(R)-Coclaurine

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  • Identifiers

    CAS number
    2196-60-3

    Molecular formula
    C17H19NO3

    SMILES
    COC1=C(C=C2[C@H](NCCC2=C1)CC3=CC=C(C=C3)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 48.9%
    Odorless 40.1%
    Vanilla 39.51%
    Sweet 37.9%
    Spicy 36.54%
    Smoky 33.8%
    Animal 29.98%
    Burnt 26.16%
    Balsamic 23.71%
    Savory 23.41%

     

    Flavor
    Bitter 77.77%
    Fruity 39.27%
    Sweet 32.13%
    Mild 22.28%
    Sweet-like 20.62%
    Orange blossom 20.43%
    Orange flower 20.18%
    Very strong 20.0%
    Animal 19.86%
    Naphthalic 19.76%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    9.82 (weak base)

    Molecular weight
    285.34 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    576°C

    Flash point

    • 210.34 ˚C est.

  • Synonyms

    • (R)-Coclaurine
    • (1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
    • CHEBI:27482
    • (1R)-1-(4-hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
    • (R)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7-isoquinolinol
    • 6-Methoxy-7-hydroxy-(1R)-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline
    • (1R)-1-((4-hydroxyphenyl)methyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
    • (R)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6-methoxy-7-isoquinolinol
    • 6-Methoxy-7-hydroxy-(1R)-((4-hydroxyphenyl)methyl)-1,2,3,4-tetrahydroisoquinoline
    • RefChem:1051081
    • (+)-Coclaurine
    • 2196-60-3
    • d-Coclaurine
    • Sanjoinine K
    • (R)-d-Coclaurine
    • CHEMBL256448
    • 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-6-methoxy-, (R)-
    • 7-ISOQUINOLINOL,1,2,3,4-TETRAHYDRO-1-[(4-HYDROXYPHENYL)METHYL]-6-METHOXY-, (1R)-
    • (+)-R-Coclaurine
    • (+)-(R)-Coclaurine
    • (+)-1(R)-Coclaurine
    • orb1301510
    • SCHEMBL21008643
    • DTXSID70176367
    • HY-N2550
    • BDBM50241488
    • AKOS040758806
    • AC-34837
    • DA-59429
    • TS-09149
    • CS-0022822
    • C06349
    • E87186
    • Q27103156
    • (R)-1-(4-hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
    • 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-, (1R)-
    • 2196-60-3

  • Applications

    (R)-Coclaurine, CAS 2196-60-3, is a benzylisoquinoline alkaloid primarily used as a synthetic intermediate and a chiral building block in the preparation of benzylisoquinoline alkaloids and related isoquinoline compounds; it is commonly employed as a precursor for enantioselective synthesis, supporting medicinal chemistry and the development of isoquinoline alkaloid frameworks. In the laboratory, it serves as a material for method development and optimization in synthesis and analytical workflows, and can be used to assemble compound libraries for SAR studies. Depending on local regulations and formulation constraints, it may also function as a reference standard or starting material in synthetic routes toward more complex alkaloids.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 14.04
    methanol 43.3
    isopropanol 15.61
    water 0.11
    ethyl acetate 26.06
    n-propanol 17.87
    acetone 26.93
    n-butanol 21.42
    acetonitrile 10.76
    DMF 34.09
    toluene 5.2
    isobutanol 10.73
    1,4-dioxane 83.25
    methyl acetate 18.27
    THF 153.35
    2-butanone 23.72
    n-pentanol 12.78
    sec-butanol 9.4
    n-hexane 0.06
    ethylene glycol 16.91
    NMP 7.56
    cyclohexane 0.31
    DMSO 257.2
    n-butyl acetate 8.25
    n-octanol 6.84
    chloroform 14.39
    n-propyl acetate 10.29
    acetic acid 44.42
    dichloromethane 10.25
    cyclohexanone 29.69
    propylene glycol 20.49
    isopropyl acetate 15.33
    DMAc 69.0
    2-ethoxyethanol 88.9
    isopentanol 16.68
    n-heptane 0.51
    ethyl formate 17.56
    1,2-dichloroethane 12.2
    n-hexanol 11.84
    2-methoxyethanol 158.74
    isobutyl acetate 7.3
    tetrachloromethane 2.06
    n-pentyl acetate 8.98
    transcutol 164.32
    n-heptanol 9.84
    ethylbenzene 2.11
    MIBK 15.02
    2-propoxyethanol 64.8
    tert-butanol 26.04
    MTBE 9.4
    2-butoxyethanol 32.35
    propionic acid 15.23
    o-xylene 3.75
    formic acid 40.25
    diethyl ether 8.66
    m-xylene 4.37
    p-xylene 2.48
    chlorobenzene 5.92
    dimethyl carbonate 16.84
    n-octane 0.38
    formamide 76.07
    cyclopentanone 36.11
    2-pentanone 21.74
    anisole 10.74
    cyclopentyl methyl ether 19.44
    gamma-butyrolactone 39.05
    1-methoxy-2-propanol 92.36
    pyridine 25.18
    3-pentanone 14.0
    furfural 47.2
    n-dodecane 0.4
    diethylene glycol 82.06
    diisopropyl ether 2.78
    tert-amyl alcohol 13.8
    acetylacetone 40.18
    n-hexadecane 0.46
    acetophenone 13.04
    methyl propionate 19.93
    isopentyl acetate 10.23
    trichloroethylene 30.38
    n-nonanol 8.15
    cyclohexanol 12.92
    benzyl alcohol 16.84
    2-ethylhexanol 6.54
    isooctanol 8.6
    dipropyl ether 7.59
    1,2-dichlorobenzene 6.44
    ethyl lactate 13.53
    propylene carbonate 15.3
    n-methylformamide 31.21
    2-pentanol 9.82
    n-pentane 0.1
    1-propoxy-2-propanol 33.76
    1-methoxy-2-propyl acetate 26.62
    2-(2-methoxypropoxy) propanol 29.27
    mesitylene 2.81
    ε-caprolactone 20.01
    p-cymene 3.15
    epichlorohydrin 71.99
    1,1,1-trichloroethane 7.96
    2-aminoethanol 27.66
    morpholine-4-carbaldehyde 48.9
    sulfolane 53.0
    2,2,4-trimethylpentane 0.24
    2-methyltetrahydrofuran 21.35
    n-hexyl acetate 10.7
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 47.52
    sec-butyl acetate 7.4
    tert-butyl acetate 18.78
    decalin 0.33
    glycerin 60.47
    diglyme 97.03
    acrylic acid 17.62
    isopropyl myristate 6.05
    n-butyric acid 31.45
    acetyl acetate 18.3
    di(2-ethylhexyl) phthalate 8.2
    ethyl propionate 9.6
    nitromethane 90.73
    1,2-diethoxyethane 32.61
    benzonitrile 11.11
    trioctyl phosphate 5.98
    1-bromopropane 2.85
    gamma-valerolactone 69.96
    n-decanol 6.36
    triethyl phosphate 8.25
    4-methyl-2-pentanol 7.31
    propionitrile 10.2
    vinylene carbonate 16.87
    1,1,2-trichlorotrifluoroethane 63.78
    DMS 13.09
    cumene 1.93
    2-octanol 5.31
    2-hexanone 10.58
    octyl acetate 7.62
    limonene 3.78
    1,2-dimethoxyethane 94.21
    ethyl orthosilicate 8.39
    tributyl phosphate 6.64
    diacetone alcohol 33.5
    N,N-dimethylaniline 7.44
    acrylonitrile 17.21
    aniline 14.54
    1,3-propanediol 68.2
    bromobenzene 4.62
    dibromomethane 4.45
    1,1,2,2-tetrachloroethane 26.91
    2-methyl-cyclohexyl acetate 10.31
    tetrabutyl urea 9.79
    diisobutyl methanol 5.68
    2-phenylethanol 15.69
    styrene 2.42
    dioctyl adipate 10.51
    dimethyl sulfate 26.72
    ethyl butyrate 9.06
    methyl lactate 24.07
    butyl lactate 11.88
    diethyl carbonate 7.76
    propanediol butyl ether 23.84
    triethyl orthoformate 10.69
    p-tert-butyltoluene 3.29
    methyl 4-tert-butylbenzoate 18.67
    morpholine 83.07
    tert-butylamine 6.35
    n-dodecanol 4.89
    dimethoxymethane 85.74
    ethylene carbonate 16.01
    cyrene 25.75
    2-ethoxyethyl acetate 24.35
    2-ethylhexyl acetate 6.61
    1,2,4-trichlorobenzene 8.8
    4-methylpyridine 14.78
    dibutyl ether 7.27
    2,6-dimethyl-4-heptanol 5.68
    DEF 17.24
    dimethyl isosorbide 46.19
    tetrachloroethylene 17.43
    eugenol 20.78
    triacetin 19.21
    span 80 18.5
    1,4-butanediol 21.7
    1,1-dichloroethane 6.25
    2-methyl-1-pentanol 10.47
    methyl formate 27.44
    2-methyl-1-butanol 11.67
    n-decane 0.65
    butyronitrile 10.03
    3,7-dimethyl-1-octanol 7.39
    1-chlorooctane 2.88
    1-chlorotetradecane 1.37
    n-nonane 0.48
    undecane 0.5
    tert-butylcyclohexane 0.3
    cyclooctane 0.24
    cyclopentanol 12.43
    tetrahydropyran 30.9
    tert-amyl methyl ether 7.3
    2,5,8-trioxanonane 67.1
    1-hexene 0.41
    2-isopropoxyethanol 41.73
    2,2,2-trifluoroethanol 18.19
    methyl butyrate 12.22

    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