Sinomenine

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  • Identifiers

    CAS number
    115-53-7

    Molecular formula
    C19H23NO4

    SMILES
    CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 45.06%
    Vanilla 30.23%
    Spicy 27.4%
    Sweet 26.63%
    Phenolic 22.58%
    Burnt 21.5%
    Smoky 20.32%
    Woody 19.68%
    Savory 19.07%
    Milky 18.65%

     

    Flavor
    Bitter 92.5%
    Bland 22.28%
    Sweet-like 21.22%
    Cedarleaf 20.95%
    Parsley 19.82%
    Lovage 19.66%
    Ripe apricot 18.82%
    Cereal 18.37%
    Alkaline 18.37%
    Leaves 18.28%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    7.23 (neutral)

    Molecular weight
    329.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    694°C

    Flash point

    • 213.72 ˚C est.

  • Synonyms

    • Sinomenine
    • 115-53-7
    • Kukoline
    • Cucoline
    • Coculine
    • Sabianine A
    • morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-
    • 63LT81K70N
    • (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
    • cuculine
    • (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo(7.5.3.01,10.02,7)heptadeca-2(7),3,5,11-tetraen-13-one
    • RefChem:183169
    • 4-hydroxy-3,7-dimethoxy-17-methylmorphin-7-en-6-one
    • 204-094-6
    • CCRIS 1550
    • SINOMENIN
    • CHEMBL248095
    • (1R,9S,10R)-3-Hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
    • (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
    • (4bR,8aS,9S)-4-hydroxy-3,7-dimethoxy-11-methyl-9,10-dihydro-5H-9,4b-(epiminoethano)phenanthren-6(8aH)-one
    • morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-, hydrochloride
    • NSC76021
    • SR-05000002170
    • EINECS 204-094-6
    • BRN 0095280
    • UNII-63LT81K70N
    • Sinomenine CRS
    • Orientvine stem HRS
    • Sinomenine (Cucoline)
    • SINOMENINE [MI]
    • Spectrum2_001242
    • Spectrum3_001134
    • Spectrum4_001981
    • Spectrum5_001621
    • UPCMLD-DP085
    • 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-morphinan-6-one
    • SINOMENINE [WHO-DD]
    • BSPBio_002627
    • KBioGR_002508
    • 5-21-13-00516 (Beilstein Handbook Reference)
    • SCHEMBL363812
    • SPECTRUM1505253
    • SPBio_001144
    • 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
    • CHEBI:9163
    • NP51
    • orb1305106
    • SCHEMBL29474810
    • UPCMLD-DP085:001
    • BCBcMAP01_000195
    • KBio3_002127
    • DTXSID00871595
    • BDBM224031
    • ALBB-020908
    • MSK10242
    • BDBM50241298
    • CCG-39100
    • EBC-11066
    • NSC785175
    • s2359
    • AKOS000265568
    • AKOS015960539
    • AKOS016023715
    • AC-8025
    • FS09811
    • NSC-785175
    • 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-
    • Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9|A,13|A,14|A)-
    • SMP1_000273
    • NCGC00161641-01
    • NCGC00161641-02
    • NCGC00161641-04
    • NCGC00161641-05
    • BS-42101
    • HY-15122
    • Sinomenine 100 microg/mL in Acetonitrile
    • CS-0003778
    • NS00018030
    • SW219295-1
    • C09643
    • 115S537
    • Sinomenine, 0.3 mol chloroform of crystallization
    • Q7524904
    • SR-05000002170-2
    • SR-05000002170-3
    • BRD-K83459933-001-02-1
    • BRD-K83459933-001-05-4
    • (9|_,13|_,14|_)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
    • 4-Hydroxy-3,7-dimethoxy-17-methyl-9alpha,13alpha,14alpha-7,8-didehydromorphinan-6-one
    • Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9a,13a,14a)-
    • (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0(1),(1)?.0(2),?]heptadeca-2(7),3,5,11-tetraen-13-one
    • (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one
    • MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4-HYDROXY-3,7-DIMETHOXY-17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.)-
    • 115-53-7

  • Applications

    Sinomenine (CAS 115-53-7) is primarily employed as an active constituent in traditional medicine–based formulations and related pharmaceutical applications, while also serving as a lead scaffold for pharmacological research on anti-inflammatory mechanisms and signaling relevant to pain management. In chemical manufacturing, it can function as an intermediate or core framework for the synthesis of related alkaloids. In analytical science, sinomenine is used as a reference standard for method development and quantitative analysis of products containing this alkaloid. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.88
    methanol 8.94
    isopropanol 2.23
    water 0.27
    ethyl acetate 5.76
    n-propanol 2.9
    acetone 5.01
    n-butanol 2.81
    acetonitrile 2.9
    DMF 24.41
    toluene 1.98
    isobutanol 2.23
    1,4-dioxane 10.82
    methyl acetate 4.5
    THF 6.59
    2-butanone 3.97
    n-pentanol 1.9
    sec-butanol 0.86
    n-hexane 0.05
    ethylene glycol 6.79
    NMP 15.88
    cyclohexane 0.26
    DMSO 24.82
    n-butyl acetate 6.6
    n-octanol 1.9
    chloroform 19.67
    n-propyl acetate 4.87
    acetic acid 29.75
    dichloromethane 16.53
    cyclohexanone 15.59
    propylene glycol 1.33
    isopropyl acetate 5.05
    DMAc 25.68
    2-ethoxyethanol 11.68
    isopentanol 3.62
    n-heptane 0.1
    ethyl formate 7.92
    1,2-dichloroethane 10.49
    n-hexanol 3.67
    2-methoxyethanol 23.78
    isobutyl acetate 4.54
    tetrachloromethane 4.14
    n-pentyl acetate 7.0
    transcutol 29.67
    n-heptanol 3.9
    ethylbenzene 1.23
    MIBK 4.94
    2-propoxyethanol 21.87
    tert-butanol 2.83
    MTBE 0.76
    2-butoxyethanol 17.04
    propionic acid 6.01
    o-xylene 2.16
    formic acid 32.35
    diethyl ether 1.64
    m-xylene 2.12
    p-xylene 1.86
    chlorobenzene 4.96
    dimethyl carbonate 11.1
    n-octane 0.09
    formamide 38.21
    cyclopentanone 10.82
    2-pentanone 4.51
    anisole 3.11
    cyclopentyl methyl ether 2.98
    gamma-butyrolactone 16.38
    1-methoxy-2-propanol 12.76
    pyridine 9.82
    3-pentanone 4.08
    furfural 30.22
    n-dodecane 0.1
    diethylene glycol 35.01
    diisopropyl ether 0.7
    tert-amyl alcohol 1.33
    acetylacetone 11.0
    n-hexadecane 0.12
    acetophenone 7.97
    methyl propionate 6.08
    isopentyl acetate 7.22
    trichloroethylene 25.04
    n-nonanol 2.46
    cyclohexanol 3.1
    benzyl alcohol 6.83
    2-ethylhexanol 2.56
    isooctanol 3.54
    dipropyl ether 1.88
    1,2-dichlorobenzene 7.52
    ethyl lactate 6.94
    propylene carbonate 12.92
    n-methylformamide 15.01
    2-pentanol 1.11
    n-pentane 0.08
    1-propoxy-2-propanol 10.43
    1-methoxy-2-propyl acetate 13.02
    2-(2-methoxypropoxy) propanol 13.15
    mesitylene 1.53
    ε-caprolactone 12.85
    p-cymene 2.23
    epichlorohydrin 15.92
    1,1,1-trichloroethane 6.79
    2-aminoethanol 5.59
    morpholine-4-carbaldehyde 33.09
    sulfolane 26.46
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 2.52
    n-hexyl acetate 5.85
    isooctane 0.07
    2-(2-butoxyethoxy)ethanol 16.76
    sec-butyl acetate 3.16
    tert-butyl acetate 5.29
    decalin 0.2
    glycerin 10.7
    diglyme 31.99
    acrylic acid 11.41
    isopropyl myristate 2.91
    n-butyric acid 10.86
    acetyl acetate 10.21
    di(2-ethylhexyl) phthalate 7.06
    ethyl propionate 4.37
    nitromethane 31.63
    1,2-diethoxyethane 6.32
    benzonitrile 8.19
    trioctyl phosphate 4.6
    1-bromopropane 2.06
    gamma-valerolactone 30.95
    n-decanol 1.83
    triethyl phosphate 5.99
    4-methyl-2-pentanol 1.71
    propionitrile 3.68
    vinylene carbonate 20.92
    1,1,2-trichlorotrifluoroethane 37.52
    DMS 10.44
    cumene 1.25
    2-octanol 1.64
    2-hexanone 3.68
    octyl acetate 3.93
    limonene 2.19
    1,2-dimethoxyethane 15.09
    ethyl orthosilicate 5.21
    tributyl phosphate 4.68
    diacetone alcohol 9.65
    N,N-dimethylaniline 3.32
    acrylonitrile 7.56
    aniline 5.08
    1,3-propanediol 11.64
    bromobenzene 4.03
    dibromomethane 8.06
    1,1,2,2-tetrachloroethane 17.08
    2-methyl-cyclohexyl acetate 7.43
    tetrabutyl urea 6.84
    diisobutyl methanol 1.88
    2-phenylethanol 10.08
    styrene 1.34
    dioctyl adipate 6.18
    dimethyl sulfate 18.24
    ethyl butyrate 5.35
    methyl lactate 9.78
    butyl lactate 9.16
    diethyl carbonate 5.67
    propanediol butyl ether 9.51
    triethyl orthoformate 5.63
    p-tert-butyltoluene 1.89
    methyl 4-tert-butylbenzoate 12.62
    morpholine 9.71
    tert-butylamine 1.05
    n-dodecanol 1.38
    dimethoxymethane 18.6
    ethylene carbonate 17.53
    cyrene 18.2
    2-ethoxyethyl acetate 14.53
    2-ethylhexyl acetate 5.6
    1,2,4-trichlorobenzene 9.94
    4-methylpyridine 6.69
    dibutyl ether 1.46
    2,6-dimethyl-4-heptanol 1.88
    DEF 8.47
    dimethyl isosorbide 22.73
    tetrachloroethylene 18.8
    eugenol 15.34
    triacetin 11.98
    span 80 10.24
    1,4-butanediol 4.0
    1,1-dichloroethane 4.49
    2-methyl-1-pentanol 2.39
    methyl formate 14.79
    2-methyl-1-butanol 2.03
    n-decane 0.16
    butyronitrile 2.96
    3,7-dimethyl-1-octanol 2.32
    1-chlorooctane 0.85
    1-chlorotetradecane 0.46
    n-nonane 0.11
    undecane 0.12
    tert-butylcyclohexane 0.13
    cyclooctane 0.11
    cyclopentanol 2.22
    tetrahydropyran 3.6
    tert-amyl methyl ether 0.82
    2,5,8-trioxanonane 23.7
    1-hexene 0.25
    2-isopropoxyethanol 7.58
    2,2,2-trifluoroethanol 23.26
    methyl butyrate 5.81

    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