4-Hydroxy-3-methoxycinnamaldehyde

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    458-36-6

    Molecular formula
    C10H10O3

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

    Retention indicies (RI)

    • DB5: 1482.0

  • Odor profile

    Sweet 84.76%
    Spicy 79.27%
    Vanilla 76.35%
    Cinnamon 55.36%
    Balsamic 50.05%
    Creamy 48.77%
    Warm 45.46%
    Clove 45.29%
    Powdery 42.91%
    Woody 41.53%

    Scent© AI

  • Properties

    XLogP3-AA
    1.5

    Molecular weight
    178.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    343°C

    Flash point est.
    145.07 ˚C

  • Synonyms

    • Coniferaldehyde
    • Coniferyl aldehyde
    • 4-HYDROXY-3-METHOXYCINNAMALDEHYDE
    • 458-36-6
    • 20649-42-7
    • Ferulaldehyde
    • 3-(4-Hydroxy-3-methoxyphenyl)acrylaldehyde
    • Ferulyl aldehyde
    • coniferylaldehyde
    • p-Coniferaldehyde
    • trans-coniferyl aldehyde
    • (E)-Ferulaldehyde
    • 3-Methoxy-4-hydroxycinnamaldehyde
    • trans-Coniferaldehyde
    • 3-(4-Hydroxy-3-methoxyphenyl)prop-2-enal
    • trans-Ferulaldehyde
    • 2-Propenal, 3-(4-hydroxy-3-methoxyphenyl)-, (2E)-
    • Cinnamaldehyde, 4-hydroxy-3-methoxy-
    • (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal
    • (2e)-3-(4-Hydroxy-3-Methoxyphenyl)prop-2-Enal
    • (E)-3-(4-Hydroxy-3-methoxyphenyl)acrylaldehyde
    • 2-Methoxy-4-(3-oxo-1-propenyl)phenol
    • 4-Hydroxy-3-methoxy-trans-cinnamaldehyde
    • 3-(4-Hydroxy-3-methoxyphenyl)-2-propenal
    • 06TPT01AD5
    • CHEMBL242529
    • CHEBI:16547
    • 2-Propenal, 3-(4-hydroxy-3-methoxyphenyl), (E)-
    • UNII-06TPT01AD5
    • Ferulic Aldehyde
    • Coniferylic aldehyde
    • (E)-coniferaldehyde
    • MFCD00075811
    • Trans-Coniferylaldehyde
    • bmse000422
    • bmse000601
    • bmse010076
    • SCHEMBL167835
    • E-Coniferyl aldehyde; trans-Coniferaldehyde; trans-Coniferyl aldehyde
    • DTXSID10174685
    • 4-Hydroxy3-Methoxy Cinnamaldehyde
    • HY-N2535
    • HY-N3616
    • STR05037
    • 4-hydroxy-3-methoxycinnamic aldehyde
    • BDBM50211193
    • s9221
    • STL479559
    • AKOS015916118
    • CCG-266411
    • FH74153
    • 4-Hydroxy-3-methoxycinnamaldehyde, 98%
    • AC-34773
    • DA-62455
    • CS-0022807
    • CS-0023941
    • NS00066975
    • C02666
    • Coniferaldehyde;4-Hydroxy-3-methoxycinnamaldehyde
    • (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenal
    • (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enal
    • Q63390505
    • Z1255419416
    • 5DF06912-B0DD-4C76-B493-29D29F746430
    • InChI=1/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2

  • Applications

    4-Hydroxy-3-methoxycinnamaldehyde (coniferaldehyde, CAS 458-36-6) is used as a phenylpropanoid building block in organic synthesis (forming Schiff bases/imines with amines, participating in Michael/Knoevenagel reactions, and serving as a probe for chemoselective reduction of C=C vs C=O), as a precursor/model substrate in lignin biotransformation and vanillin production, and as an analytical standard for HPLC/GC-MS quantification of monolignols and lignin-degradation products; in materials and polymer science it is derivatized or grafted onto chitosan, gelatin, epoxies or polyurethanes to introduce crosslinking, adhesion and antioxidant functionality, and related cinnamate derivatives are developed for bio-based photo-crosslinkable systems; in biomedical and agrochemical research the compound and its derivatives have been evaluated in vitro for antioxidant, antimicrobial, anti-inflammatory and tyrosinase-inhibitory activities, supporting natural-product lead discovery and preservation/anti-browning applications; additionally, it is a common substrate/control in enzyme assays (e.g., with cinnamyl alcohol dehydrogenase) and a benchmark molecule for catalytic mechanism studies because it combines a conjugated aldehyde with an α,β-unsaturated double bond.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 77.96
    methanol 103.5
    isopropanol 43.59
    water 0.56
    ethyl acetate 161.01
    n-propanol 48.33
    acetone 161.49
    n-butanol 32.95
    acetonitrile 105.35
    DMF 156.29
    toluene 26.75
    isobutanol 28.87
    1,4-dioxane 263.18
    methyl acetate 165.35
    THF 318.8
    2-butanone 111.19
    n-pentanol 34.85
    sec-butanol 39.1
    n-hexane 1.69
    ethylene glycol 71.7
    NMP 89.65
    cyclohexane 2.97
    DMSO 371.95
    n-butyl acetate 60.41
    n-octanol 25.29
    chloroform 104.44
    n-propyl acetate 86.46
    acetic acid 133.12
    dichloromethane 151.09
    cyclohexanone 93.97
    propylene glycol 49.39
    isopropyl acetate 61.47
    DMAc 155.28
    2-ethoxyethanol 145.72
    isopentanol 35.93
    n-heptane 4.05
    ethyl formate 84.86
    1,2-dichloroethane 127.55
    n-hexanol 41.91
    2-methoxyethanol 186.39
    isobutyl acetate 46.84
    tetrachloromethane 12.26
    n-pentyl acetate 32.76
    transcutol 265.12
    n-heptanol 25.43
    ethylbenzene 21.06
    MIBK 55.61
    2-propoxyethanol 104.07
    tert-butanol 162.15
    MTBE 75.17
    2-butoxyethanol 60.86
    propionic acid 74.65
    o-xylene 24.22
    formic acid 84.62
    diethyl ether 70.21
    m-xylene 22.97
    p-xylene 24.88
    chlorobenzene 36.27
    dimethyl carbonate 68.09
    n-octane 2.98
    formamide 196.55
    cyclopentanone 151.01
    2-pentanone 73.31
    anisole 74.88
    cyclopentyl methyl ether 72.76
    gamma-butyrolactone 211.79
    1-methoxy-2-propanol 109.78
    pyridine 91.24
    3-pentanone 58.94
    furfural 159.1
    n-dodecane 3.35
    diethylene glycol 135.77
    diisopropyl ether 19.76
    tert-amyl alcohol 79.83
    acetylacetone 118.24
    n-hexadecane 3.68
    acetophenone 66.44
    methyl propionate 103.47
    isopentyl acetate 52.35
    trichloroethylene 186.78
    n-nonanol 24.2
    cyclohexanol 35.88
    benzyl alcohol 56.05
    2-ethylhexanol 29.98
    isooctanol 22.83
    dipropyl ether 36.08
    1,2-dichlorobenzene 39.62
    ethyl lactate 50.61
    propylene carbonate 93.85
    n-methylformamide 114.69
    2-pentanol 27.19
    n-pentane 1.4
    1-propoxy-2-propanol 66.12
    1-methoxy-2-propyl acetate 75.6
    2-(2-methoxypropoxy) propanol 75.77
    mesitylene 18.11
    ε-caprolactone 89.04
    p-cymene 18.36
    epichlorohydrin 248.73
    1,1,1-trichloroethane 76.07
    2-aminoethanol 73.76
    morpholine-4-carbaldehyde 151.76
    sulfolane 214.88
    2,2,4-trimethylpentane 3.03
    2-methyltetrahydrofuran 124.42
    n-hexyl acetate 45.45
    isooctane 2.79
    2-(2-butoxyethoxy)ethanol 91.69
    sec-butyl acetate 51.37
    tert-butyl acetate 80.16
    decalin 4.75
    glycerin 96.47
    diglyme 176.07
    acrylic acid 75.78
    isopropyl myristate 25.04
    n-butyric acid 73.82
    acetyl acetate 77.16
    di(2-ethylhexyl) phthalate 25.03
    ethyl propionate 68.6
    nitromethane 280.41
    1,2-diethoxyethane 81.26
    benzonitrile 53.9
    trioctyl phosphate 19.84
    1-bromopropane 38.44
    gamma-valerolactone 169.38
    n-decanol 20.19
    triethyl phosphate 36.86
    4-methyl-2-pentanol 23.46
    propionitrile 76.51
    vinylene carbonate 88.06
    1,1,2-trichlorotrifluoroethane 146.72
    DMS 62.41
    cumene 17.96
    2-octanol 17.89
    2-hexanone 64.4
    octyl acetate 29.53
    limonene 23.92
    1,2-dimethoxyethane 200.88
    ethyl orthosilicate 32.73
    tributyl phosphate 24.11
    diacetone alcohol 102.58
    N,N-dimethylaniline 46.6
    acrylonitrile 106.0
    aniline 47.25
    1,3-propanediol 89.63
    bromobenzene 33.36
    dibromomethane 79.97
    1,1,2,2-tetrachloroethane 125.95
    2-methyl-cyclohexyl acetate 45.31
    tetrabutyl urea 33.74
    diisobutyl methanol 23.86
    2-phenylethanol 50.83
    styrene 26.41
    dioctyl adipate 39.33
    dimethyl sulfate 103.78
    ethyl butyrate 52.52
    methyl lactate 63.4
    butyl lactate 33.07
    diethyl carbonate 45.51
    propanediol butyl ether 53.73
    triethyl orthoformate 41.01
    p-tert-butyltoluene 18.52
    methyl 4-tert-butylbenzoate 58.96
    morpholine 219.83
    tert-butylamine 53.48
    n-dodecanol 17.25
    dimethoxymethane 155.48
    ethylene carbonate 73.79
    cyrene 79.49
    2-ethoxyethyl acetate 63.2
    2-ethylhexyl acetate 39.17
    1,2,4-trichlorobenzene 49.27
    4-methylpyridine 65.22
    dibutyl ether 31.49
    2,6-dimethyl-4-heptanol 23.86
    DEF 75.12
    dimethyl isosorbide 116.75
    tetrachloroethylene 76.54
    eugenol 59.92
    triacetin 64.0
    span 80 48.57
    1,4-butanediol 40.99
    1,1-dichloroethane 84.56
    2-methyl-1-pentanol 34.74
    methyl formate 126.73
    2-methyl-1-butanol 28.88
    n-decane 4.6
    butyronitrile 51.78
    3,7-dimethyl-1-octanol 27.88
    1-chlorooctane 17.97
    1-chlorotetradecane 9.53
    n-nonane 4.11
    undecane 3.86
    tert-butylcyclohexane 4.83
    cyclooctane 1.93
    cyclopentanol 45.72
    tetrahydropyran 120.34
    tert-amyl methyl ether 51.23
    2,5,8-trioxanonane 133.09
    1-hexene 10.23
    2-isopropoxyethanol 92.79
    2,2,2-trifluoroethanol 67.78
    methyl butyrate 82.73

    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 1.4%