Sinapyl alcohol

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  • Identifiers

    CAS number
    537-33-7

    Molecular formula
    C11H14O4

    SMILES
    COC1=CC(=CC(=C1O)OC)/C=C/CO

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Vanilla 68.89%
    Spicy 62.74%
    Sweet 60.3%
    Balsamic 52.71%
    Floral 50.84%
    Powdery 40.33%
    Phenolic 38.8%
    Clove 36.93%
    Smoky 36.17%
    Creamy 34.4%

     

    Flavor
    Sweet 63.47%
    Woody 42.68%
    Spicy 42.16%
    Vanilla 41.71%
    Spice 36.22%
    Creamy 33.96%
    Clove 32.57%
    Smoky 32.2%
    Powdery 31.14%
    Flower 28.78%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    9.55 (weak base)

    Molecular weight
    210.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    424°C

    Melting point expt.

    • 61 - 65 °C

    Flash point

    • 169.71 ˚C est.

  • Synonyms

    • Sinapyl alcohol
    • 537-33-7
    • Sinapoyl alcohol
    • 4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenol
    • 4-Hydroxy-3,5-dimethoxycinnamyl alcohol
    • 8O6NO04SMV
    • CHEBI:28813
    • 4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol
    • 4-((1E)-3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenol
    • RefChem:886350
    • Phenol, 4-((1E)-3-hydroxy-1-propen-1-yl)-2,6-dimethoxy-
    • 664-272-8
    • Sinapic alcohol
    • 4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenol
    • trans-sinapyl alcohol
    • 20675-96-1
    • 4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenol
    • SINAPYL-ALCOHOL
    • Sinapyl alcohol, (E)
    • (E)-4-(3-Hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenol
    • Sinapyl Alcohol (>85%)
    • ST069367
    • MFCD00192441
    • 2-Propen-1-ol, 3-(4-hydroxy-3,5-dimethoxyphenyl), (E)-
    • (E)-Sinapyl alcohol
    • UNII-8O6NO04SMV
    • synapil alcohol
    • Sinapyl alcohol(e)
    • (E)-sinapoyl alcohol
    • 3,5-Dimethoxy-4-hydroxycinnamyl alcohol
    • bmse000612
    • bmse010286
    • SCHEMBL807443
    • orb1297147
    • CHEMBL1800816
    • CHEBI:64557
    • Sinapyl alcohol; sinapoyl alcohol
    • DTXSID501314695
    • AKOS015966876
    • EBC-493077
    • HY-W109812
    • Sinapyl alcohol, technical grade, 80%
    • 4-hydroxy-3,5-dimethoxy cinnamyl alcohol
    • AS-76705
    • DA-77852
    • FS137914
    • SY076098
    • CS-0163319
    • CS-0369210
    • C02325
    • D94780
    • 4-(3-hydroxy-1-propenyl)-2,6-dimethoxy-Phenol
    • EN300-1866966
    • F758448
    • Q418975
    • Phenol, 4-(3-hydroxy-1-propenyl)-2,6-dimethoxy-
    • 4-((1E)-3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol
    • 4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxy-phenol
    • (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-Propen-1-ol
    • Phenol, 4-(3-hydroxy-1-propenyl)-2,6-dimethoxy-, (E)-
    • Phenol, 4-[(1E)-3-hydroxy-1-propenyl]-2,6-dimethoxy-
    • 2-Propen-1-ol, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (E)-
    • 2EC125E6-3813-49EE-903E-5730561A1B09
    • InChI=1/C11H14O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-4,6-7,12-13H,5H2,1-2H3/b4-3
    • 537-33-7

  • Applications

    Sinapyl alcohol is a monolignol that serves as a natural building block in lignin. In industry, it is used as a chemical intermediate for the preparation of lignin-derived polymers and bio-based resins, supporting renewable material formulations in the polymer and plastics sector. It also participates in phenolic resin chemistry for coatings and adhesive systems, where syringyl-type units derived from sinapyl alcohol help tailor polymer properties. It functions as a precursor in the synthesis of aromatic derivatives and specialty chemicals in industrial manufacturing. In research and development, it is widely used as a model compound to study lignin structure, depolymerization, and valorization toward value-added materials. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 103.03
    methanol 138.88
    isopropanol 45.96
    water 0.95
    ethyl acetate 86.36
    n-propanol 59.38
    acetone 149.13
    n-butanol 40.97
    acetonitrile 74.64
    DMF 283.52
    toluene 9.38
    isobutanol 32.24
    1,4-dioxane 189.9
    methyl acetate 108.62
    THF 232.32
    2-butanone 74.39
    n-pentanol 35.94
    sec-butanol 34.89
    n-hexane 0.93
    ethylene glycol 146.14
    NMP 136.3
    cyclohexane 4.09
    DMSO 649.09
    n-butyl acetate 33.43
    n-octanol 22.77
    chloroform 93.17
    n-propyl acetate 47.94
    acetic acid 211.67
    dichloromethane 121.61
    cyclohexanone 92.77
    propylene glycol 83.11
    isopropyl acetate 31.32
    DMAc 174.86
    2-ethoxyethanol 180.85
    isopentanol 32.73
    n-heptane 2.22
    ethyl formate 101.63
    1,2-dichloroethane 110.92
    n-hexanol 36.6
    2-methoxyethanol 303.85
    isobutyl acetate 24.94
    tetrachloromethane 17.38
    n-pentyl acetate 23.48
    transcutol 165.08
    n-heptanol 25.26
    ethylbenzene 10.14
    MIBK 28.58
    2-propoxyethanol 109.17
    tert-butanol 95.92
    MTBE 37.18
    2-butoxyethanol 65.18
    propionic acid 82.05
    o-xylene 13.25
    formic acid 162.39
    diethyl ether 31.76
    m-xylene 9.75
    p-xylene 12.62
    chlorobenzene 27.25
    dimethyl carbonate 59.13
    n-octane 1.71
    formamide 283.82
    cyclopentanone 152.19
    2-pentanone 49.07
    anisole 41.89
    cyclopentyl methyl ether 46.0
    gamma-butyrolactone 224.73
    1-methoxy-2-propanol 140.1
    pyridine 83.52
    3-pentanone 35.69
    furfural 198.64
    n-dodecane 2.13
    diethylene glycol 174.15
    diisopropyl ether 7.8
    tert-amyl alcohol 61.24
    acetylacetone 97.1
    n-hexadecane 2.37
    acetophenone 51.87
    methyl propionate 79.79
    isopentyl acetate 29.35
    trichloroethylene 168.76
    n-nonanol 21.8
    cyclohexanol 43.14
    benzyl alcohol 54.81
    2-ethylhexanol 22.41
    isooctanol 21.08
    dipropyl ether 18.51
    1,2-dichlorobenzene 35.34
    ethyl lactate 50.22
    propylene carbonate 103.83
    n-methylformamide 187.34
    2-pentanol 20.13
    n-pentane 1.07
    1-propoxy-2-propanol 58.4
    1-methoxy-2-propyl acetate 48.86
    2-(2-methoxypropoxy) propanol 54.42
    mesitylene 8.13
    ε-caprolactone 93.55
    p-cymene 11.68
    epichlorohydrin 234.51
    1,1,1-trichloroethane 59.16
    2-aminoethanol 133.23
    morpholine-4-carbaldehyde 173.22
    sulfolane 278.23
    2,2,4-trimethylpentane 1.97
    2-methyltetrahydrofuran 84.22
    n-hexyl acetate 32.71
    isooctane 1.38
    2-(2-butoxyethoxy)ethanol 77.38
    sec-butyl acetate 23.17
    tert-butyl acetate 42.78
    decalin 3.36
    glycerin 172.14
    diglyme 156.68
    acrylic acid 101.6
    isopropyl myristate 15.05
    n-butyric acid 90.62
    acetyl acetate 55.23
    di(2-ethylhexyl) phthalate 22.07
    ethyl propionate 37.53
    nitromethane 353.07
    1,2-diethoxyethane 39.89
    benzonitrile 47.38
    trioctyl phosphate 18.14
    1-bromopropane 23.96
    gamma-valerolactone 191.25
    n-decanol 17.34
    triethyl phosphate 26.69
    4-methyl-2-pentanol 15.0
    propionitrile 46.47
    vinylene carbonate 100.25
    1,1,2-trichlorotrifluoroethane 237.29
    DMS 41.78
    cumene 10.09
    2-octanol 14.69
    2-hexanone 38.2
    octyl acetate 21.24
    limonene 16.97
    1,2-dimethoxyethane 191.13
    ethyl orthosilicate 23.82
    tributyl phosphate 19.31
    diacetone alcohol 79.16
    N,N-dimethylaniline 31.74
    acrylonitrile 83.9
    aniline 38.61
    1,3-propanediol 146.4
    bromobenzene 22.3
    dibromomethane 67.06
    1,1,2,2-tetrachloroethane 130.39
    2-methyl-cyclohexyl acetate 32.24
    tetrabutyl urea 27.13
    diisobutyl methanol 14.68
    2-phenylethanol 47.08
    styrene 12.85
    dioctyl adipate 29.2
    dimethyl sulfate 111.68
    ethyl butyrate 31.02
    methyl lactate 80.46
    butyl lactate 30.78
    diethyl carbonate 29.6
    propanediol butyl ether 59.5
    triethyl orthoformate 26.81
    p-tert-butyltoluene 11.62
    methyl 4-tert-butylbenzoate 47.72
    morpholine 196.29
    tert-butylamine 34.56
    n-dodecanol 14.0
    dimethoxymethane 165.67
    ethylene carbonate 81.27
    cyrene 80.13
    2-ethoxyethyl acetate 41.5
    2-ethylhexyl acetate 21.56
    1,2,4-trichlorobenzene 44.28
    4-methylpyridine 52.36
    dibutyl ether 16.31
    2,6-dimethyl-4-heptanol 14.68
    DEF 74.11
    dimethyl isosorbide 88.35
    tetrachloroethylene 98.1
    eugenol 54.35
    triacetin 45.66
    span 80 46.05
    1,4-butanediol 69.58
    1,1-dichloroethane 55.64
    2-methyl-1-pentanol 31.24
    methyl formate 192.91
    2-methyl-1-butanol 29.33
    n-decane 2.96
    butyronitrile 38.63
    3,7-dimethyl-1-octanol 19.3
    1-chlorooctane 12.35
    1-chlorotetradecane 6.14
    n-nonane 2.52
    undecane 2.46
    tert-butylcyclohexane 2.78
    cyclooctane 1.69
    cyclopentanol 54.48
    tetrahydropyran 74.94
    tert-amyl methyl ether 28.4
    2,5,8-trioxanonane 110.59
    1-hexene 4.46
    2-isopropoxyethanol 87.01
    2,2,2-trifluoroethanol 105.03
    methyl butyrate 56.0

    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