol 9.63
    tert-butanol 1.47
    MTBE 1.22
    2-butoxyethanol 7.9
    propionic acid 1.46
    o-xylene 1.56
    formic acid 3.99
    diethyl ether 2.15
    m-xylene 1.68
    p-xylene 1.61
    chlorobenzene 2.24
    dimethyl carbonate 4.14
    n-octane 0.16
    formamide 7.08
    cyclopentanone 5.23
    2-pentanone 3.04
    anisole 2.83
    cyclopentyl methyl ether 3.07
    gamma-butyrolactone 5.82
    1-methoxy-2-propanol 4.75
    pyridine 8.4
    3-pentanone 2.68
    furfural 10.93
    n-dodecane 0.18
    diethylene glycol 12.19
    diisopropyl ether 1.06
    tert-amyl alcohol 0.88
    acetylacetone 7.35
    n-hexadecane 0.22
    acetophenone 4.3
    methyl propionate 2.78
    isopentyl acetate 4.73
    trichloroethylene 13.45
    n-nonanol 1.79
    cyclohexanol 1.28
    benzyl alcohol 3.12
    2-ethylhexanol 1.58
    isooctanol 2.19
    dipropyl ether 2.8
    1,2-dichlorobenzene 3.35
    ethyl lactate 2.24
    propylene carbonate 3.39
    n-methylformamide 2.21
    2-pentanol 0.78
    n-pentane 0.07
    1-propoxy-2-propanol 5.07
    1-methoxy-2-propyl acetate 7.71
    2-(2-methoxypropoxy) propanol 8.08
    mesitylene 1.22
    ε-caprolactone 4.59
    p-cymene 1.74
    epichlorohydrin 12.4
    1,1,1-trichloroethane 3.91
    2-aminoethanol 0.93
    morpholine-4-carbaldehyde 8.03
    sulfolane 7.01
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 2.9
    n-hexyl acetate 3.86
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 10.71
    sec-butyl acetate 2.76
    tert-butyl acetate 5.04
    decalin 0.17
    glycerin 2.5
    diglyme 24.74
    acrylic acid 2.35
    isopropyl myristate 2.95
    n-butyric acid 3.59
    acetyl acetate 5.79
    di(2-ethylhexyl) phthalate 3.56
    ethyl propionate 3.21
    nitromethane 10.18
    1,2-diethoxyethane 8.65
    benzonitrile 3.68
    trioctyl phosphate 2.42
    1-bromopropane 1.79
    gamma-valerolactone 11.48
    n-decanol 1.45
    triethyl phosphate 3.78
    4-methyl-2-pentanol 1.1
    propionitrile 2.27
    vinylene carbonate 5.2
    1,1,2-trichlorotrifluoroethane 14.33
    DMS 5.19
    cumene 1.12
    2-octanol 1.17
    2-hexanone 2.71
    octyl acetate 3.02
    limonene 1.51
    1,2-dimethoxyethane 12.19
    ethyl orthosilicate 3.73
    tributyl phosphate 2.89
    diacetone alcohol 5.56
    N,N-dimethylaniline 2.48
    acrylonitrile 3.79
    aniline 2.81
    1,3-propanediol 3.32
    bromobenzene 2.42
    dibromomethane 4.68
    1,1,2,2-tetrachloroethane 8.93
    2-methyl-cyclohexyl acetate 4.81
    tetrabutyl urea 4.18
    diisobutyl methanol 1.68
    2-phenylethanol 4.82
    styrene 1.18
    dioctyl adipate 4.53
    dimethyl sulfate 6.31
    ethyl butyrate 3.83
    methyl lactate 2.59
    butyl lactate 3.51
    diethyl carbonate 3.9
    propanediol butyl ether 3.28
    triethyl orthoformate 4.37
    p-tert-butyltoluene 1.59
    methyl 4-tert-butylbenzoate 7.63
    morpholine 6.35
    tert-butylamine 0.63
    n-dodecanol 1.2
    dimethoxymethane 9.08
    ethylene carbonate 4.39
    cyrene 5.95
    2-ethoxyethyl acetate 9.82
    2-ethylhexyl acetate 3.51
    1,2,4-trichlorobenzene 4.13
    4-methylpyridine 3.73
    dibutyl ether 2.46
    2,6-dimethyl-4-heptanol 1.68
    DEF 3.25
    dimethyl isosorbide 14.99
    tetrachloroethylene 8.36
    eugenol 7.92
    triacetin 6.79
    span 80 4.67
    1,4-butanediol 1.06
    1,1-dichloroethane 2.59
    2-methyl-1-pentanol 1.43
    methyl formate 2.36
    2-methyl-1-butanol 0.98
    n-decane 0.28
    butyronitrile 1.84
    3,7-dimethyl-1-octanol 1.78
    1-chlorooctane 0.99
    1-chlorotetradecane 0.61
    n-nonane 0.2
    undecane 0.21
    tert-butylcyclohexane 0.13
    cyclooctane 0.12
    cyclopentanol 1.02
    tetrahydropyran 3.84
    tert-amyl methyl ether 1.11
    2,5,8-trioxanonane 19.42
    1-hexene 0.25
    2-isopropoxyethanol 4.7
    2,2,2-trifluoroethanol 3.62
    methyl butyrate 3.1

    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