Methyl 3-Coumarate

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  • Identifiers

    CAS number
    66417-46-7

    Molecular formula
    C10H10O3

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

    Safety labels

  • Odor profile

    Fragrance
    Fruity 55.68%
    Sweet 49.1%
    Spicy 47.73%
    Phenolic 47.26%
    Balsamic 43.34%
    Vanilla 34.13%
    Floral 30.68%
    Aromatic 30.17%
    Cherry 29.82%
    Honey 29.19%

     

    Flavor
    Odorless 29.62%
    Bitter 27.24%
    Balsam 26.35%
    Wintergreen 23.27%
    Fruity 23.21%
    Faint 21.78%
    Ethyl benzoate 20.96%
    Orange flower 20.49%
    Cadaverous 20.37%
    Aniseed 20.12%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    8.5 (weak base)

    Molecular weight
    178.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    333°C

    Flash point

    • 148.65 ˚C est.

  • Synonyms

    • methyl (E)-3-(3-hydroxyphenyl)prop-2-enoate
    • Methyl 3-Coumarate
    • RefChem:1089407
    • 66417-46-7
    • Methyl trans-3-Hydroxycinnamate
    • 3-Hydroxycinnamic acid methyl ester
    • 2-Propenoic acid, 3-(3-hydroxyphenyl)-, methyl ester, (2E)-
    • MFCD09259949
    • methyl (2E)-3-(3-hydroxyphenyl)prop-2-enoate
    • Methyl 3-(3-hydroxyphenyl)acrylate
    • trans-3-(3-hydroxyphenyl)acrylic acid methyl ester
    • 2-Propenoic acid, 3-(3-hydroxyphenyl)-, methyl ester
    • 3943-95-1
    • Cinnamic acid, m-hydroxy-, methyl ester
    • Methyl (E)-3-(3-hydroxyphenyl)acrylate
    • Methyl 3-(3-hydroxyphenyl)-2-propenoate
    • m-coumaric methyl ester
    • Methyl m-hydroxycinnamate
    • methyl 3-hydroxycinnamate
    • methyl trans-3-coumarate
    • methyl (E)-3-hydroxycinnamate
    • CHEMBL151178
    • SCHEMBL2631340
    • SCHEMBL30676338
    • CHEBI:131393
    • m-hydroxycinnamic acid-methyl ester
    • m-Hydroxycinnamic acid, methyl ester
    • AKOS006331414
    • Methyl ester of m-hydroxycinnamic acid
    • (E)-methyl 3-(3-hydroxyphenyl)acrylate
    • AS-70747
    • FM158183
    • SY029355
    • methyl (2E)-3-(3-hydroxyphenyl)acrylate
    • DB-230824
    • CS-0313933
    • A11407
    • (E)-3-(3-hydroxyphenyl)-acrylic acid methyl ester
    • 3943-95-1

  • Applications

    Methyl 3-Coumarate (CAS 66417-46-7) is primarily a chemical building block in fragrance chemistry, serving as a precursor to hydroxycinnamate-derived aroma compounds, and it is also used as a flavor precursor in flavor chemistry. In perfumery and cosmetics it may function as a fragrance ingredient or scent precursor, contributing distinct aroma notes. It is commonly evaluated as an intermediate in industrial manufacturing for the synthesis of specialty aroma chemicals and related intermediates. In coatings, inks and polymers it may be explored as a functional additive or starting point for polymerizable derivatives. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 132.55
    methanol 143.1
    isopropanol 91.91
    water 0.22
    ethyl acetate 102.83
    n-propanol 89.6
    acetone 103.05
    n-butanol 68.06
    acetonitrile 100.66
    DMF 200.47
    toluene 34.16
    isobutanol 44.94
    1,4-dioxane 246.21
    methyl acetate 133.0
    THF 251.03
    2-butanone 131.23
    n-pentanol 51.46
    sec-butanol 85.59
    n-hexane 1.04
    ethylene glycol 50.1
    NMP 98.69
    cyclohexane 1.25
    DMSO 319.9
    n-butyl acetate 39.54
    n-octanol 14.22
    chloroform 93.85
    n-propyl acetate 47.26
    acetic acid 87.89
    dichloromethane 88.72
    cyclohexanone 69.18
    propylene glycol 66.68
    isopropyl acetate 41.88
    DMAc 297.96
    2-ethoxyethanol 179.03
    isopentanol 54.88
    n-heptane 1.01
    ethyl formate 42.96
    1,2-dichloroethane 77.7
    n-hexanol 40.37
    2-methoxyethanol 259.26
    isobutyl acetate 22.86
    tetrachloromethane 6.97
    n-pentyl acetate 17.59
    transcutol 403.32
    n-heptanol 15.07
    ethylbenzene 18.21
    MIBK 43.17
    2-propoxyethanol 111.13
    tert-butanol 176.36
    MTBE 87.1
    2-butoxyethanol 50.7
    propionic acid 67.52
    o-xylene 22.61
    formic acid 69.64
    diethyl ether 94.65
    m-xylene 17.52
    p-xylene 18.48
    chlorobenzene 26.07
    dimethyl carbonate 45.35
    n-octane 0.56
    formamide 170.78
    cyclopentanone 98.28
    2-pentanone 67.87
    anisole 83.3
    cyclopentyl methyl ether 59.04
    gamma-butyrolactone 119.18
    1-methoxy-2-propanol 155.14
    pyridine 112.58
    3-pentanone 58.78
    furfural 119.54
    n-dodecane 0.73
    diethylene glycol 119.29
    diisopropyl ether 14.18
    tert-amyl alcohol 126.43
    acetylacetone 83.53
    n-hexadecane 0.85
    acetophenone 57.33
    methyl propionate 88.18
    isopentyl acetate 37.01
    trichloroethylene 143.96
    n-nonanol 14.32
    cyclohexanol 41.76
    benzyl alcohol 60.31
    2-ethylhexanol 22.35
    isooctanol 13.51
    dipropyl ether 23.18
    1,2-dichlorobenzene 25.74
    ethyl lactate 33.16
    propylene carbonate 48.51
    n-methylformamide 113.13
    2-pentanol 43.73
    n-pentane 0.74
    1-propoxy-2-propanol 63.54
    1-methoxy-2-propyl acetate 60.96
    2-(2-methoxypropoxy) propanol 78.66
    mesitylene 9.6
    ε-caprolactone 66.52
    p-cymene 10.19
    epichlorohydrin 191.81
    1,1,1-trichloroethane 43.63
    2-aminoethanol 95.14
    morpholine-4-carbaldehyde 168.44
    sulfolane 141.02
    2,2,4-trimethylpentane 2.1
    2-methyltetrahydrofuran 125.9
    n-hexyl acetate 29.46
    isooctane 1.2
    2-(2-butoxyethoxy)ethanol 97.19
    sec-butyl acetate 32.57
    tert-butyl acetate 60.9
    decalin 2.28
    glycerin 104.87
    diglyme 178.46
    acrylic acid 61.69
    isopropyl myristate 14.3
    n-butyric acid 60.33
    acetyl acetate 43.39
    di(2-ethylhexyl) phthalate 18.15
    ethyl propionate 47.16
    nitromethane 188.12
    1,2-diethoxyethane 73.46
    benzonitrile 43.52
    trioctyl phosphate 11.2
    1-bromopropane 34.18
    gamma-valerolactone 142.14
    n-decanol 11.27
    triethyl phosphate 24.41
    4-methyl-2-pentanol 25.57
    propionitrile 68.62
    vinylene carbonate 48.44
    1,1,2-trichlorotrifluoroethane 128.21
    DMS 41.76
    cumene 12.05
    2-octanol 9.49
    2-hexanone 49.12
    octyl acetate 17.66
    limonene 13.83
    1,2-dimethoxyethane 204.08
    ethyl orthosilicate 22.56
    tributyl phosphate 15.86
    diacetone alcohol 105.32
    N,N-dimethylaniline 47.51
    acrylonitrile 83.3
    aniline 72.33
    1,3-propanediol 115.18
    bromobenzene 21.64
    dibromomethane 51.39
    1,1,2,2-tetrachloroethane 110.53
    2-methyl-cyclohexyl acetate 30.31
    tetrabutyl urea 23.19
    diisobutyl methanol 15.07
    2-phenylethanol 45.28
    styrene 25.11
    dioctyl adipate 26.19
    dimethyl sulfate 80.58
    ethyl butyrate 34.49
    methyl lactate 53.51
    butyl lactate 23.34
    diethyl carbonate 28.56
    propanediol butyl ether 50.36
    triethyl orthoformate 28.39
    p-tert-butyltoluene 10.53
    methyl 4-tert-butylbenzoate 43.47
    morpholine 284.54
    tert-butylamine 65.39
    n-dodecanol 9.02
    dimethoxymethane 149.4
    ethylene carbonate 37.11
    cyrene 63.12
    2-ethoxyethyl acetate 42.78
    2-ethylhexyl acetate 27.04
    1,2,4-trichlorobenzene 37.35
    4-methylpyridine 90.78
    dibutyl ether 19.39
    2,6-dimethyl-4-heptanol 15.07
    DEF 79.96
    dimethyl isosorbide 100.01
    tetrachloroethylene 59.07
    eugenol 49.1
    triacetin 45.11
    span 80 44.66
    1,4-butanediol 42.37
    1,1-dichloroethane 57.11
    2-methyl-1-pentanol 48.64
    methyl formate 70.95
    2-methyl-1-butanol 50.92
    n-decane 1.12
    butyronitrile 47.45
    3,7-dimethyl-1-octanol 20.26
    1-chlorooctane 6.89
    1-chlorotetradecane 3.23
    n-nonane 0.91
    undecane 0.88
    tert-butylcyclohexane 2.47
    cyclooctane 0.61
    cyclopentanol 42.23
    tetrahydropyran 121.68
    tert-amyl methyl ether 68.36
    2,5,8-trioxanonane 133.76
    1-hexene 9.81
    2-isopropoxyethanol 99.52
    2,2,2-trifluoroethanol 35.52
    methyl butyrate 53.27

    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