Methyl Caffeate

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  • Identifiers

    CAS number
    3843-74-1

    Molecular formula
    C10H10O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 46.6%
    Odorless 45.6%
    Vanilla 42.99%
    Spicy 42.71%
    Balsamic 36.38%
    Burnt 34.25%
    Caramellic 28.54%
    Sweet 27.39%
    Milky 25.51%
    Smoky 25.32%

     

    Flavor
    Bitter 45.31%
    Odorless 36.54%
    Mild 26.04%
    Faint 22.48%
    Wintergreen 22.24%
    Powdery 22.07%
    Ethyl benzoate 21.01%
    Orange flower 20.84%
    Cadaverous 20.69%
    Heliotropin 20.45%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    9.33 (weak base)

    Molecular weight
    194.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    380°C

    Flash point

    • 162.24 ˚C est.

  • Synonyms

    • Methyl caffeate
    • 3843-74-1
    • Caffeic acid methyl ester
    • METHYLCAFFEATE
    • methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
    • Caffeic acid, methyl ester
    • methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
    • DTXSID401030290
    • N79173B9HF
    • CHEBI:6856
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester
    • RefChem:30878
    • DTXCID601515387
    • 808-143-8
    • 67667-67-8
    • methyl 3-(3,4-dihydroxyphenyl)acrylate
    • (E)-methyl 3-(3,4-dihydroxyphenyl)acrylate
    • Methyl 3,4-dihydroxycinnamate
    • MFCD00210468
    • (E)-3,4-Dihydroxycinnamic Acid Methyl Ester
    • Methyl caffeate acid
    • methyl (2E)-3-(3,4-dihydroxyphenyl)acrylate
    • CHEMBL17001
    • 142234-81-9
    • methyl (E)-3-(3,4-dihydroxyphenyl)acrylate
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (2E)-
    • METHYL CAFFEOATE
    • E-Caffeic acid methyl ester
    • UNII-N79173B9HF
    • caffeic methyl ester
    • methyl (E)-caffeate
    • (E)-Methyl3-(3,4-dihydroxyphenyl)acrylate
    • 3-(3,4-Dihydroxy-phenyl)-acrylic acid methyl ester
    • Cinnamic acid, 3,4-dihydroxy-, methyl ester
    • t-caffeic acid methyl ester
    • trans-caffeic acid methylate
    • SCHEMBL817520
    • methyl-3,4-dihydroxy cinnamate
    • orb2939678
    • SCHEMBL30963730
    • ALBB-024360
    • HY-N6005
    • AC9787
    • BDBM50029209
    • SBB000325
    • STK523948
    • AKOS003263230
    • EBC-462060
    • FM46133
    • AS-56651
    • AS-65428
    • DA-55392
    • ST094769
    • SY057957
    • SY237763
    • DB-230642
    • DB-320084
    • CS-0032054
    • E80647
    • Methyl 1-(3'',4''-dihydroxyphenyl)propenate
    • A824271
    • Q6823935
    • (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid methyl ester
    • methyl (E)-3-[3,4-bis(oxidanyl)phenyl]prop-2-enoate
    • (E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid methyl ester
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (E)-
    • 3843-74-1

  • Applications

    Methyl caffeate is the methyl ester of caffeic acid and is commonly employed as an intermediate in organic synthesis to access complex polyphenols; in the plastics and coatings sector it can act as an antioxidant and stabilizer to retard oxidation and extend material life; in cosmetics and personal care it may serve as an antioxidant and as a precursor to other polyphenol-derived compounds; in the field of fragrance, it can be considered as a precursor to certain fragrance ingredients, and at a research level it may function as a starting material for dyes or colorants or related additives for printing and coating systems.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 109.77
    methanol 134.36
    isopropanol 77.38
    water 0.41
    ethyl acetate 88.04
    n-propanol 71.69
    acetone 107.19
    n-butanol 50.22
    acetonitrile 41.41
    DMF 81.67
    toluene 9.84
    isobutanol 32.46
    1,4-dioxane 183.01
    methyl acetate 106.14
    THF 350.71
    2-butanone 95.64
    n-pentanol 34.64
    sec-butanol 70.53
    n-hexane 0.27
    ethylene glycol 47.42
    NMP 27.04
    cyclohexane 0.62
    DMSO 168.97
    n-butyl acetate 15.69
    n-octanol 13.09
    chloroform 8.24
    n-propyl acetate 27.8
    acetic acid 63.88
    dichloromethane 10.13
    cyclohexanone 37.44
    propylene glycol 48.34
    isopropyl acetate 31.85
    DMAc 161.49
    2-ethoxyethanol 176.38
    isopentanol 41.19
    n-heptane 0.93
    ethyl formate 37.96
    1,2-dichloroethane 13.67
    n-hexanol 25.22
    2-methoxyethanol 258.91
    isobutyl acetate 9.9
    tetrachloromethane 1.26
    n-pentyl acetate 12.18
    transcutol 148.6
    n-heptanol 15.97
    ethylbenzene 6.99
    MIBK 29.14
    2-propoxyethanol 80.64
    tert-butanol 238.84
    MTBE 74.14
    2-butoxyethanol 43.6
    propionic acid 39.94
    o-xylene 9.87
    formic acid 84.55
    diethyl ether 49.86
    m-xylene 6.83
    p-xylene 7.84
    chlorobenzene 4.68
    dimethyl carbonate 35.2
    n-octane 0.78
    formamide 241.01
    cyclopentanone 60.59
    2-pentanone 51.77
    anisole 39.67
    cyclopentyl methyl ether 36.7
    gamma-butyrolactone 83.25
    1-methoxy-2-propanol 141.95
    pyridine 45.6
    3-pentanone 32.67
    furfural 60.31
    n-dodecane 0.86
    diethylene glycol 101.03
    diisopropyl ether 8.68
    tert-amyl alcohol 137.31
    acetylacetone 61.2
    n-hexadecane 0.95
    acetophenone 28.28
    methyl propionate 63.51
    isopentyl acetate 16.87
    trichloroethylene 22.71
    n-nonanol 14.04
    cyclohexanol 30.71
    benzyl alcohol 35.63
    2-ethylhexanol 12.79
    isooctanol 13.33
    dipropyl ether 14.06
    1,2-dichlorobenzene 5.33
    ethyl lactate 21.63
    propylene carbonate 26.26
    n-methylformamide 83.71
    2-pentanol 35.56
    n-pentane 0.34
    1-propoxy-2-propanol 41.49
    1-methoxy-2-propyl acetate 34.32
    2-(2-methoxypropoxy) propanol 50.31
    mesitylene 5.01
    ε-caprolactone 39.47
    p-cymene 5.35
    epichlorohydrin 119.33
    1,1,1-trichloroethane 7.31
    2-aminoethanol 75.92
    morpholine-4-carbaldehyde 84.06
    sulfolane 61.46
    2,2,4-trimethylpentane 0.89
    2-methyltetrahydrofuran 105.78
    n-hexyl acetate 16.63
    isooctane 0.55
    2-(2-butoxyethoxy)ethanol 64.55
    sec-butyl acetate 17.14
    tert-butyl acetate 46.56
    decalin 0.81
    glycerin 84.43
    diglyme 109.93
    acrylic acid 31.47
    isopropyl myristate 9.59
    n-butyric acid 42.44
    acetyl acetate 28.92
    di(2-ethylhexyl) phthalate 10.94
    ethyl propionate 28.32
    nitromethane 154.45
    1,2-diethoxyethane 40.21
    benzonitrile 15.2
    trioctyl phosphate 7.95
    1-bromopropane 6.45
    gamma-valerolactone 86.43
    n-decanol 11.71
    triethyl phosphate 13.18
    4-methyl-2-pentanol 19.69
    propionitrile 30.38
    vinylene carbonate 23.0
    1,1,2-trichlorotrifluoroethane 60.09
    DMS 19.36
    cumene 5.21
    2-octanol 10.18
    2-hexanone 27.81
    octyl acetate 12.58
    limonene 7.03
    1,2-dimethoxyethane 175.38
    ethyl orthosilicate 13.21
    tributyl phosphate 8.96
    diacetone alcohol 89.73
    N,N-dimethylaniline 24.84
    acrylonitrile 36.93
    aniline 27.99
    1,3-propanediol 112.0
    bromobenzene 3.44
    dibromomethane 5.37
    1,1,2,2-tetrachloroethane 19.55
    2-methyl-cyclohexyl acetate 16.0
    tetrabutyl urea 15.49
    diisobutyl methanol 11.12
    2-phenylethanol 26.93
    styrene 7.95
    dioctyl adipate 15.87
    dimethyl sulfate 43.2
    ethyl butyrate 16.13
    methyl lactate 41.33
    butyl lactate 14.74
    diethyl carbonate 13.26
    propanediol butyl ether 33.66
    triethyl orthoformate 14.48
    p-tert-butyltoluene 5.92
    methyl 4-tert-butylbenzoate 28.47
    morpholine 203.49
    tert-butylamine 59.38
    n-dodecanol 9.5
    dimethoxymethane 152.14
    ethylene carbonate 19.54
    cyrene 41.21
    2-ethoxyethyl acetate 28.41
    2-ethylhexyl acetate 10.82
    1,2,4-trichlorobenzene 8.28
    4-methylpyridine 30.47
    dibutyl ether 12.26
    2,6-dimethyl-4-heptanol 11.12
    DEF 44.88
    dimethyl isosorbide 64.26
    tetrachloroethylene 11.79
    eugenol 30.54
    triacetin 23.8
    span 80 28.25
    1,4-butanediol 40.89
    1,1-dichloroethane 8.15
    2-methyl-1-pentanol 30.56
    methyl formate 69.02
    2-methyl-1-butanol 36.39
    n-decane 1.2
    butyronitrile 22.61
    3,7-dimethyl-1-octanol 14.13
    1-chlorooctane 4.57
    1-chlorotetradecane 2.54
    n-nonane 0.97
    undecane 1.0
    tert-butylcyclohexane 0.87
    cyclooctane 0.42
    cyclopentanol 33.64
    tetrahydropyran 74.82
    tert-amyl methyl ether 52.07
    2,5,8-trioxanonane 92.1
    1-hexene 2.68
    2-isopropoxyethanol 88.11
    2,2,2-trifluoroethanol 29.78
    methyl butyrate 32.27

    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