(E)-3,4-Methylenedioxycinnamaldehyde

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    14756-00-4

    Molecular formula
    C10H8O3

    SMILES
    C1OC2=C(O1)C=C(C=C2)/C=C/C=O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Sweet 86.02%
    Spicy 85.02%
    Cinnamon 73.18%
    Floral 58.8%
    Vanilla 57.88%
    Warm 53.53%
    Balsamic 48.31%
    Powdery 47.61%
    Clove 36.94%
    Coumarinic 36.14%

    Scent© AI

  • Properties

    XLogP3-AA
    2.0

    Molecular weight
    176.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    337°C

    Flash point est.
    148.98 ˚C

  • Synonyms

    • 58095-77-5
    • (2E)-3-(1,3-dioxaindan-5-yl)prop-2-enal
    • (E)-3,4-Methylenedioxycinnamaldehyde
    • 3,4-Methylenedioxycinnamaldehyde
    • (2E)-3-(2H-1,3-BENZODIOXOL-5-YL)PROP-2-ENAL
    • 14756-00-4
    • DTXSID301291225
    • 3-(1,3-Benzodioxol-5-yl)acrylaldehyde
    • 2-Propenal, 3-(1,3-benzodioxol-5-yl)-
    • (E)-3-(1,3-benzodioxol-5-yl)prop-2-enal
    • 3,4-Methylendioxy-zimtaldehyd
    • SCHEMBL2757691
    • CHEMBL2299415
    • DTXCID801721823
    • STK029556
    • AKOS005380753
    • NCGC00170990-01
    • NS00053102
    • PK04_096311
    • (2E)-3-(1,3-benzodioxol-5-yl)prop-2-enal
    • G59239
    • EN300-1703969
    • (2E)-3-(1,3-Benzodioxol-5-yl)-2-propenal #
    • BRD-K84921179-001-01-4
    • Z1251353395
    • 864-677-1

  • Applications

    (E)-3,4-Methylenedioxycinnamaldehyde (CAS 14756-00-4) is an aromatic aldehyde featuring a benzodioxole ring and an α,β-conjugated unit, used broadly in fragrance chemistry and synthesis: as a fragrance/flavor ingredient or modulator in perfumes and personal care with warm spicy, balsamic–vanillic and woody notes; as an intermediate/building block to access pharma and agrochemical derivatives (e.g., imines, oximes, hydrazones, urethanes, and redox or Michael adducts) leveraged in medicinal chemistry via its electrophilic Michael acceptor toward cysteine thiols; as a linker or functional monomer for UV-responsive and cinnamyl-conjugated materials, for surface grafting onto polymers or silica, and as a precursor to molecularly imprinted polymers; investigated for natural-product-inspired antimicrobial, antifungal, antioxidant and insect-repellent functions in smart packaging, antimicrobial coatings, stored-crop treatment and wood protection; used as an analytical reference standard in HPLC/GC/MS and as a derivatization agent for trace analysis; and as a common motif in natural product chemistry to assemble lignans/benzodioxoles, biochemical probes, and to promote Knoevenagel/Michael/coupling transformations in advanced synthesis.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 28.96
    methanol 36.28
    isopropanol 22.13
    water 0.76
    ethyl acetate 71.19
    n-propanol 20.72
    acetone 61.05
    n-butanol 17.77
    acetonitrile 82.24
    DMF 89.82
    toluene 20.21
    isobutanol 15.45
    1,4-dioxane 149.3
    methyl acetate 82.43
    THF 93.58
    2-butanone 54.1
    n-pentanol 22.48
    sec-butanol 19.59
    n-hexane 0.58
    ethylene glycol 51.87
    NMP 52.77
    cyclohexane 1.07
    DMSO 150.68
    n-butyl acetate 32.43
    n-octanol 15.36
    chloroform 77.55
    n-propyl acetate 48.62
    acetic acid 57.15
    dichloromethane 102.49
    cyclohexanone 48.62
    propylene glycol 33.86
    isopropyl acetate 41.55
    DMAc 132.78
    2-ethoxyethanol 114.61
    isopentanol 21.8
    n-heptane 1.97
    ethyl formate 36.83
    1,2-dichloroethane 69.94
    n-hexanol 22.39
    2-methoxyethanol 137.02
    isobutyl acetate 32.82
    tetrachloromethane 7.14
    n-pentyl acetate 19.62
    transcutol 332.32
    n-heptanol 13.39
    ethylbenzene 14.31
    MIBK 35.96
    2-propoxyethanol 79.36
    tert-butanol 48.49
    MTBE 29.65
    2-butoxyethanol 41.73
    propionic acid 37.06
    o-xylene 18.5
    formic acid 55.06
    diethyl ether 31.98
    m-xylene 18.24
    p-xylene 19.85
    chlorobenzene 27.9
    dimethyl carbonate 53.32
    n-octane 1.4
    formamide 120.15
    cyclopentanone 60.74
    2-pentanone 38.25
    anisole 59.19
    cyclopentyl methyl ether 35.93
    gamma-butyrolactone 86.6
    1-methoxy-2-propanol 96.36
    pyridine 80.18
    3-pentanone 35.49
    furfural 96.34
    n-dodecane 2.3
    diethylene glycol 116.65
    diisopropyl ether 12.73
    tert-amyl alcohol 33.74
    acetylacetone 76.95
    n-hexadecane 2.56
    acetophenone 54.22
    methyl propionate 60.65
    isopentyl acetate 34.01
    trichloroethylene 125.81
    n-nonanol 16.01
    cyclohexanol 20.57
    benzyl alcohol 45.86
    2-ethylhexanol 17.9
    isooctanol 14.21
    dipropyl ether 22.21
    1,2-dichlorobenzene 31.78
    ethyl lactate 37.77
    propylene carbonate 48.31
    n-methylformamide 66.19
    2-pentanol 16.06
    n-pentane 0.48
    1-propoxy-2-propanol 49.4
    1-methoxy-2-propyl acetate 58.23
    2-(2-methoxypropoxy) propanol 74.59
    mesitylene 12.98
    ε-caprolactone 51.2
    p-cymene 13.17
    epichlorohydrin 127.11
    1,1,1-trichloroethane 41.45
    2-aminoethanol 45.33
    morpholine-4-carbaldehyde 125.76
    sulfolane 86.93
    2,2,4-trimethylpentane 1.28
    2-methyltetrahydrofuran 53.86
    n-hexyl acetate 29.38
    isooctane 1.26
    2-(2-butoxyethoxy)ethanol 84.37
    sec-butyl acetate 35.41
    tert-butyl acetate 47.05
    decalin 2.59
    glycerin 82.8
    diglyme 157.71
    acrylic acid 44.2
    isopropyl myristate 19.45
    n-butyric acid 37.05
    acetyl acetate 46.98
    di(2-ethylhexyl) phthalate 22.25
    ethyl propionate 46.83
    nitromethane 159.74
    1,2-diethoxyethane 71.67
    benzonitrile 46.52
    trioctyl phosphate 14.32
    1-bromopropane 19.92
    gamma-valerolactone 95.69
    n-decanol 14.3
    triethyl phosphate 27.53
    4-methyl-2-pentanol 15.91
    propionitrile 50.51
    vinylene carbonate 51.12
    1,1,2-trichlorotrifluoroethane 92.49
    DMS 52.89
    cumene 12.65
    2-octanol 10.46
    2-hexanone 37.56
    octyl acetate 21.46
    limonene 14.23
    1,2-dimethoxyethane 134.79
    ethyl orthosilicate 24.87
    tributyl phosphate 19.34
    diacetone alcohol 66.43
    N,N-dimethylaniline 38.18
    acrylonitrile 78.28
    aniline 41.0
    1,3-propanediol 58.13
    bromobenzene 27.99
    dibromomethane 44.06
    1,1,2,2-tetrachloroethane 82.27
    2-methyl-cyclohexyl acetate 32.15
    tetrabutyl urea 26.56
    diisobutyl methanol 15.43
    2-phenylethanol 37.76
    styrene 18.39
    dioctyl adipate 30.54
    dimethyl sulfate 75.82
    ethyl butyrate 34.78
    methyl lactate 52.79
    butyl lactate 23.47
    diethyl carbonate 33.42
    propanediol butyl ether 41.76
    triethyl orthoformate 31.38
    p-tert-butyltoluene 12.67
    methyl 4-tert-butylbenzoate 43.34
    morpholine 125.48
    tert-butylamine 19.05
    n-dodecanol 13.09
    dimethoxymethane 104.44
    ethylene carbonate 42.25
    cyrene 58.16
    2-ethoxyethyl acetate 45.34
    2-ethylhexyl acetate 26.6
    1,2,4-trichlorobenzene 40.43
    4-methylpyridine 55.46
    dibutyl ether 22.48
    2,6-dimethyl-4-heptanol 15.43
    DEF 53.38
    dimethyl isosorbide 95.52
    tetrachloroethylene 50.08
    eugenol 50.43
    triacetin 52.65
    span 80 39.82
    1,4-butanediol 33.91
    1,1-dichloroethane 47.38
    2-methyl-1-pentanol 23.11
    methyl formate 61.17
    2-methyl-1-butanol 17.44
    n-decane 2.83
    butyronitrile 33.59
    3,7-dimethyl-1-octanol 20.83
    1-chlorooctane 10.87
    1-chlorotetradecane 7.23
    n-nonane 2.31
    undecane 2.52
    tert-butylcyclohexane 2.48
    cyclooctane 0.8
    cyclopentanol 21.31
    tetrahydropyran 48.78
    tert-amyl methyl ether 26.9
    2,5,8-trioxanonane 132.4
    1-hexene 3.75
    2-isopropoxyethanol 75.65
    2,2,2-trifluoroethanol 44.55
    methyl butyrate 49.2

    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
Sassafras 1 8006-80-2 Sassafras albidum (Nutt.) Nees, fam. Lauraceae 2.2%