(-)-Chicoric acid

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  • Identifiers

    CAS number
    70831-56-0

    Molecular formula
    C22H18O12

    SMILES
    C1=CC(=C(C=C1/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC(=C(C=C2)O)O)C(=O)O)O)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 71.7%
    Balsamic 24.02%
    Savory 23.9%
    Burnt 22.82%
    Milky 19.8%
    Cooked 19.28%
    Sour 17.05%
    Caramellic 16.89%
    Phenolic 16.49%
    Bitter 16.13%

     

    Flavor
    Odorless 58.87%
    Bitter 51.44%
    Very mild 35.21%
    Bland 32.07%
    Mild 27.44%
    Sweet-like 22.2%
    Yeast 20.52%
    Faint 19.67%
    Nitrile 19.34%
    Ethyl benzoate 18.69%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    5.11 (weak acid)

    Molecular weight
    474.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    742°C

    Flash point

    • 312.64 ˚C est.

  • Synonyms

    • Chicoric acid
    • L-Chicoric acid
    • 70831-56-0
    • (-)-Chicoric acid
    • dicaffeoyltartaric acid
    • (-)-L-Chicoric acid
    • S4YY3V8YHD
    • NSC-699173
    • NSC-99173
    • RefChem:575494
    • GlyTouCan:G45391HQ
    • (2S,3S)-2,3-bis((((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy))butanedioic acid
    • G45391HQ
    • (2R,3R)-2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-butanedioic acid
    • 636-229-3
    • (2S,3S)-2,3-bis(((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioic acid
    • D-Chicoric acid
    • Cichoric Acid
    • 6537-80-0
    • (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
    • ChicoricAcid
    • L-Cichoric acid
    • NSC 699173
    • (2R,3R)-2,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid
    • L-DCTA
    • Chicoric acid, (-)-
    • NSC699173
    • Dicaffeoyl-L-tartaric acid
    • CHEMBL282731
    • DTXSID0033332
    • (2R,3R)-2,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid
    • 2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid
    • (R-(R*,R*-(E,E)))-2,3-Bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid
    • C22H18O12
    • (2R,3R)-2,3-Bis[[(E)-3-(3,4-dihydroxyphenyl)acryloyl]oxy]succinic Acid
    • (2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
    • MFCD22683653
    • Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)-
    • Dicaffeoyl tartaric acid
    • UNII-S4YY3V8YHD
    • L-Chicoricacid
    • 1-chicoricacid
    • Cichoric-Acid
    • l-Chicoric-acid
    • MFCD00189418
    • GKP
    • (-)-Chicoric acid;trans-Caffeoyltartaric acid
    • L-CA
    • trans-Caffeoyltartaric acid
    • (-)-CICHORIC ACID
    • CHEBI:3594
    • orb1300155
    • CHICORIC ACID [USP-RS]
    • DTXCID8013332
    • SCHEMBL15532218
    • SCHEMBL29349701
    • SCHEMBL29385936
    • (2R,3R)-2,3-bis{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
    • YDDGKXBLOXEEMN-IABMMNSOSA-N
    • GLXC-10979
    • GLXC-19344
    • Chicoric Acid, >=95% (HPLC)
    • HY-N0457
    • MSK40121
    • Tox21_201055
    • BDBM50076273
    • MSK181147
    • s9133
    • AKOS000278435
    • CCG-269487
    • CS-4262
    • EBC-618421
    • FC65730
    • (2R,3R)-2,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid
    • Butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (2R,3R)-
    • ( -)-Chicoric acid, analytical standard
    • NCGC00091914-01
    • NCGC00091914-02
    • NCGC00091914-04
    • NCGC00258608-01
    • AC-34315
    • AC-36990
    • AS-56447
    • Butanedioic acid, 2,3-bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*-(E,E)))-
    • DA-72145
    • DA-72146
    • SY076698
    • CAS-70831-56-0
    • C3450
    • NS00037116
    • D78144
    • 831C560
    • Q5119402
    • TARTARIC ACID, BIS(3,4-DIHYDROXYCINNAMATE)
    • Chicoric Acid, United States Pharmacopeia (USP) Reference Standard
    • (2R,3R)-2,3-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-succinic acid
    • [S-(R*,R*)]-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid
    • butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (2R,3R)-
    • Butanedioic acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*))-
    • Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)- (9CI)
    • Butanedioic acid, 2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [R-[R*,R*-(E,E)]]-
    • NCGC00091914-04!(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
    • 6537-80-0

  • Applications

    (-)-Chicoric acid (CAS 70831-56-0) is a natural polyphenol with reported occurrence in chicory and Echinacea. In industrial practice, it is primarily used as an analytical reference standard to quantify chicoric acid in plant extracts by HPLC and related analytical methods, supporting quality control of products. It is also investigated as a bioactive compound with antioxidant, anti-inflammatory, and antimicrobial potentials, making it a candidate for cosmetic and personal care formulations as an antioxidant ingredient and stabilizer. Additionally, chicoric acid is commonly evaluated in pharmaceuticals and pharmacological research as a plant-derived lead compound; it is also considered for nutritional supplements or dietary functional foods. In food technology, it may be used as a natural antioxidant depending on local regulations. Finally, it is used in agricultural research and for standardization of plant extract quality.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 101.72
    methanol 74.92
    isopropanol 86.2
    water 2.01
    ethyl acetate 30.21
    n-propanol 76.92
    acetone 265.72
    n-butanol 29.52
    acetonitrile 35.5
    DMF 403.9
    toluene 2.38
    isobutanol 22.57
    1,4-dioxane 158.66
    methyl acetate 86.81
    THF 634.49
    2-butanone 135.96
    n-pentanol 15.24
    sec-butanol 57.93
    n-hexane 0.42
    ethylene glycol 72.09
    NMP 206.57
    cyclohexane 0.95
    DMSO 2158.93
    n-butyl acetate 3.87
    n-octanol 5.39
    chloroform 3.13
    n-propyl acetate 9.05
    acetic acid 142.06
    dichloromethane 5.69
    cyclohexanone 40.59
    propylene glycol 83.3
    isopropyl acetate 11.57
    DMAc 508.99
    2-ethoxyethanol 188.15
    isopentanol 10.98
    n-heptane 0.52
    ethyl formate 24.44
    1,2-dichloroethane 10.0
    n-hexanol 4.17
    2-methoxyethanol 414.5
    isobutyl acetate 1.4
    tetrachloromethane 0.62
    n-pentyl acetate 3.69
    transcutol 65.75
    n-heptanol 4.48
    ethylbenzene 0.9
    MIBK 6.7
    2-propoxyethanol 49.28
    tert-butanol 62.13
    MTBE 29.2
    2-butoxyethanol 22.59
    propionic acid 55.98
    o-xylene 1.66
    formic acid 106.25
    diethyl ether 38.66
    m-xylene 0.84
    p-xylene 0.96
    chlorobenzene 0.73
    dimethyl carbonate 32.11
    n-octane 0.34
    formamide 275.48
    cyclopentanone 153.19
    2-pentanone 39.57
    anisole 7.44
    cyclopentyl methyl ether 37.18
    gamma-butyrolactone 152.03
    1-methoxy-2-propanol 176.24
    pyridine 54.15
    3-pentanone 27.91
    furfural 43.05
    n-dodecane 0.27
    diethylene glycol 53.19
    diisopropyl ether 2.95
    tert-amyl alcohol 45.33
    acetylacetone 48.74
    n-hexadecane 0.31
    acetophenone 6.18
    methyl propionate 46.53
    isopentyl acetate 1.94
    trichloroethylene 8.68
    n-nonanol 5.52
    cyclohexanol 19.62
    benzyl alcohol 8.34
    2-ethylhexanol 1.29
    isooctanol 2.29
    dipropyl ether 10.48
    1,2-dichlorobenzene 0.42
    ethyl lactate 7.92
    propylene carbonate 12.94
    n-methylformamide 171.7
    2-pentanol 14.69
    n-pentane 0.71
    1-propoxy-2-propanol 24.93
    1-methoxy-2-propyl acetate 8.61
    2-(2-methoxypropoxy) propanol 16.07
    mesitylene 0.43
    ε-caprolactone 33.29
    p-cymene 0.33
    epichlorohydrin 136.01
    1,1,1-trichloroethane 2.61
    2-aminoethanol 114.31
    morpholine-4-carbaldehyde 165.9
    sulfolane 226.12
    2,2,4-trimethylpentane 0.18
    2-methyltetrahydrofuran 128.65
    n-hexyl acetate 4.99
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 29.18
    sec-butyl acetate 3.76
    tert-butyl acetate 10.02
    decalin 0.15
    glycerin 119.38
    diglyme 67.57
    acrylic acid 48.94
    isopropyl myristate 2.11
    n-butyric acid 26.3
    acetyl acetate 8.79
    di(2-ethylhexyl) phthalate 1.17
    ethyl propionate 9.88
    nitromethane 322.91
    1,2-diethoxyethane 19.17
    benzonitrile 2.0
    trioctyl phosphate 1.55
    1-bromopropane 4.49
    gamma-valerolactone 188.48
    n-decanol 4.1
    triethyl phosphate 1.92
    4-methyl-2-pentanol 2.84
    propionitrile 14.32
    vinylene carbonate 8.28
    1,1,2-trichlorotrifluoroethane 49.42
    DMS 4.83
    cumene 0.4
    2-octanol 2.97
    2-hexanone 12.22
    octyl acetate 3.79
    limonene 0.66
    1,2-dimethoxyethane 168.92
    ethyl orthosilicate 2.05
    tributyl phosphate 1.34
    diacetone alcohol 29.34
    N,N-dimethylaniline 4.22
    acrylonitrile 19.63
    aniline 11.51
    1,3-propanediol 122.79
    bromobenzene 0.46
    dibromomethane 2.82
    1,1,2,2-tetrachloroethane 9.77
    2-methyl-cyclohexyl acetate 1.61
    tetrabutyl urea 4.4
    diisobutyl methanol 0.9
    2-phenylethanol 2.79
    styrene 1.11
    dioctyl adipate 3.17
    dimethyl sulfate 56.69
    ethyl butyrate 4.13
    methyl lactate 38.56
    butyl lactate 4.03
    diethyl carbonate 2.25
    propanediol butyl ether 16.58
    triethyl orthoformate 4.06
    p-tert-butyltoluene 0.38
    methyl 4-tert-butylbenzoate 4.75
    morpholine 272.74
    tert-butylamine 15.53
    n-dodecanol 2.99
    dimethoxymethane 222.94
    ethylene carbonate 8.66
    cyrene 18.08
    2-ethoxyethyl acetate 8.93
    2-ethylhexyl acetate 1.18
    1,2,4-trichlorobenzene 0.98
    4-methylpyridine 19.12
    dibutyl ether 6.21
    2,6-dimethyl-4-heptanol 0.9
    DEF 51.16
    dimethyl isosorbide 14.11
    tetrachloroethylene 4.39
    eugenol 4.42
    triacetin 5.36
    span 80 9.94
    1,4-butanediol 37.65
    1,1-dichloroethane 5.08
    2-methyl-1-pentanol 6.01
    methyl formate 113.02
    2-methyl-1-butanol 14.51
    n-decane 0.51
    butyronitrile 8.18
    3,7-dimethyl-1-octanol 1.93
    1-chlorooctane 1.32
    1-chlorotetradecane 0.59
    n-nonane 0.46
    undecane 0.36
    tert-butylcyclohexane 0.09
    cyclooctane 0.27
    cyclopentanol 63.15
    tetrahydropyran 88.15
    tert-amyl methyl ether 20.9
    2,5,8-trioxanonane 43.6
    1-hexene 1.59
    2-isopropoxyethanol 54.82
    2,2,2-trifluoroethanol 44.32
    methyl butyrate 12.27

    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