(+)-Boldine

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  • Identifiers

    CAS number
    476-70-0

    Molecular formula
    C19H21NO4

    SMILES
    CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 43.94%
    Odorless 43.66%
    Spicy 33.52%
    Vanilla 33.47%
    Smoky 32.31%
    Burnt 28.68%
    Sweet 25.4%
    Balsamic 23.53%
    Powdery 22.44%
    Animal 22.31%

     

    Flavor
    Bitter 93.7%
    Bland 26.59%
    Odorless 22.14%
    Sweet-like 21.91%
    Cedarleaf 20.6%
    Parsley 19.95%
    Eugenol 19.01%
    Very strong 18.74%
    Indole 18.68%
    Lovage 18.63%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    8.9 (weak base)

    Molecular weight
    327.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    816°C

    Flash point

    • 241.1 ˚C est.

  • Synonyms

    • Boldine
    • 476-70-0
    • (S)-Boldine
    • (+)-Boldine
    • 1,10-Dimethoxy-2,9-dihydroxyaporphine
    • DTXSID40883394
    • 8I91GE2769
    • 4H-Dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-
    • 4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-
    • NSC-65689
    • RefChem:30175
    • DTXCID801022928
    • 207-509-9
    • Uniboldina
    • Boldin
    • Boldine chloroform
    • NSC 65689
    • (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
    • MFCD00135040
    • CHEMBL388342
    • (S)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
    • 4H-Dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-
    • (+)-(S)-Boldine
    • EINECS 207-509-9
    • 2,9-Dihydroxy-1,10-dimethoxyaporphine
    • BRN 0094036
    • ex Peumus boldus
    • UNII-8I91GE2769
    • 1,10-Dimethoxy-6a-alpha-aporphine-2,9-diol
    • Aprophine alkaloid
    • Boldine CRS
    • 4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-
    • Prestwick_46
    • Boldine (Standard)
    • (S)-(+)-Boldine
    • BOLDINE [MI]
    • Prestwick3_000600
    • BOLDINE [WHO-DD]
    • 6aalpha-Aporphine-2,9-diol, 1,10-dimethoxy-
    • Boldine, analytical standard
    • BSPBio_000480
    • 5-21-06-00118 (Beilstein Handbook Reference)
    • cid_10154
    • MLS002153899
    • SCHEMBL177550
    • BOLDINE [EP MONOGRAPH]
    • 6a-alpha-APORPHINE-2,9-DIOL, 1,10-DIMETHOXY-
    • BPBio1_000528
    • CHEBI:3148
    • cid_248507
    • orb1301554
    • SCHEMBL30184400
    • HY-N6973R
    • HMS2096H22
    • HMS2235B04
    • HY-N6973
    • TNP00245
    • BDBM50202318
    • MSK159059
    • s9050
    • ZB1855
    • Boldine, analytical reference material
    • 2,6-dihydroxy-3,5-dimethoxyaporphine
    • AKOS015912953
    • CCG-208461
    • EBC-616755
    • FB70015
    • 5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol
    • NCGC00016454-01
    • NCGC00016454-02
    • NCGC00017314-01
    • NCGC00179547-01
    • AC-34043
    • AS-17759
    • CAS-476-70-0
    • SMR001233248
    • CS-0013445
    • NS00004847
    • C09365
    • 1,10-Dimethoxy-6a-.alpha.-aporphine-2,9-diol
    • 476B700
    • 6a.alpha.-Aporphine-2,9-diol, 1,10-dimethoxy-
    • Q2070105
    • 1,10-DIMETHOXY-6A.ALPHA.-APORPHINE-2,9-DIOL
    • BRD-K03440695-001-02-6
    • Boldine, European Pharmacopoeia (EP) Reference Standard
    • 1,10-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol, (S)-
    • (6AS)-5,6,6A,7-TETRAHYDRO-1,10-DIMETHOXY-6-METHYL-4H-DIBENZO(DE,G)QUINOLINE-2,9-DIOL
    • (9S)-4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,13(17),14-hexaene-5,15-diol
    • 476-70-0

  • Applications

    (+)-Boldine, CAS 476-70-0, is primarily used in scientific research as a natural product and analytical reference material, commonly serving as a standard for HPLC and spectroscopy to identify and quantify aporphine alkaloids in plant samples. It is evaluated for antioxidant activity and is often viewed as a lead scaffold for the synthesis of aporphine alkaloids in organic chemistry. In cosmetic science and personal care R&D, it is explored as a natural bioactive ingredient with antioxidant potential in formulational studies. It may also function as an intermediate or starting point for the synthesis of related alkaloids for medicinal chemistry and phytochemical research, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.93
    methanol 8.93
    isopropanol 3.78
    water 0.16
    ethyl acetate 6.54
    n-propanol 6.06
    acetone 5.61
    n-butanol 5.25
    acetonitrile 2.59
    DMF 27.09
    toluene 0.85
    isobutanol 3.96
    1,4-dioxane 7.15
    methyl acetate 5.97
    THF 9.52
    2-butanone 5.51
    n-pentanol 3.99
    sec-butanol 2.4
    n-hexane 0.09
    ethylene glycol 8.53
    NMP 20.69
    cyclohexane 0.2
    DMSO 33.67
    n-butyl acetate 9.81
    n-octanol 2.72
    chloroform 13.54
    n-propyl acetate 7.72
    acetic acid 36.71
    dichloromethane 12.48
    cyclohexanone 13.7
    propylene glycol 2.81
    isopropyl acetate 5.39
    DMAc 34.27
    2-ethoxyethanol 20.32
    isopentanol 5.8
    n-heptane 0.18
    ethyl formate 9.5
    1,2-dichloroethane 9.31
    n-hexanol 6.15
    2-methoxyethanol 32.65
    isobutyl acetate 5.77
    tetrachloromethane 3.81
    n-pentyl acetate 9.66
    transcutol 39.6
    n-heptanol 5.63
    ethylbenzene 0.89
    MIBK 5.08
    2-propoxyethanol 28.16
    tert-butanol 4.99
    MTBE 1.61
    2-butoxyethanol 22.45
    propionic acid 10.23
    o-xylene 1.28
    formic acid 31.9
    diethyl ether 2.28
    m-xylene 1.2
    p-xylene 1.29
    chlorobenzene 2.82
    dimethyl carbonate 11.55
    n-octane 0.15
    formamide 39.23
    cyclopentanone 12.18
    2-pentanone 5.18
    anisole 2.81
    cyclopentyl methyl ether 3.55
    gamma-butyrolactone 19.6
    1-methoxy-2-propanol 18.15
    pyridine 6.6
    3-pentanone 4.11
    furfural 28.19
    n-dodecane 0.15
    diethylene glycol 41.76
    diisopropyl ether 0.95
    tert-amyl alcohol 3.56
    acetylacetone 9.21
    n-hexadecane 0.17
    acetophenone 7.53
    methyl propionate 7.4
    isopentyl acetate 10.02
    trichloroethylene 18.81
    n-nonanol 3.32
    cyclohexanol 4.01
    benzyl alcohol 6.62
    2-ethylhexanol 4.19
    isooctanol 4.98
    dipropyl ether 3.0
    1,2-dichlorobenzene 4.87
    ethyl lactate 10.4
    propylene carbonate 15.68
    n-methylformamide 19.38
    2-pentanol 2.45
    n-pentane 0.12
    1-propoxy-2-propanol 14.95
    1-methoxy-2-propyl acetate 16.65
    2-(2-methoxypropoxy) propanol 16.35
    mesitylene 0.99
    ε-caprolactone 15.72
    p-cymene 2.3
    epichlorohydrin 18.78
    1,1,1-trichloroethane 5.88
    2-aminoethanol 8.69
    morpholine-4-carbaldehyde 35.77
    sulfolane 32.69
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 3.76
    n-hexyl acetate 7.43
    isooctane 0.11
    2-(2-butoxyethoxy)ethanol 21.31
    sec-butyl acetate 4.66
    tert-butyl acetate 6.33
    decalin 0.23
    glycerin 17.11
    diglyme 38.39
    acrylic acid 15.62
    isopropyl myristate 3.52
    n-butyric acid 15.4
    acetyl acetate 8.01
    di(2-ethylhexyl) phthalate 7.27
    ethyl propionate 6.16
    nitromethane 35.77
    1,2-diethoxyethane 9.13
    benzonitrile 6.32
    trioctyl phosphate 5.64
    1-bromopropane 2.41
    gamma-valerolactone 31.2
    n-decanol 2.51
    triethyl phosphate 8.5
    4-methyl-2-pentanol 2.69
    propionitrile 3.74
    vinylene carbonate 20.03
    1,1,2-trichlorotrifluoroethane 48.44
    DMS 11.55
    cumene 1.09
    2-octanol 2.57
    2-hexanone 5.2
    octyl acetate 4.87
    limonene 2.54
    1,2-dimethoxyethane 20.16
    ethyl orthosilicate 7.44
    tributyl phosphate 6.04
    diacetone alcohol 13.33
    N,N-dimethylaniline 3.44
    acrylonitrile 7.16
    aniline 3.41
    1,3-propanediol 15.86
    bromobenzene 2.2
    dibromomethane 6.3
    1,1,2,2-tetrachloroethane 16.48
    2-methyl-cyclohexyl acetate 9.15
    tetrabutyl urea 8.32
    diisobutyl methanol 2.72
    2-phenylethanol 9.72
    styrene 0.92
    dioctyl adipate 7.13
    dimethyl sulfate 21.88
    ethyl butyrate 7.96
    methyl lactate 14.5
    butyl lactate 12.36
    diethyl carbonate 8.27
    propanediol butyl ether 12.87
    triethyl orthoformate 8.37
    p-tert-butyltoluene 2.04
    methyl 4-tert-butylbenzoate 13.91
    morpholine 10.04
    tert-butylamine 1.92
    n-dodecanol 1.9
    dimethoxymethane 19.0
    ethylene carbonate 16.85
    cyrene 21.47
    2-ethoxyethyl acetate 18.24
    2-ethylhexyl acetate 7.91
    1,2,4-trichlorobenzene 6.92
    4-methylpyridine 4.99
    dibutyl ether 2.21
    2,6-dimethyl-4-heptanol 2.72
    DEF 11.15
    dimethyl isosorbide 25.57
    tetrachloroethylene 16.69
    eugenol 16.38
    triacetin 13.56
    span 80 12.32
    1,4-butanediol 6.45
    1,1-dichloroethane 4.03
    2-methyl-1-pentanol 4.53
    methyl formate 16.65
    2-methyl-1-butanol 4.13
    n-decane 0.23
    butyronitrile 3.68
    3,7-dimethyl-1-octanol 3.17
    1-chlorooctane 1.13
    1-chlorotetradecane 0.6
    n-nonane 0.17
    undecane 0.17
    tert-butylcyclohexane 0.19
    cyclooctane 0.1
    cyclopentanol 3.91
    tetrahydropyran 3.54
    tert-amyl methyl ether 1.79
    2,5,8-trioxanonane 27.91
    1-hexene 0.47
    2-isopropoxyethanol 12.76
    2,2,2-trifluoroethanol 26.81
    methyl butyrate 8.69

    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