cis-Coutaric acid

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  • Identifiers

    CAS number
    67920-37-0

    Molecular formula
    C13H12O8

    SMILES
    C1=CC(=CC=C1/C=C\C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 52.02%
    Caramellic 32.75%
    Sour 27.95%
    Burnt 27.21%
    Balsamic 26.64%
    Sweet 25.35%
    Fruity 24.67%
    Savory 23.49%
    Winey 23.25%
    Cooked 23.14%

     

    Flavor
    Odorless 61.04%
    Very mild 39.56%
    Mild 29.58%
    Bland 26.86%
    Sour 22.89%
    Bitter 22.3%
    Faint 22.01%
    Yeast 21.66%
    Sweet-like 21.21%
    Caramellic 20.37%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    4.72 (weak acid)

    Molecular weight
    296.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    588°C

    Flash point

    • 258.26 ˚C est.

  • Synonyms

    • cis-coutaric acid
    • 67920-37-0
    • cis-p-Coumaroyltartaric acid
    • cis-Coutarate
    • 2-Hydroxy-3-(((2Z)-3-(4-hydroxyphenyl)prop-2-enoyl)oxy)butanedioate
    • 2-Hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioate
    • RefChem:126439
    • DTXSID201316428
    • (2R,3R)-2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
    • 67920-37-0

  • Applications

    cis-Coutaric acid (CAS 67920-37-0) is a multifunctional dicarboxylic acid used primarily as an intermediate in organic synthesis and as a building block for specialty polymers and resins. In industry it may be used as a co-monomer or crosslinking component for coatings and polyester polymers; as a chelating agent or formulation additive in cleaning products and protective coatings; as a reactive building block in pharmaceutical synthesis; and it may be evaluated for cosmetic/personal care applications as a chelating agent or pH modifier, subject to regulatory requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 168.05
    methanol 264.93
    isopropanol 125.29
    water 10.05
    ethyl acetate 32.23
    n-propanol 127.2
    acetone 245.88
    n-butanol 58.55
    acetonitrile 41.76
    DMF 492.54
    toluene 2.18
    isobutanol 40.75
    1,4-dioxane 127.06
    methyl acetate 73.86
    THF 336.44
    2-butanone 102.89
    n-pentanol 30.66
    sec-butanol 82.54
    n-hexane 0.42
    ethylene glycol 226.07
    NMP 148.6
    cyclohexane 0.8
    DMSO 1141.08
    n-butyl acetate 4.52
    n-octanol 5.55
    chloroform 0.72
    n-propyl acetate 10.97
    acetic acid 115.39
    dichloromethane 1.4
    cyclohexanone 31.61
    propylene glycol 173.5
    isopropyl acetate 14.0
    DMAc 557.99
    2-ethoxyethanol 320.18
    isopentanol 32.4
    n-heptane 0.83
    ethyl formate 24.27
    1,2-dichloroethane 4.65
    n-hexanol 10.81
    2-methoxyethanol 742.74
    isobutyl acetate 2.19
    tetrachloromethane 0.25
    n-pentyl acetate 3.21
    transcutol 85.41
    n-heptanol 7.35
    ethylbenzene 1.6
    MIBK 13.34
    2-propoxyethanol 89.59
    tert-butanol 142.28
    MTBE 33.93
    2-butoxyethanol 37.51
    propionic acid 51.28
    o-xylene 2.69
    formic acid 222.19
    diethyl ether 36.33
    m-xylene 1.46
    p-xylene 1.57
    chlorobenzene 0.59
    dimethyl carbonate 42.13
    n-octane 0.49
    formamide 560.03
    cyclopentanone 89.65
    2-pentanone 46.24
    anisole 12.6
    cyclopentyl methyl ether 37.23
    gamma-butyrolactone 86.94
    1-methoxy-2-propanol 326.07
    pyridine 30.76
    3-pentanone 29.08
    furfural 36.35
    n-dodecane 0.42
    diethylene glycol 139.49
    diisopropyl ether 4.79
    tert-amyl alcohol 86.36
    acetylacetone 58.28
    n-hexadecane 0.46
    acetophenone 10.18
    methyl propionate 50.73
    isopentyl acetate 3.38
    trichloroethylene 3.41
    n-nonanol 6.12
    cyclohexanol 27.39
    benzyl alcohol 16.64
    2-ethylhexanol 3.83
    isooctanol 4.5
    dipropyl ether 13.35
    1,2-dichlorobenzene 0.55
    ethyl lactate 16.02
    propylene carbonate 11.38
    n-methylformamide 263.33
    2-pentanol 29.28
    n-pentane 0.58
    1-propoxy-2-propanol 36.4
    1-methoxy-2-propyl acetate 13.39
    2-(2-methoxypropoxy) propanol 30.47
    mesitylene 1.06
    ε-caprolactone 27.13
    p-cymene 1.08
    epichlorohydrin 87.73
    1,1,1-trichloroethane 1.1
    2-aminoethanol 298.78
    morpholine-4-carbaldehyde 170.91
    sulfolane 114.27
    2,2,4-trimethylpentane 0.33
    2-methyltetrahydrofuran 90.31
    n-hexyl acetate 4.38
    isooctane 0.16
    2-(2-butoxyethoxy)ethanol 50.09
    sec-butyl acetate 5.56
    tert-butyl acetate 15.51
    decalin 0.37
    glycerin 280.92
    diglyme 93.62
    acrylic acid 46.72
    isopropyl myristate 2.59
    n-butyric acid 30.98
    acetyl acetate 10.8
    di(2-ethylhexyl) phthalate 2.56
    ethyl propionate 13.18
    nitromethane 301.12
    1,2-diethoxyethane 18.18
    benzonitrile 3.11
    trioctyl phosphate 2.49
    1-bromopropane 2.16
    gamma-valerolactone 125.08
    n-decanol 5.08
    triethyl phosphate 3.91
    4-methyl-2-pentanol 8.32
    propionitrile 20.77
    vinylene carbonate 7.62
    1,1,2-trichlorotrifluoroethane 49.45
    DMS 6.18
    cumene 1.05
    2-octanol 3.87
    2-hexanone 14.6
    octyl acetate 4.27
    limonene 1.74
    1,2-dimethoxyethane 212.24
    ethyl orthosilicate 4.12
    tributyl phosphate 2.31
    diacetone alcohol 58.97
    N,N-dimethylaniline 9.99
    acrylonitrile 27.4
    aniline 11.54
    1,3-propanediol 275.37
    bromobenzene 0.37
    dibromomethane 0.72
    1,1,2,2-tetrachloroethane 4.44
    2-methyl-cyclohexyl acetate 3.73
    tetrabutyl urea 6.78
    diisobutyl methanol 2.63
    2-phenylethanol 7.47
    styrene 1.61
    dioctyl adipate 4.47
    dimethyl sulfate 56.93
    ethyl butyrate 5.47
    methyl lactate 67.12
    butyl lactate 5.54
    diethyl carbonate 3.91
    propanediol butyl ether 23.89
    triethyl orthoformate 6.29
    p-tert-butyltoluene 1.13
    methyl 4-tert-butylbenzoate 9.94
    morpholine 218.26
    tert-butylamine 28.9
    n-dodecanol 4.07
    dimethoxymethane 296.64
    ethylene carbonate 8.28
    cyrene 39.27
    2-ethoxyethyl acetate 8.15
    2-ethylhexyl acetate 2.16
    1,2,4-trichlorobenzene 1.22
    4-methylpyridine 14.84
    dibutyl ether 5.43
    2,6-dimethyl-4-heptanol 2.63
    DEF 66.01
    dimethyl isosorbide 31.95
    tetrachloroethylene 2.41
    eugenol 11.7
    triacetin 7.28
    span 80 15.29
    1,4-butanediol 99.24
    1,1-dichloroethane 2.05
    2-methyl-1-pentanol 17.07
    methyl formate 149.96
    2-methyl-1-butanol 32.85
    n-decane 0.65
    butyronitrile 12.48
    3,7-dimethyl-1-octanol 3.25
    1-chlorooctane 1.31
    1-chlorotetradecane 0.79
    n-nonane 0.58
    undecane 0.51
    tert-butylcyclohexane 0.24
    cyclooctane 0.37
    cyclopentanol 63.8
    tetrahydropyran 59.42
    tert-amyl methyl ether 29.22
    2,5,8-trioxanonane 77.49
    1-hexene 1.8
    2-isopropoxyethanol 101.01
    2,2,2-trifluoroethanol 44.11
    methyl butyrate 15.84

    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