Ethyl Caffeate

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  • Identifiers

    CAS number
    102-37-4

    Molecular formula
    C11H12O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Spicy 45.57%
    Odorless 44.31%
    Vanilla 43.94%
    Phenolic 42.47%
    Balsamic 40.4%
    Burnt 31.39%
    Sweet 27.86%
    Caramellic 27.03%
    Fruity 25.45%
    Smoky 24.98%

     

    Flavor
    Bitter 44.11%
    Odorless 34.85%
    Mild 26.76%
    Faint 23.81%
    Powdery 23.12%
    Wintergreen 23.05%
    Sweet 22.51%
    Ethyl benzoate 21.39%
    Balsam 21.14%
    Bland 20.47%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    9.59 (weak base)

    Molecular weight
    208.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    375°C

    Flash point

    • 173.64 ˚C est.

  • Synonyms

    • Ethyl caffeate
    • 102-37-4
    • Ethyl 3,4-dihydroxycinnamate
    • ethyl trans-caffeate
    • Caffeic acid ethyl ester
    • ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
    • 76GBB1JU5Y
    • CHEBI:132714
    • DTXSID70876375
    • RefChem:596426
    • DTXCID801014480
    • 108-430-1
    • 66648-50-8
    • Ethyl 3-(3,4-dihydroxyphenyl)acrylate
    • (E)-Ethyl Dihydroxycinnamate
    • (E)-ethyl caffeate
    • Ethyl (2e)-3-(3,4-Dihydroxyphenyl)prop-2-Enoate
    • (E)-ethyl 3-(3,4-dihydroxyphenyl)acrylate
    • CHEMBL17347
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester
    • MFCD00045754
    • UNII-76GBB1JU5Y
    • 4gqq
    • CAEE
    • 3,4-Dihydroxycinnamic acid ethyl ester
    • 3-(3,4-Dihydroxy-phenyl)-acrylic acid ethyl ester
    • SCHEMBL782032
    • orb1303444
    • SCHEMBL30602576
    • CHEBI:69656
    • HY-N6966A
    • (E)-ethyl 3,4-dihydroxycinnamate
    • ethyl trans-3,4-dihydroxycinnamate
    • HY-N6966
    • BDBM50029196
    • MSK167830
    • NSC619661
    • AKOS005167063
    • AKOS025310508
    • CCG-266637
    • CS-W019100
    • EBC-466110
    • NSC-619661
    • AC-34380
    • AS-18100
    • AS-69825
    • DA-53029
    • Ethyl 3,4-dihydroxycinnamate, AldrichCPR
    • SY121016
    • CS-0181967
    • Ethyl (E)-3-(3,4-dihydroxyphenyl)acrylate
    • ethyl 3-(3,4-dihydroxyphenyl)-2-propenoate
    • NS00126254
    • S5640
    • ethyl (2E)-3-(3,4-dihydroxyphenyl)acrylate
    • Ethyl 1-(3'',4''-dihydroxyphenyl)propenate
    • G79794
    • (E)-Ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
    • 102E374
    • F866169
    • Q5404446
    • (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid ethyl ester
    • 102-37-4

  • Applications

    Ethyl caffeate (CAS 102-37-4) is primarily used as an intermediate in organic synthesis; it is also encountered in fragrance and flavor applications as an odorant or aroma component rooted in the caffeic acid framework; in cosmetics and personal care it is considered an antioxidant and a formulation stabilizer; in the polymer and materials sector it is studied as an antioxidant additive or stabilizer; and it serves as a building block for the synthesis of more complex caffeic acid derivatives in pharmaceutical research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 150.5
    methanol 231.56
    isopropanol 105.11
    water 0.2
    ethyl acetate 142.09
    n-propanol 103.91
    acetone 260.8
    n-butanol 76.21
    acetonitrile 79.76
    DMF 250.38
    toluene 14.6
    isobutanol 47.76
    1,4-dioxane 255.5
    methyl acetate 158.63
    THF 493.66
    2-butanone 172.04
    n-pentanol 56.64
    sec-butanol 91.61
    n-hexane 0.84
    ethylene glycol 43.79
    NMP 71.58
    cyclohexane 0.92
    DMSO 433.79
    n-butyl acetate 54.37
    n-octanol 19.68
    chloroform 32.32
    n-propyl acetate 59.58
    acetic acid 121.48
    dichloromethane 43.12
    cyclohexanone 80.19
    propylene glycol 50.96
    isopropyl acetate 60.84
    DMAc 294.17
    2-ethoxyethanol 224.0
    isopentanol 67.98
    n-heptane 1.21
    ethyl formate 54.45
    1,2-dichloroethane 55.72
    n-hexanol 45.36
    2-methoxyethanol 320.04
    isobutyl acetate 27.98
    tetrachloromethane 2.71
    n-pentyl acetate 26.05
    transcutol 264.06
    n-heptanol 22.57
    ethylbenzene 12.87
    MIBK 58.43
    2-propoxyethanol 122.39
    tert-butanol 349.17
    MTBE 133.72
    2-butoxyethanol 61.57
    propionic acid 66.18
    o-xylene 14.13
    formic acid 78.75
    diethyl ether 99.13
    m-xylene 11.41
    p-xylene 15.29
    chlorobenzene 14.8
    dimethyl carbonate 55.23
    n-octane 1.09
    formamide 201.02
    cyclopentanone 135.2
    2-pentanone 102.54
    anisole 65.34
    cyclopentyl methyl ether 62.61
    gamma-butyrolactone 145.47
    1-methoxy-2-propanol 193.65
    pyridine 70.51
    3-pentanone 62.34
    furfural 106.78
    n-dodecane 1.67
    diethylene glycol 141.25
    diisopropyl ether 16.49
    tert-amyl alcohol 185.14
    acetylacetone 133.02
    n-hexadecane 1.85
    acetophenone 47.86
    methyl propionate 95.07
    isopentyl acetate 48.67
    trichloroethylene 74.48
    n-nonanol 20.86
    cyclohexanol 41.77
    benzyl alcohol 51.84
    2-ethylhexanol 23.55
    isooctanol 19.5
    dipropyl ether 27.1
    1,2-dichlorobenzene 16.91
    ethyl lactate 36.39
    propylene carbonate 53.69
    n-methylformamide 117.16
    2-pentanol 53.44
    n-pentane 0.59
    1-propoxy-2-propanol 72.48
    1-methoxy-2-propyl acetate 68.38
    2-(2-methoxypropoxy) propanol 79.11
    mesitylene 8.22
    ε-caprolactone 71.2
    p-cymene 10.46
    epichlorohydrin 199.72
    1,1,1-trichloroethane 26.12
    2-aminoethanol 81.14
    morpholine-4-carbaldehyde 145.61
    sulfolane 156.11
    2,2,4-trimethylpentane 1.79
    2-methyltetrahydrofuran 151.8
    n-hexyl acetate 35.11
    isooctane 1.24
    2-(2-butoxyethoxy)ethanol 100.78
    sec-butyl acetate 39.48
    tert-butyl acetate 92.53
    decalin 1.9
    glycerin 86.61
    diglyme 170.9
    acrylic acid 52.87
    isopropyl myristate 20.54
    n-butyric acid 72.31
    acetyl acetate 53.6
    di(2-ethylhexyl) phthalate 21.12
    ethyl propionate 52.67
    nitromethane 267.42
    1,2-diethoxyethane 82.03
    benzonitrile 34.64
    trioctyl phosphate 15.75
    1-bromopropane 22.86
    gamma-valerolactone 157.76
    n-decanol 18.11
    triethyl phosphate 26.36
    4-methyl-2-pentanol 33.02
    propionitrile 60.99
    vinylene carbonate 48.01
    1,1,2-trichlorotrifluoroethane 95.62
    DMS 43.68
    cumene 10.38
    2-octanol 15.94
    2-hexanone 59.36
    octyl acetate 25.19
    limonene 14.19
    1,2-dimethoxyethane 259.03
    ethyl orthosilicate 24.84
    tributyl phosphate 20.13
    diacetone alcohol 140.66
    N,N-dimethylaniline 38.46
    acrylonitrile 75.59
    aniline 38.71
    1,3-propanediol 131.16
    bromobenzene 11.31
    dibromomethane 23.43
    1,1,2,2-tetrachloroethane 61.67
    2-methyl-cyclohexyl acetate 32.51
    tetrabutyl urea 30.31
    diisobutyl methanol 20.0
    2-phenylethanol 44.49
    styrene 16.47
    dioctyl adipate 31.46
    dimethyl sulfate 86.13
    ethyl butyrate 37.85
    methyl lactate 57.93
    butyl lactate 27.93
    diethyl carbonate 31.3
    propanediol butyl ether 50.4
    triethyl orthoformate 31.24
    p-tert-butyltoluene 11.21
    methyl 4-tert-butylbenzoate 47.23
    morpholine 264.53
    tert-butylamine 91.51
    n-dodecanol 15.52
    dimethoxymethane 239.54
    ethylene carbonate 41.71
    cyrene 61.64
    2-ethoxyethyl acetate 53.22
    2-ethylhexyl acetate 32.29
    1,2,4-trichlorobenzene 22.71
    4-methylpyridine 53.13
    dibutyl ether 25.88
    2,6-dimethyl-4-heptanol 20.0
    DEF 85.81
    dimethyl isosorbide 104.65
    tetrachloroethylene 32.22
    eugenol 51.36
    triacetin 45.2
    span 80 47.09
    1,4-butanediol 49.24
    1,1-dichloroethane 34.12
    2-methyl-1-pentanol 51.79
    methyl formate 97.74
    2-methyl-1-butanol 55.81
    n-decane 2.17
    butyronitrile 44.9
    3,7-dimethyl-1-octanol 24.12
    1-chlorooctane 9.92
    1-chlorotetradecane 5.8
    n-nonane 1.67
    undecane 1.9
    tert-butylcyclohexane 2.17
    cyclooctane 0.57
    cyclopentanol 45.42
    tetrahydropyran 123.71
    tert-amyl methyl ether 92.69
    2,5,8-trioxanonane 144.7
    1-hexene 8.25
    2-isopropoxyethanol 119.3
    2,2,2-trifluoroethanol 38.68
    methyl butyrate 61.05

    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