Sinapine

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  • Identifiers

    CAS number
    18696-26-9

    Molecular formula
    C16H24NO5+

    SMILES
    C[N+](C)(C)CCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC

    Safety labels

  • Odor profile

    Fragrance
    Fruity 46.54%
    Floral 44.26%
    Sweet 39.48%
    Spicy 37.71%
    Balsamic 36.37%
    Woody 35.28%
    Vanilla 31.72%
    Powdery 29.03%
    Dry 28.03%
    Warm 25.84%

     

    Flavor
    Bitter 47.41%
    Bland 28.91%
    Odorless 26.22%
    Fruity 21.11%
    Mild 21.06%
    Parsley 20.42%
    Heather 20.0%
    Broom 19.83%
    Genet 19.7%
    Cedarleaf 19.25%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    8.0 (neutral)

    Molecular weight
    310.36 g/mol

    Flash point

    • 10.54 ˚C est.

  • Synonyms

    • Sinapine
    • 18696-26-9
    • Sinapoylcholine
    • O-sinapoylcholine
    • sinapin
    • Sinapine cation
    • trans-Sinapine
    • Sinapine ion
    • Sinapine bisulphate
    • 4-Hydroxy-3,5-dimethoxycinnamate choline
    • 09211A0HHL
    • Ethanaminium, 2-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethyl-
    • CHEBI:16353
    • DTXSID10171957
    • Choline, 4-hydroxy-3,5-dimethoxycinnamate (ester)
    • 2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium
    • Cinnamic acid, 4-hydroxy-3,5-dimethoxy-, choline ester
    • 2-((3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl)oxy)-N,N,N-trimethylethanaminium
    • 84123-22-8
    • Ethanaminium, 2-(((2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl)oxy)-N,N,N-trimethyl-
    • Ethanaminium, 2-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl)oxy)-N,N,N-trimethyl-
    • 2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy]-N,N,N-trimethylethanaminium
    • 2-(3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy)ethyl-trimethylazanium
    • 2-[3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy]ethyl-trimethylazanium
    • 2-((2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy)-N,N,N-trimethylethanaminium
    • 2-((E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl)oxyethyl-trimethylazanium
    • RefChem:183144
    • DTXCID5094448
    • Sinapine [MI]
    • trans-Sinapoylcholine
    • 2-((3-(4-Hydroxy-3,5-dimethoxyphenyl)acryloyl)oxy)-N,N,N-trimethylethan-1-aminium
    • 2-(4-hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminium
    • SCHEMBL424527
    • UNII-09211A0HHL
    • SCHEMBL424529
    • MEGxp0_001763
    • ACon1_000255
    • HY-N5077
    • MFCD09837796
    • s3235
    • AKOS030626997
    • 2-((3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethylethanaminium
    • AC-34366
    • DA-77851
    • SY231623
    • CS-0032305
    • NS00097137
    • C00933
    • Choline 4-hydroxy-3,5-dimethoxycinnamate, 8CI
    • Q891772
    • BRD-K21295184-064-01-0
    • 2-[[3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]oxy]-N,N,N- trimethylethanaminium, 9CI
    • 2-{[(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-N,N,N-trimethylethan-1-aminium
    • 18696-26-9

  • Applications

    Sinapine (CAS 18696-26-9) is the choline ester of sinapic acid, commonly found in seeds of Brassicaceae, and is mainly used in phytochemical research and analytical chemistry as a marker and reference standard for sinapic acid related esters in HPLC/LC-MS methods. In plant sciences and seed science, it is regarded as a natural defense metabolite and is used to assess seed composition, ripeness, and processing of oilseed meals containing sinapine. In food processing and animal feed, it is treated as an anti-nutritional factor and is often reduced during processing of rapeseed meal to improve palatability and nutritional value; upon hydrolysis, sinapine releases choline and sinapinic acid, providing a potential choline source in certain chemical or biochemical workflows. In analytical chemistry and laboratory research, sinapine may serve as a precursor to sinapic acid esters or related derivatives in synthetic studies.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 166.5
    methanol 299.74
    isopropanol 50.55
    water 6.58
    ethyl acetate 39.96
    n-propanol 85.19
    acetone 64.04
    n-butanol 39.45
    acetonitrile 42.46
    DMF 130.17
    toluene 5.83
    isobutanol 31.55
    1,4-dioxane 80.73
    methyl acetate 67.9
    THF 96.4
    2-butanone 40.32
    n-pentanol 25.97
    sec-butanol 40.29
    n-hexane 0.4
    ethylene glycol 143.09
    NMP 106.34
    cyclohexane 1.58
    DMSO 287.6
    n-butyl acetate 10.8
    n-octanol 9.11
    chloroform 123.62
    n-propyl acetate 18.02
    acetic acid 416.54
    dichloromethane 110.72
    cyclohexanone 59.17
    propylene glycol 150.79
    isopropyl acetate 11.24
    DMAc 146.25
    2-ethoxyethanol 147.81
    isopentanol 18.66
    n-heptane 0.6
    ethyl formate 66.65
    1,2-dichloroethane 53.6
    n-hexanol 19.28
    2-methoxyethanol 340.73
    isobutyl acetate 9.76
    tetrachloromethane 14.18
    n-pentyl acetate 9.3
    transcutol 110.56
    n-heptanol 13.35
    ethylbenzene 4.19
    MIBK 8.56
    2-propoxyethanol 81.17
    tert-butanol 46.0
    MTBE 9.08
    2-butoxyethanol 47.01
    propionic acid 125.76
    o-xylene 6.26
    formic acid 489.14
    diethyl ether 8.61
    m-xylene 4.49
    p-xylene 6.36
    chlorobenzene 16.13
    dimethyl carbonate 27.44
    n-octane 0.45
    formamide 474.65
    cyclopentanone 81.79
    2-pentanone 16.76
    anisole 14.99
    cyclopentyl methyl ether 15.76
    gamma-butyrolactone 139.11
    1-methoxy-2-propanol 131.95
    pyridine 61.85
    3-pentanone 14.38
    furfural 126.4
    n-dodecane 0.47
    diethylene glycol 144.49
    diisopropyl ether 1.64
    tert-amyl alcohol 33.7
    acetylacetone 37.93
    n-hexadecane 0.5
    acetophenone 25.62
    methyl propionate 44.01
    isopentyl acetate 9.72
    trichloroethylene 131.25
    n-nonanol 9.57
    cyclohexanol 33.82
    benzyl alcohol 39.19
    2-ethylhexanol 8.36
    isooctanol 9.94
    dipropyl ether 5.23
    1,2-dichlorobenzene 18.93
    ethyl lactate 28.51
    propylene carbonate 59.38
    n-methylformamide 163.75
    2-pentanol 12.86
    n-pentane 0.46
    1-propoxy-2-propanol 32.35
    1-methoxy-2-propyl acetate 20.86
    2-(2-methoxypropoxy) propanol 36.22
    mesitylene 2.56
    ε-caprolactone 64.08
    p-cymene 4.07
    epichlorohydrin 125.06
    1,1,1-trichloroethane 37.9
    2-aminoethanol 195.99
    morpholine-4-carbaldehyde 118.83
    sulfolane 139.49
    2,2,4-trimethylpentane 0.55
    2-methyltetrahydrofuran 36.9
    n-hexyl acetate 12.29
    isooctane 0.26
    2-(2-butoxyethoxy)ethanol 50.53
    sec-butyl acetate 8.46
    tert-butyl acetate 12.35
    decalin 0.87
    glycerin 239.32
    diglyme 77.27
    acrylic acid 145.97
    isopropyl myristate 4.78
    n-butyric acid 99.34
    acetyl acetate 28.76
    di(2-ethylhexyl) phthalate 12.39
    ethyl propionate 15.22
    nitromethane 357.26
    1,2-diethoxyethane 14.68
    benzonitrile 26.33
    trioctyl phosphate 8.09
    1-bromopropane 13.03
    gamma-valerolactone 142.12
    n-decanol 7.17
    triethyl phosphate 10.63
    4-methyl-2-pentanol 6.27
    propionitrile 28.46
    vinylene carbonate 70.56
    1,1,2-trichlorotrifluoroethane 213.48
    DMS 19.95
    cumene 3.62
    2-octanol 6.2
    2-hexanone 13.71
    octyl acetate 8.03
    limonene 4.81
    1,2-dimethoxyethane 74.27
    ethyl orthosilicate 9.44
    tributyl phosphate 8.85
    diacetone alcohol 39.44
    N,N-dimethylaniline 11.58
    acrylonitrile 54.68
    aniline 29.18
    1,3-propanediol 218.99
    bromobenzene 11.94
    dibromomethane 53.41
    1,1,2,2-tetrachloroethane 98.42
    2-methyl-cyclohexyl acetate 14.01
    tetrabutyl urea 12.26
    diisobutyl methanol 4.39
    2-phenylethanol 28.89
    styrene 4.96
    dioctyl adipate 12.19
    dimethyl sulfate 50.17
    ethyl butyrate 10.3
    methyl lactate 60.9
    butyl lactate 18.78
    diethyl carbonate 10.33
    propanediol butyl ether 45.43
    triethyl orthoformate 9.55
    p-tert-butyltoluene 3.78
    methyl 4-tert-butylbenzoate 23.96
    morpholine 125.85
    tert-butylamine 12.61
    n-dodecanol 5.23
    dimethoxymethane 65.98
    ethylene carbonate 50.61
    cyrene 56.94
    2-ethoxyethyl acetate 23.49
    2-ethylhexyl acetate 7.36
    1,2,4-trichlorobenzene 28.3
    4-methylpyridine 35.36
    dibutyl ether 3.92
    2,6-dimethyl-4-heptanol 4.39
    DEF 30.38
    dimethyl isosorbide 49.58
    tetrachloroethylene 74.41
    eugenol 30.82
    triacetin 25.38
    span 80 32.84
    1,4-butanediol 75.26
    1,1-dichloroethane 37.21
    2-methyl-1-pentanol 16.72
    methyl formate 143.05
    2-methyl-1-butanol 21.63
    n-decane 0.64
    butyronitrile 20.65
    3,7-dimethyl-1-octanol 7.45
    1-chlorooctane 3.15
    1-chlorotetradecane 1.56
    n-nonane 0.53
    undecane 0.53
    tert-butylcyclohexane 0.7
    cyclooctane 0.52
    cyclopentanol 49.98
    tetrahydropyran 32.95
    tert-amyl methyl ether 8.41
    2,5,8-trioxanonane 61.25
    1-hexene 1.75
    2-isopropoxyethanol 58.96
    2,2,2-trifluoroethanol 180.0
    methyl butyrate 24.31

    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