(2E)-3-(3,4-dimethoxyphenyl)prop-2-enal

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  • Identifiers

    CAS number
    4497-40-9

    Molecular formula
    C11H12O3

    SMILES
    COC1=C(C=C(C=C1)/C=C/C=O)OC

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Sweet 86.97%
    Spicy 79.85%
    Vanilla 69.94%
    Floral 58.37%
    Cinnamon 58.0%
    Woody 54.6%
    Warm 51.33%
    Powdery 49.71%
    Balsamic 46.67%
    Clove 44.57%

    Scent© AI

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    6.61 (neutral)

    Molecular weight
    192.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    346°C

    Flash point est.
    130.4 ˚C

  • Synonyms

    • 3,4-dimethoxy cinnamaldehyde
    • Methylconiferylaldehyde
    • 58045-88-8
    • 3,4-Dimethoxycinnamaldehyde
    • (E)-3-(3,4-dimethoxyphenyl)prop-2-enal
    • 4497-40-9
    • 2-Propenal, 3-(3,4-dimethoxyphenyl)-
    • (E)-3,4-Dimethoxycinnamaldehyde
    • (2E)-3-(3,4-dimethoxyphenyl)prop-2-enal
    • bmse010082
    • CHEBI:86548
    • (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde
    • 3-(3,4-dimethoxyphenyl)prop-2-enal
    • 2-Propenal, 3-(3,4-dimethoxyphenyl)-, (2E)-
    • AC1NT9G2
    • Cinnamaldehyde, 3,4-dimethoxy-
    • trans-3,4-dimethoxycinnamaldehyde
    • Coniferaldehyde methyl ether
    • SCHEMBL563071
    • CHEMBL465888
    • KNUFNLWDGZQKKJ-ONEGZZNKSA-N
    • DTXSID701025105
    • AKOS022342873
    • (E)-3-(3,4-Dimethoxy-phenyl)-propenal
    • CS-0260531
    • (2E)-3-(3,4-Dimethoxyphenyl)-2-propenal #
    • EN300-1846839
    • EN300-7539373
    • trans-3-(3,4-dimethoxyphenyl)-2-propenaldehyde
    • Q27159234
    • 849-531-7

  • Applications

    (2E)-3-(3,4-dimethoxyphenyl)prop-2-enal (CAS 4497-40-9), also known as 3,4-dimethoxycinnamaldehyde, is used as a fragrance and flavor-note modifier in perfumes, personal care, scented candles, and food flavorings owing to its warm, sweet, mildly spicy cinnamon–vanilla nuances; as a versatile intermediate in fine-chemical and pharmaceutical synthesis via Schiff base formation, aldol/Knoevenagel condensations, and redox transformations to access the corresponding alcohols, acids, chalcones, and related heterocycles; as a building block for push–pull chromophores, emissive materials, and nonlinear-optical systems; to introduce imine linkages on biopolymers (e.g., chitosan, gelatin) for functional films and antimicrobial coatings; as a reference/marker in LC/GC method development for plant extracts enriched in cinnamaldehyde-type constituents; and in pharmacology research, where the compound and its derivatives are investigated for antioxidant, antimicrobial, anti-inflammatory, aldose reductase–inhibitory, and NF-κB–modulating activities, supporting hit identification and structure–activity optimization.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 49.26
    methanol 58.38
    isopropanol 30.66
    water 0.73
    ethyl acetate 235.44
    n-propanol 36.64
    acetone 212.39
    n-butanol 29.55
    acetonitrile 193.32
    DMF 224.52
    toluene 48.43
    isobutanol 26.96
    1,4-dioxane 355.76
    methyl acetate 198.52
    THF 324.6
    2-butanone 128.46
    n-pentanol 33.31
    sec-butanol 32.19
    n-hexane 7.84
    ethylene glycol 53.89
    NMP 161.14
    cyclohexane 22.17
    DMSO 386.99
    n-butyl acetate 89.49
    n-octanol 25.45
    chloroform 469.48
    n-propyl acetate 117.9
    acetic acid 162.96
    dichloromethane 582.27
    cyclohexanone 172.65
    propylene glycol 30.5
    isopropyl acetate 90.11
    DMAc 187.66
    2-ethoxyethanol 147.6
    isopentanol 32.82
    n-heptane 11.14
    ethyl formate 145.23
    1,2-dichloroethane 405.68
    n-hexanol 42.72
    2-methoxyethanol 186.62
    isobutyl acetate 66.24
    tetrachloromethane 79.38
    n-pentyl acetate 51.2
    transcutol 221.74
    n-heptanol 24.35
    ethylbenzene 43.68
    MIBK 65.25
    2-propoxyethanol 111.84
    tert-butanol 84.4
    MTBE 75.33
    2-butoxyethanol 59.41
    propionic acid 89.13
    o-xylene 47.96
    formic acid 72.75
    diethyl ether 115.52
    m-xylene 42.51
    p-xylene 54.41
    chlorobenzene 104.84
    dimethyl carbonate 100.99
    n-octane 6.73
    formamide 148.97
    cyclopentanone 241.99
    2-pentanone 98.72
    anisole 109.82
    cyclopentyl methyl ether 114.34
    gamma-butyrolactone 349.33
    1-methoxy-2-propanol 106.15
    pyridine 181.44
    3-pentanone 98.47
    furfural 284.32
    n-dodecane 6.39
    diethylene glycol 133.55
    diisopropyl ether 33.86
    tert-amyl alcohol 54.01
    acetylacetone 171.84
    n-hexadecane 7.29
    acetophenone 105.24
    methyl propionate 153.81
    isopentyl acetate 76.32
    trichloroethylene 581.15
    n-nonanol 25.73
    cyclohexanol 51.43
    benzyl alcohol 74.17
    2-ethylhexanol 37.63
    isooctanol 23.74
    dipropyl ether 62.44
    1,2-dichlorobenzene 115.46
    ethyl lactate 69.62
    propylene carbonate 179.1
    n-methylformamide 135.77
    2-pentanol 25.08
    n-pentane 5.81
    1-propoxy-2-propanol 70.65
    1-methoxy-2-propyl acetate 100.21
    2-(2-methoxypropoxy) propanol 74.83
    mesitylene 34.95
    ε-caprolactone 158.63
    p-cymene 33.28
    epichlorohydrin 429.54
    1,1,1-trichloroethane 288.38
    2-aminoethanol 50.47
    morpholine-4-carbaldehyde 218.3
    sulfolane 350.05
    2,2,4-trimethylpentane 6.66
    2-methyltetrahydrofuran 166.02
    n-hexyl acetate 62.19
    isooctane 5.45
    2-(2-butoxyethoxy)ethanol 87.06
    sec-butyl acetate 70.17
    tert-butyl acetate 101.62
    decalin 15.72
    glycerin 71.62
    diglyme 206.56
    acrylic acid 102.89
    isopropyl myristate 34.35
    n-butyric acid 101.42
    acetyl acetate 142.64
    di(2-ethylhexyl) phthalate 32.98
    ethyl propionate 105.25
    nitromethane 378.4
    1,2-diethoxyethane 104.08
    benzonitrile 98.04
    trioctyl phosphate 23.92
    1-bromopropane 113.5
    gamma-valerolactone 270.25
    n-decanol 22.03
    triethyl phosphate 64.92
    4-methyl-2-pentanol 21.44
    propionitrile 113.57
    vinylene carbonate 182.53
    1,1,2-trichlorotrifluoroethane 251.11
    DMS 104.17
    cumene 34.69
    2-octanol 18.66
    2-hexanone 86.15
    octyl acetate 39.29
    limonene 44.09
    1,2-dimethoxyethane 265.62
    ethyl orthosilicate 56.98
    tributyl phosphate 33.13
    diacetone alcohol 97.04
    N,N-dimethylaniline 71.33
    acrylonitrile 164.31
    aniline 75.75
    1,3-propanediol 68.51
    bromobenzene 109.44
    dibromomethane 334.49
    1,1,2,2-tetrachloroethane 414.72
    2-methyl-cyclohexyl acetate 72.43
    tetrabutyl urea 43.57
    diisobutyl methanol 28.55
    2-phenylethanol 65.93
    styrene 55.51
    dioctyl adipate 54.87
    dimethyl sulfate 154.57
    ethyl butyrate 91.15
    methyl lactate 77.75
    butyl lactate 41.48
    diethyl carbonate 81.72
    propanediol butyl ether 45.47
    triethyl orthoformate 68.58
    p-tert-butyltoluene 31.64
    methyl 4-tert-butylbenzoate 76.01
    morpholine 280.38
    tert-butylamine 45.86
    n-dodecanol 19.4
    dimethoxymethane 205.38
    ethylene carbonate 155.85
    cyrene 101.24
    2-ethoxyethyl acetate 85.93
    2-ethylhexyl acetate 63.75
    1,2,4-trichlorobenzene 135.41
    4-methylpyridine 123.19
    dibutyl ether 46.07
    2,6-dimethyl-4-heptanol 28.55
    DEF 122.56
    dimethyl isosorbide 142.55
    tetrachloroethylene 282.84
    eugenol 74.83
    triacetin 90.53
    span 80 50.18
    1,4-butanediol 36.66
    1,1-dichloroethane 253.3
    2-methyl-1-pentanol 34.64
    methyl formate 167.34
    2-methyl-1-butanol 28.48
    n-decane 8.88
    butyronitrile 86.64
    3,7-dimethyl-1-octanol 28.96
    1-chlorooctane 29.25
    1-chlorotetradecane 16.54
    n-nonane 8.48
    undecane 7.39
    tert-butylcyclohexane 12.63
    cyclooctane 9.79
    cyclopentanol 64.62
    tetrahydropyran 182.24
    tert-amyl methyl ether 62.2
    2,5,8-trioxanonane 144.27
    1-hexene 25.11
    2-isopropoxyethanol 97.03
    2,2,2-trifluoroethanol 102.7
    methyl butyrate 132.72

    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

Botanical

Name CAS Botanical Proportion
Empleurum fragrans Empleurum fragrans Glover, fam. Diosmeae 2.1%
Zingiber cassumunar root (Indonesia) 2 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.7%