Cis-P-Coumaric Acid

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  • Identifiers

    CAS number
    4501-31-9

    Molecular formula
    C9H8O3

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

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 57.02%
    Balsamic 54.87%
    Spicy 41.66%
    Odorless 39.28%
    Burnt 33.88%
    Vanilla 31.31%
    Aromatic 31.06%
    Nutty 30.77%
    Medicinal 29.64%
    Sweet 29.25%

     

    Flavor
    Balsam 51.65%
    Phenolic 42.92%
    Odorless 41.81%
    Nutty 40.89%
    Balsamic 37.48%
    Mild 35.59%
    Faint 34.0%
    Honey 32.6%
    Sweet 30.84%
    Cinnamon 27.5%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    8.49 (weak base)

    Molecular weight
    164.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    364°C

    Melting point expt.

    • 134 - 134.5 °C

    Flash point

    • 181.97 ˚C est.

  • Synonyms

    • cis-p-Coumaric acid
    • 4501-31-9
    • (2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid
    • (Z)-3-(4-hydroxyphenyl)prop-2-enoic acid
    • DTXSID901315564
    • RefChem:1081972
    • DTXCID20842085
    • cis-4-Hydroxycinnamic acid
    • cis-p-Hydroxycinnamic acid
    • (Z)-p-Coumaric acid
    • cis-p-Cumaric acid
    • cis-4-coumaric acid
    • cis-p-Coumarinic acid
    • (Z)-3-(4-Hydroxyphenyl)-2-propenoic acid
    • (Z)-p-hydroxycinnamic acid
    • cis-p-Coumarate
    • (2Z)-3-(4-Hydroxyphenyl)-2-propenoic Acid
    • 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (Z)-
    • EINECS 224-813-7
    • CINNAMIC ACID, p-HYDROXY-, (Z)-
    • (Z)-3-(4-hydroxyphenyl)acrylic acid
    • (2Z)-3-(4-hydroxyphenyl)acrylic acid
    • SCHEMBL434720
    • orb1984131
    • CHEMBL2336752
    • CHEBI:17450
    • Cinnamic acid, 4-hydroxy-, cis-
    • NSC90284
    • MFCD00064995
    • NSC 90284
    • NSC-90284
    • AKOS040763716
    • FH24323
    • SY027398
    • NS00082097
    • C06738
    • H59364
    • 501H319
    • Q27102404
    • 15F90638-DCF1-4922-AFB2-BAF5EA308C8C
    • 4501-31-9

  • Applications

    Cis-P-Coumaric Acid (CAS 4501-31-9) is primarily used as a chemical intermediate and building block in organic synthesis; in practice it serves as a precursor for hydroxycinnamate derivatives used in flavors, fragrances, and polymer-related materials. It is often evaluated as a starting point for the derivatization of esters and ethers for cosmetic and personal care formulations, contributing to antioxidant or matrix-stabilizing functionalities after modification. In pharmaceutical and medicinal chemistry research, it provides a scaffold for the synthesis of plant-derived phenolic compounds and related intermediates. In coatings, inks, and specialty polymers, the hydroxycinnamate functionality can be incorporated to impart UV-absorption and radical-scavenging properties, subject to formulation limits. Additionally, it is used as an intermediate in agrochemical research for the synthesis of related phenolic compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 160.45
    methanol 195.65
    isopropanol 75.76
    water 1.28
    ethyl acetate 23.95
    n-propanol 94.88
    acetone 108.87
    n-butanol 72.76
    acetonitrile 15.79
    DMF 165.2
    toluene 2.14
    isobutanol 42.99
    1,4-dioxane 50.26
    methyl acetate 43.45
    THF 158.66
    2-butanone 57.56
    n-pentanol 49.17
    sec-butanol 51.7
    n-hexane 0.12
    ethylene glycol 60.27
    NMP 48.39
    cyclohexane 0.07
    DMSO 81.17
    n-butyl acetate 26.91
    n-octanol 19.71
    chloroform 0.48
    n-propyl acetate 22.62
    acetic acid 43.86
    dichloromethane 0.74
    cyclohexanone 23.17
    propylene glycol 78.94
    isopropyl acetate 22.98
    DMAc 137.68
    2-ethoxyethanol 158.19
    isopentanol 51.22
    n-heptane 0.59
    ethyl formate 24.54
    1,2-dichloroethane 1.63
    n-hexanol 35.27
    2-methoxyethanol 236.49
    isobutyl acetate 15.02
    tetrachloromethane 0.19
    n-pentyl acetate 18.83
    transcutol 154.94
    n-heptanol 23.99
    ethylbenzene 2.85
    MIBK 33.96
    2-propoxyethanol 124.67
    tert-butanol 94.93
    MTBE 30.23
    2-butoxyethanol 66.94
    propionic acid 31.06
    o-xylene 3.07
    formic acid 61.09
    diethyl ether 15.87
    m-xylene 3.68
    p-xylene 2.94
    chlorobenzene 1.34
    dimethyl carbonate 20.63
    n-octane 0.45
    formamide 121.22
    cyclopentanone 57.5
    2-pentanone 41.88
    anisole 20.06
    cyclopentyl methyl ether 21.01
    gamma-butyrolactone 67.79
    1-methoxy-2-propanol 156.53
    pyridine 12.95
    3-pentanone 14.48
    furfural 41.36
    n-dodecane 0.84
    diethylene glycol 123.56
    diisopropyl ether 6.08
    tert-amyl alcohol 62.07
    acetylacetone 44.65
    n-hexadecane 0.88
    acetophenone 19.46
    methyl propionate 28.09
    isopentyl acetate 26.68
    trichloroethylene 2.84
    n-nonanol 19.78
    cyclohexanol 13.21
    benzyl alcohol 24.13
    2-ethylhexanol 16.47
    isooctanol 19.14
    dipropyl ether 16.67
    1,2-dichlorobenzene 1.79
    ethyl lactate 26.19
    propylene carbonate 27.02
    n-methylformamide 93.01
    2-pentanol 33.73
    n-pentane 0.13
    1-propoxy-2-propanol 76.43
    1-methoxy-2-propyl acetate 47.74
    2-(2-methoxypropoxy) propanol 61.19
    mesitylene 3.26
    ε-caprolactone 27.96
    p-cymene 5.02
    epichlorohydrin 55.22
    1,1,1-trichloroethane 1.35
    2-aminoethanol 102.03
    morpholine-4-carbaldehyde 79.28
    sulfolane 50.41
    2,2,4-trimethylpentane 0.42
    2-methyltetrahydrofuran 48.07
    n-hexyl acetate 23.19
    isooctane 0.61
    2-(2-butoxyethoxy)ethanol 83.33
    sec-butyl acetate 17.07
    tert-butyl acetate 38.66
    decalin 0.36
    glycerin 108.44
    diglyme 110.18
    acrylic acid 24.92
    isopropyl myristate 13.93
    n-butyric acid 35.06
    acetyl acetate 13.35
    di(2-ethylhexyl) phthalate 15.35
    ethyl propionate 18.75
    nitromethane 74.44
    1,2-diethoxyethane 43.29
    benzonitrile 9.92
    trioctyl phosphate 12.43
    1-bromopropane 0.96
    gamma-valerolactone 85.37
    n-decanol 17.23
    triethyl phosphate 13.1
    4-methyl-2-pentanol 23.19
    propionitrile 14.68
    vinylene carbonate 18.45
    1,1,2-trichlorotrifluoroethane 33.91
    DMS 17.33
    cumene 3.57
    2-octanol 14.52
    2-hexanone 28.79
    octyl acetate 18.85
    limonene 5.42
    1,2-dimethoxyethane 132.38
    ethyl orthosilicate 12.94
    tributyl phosphate 12.87
    diacetone alcohol 85.57
    N,N-dimethylaniline 17.33
    acrylonitrile 19.32
    aniline 8.1
    1,3-propanediol 121.7
    bromobenzene 0.8
    dibromomethane 0.35
    1,1,2,2-tetrachloroethane 2.88
    2-methyl-cyclohexyl acetate 19.84
    tetrabutyl urea 23.9
    diisobutyl methanol 14.31
    2-phenylethanol 25.45
    styrene 2.71
    dioctyl adipate 20.48
    dimethyl sulfate 26.15
    ethyl butyrate 21.67
    methyl lactate 38.59
    butyl lactate 23.92
    diethyl carbonate 14.21
    propanediol butyl ether 51.59
    triethyl orthoformate 18.17
    p-tert-butyltoluene 5.23
    methyl 4-tert-butylbenzoate 33.77
    morpholine 79.56
    tert-butylamine 24.93
    n-dodecanol 13.56
    dimethoxymethane 104.11
    ethylene carbonate 14.98
    cyrene 58.95
    2-ethoxyethyl acetate 33.47
    2-ethylhexyl acetate 15.96
    1,2,4-trichlorobenzene 2.71
    4-methylpyridine 13.15
    dibutyl ether 15.19
    2,6-dimethyl-4-heptanol 14.31
    DEF 36.04
    dimethyl isosorbide 93.56
    tetrachloroethylene 1.5
    eugenol 40.78
    triacetin 26.7
    span 80 38.97
    1,4-butanediol 57.06
    1,1-dichloroethane 1.36
    2-methyl-1-pentanol 35.94
    methyl formate 61.49
    2-methyl-1-butanol 40.41
    n-decane 0.99
    butyronitrile 18.32
    3,7-dimethyl-1-octanol 18.39
    1-chlorooctane 3.88
    1-chlorotetradecane 2.63
    n-nonane 0.73
    undecane 0.92
    tert-butylcyclohexane 0.62
    cyclooctane 0.1
    cyclopentanol 25.51
    tetrahydropyran 20.03
    tert-amyl methyl ether 24.63
    2,5,8-trioxanonane 101.38
    1-hexene 1.17
    2-isopropoxyethanol 82.63
    2,2,2-trifluoroethanol 17.43
    methyl butyrate 25.48

    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