cis,trans-4-Methoxycinnamonitrile

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  • Identifiers

    CAS number
    28446-68-6

    Molecular formula
    C10H9NO

    SMILES
    COC1=CC=C(C=C1)/C=C/C#N

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Spicy 71.79%
    Sweet 60.33%
    Floral 58.77%
    Cinnamon 50.1%
    Anisic 32.58%
    Warm 31.01%
    Almond 30.3%
    Powdery 29.58%
    Vanilla 29.5%
    Cherry 28.71%

     

    Flavor
    Bitter 44.61%
    Cinnamon 28.54%
    Nitrile 22.97%
    Balsam 22.06%
    Sweet 21.41%
    Almond shell 19.93%
    Red hots 19.66%
    Oriental 19.23%
    Spicy 19.09%
    Butyric 18.94%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    6.14 (neutral)

    Molecular weight
    159.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    346°C

    Flash point

    • 127.28 ˚C est.

  • Synonyms

    • cis,trans-4-Methoxycinnamonitrile
    • RefChem:577260
    • 249-022-4
    • 4-Methoxycinnamonitrile
    • 28446-68-6
    • p-Methoxycinnamonitrile
    • 2-Propenenitrile, 3-(4-methoxyphenyl)-
    • 14482-11-2
    • CINNAMONITRILE, p-METHOXY-
    • (E)-3-(4-methoxyphenyl)acrylonitrile
    • 3-(4-methoxyphenyl)acrylonitrile
    • (E)-3-(4-methoxyphenyl)prop-2-enenitrile
    • MFCD00001934
    • 4-Methoxycinnamonitrile,c&t
    • (2E)-3-(4-methoxyphenyl)prop-2-enenitrile
    • 4-Methoxycinnamonitrile (cis- and trans- mixture)
    • 4-Methoxycinnamonitrile cis + trans
    • 3-(4-Methoxyphenyl)-2-propenenitrile
    • NSC-379284
    • 2-Propenenitrile, 3-(4-methoxyphenyl)-, (2E)-
    • EINECS 249-022-4
    • NSC 379284
    • (E)-4-Methoxycinnamonitrile
    • trans-4-Methoxycinnamonitrile
    • NSC379284
    • ET8BLJ6LJ4
    • 3-(p-Anisyl)acrylonitrile
    • Cambridge id 5106708
    • SCHEMBL442274
    • DTXSID401035107
    • HMS1538L04
    • beta-(4-Methoxyphenyl)acrylonitrile
    • Cinnamonitrile, p-methoxy-, (E)-
    • STL308391
    • 4-Methoxycinnamonitrile, Cis + Trans
    • AKOS008967971
    • (2E)-3-(4-Methoxyphenyl)acrylonitrile
    • (E)-3-(4-methoxyphenyl)-acrylonitrile
    • 2-Propenenitrile,3-(4-methoxyphenyl)-
    • NCGC00174201-01
    • AS-86582
    • ST023630
    • (2E)-3-(4-Methoxyphenyl)-2-propenenitrile
    • CS-0210675
    • NS00047827
    • (2E)-3-(4-Methoxyphenyl)-2-propenenitrile #
    • D91428
    • 28446-68-6

  • Applications

    cis,trans-4-Methoxycinnamonitrile (CAS 28446-68-6) is typically used as an aroma-related intermediate in perfumery and flavor chemistry, serving as a precursor to cinnamaldehyde-type aroma compounds and contributing to cinnamon notes in fragrance formulations. It may be used in cosmetics and personal care as a fragrance ingredient and in household products such as air fresheners and cleaners to impart a cinnamon-like scent. In industrial manufacturing, it is employed as a specialty intermediate for further synthesis of aroma chemicals and related nitrile derivatives. Depending on regulatory constraints and formulation limits, it may also be evaluated for additional applications within fragrance, flavor, and materials synthesis.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 122.89
    methanol 169.12
    isopropanol 61.97
    water 2.15
    ethyl acetate 578.83
    n-propanol 77.92
    acetone 485.49
    n-butanol 47.09
    acetonitrile 522.3
    DMF 606.83
    toluene 153.9
    isobutanol 42.15
    1,4-dioxane 874.91
    methyl acetate 500.87
    THF 538.5
    2-butanone 288.44
    n-pentanol 45.44
    sec-butanol 46.34
    n-hexane 4.09
    ethylene glycol 117.58
    NMP 354.8
    cyclohexane 17.49
    DMSO 880.49
    n-butyl acetate 132.6
    n-octanol 26.82
    chloroform 917.65
    n-propyl acetate 180.63
    acetic acid 328.74
    dichloromethane 1130.36
    cyclohexanone 297.68
    propylene glycol 80.93
    isopropyl acetate 180.91
    DMAc 595.97
    2-ethoxyethanol 203.81
    isopentanol 34.27
    n-heptane 9.89
    ethyl formate 226.98
    1,2-dichloroethane 606.38
    n-hexanol 45.12
    2-methoxyethanol 283.44
    isobutyl acetate 87.64
    tetrachloromethane 73.2
    n-pentyl acetate 62.16
    transcutol 662.12
    n-heptanol 23.44
    ethylbenzene 41.92
    MIBK 71.69
    2-propoxyethanol 144.02
    tert-butanol 93.41
    MTBE 96.71
    2-butoxyethanol 73.32
    propionic acid 207.1
    o-xylene 63.85
    formic acid 199.17
    diethyl ether 201.25
    m-xylene 58.96
    p-xylene 61.39
    chlorobenzene 209.83
    dimethyl carbonate 275.59
    n-octane 4.19
    formamide 440.14
    cyclopentanone 397.87
    2-pentanone 165.4
    anisole 162.07
    cyclopentyl methyl ether 161.2
    gamma-butyrolactone 640.92
    1-methoxy-2-propanol 161.19
    pyridine 606.28
    3-pentanone 199.31
    furfural 475.28
    n-dodecane 4.94
    diethylene glycol 199.14
    diisopropyl ether 40.51
    tert-amyl alcohol 54.82
    acetylacetone 406.73
    n-hexadecane 5.58
    acetophenone 145.52
    methyl propionate 400.24
    isopentyl acetate 94.15
    trichloroethylene 1106.84
    n-nonanol 27.19
    cyclohexanol 63.35
    benzyl alcohol 103.76
    2-ethylhexanol 31.23
    isooctanol 21.19
    dipropyl ether 82.05
    1,2-dichlorobenzene 156.46
    ethyl lactate 84.53
    propylene carbonate 267.94
    n-methylformamide 367.35
    2-pentanol 28.51
    n-pentane 3.99
    1-propoxy-2-propanol 88.55
    1-methoxy-2-propyl acetate 186.89
    2-(2-methoxypropoxy) propanol 111.0
    mesitylene 35.26
    ε-caprolactone 243.26
    p-cymene 28.59
    epichlorohydrin 661.41
    1,1,1-trichloroethane 415.36
    2-aminoethanol 100.18
    morpholine-4-carbaldehyde 509.37
    sulfolane 491.76
    2,2,4-trimethylpentane 3.48
    2-methyltetrahydrofuran 267.84
    n-hexyl acetate 81.92
    isooctane 2.81
    2-(2-butoxyethoxy)ethanol 145.67
    sec-butyl acetate 101.1
    tert-butyl acetate 146.73
    decalin 8.83
    glycerin 143.63
    diglyme 380.17
    acrylic acid 231.81
    isopropyl myristate 41.85
    n-butyric acid 162.37
    acetyl acetate 405.51
    di(2-ethylhexyl) phthalate 41.69
    ethyl propionate 173.08
    nitromethane 1070.55
    1,2-diethoxyethane 216.84
    benzonitrile 147.75
    trioctyl phosphate 26.37
    1-bromopropane 154.11
    gamma-valerolactone 506.74
    n-decanol 22.69
    triethyl phosphate 70.83
    4-methyl-2-pentanol 18.22
    propionitrile 219.6
    vinylene carbonate 302.07
    1,1,2-trichlorotrifluoroethane 449.93
    DMS 203.3
    cumene 25.45
    2-octanol 15.13
    2-hexanone 105.8
    octyl acetate 50.81
    limonene 40.95
    1,2-dimethoxyethane 351.31
    ethyl orthosilicate 64.24
    tributyl phosphate 39.09
    diacetone alcohol 116.11
    N,N-dimethylaniline 83.81
    acrylonitrile 326.93
    aniline 166.26
    1,3-propanediol 107.4
    bromobenzene 234.02
    dibromomethane 520.99
    1,1,2,2-tetrachloroethane 663.5
    2-methyl-cyclohexyl acetate 82.82
    tetrabutyl urea 53.0
    diisobutyl methanol 25.33
    2-phenylethanol 84.73
    styrene 75.89
    dioctyl adipate 73.32
    dimethyl sulfate 392.95
    ethyl butyrate 129.33
    methyl lactate 143.3
    butyl lactate 49.38
    diethyl carbonate 118.05
    propanediol butyl ether 65.17
    triethyl orthoformate 92.49
    p-tert-butyltoluene 28.02
    methyl 4-tert-butylbenzoate 95.69
    morpholine 594.34
    tert-butylamine 44.71
    n-dodecanol 20.09
    dimethoxymethane 420.49
    ethylene carbonate 247.47
    cyrene 118.07
    2-ethoxyethyl acetate 156.68
    2-ethylhexyl acetate 80.11
    1,2,4-trichlorobenzene 212.67
    4-methylpyridine 310.37
    dibutyl ether 56.59
    2,6-dimethyl-4-heptanol 25.33
    DEF 249.5
    dimethyl isosorbide 200.41
    tetrachloroethylene 408.74
    eugenol 91.07
    triacetin 170.56
    span 80 71.11
    1,4-butanediol 53.56
    1,1-dichloroethane 441.76
    2-methyl-1-pentanol 35.8
    methyl formate 357.18
    2-methyl-1-butanol 31.41
    n-decane 6.79
    butyronitrile 114.88
    3,7-dimethyl-1-octanol 30.39
    1-chlorooctane 26.84
    1-chlorotetradecane 14.31
    n-nonane 5.99
    undecane 5.69
    tert-butylcyclohexane 7.12
    cyclooctane 5.58
    cyclopentanol 85.04
    tetrahydropyran 367.27
    tert-amyl methyl ether 62.22
    2,5,8-trioxanonane 265.64
    1-hexene 20.0
    2-isopropoxyethanol 120.3
    2,2,2-trifluoroethanol 184.12
    methyl butyrate 183.43

    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