Caffeoylmalic Acid

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  • Identifiers

    CAS number
    149197-97-7

    Molecular formula
    C13H12O8

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

  • Odor profile

    Fragrance
    Odorless 70.14%
    Sour 25.95%
    Savory 24.84%
    Burnt 24.48%
    Milky 21.75%
    Cooked 21.5%
    Caramellic 20.83%
    Balsamic 20.55%
    Roasted 20.42%
    Clean 17.69%

     

    Flavor
    Odorless 63.99%
    Very mild 40.0%
    Mild 33.27%
    Bland 27.56%
    Sour 26.15%
    Faint 23.29%
    Yeast 22.26%
    Nutty 21.53%
    Sweet-like 21.29%
    Bitter 20.52%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    6.25 (neutral)

    Molecular weight
    296.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    540°C

    Flash point

    • 275.88 ˚C est.

  • Synonyms

    • Caffeoylmalic Acid
    • Coumaroyl malic acid
    • 2-O-Caffeoylmalic acid
    • 2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
    • 8EY7S5QS7D
    • 149197-97-7
    • 92344-57-5
    • 2-((3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)butanedioic acid
    • Butanedioic acid, ((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-
    • 2-(((2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)butanedioic acid
    • Butanedioic acid, 2-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-
    • Butanedioic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-
    • 2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
    • (-)-Phaselic acid
    • 2-((3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioate
    • 2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioate
    • 2-(((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioic acid
    • 2-((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxybutanedioic acid
    • Phaseolic acid?
    • (S)-Phaselic acid
    • UNII-8EY7S5QS7D
    • CHEMBL393293
    • 2-O-(trans-caffeoyl)malic acid
    • SCHEMBL19894754
    • CHEBI:169040
    • DTXSID301031926
    • AKOS040734961
    • Q18379746
    • (E)-2-((3-(3,4-Dihydroxyphenyl)acryloyl)oxy)succinicacid
    • (E)-2-((3-(3,4-Dihydroxyphenyl)acryloyl)oxy)succinic acid

  • Applications

    Caffeoylmalic Acid (CAS 149197-97-7) is a naturally occurring hydroxycinnamate ester that is typically valued as an antioxidant precursor and a synthetic intermediate. In cosmetics and personal care, it is commonly evaluated as an antioxidant/stabilizer additive to extend product shelf life and protect sensitive ingredients. In polymer and coating formulations, it is studied as a potential UV-absorbing or radical-scavenging additive to improve light stability and longevity. As a chemical building block, it serves as an intermediate for the preparation of more complex caffeic acid derivatives used in specialty chemicals. In analytical and process development, it is used as a reference material or starting point in natural-product isolation and green-chemistry routes. Subject to local regulations and formulation limits, its use is context-dependent.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 189.94
    methanol 266.5
    isopropanol 117.57
    water 11.71
    ethyl acetate 14.07
    n-propanol 112.5
    acetone 224.64
    n-butanol 46.87
    acetonitrile 28.79
    DMF 579.58
    toluene 0.73
    isobutanol 31.37
    1,4-dioxane 133.2
    methyl acetate 47.96
    THF 400.32
    2-butanone 81.73
    n-pentanol 26.25
    sec-butanol 70.58
    n-hexane 0.23
    ethylene glycol 154.31
    NMP 153.99
    cyclohexane 0.32
    DMSO 1538.95
    n-butyl acetate 3.28
    n-octanol 5.55
    chloroform 0.49
    n-propyl acetate 8.64
    acetic acid 80.79
    dichloromethane 1.06
    cyclohexanone 25.87
    propylene glycol 109.64
    isopropyl acetate 6.36
    DMAc 589.6
    2-ethoxyethanol 318.19
    isopentanol 24.06
    n-heptane 0.32
    ethyl formate 22.08
    1,2-dichloroethane 3.03
    n-hexanol 6.41
    2-methoxyethanol 669.41
    isobutyl acetate 1.61
    tetrachloromethane 0.13
    n-pentyl acetate 2.55
    transcutol 74.34
    n-heptanol 5.54
    ethylbenzene 0.75
    MIBK 8.43
    2-propoxyethanol 72.72
    tert-butanol 127.98
    MTBE 28.52
    2-butoxyethanol 30.47
    propionic acid 33.7
    o-xylene 1.05
    formic acid 160.99
    diethyl ether 26.68
    m-xylene 0.49
    p-xylene 0.85
    chlorobenzene 0.26
    dimethyl carbonate 25.39
    n-octane 0.23
    formamide 449.39
    cyclopentanone 82.3
    2-pentanone 27.97
    anisole 10.45
    cyclopentyl methyl ether 21.37
    gamma-butyrolactone 77.56
    1-methoxy-2-propanol 250.66
    pyridine 21.16
    3-pentanone 16.82
    furfural 34.35
    n-dodecane 0.24
    diethylene glycol 104.83
    diisopropyl ether 2.42
    tert-amyl alcohol 74.18
    acetylacetone 34.69
    n-hexadecane 0.27
    acetophenone 7.78
    methyl propionate 26.98
    isopentyl acetate 2.45
    trichloroethylene 2.11
    n-nonanol 5.83
    cyclohexanol 15.85
    benzyl alcohol 12.5
    2-ethylhexanol 2.3
    isooctanol 3.39
    dipropyl ether 9.47
    1,2-dichlorobenzene 0.28
    ethyl lactate 11.61
    propylene carbonate 9.2
    n-methylformamide 252.69
    2-pentanol 18.34
    n-pentane 0.26
    1-propoxy-2-propanol 29.01
    1-methoxy-2-propyl acetate 8.25
    2-(2-methoxypropoxy) propanol 28.37
    mesitylene 0.39
    ε-caprolactone 20.72
    p-cymene 0.49
    epichlorohydrin 86.24
    1,1,1-trichloroethane 0.55
    2-aminoethanol 229.65
    morpholine-4-carbaldehyde 173.35
    sulfolane 113.08
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 71.67
    n-hexyl acetate 4.07
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 42.94
    sec-butyl acetate 3.6
    tert-butyl acetate 8.92
    decalin 0.16
    glycerin 184.25
    diglyme 89.72
    acrylic acid 29.72
    isopropyl myristate 2.3
    n-butyric acid 18.05
    acetyl acetate 4.76
    di(2-ethylhexyl) phthalate 2.45
    ethyl propionate 8.55
    nitromethane 233.05
    1,2-diethoxyethane 17.02
    benzonitrile 2.16
    trioctyl phosphate 2.35
    1-bromopropane 1.37
    gamma-valerolactone 132.27
    n-decanol 4.73
    triethyl phosphate 3.22
    4-methyl-2-pentanol 5.13
    propionitrile 13.4
    vinylene carbonate 6.08
    1,1,2-trichlorotrifluoroethane 36.01
    DMS 4.5
    cumene 0.52
    2-octanol 3.14
    2-hexanone 14.84
    octyl acetate 3.74
    limonene 0.77
    1,2-dimethoxyethane 291.65
    ethyl orthosilicate 3.23
    tributyl phosphate 2.28
    diacetone alcohol 40.86
    N,N-dimethylaniline 7.39
    acrylonitrile 18.13
    aniline 6.47
    1,3-propanediol 211.93
    bromobenzene 0.14
    dibromomethane 0.5
    1,1,2,2-tetrachloroethane 2.89
    2-methyl-cyclohexyl acetate 2.81
    tetrabutyl urea 6.62
    diisobutyl methanol 1.65
    2-phenylethanol 4.85
    styrene 0.76
    dioctyl adipate 4.22
    dimethyl sulfate 44.35
    ethyl butyrate 4.1
    methyl lactate 38.85
    butyl lactate 4.59
    diethyl carbonate 3.08
    propanediol butyl ether 20.82
    triethyl orthoformate 4.97
    p-tert-butyltoluene 0.5
    methyl 4-tert-butylbenzoate 8.39
    morpholine 215.09
    tert-butylamine 22.71
    n-dodecanol 3.66
    dimethoxymethane 281.45
    ethylene carbonate 6.36
    cyrene 33.14
    2-ethoxyethyl acetate 6.21
    2-ethylhexyl acetate 1.52
    1,2,4-trichlorobenzene 0.63
    4-methylpyridine 11.11
    dibutyl ether 5.25
    2,6-dimethyl-4-heptanol 1.65
    DEF 49.54
    dimethyl isosorbide 28.35
    tetrachloroethylene 1.38
    eugenol 10.27
    triacetin 5.39
    span 80 13.05
    1,4-butanediol 84.0
    1,1-dichloroethane 1.03
    2-methyl-1-pentanol 12.62
    methyl formate 140.93
    2-methyl-1-butanol 24.82
    n-decane 0.4
    butyronitrile 9.4
    3,7-dimethyl-1-octanol 2.87
    1-chlorooctane 0.97
    1-chlorotetradecane 0.55
    n-nonane 0.34
    undecane 0.3
    tert-butylcyclohexane 0.11
    cyclooctane 0.13
    cyclopentanol 40.5
    tetrahydropyran 45.84
    tert-amyl methyl ether 21.26
    2,5,8-trioxanonane 72.82
    1-hexene 1.16
    2-isopropoxyethanol 92.25
    2,2,2-trifluoroethanol 29.75
    methyl butyrate 13.03

    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