Caftaric Acid

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  • Identifiers

    CAS number
    67879-58-7

    Molecular formula
    C13H12O9

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

  • Odor profile

    Fragrance
    Odorless 70.55%
    Savory 25.22%
    Caramellic 24.67%
    Burnt 24.22%
    Sour 22.9%
    Milky 22.08%
    Cooked 20.4%
    Balsamic 18.91%
    Roasted 18.16%
    Clean 17.73%

     

    Flavor
    Odorless 62.78%
    Very mild 40.03%
    Bland 29.85%
    Mild 29.5%
    Bitter 26.38%
    Sweet-like 22.3%
    Yeast 21.54%
    Sour 21.12%
    Faint 20.25%
    Caramellic 20.25%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.1

    pKa est.
    5.1 (weak acid)

    Molecular weight
    312.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 125 °C

    Boiling point

    • 618.2 °C at 760 mmHg

    Flash point

    • 274.84 ˚C est.

  • Synonyms

    • caftaric acid
    • 67879-58-7
    • CAFFEOYLTARTARICACID
    • UNII-WCV7W3174L
    • (2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid
    • WCV7W3174L
    • trans-caftaric acid
    • CAFTARIC ACID [USP-RS]
    • 1234-09-9
    • DTXSID3036866
    • Butanedioic acid, 2-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-3-hydroxy-, (R-(R*,R*-(E)))-
    • Butanedioic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3-hydroxy-, (2R,3R)-
    • CAFTARIC ACID (USP-RS)
    • (2R,3R)-2-(((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOYL)OXY)-3-HYDROXYSUCCINIC ACID
    • (2R,3R)-2-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-3-hydroxysuccinic acid
    • (2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
    • Caftarate
    • (R*,R*)-2-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-butanoic acid
    • [R*,R*]-2-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-butanoic acid
    • (2R,3R)-2-(((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)-3-hydroxybutanedioate
    • (2R,3R)-2-(((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)-3-hydroxybutanedioic acid
    • (2R,3R)-2-((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy-3-hydroxybutanedioic acid
    • (2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioate
    • Butanedioic acid, 2-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3-hydroxy-, (2R,3R)-
    • Butanedioic acid, 2-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3-hydroxy-, (2R,3R)- (9CI); Butanedioic acid, 2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3-hydroxy-, [R-[R*,R*-(E)]]-; (2R,3R)-2-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3-hydroxybutanedioic acid; trans-Caftaric acid
    • MFCD02094177
    • trans-Caffeoyl tartarate
    • Caftaric acid (Standard)
    • Caftaric acid , HPLC Grade
    • Caftaric acid, >=97.0%
    • CHEMBL558557
    • SCHEMBL16426394
    • HY-N0321R
    • DTXCID50819886
    • CHEBI:174975
    • Caftaric acid, analytical standard
    • HY-N0321
    • s3308
    • AKOS022175477
    • FC65459
    • (2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxy-butanedioic acid
    • AC-34146
    • AS-79234
    • NS00036250
    • Q5017207
    • Caftaric acid, United States Pharmacopeia (USP) Reference Standard
    • Mono-(3,4-dihydroxycinnamoyl)-tartaric acid;Caffeoyltartaric acid
    • (2R,3R)-2-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
    • 614-155-2
    • CAFTARIC ACID (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS)

  • Applications

    Caftaric acid, a grape-derived hydroxycinnamic acid ester, is used primarily in research and formulation contexts as a natural antioxidant precursor and as a substrate for polyphenol oxidase in enzymatic browning studies; in the food and beverage sector, it is examined for antioxidant activity and its role in grape-derived products; in cosmetics and personal care, it is evaluated as a polyphenol-based antioxidant ingredient for skin care formulations; in pharmaceutical/nutrition research, it serves as an intermediate for the synthesis of related polyphenolic esters and as a model compound for antioxidant testing; in analytical/biochemical applications, it is used as a substrate in PPO activity assays and enzymatic kinetics; in coatings/inks or polymers, it may be explored as a bio-based phenolic additive or precursor to polymer materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 321.51
    methanol 426.04
    isopropanol 237.24
    water 39.68
    ethyl acetate 32.69
    n-propanol 238.51
    acetone 343.5
    n-butanol 97.35
    acetonitrile 47.8
    DMF 692.98
    toluene 3.14
    isobutanol 72.2
    1,4-dioxane 186.19
    methyl acetate 73.06
    THF 545.68
    2-butanone 131.54
    n-pentanol 46.15
    sec-butanol 144.03
    n-hexane 0.83
    ethylene glycol 427.26
    NMP 215.78
    cyclohexane 1.93
    DMSO 2476.97
    n-butyl acetate 4.33
    n-octanol 10.25
    chloroform 0.83
    n-propyl acetate 10.69
    acetic acid 167.27
    dichloromethane 1.76
    cyclohexanone 43.36
    propylene glycol 276.67
    isopropyl acetate 14.34
    DMAc 651.6
    2-ethoxyethanol 459.73
    isopentanol 47.01
    n-heptane 1.61
    ethyl formate 31.57
    1,2-dichloroethane 5.84
    n-hexanol 16.37
    2-methoxyethanol 1061.78
    isobutyl acetate 1.76
    tetrachloromethane 0.39
    n-pentyl acetate 3.88
    transcutol 88.2
    n-heptanol 11.57
    ethylbenzene 1.76
    MIBK 15.71
    2-propoxyethanol 102.49
    tert-butanol 276.86
    MTBE 57.19
    2-butoxyethanol 46.5
    propionic acid 73.64
    o-xylene 3.52
    formic acid 351.15
    diethyl ether 63.35
    m-xylene 1.79
    p-xylene 1.58
    chlorobenzene 0.56
    dimethyl carbonate 44.32
    n-octane 0.95
    formamide 813.8
    cyclopentanone 132.35
    2-pentanone 60.36
    anisole 12.22
    cyclopentyl methyl ether 53.74
    gamma-butyrolactone 123.52
    1-methoxy-2-propanol 437.09
    pyridine 40.47
    3-pentanone 36.53
    furfural 42.77
    n-dodecane 0.69
    diethylene glycol 166.97
    diisopropyl ether 6.7
    tert-amyl alcohol 143.34
    acetylacetone 61.13
    n-hexadecane 0.75
    acetophenone 9.45
    methyl propionate 57.77
    isopentyl acetate 3.0
    trichloroethylene 3.51
    n-nonanol 10.33
    cyclohexanol 47.37
    benzyl alcohol 18.28
    2-ethylhexanol 4.77
    isooctanol 6.24
    dipropyl ether 19.03
    1,2-dichlorobenzene 0.44
    ethyl lactate 15.7
    propylene carbonate 11.73
    n-methylformamide 380.64
    2-pentanol 51.12
    n-pentane 1.5
    1-propoxy-2-propanol 43.39
    1-methoxy-2-propyl acetate 11.4
    2-(2-methoxypropoxy) propanol 29.59
    mesitylene 1.14
    ε-caprolactone 32.28
    p-cymene 1.04
    epichlorohydrin 112.81
    1,1,1-trichloroethane 1.2
    2-aminoethanol 516.76
    morpholine-4-carbaldehyde 213.7
    sulfolane 182.66
    2,2,4-trimethylpentane 0.57
    2-methyltetrahydrofuran 139.75
    n-hexyl acetate 5.38
    isooctane 0.23
    2-(2-butoxyethoxy)ethanol 53.84
    sec-butyl acetate 4.69
    tert-butyl acetate 16.7
    decalin 0.48
    glycerin 416.27
    diglyme 101.95
    acrylic acid 64.34
    isopropyl myristate 3.05
    n-butyric acid 39.55
    acetyl acetate 9.35
    di(2-ethylhexyl) phthalate 2.28
    ethyl propionate 12.43
    nitromethane 353.92
    1,2-diethoxyethane 20.81
    benzonitrile 2.72
    trioctyl phosphate 3.03
    1-bromopropane 3.48
    gamma-valerolactone 165.33
    n-decanol 8.36
    triethyl phosphate 3.41
    4-methyl-2-pentanol 11.64
    propionitrile 23.71
    vinylene carbonate 7.23
    1,1,2-trichlorotrifluoroethane 59.53
    DMS 5.52
    cumene 0.98
    2-octanol 6.31
    2-hexanone 16.63
    octyl acetate 5.26
    limonene 1.92
    1,2-dimethoxyethane 286.39
    ethyl orthosilicate 3.66
    tributyl phosphate 2.25
    diacetone alcohol 71.4
    N,N-dimethylaniline 9.79
    acrylonitrile 28.13
    aniline 18.58
    1,3-propanediol 412.2
    bromobenzene 0.35
    dibromomethane 0.97
    1,1,2,2-tetrachloroethane 5.05
    2-methyl-cyclohexyl acetate 3.04
    tetrabutyl urea 7.14
    diisobutyl methanol 3.07
    2-phenylethanol 7.8
    styrene 1.67
    dioctyl adipate 4.62
    dimethyl sulfate 63.11
    ethyl butyrate 5.22
    methyl lactate 74.05
    butyl lactate 5.97
    diethyl carbonate 3.31
    propanediol butyl ether 30.13
    triethyl orthoformate 5.53
    p-tert-butyltoluene 1.12
    methyl 4-tert-butylbenzoate 9.77
    morpholine 328.72
    tert-butylamine 60.86
    n-dodecanol 6.68
    dimethoxymethane 399.81
    ethylene carbonate 8.03
    cyrene 37.43
    2-ethoxyethyl acetate 8.59
    2-ethylhexyl acetate 1.89
    1,2,4-trichlorobenzene 0.96
    4-methylpyridine 18.46
    dibutyl ether 7.79
    2,6-dimethyl-4-heptanol 3.07
    DEF 85.01
    dimethyl isosorbide 27.32
    tetrachloroethylene 2.99
    eugenol 11.19
    triacetin 6.37
    span 80 16.56
    1,4-butanediol 152.91
    1,1-dichloroethane 2.39
    2-methyl-1-pentanol 19.53
    methyl formate 195.27
    2-methyl-1-butanol 51.78
    n-decane 1.14
    butyronitrile 14.48
    3,7-dimethyl-1-octanol 4.4
    1-chlorooctane 2.06
    1-chlorotetradecane 1.15
    n-nonane 1.08
    undecane 0.87
    tert-butylcyclohexane 0.3
    cyclooctane 0.76
    cyclopentanol 114.89
    tetrahydropyran 95.44
    tert-amyl methyl ether 44.81
    2,5,8-trioxanonane 78.87
    1-hexene 2.8
    2-isopropoxyethanol 128.94
    2,2,2-trifluoroethanol 62.73
    methyl butyrate 16.06

    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