1,5-O-Trans-Dicaffeoylquinic Acid

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  • Identifiers

    CAS number
    19870-46-3

    Molecular formula
    C25H24O12

    SMILES
    C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O

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  • Odor profile

    Fragrance
    Odorless 77.25%
    Balsamic 25.22%
    Savory 23.46%
    Vanilla 23.44%
    Milky 21.81%
    Burnt 21.4%
    Phenolic 20.54%
    Spicy 19.46%
    Bitter 17.37%
    Dairy 15.74%

     

    Flavor
    Bitter 73.31%
    Odorless 48.43%
    Bland 32.88%
    Very mild 28.74%
    Sweet-like 23.13%
    Mild 22.36%
    Nitrile 19.36%
    Lovage 19.15%
    Ethyl benzoate 19.11%
    Parsley 18.98%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    7.4 (neutral)

    Molecular weight
    516.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1390°C

    Flash point

    • 319.59 ˚C est.

  • Synonyms

    • 1,5-O-trans-dicaffeoylquinic acid
    • (1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
    • (1S,3R,4R,5R)-1,3-bis(((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic acid
    • RefChem:1053472
    • 19870-46-3
    • 1,3-O-Dicaffeoylquinic acid
    • 1,3-Dicaffeoylquinic acid
    • Dicaffeoylquininic acid
    • MFCD13196505
    • 1,3-di-O-Caffeoylquinic acid
    • 1,5-Dicaffeoylquinic-acid
    • 251320-66-8
    • Cyclohexanecarboxylic acid,1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-,(1S,3R,4R,5R)-
    • (1S,3R,4R,5R)-1,3-BIS({[(2E)-3-(3,4-DIHYDROXYPHENYL)PROP-2-ENOYL]OXY})-4,5-DIHYDROXYCYCLOHEXANE-1-CARBOXYLIC ACID
    • (1S,3R,4R,5R)-1,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic acid
    • (1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxy-cyclohexanecarboxylic acid
    • 1,5-DCQA
    • 1,3-di-caffeoylquinic acid
    • 1,3-O-Dicaffeoylquinicacid
    • 1,5-Dicaffeoylquinic acid?
    • 1,3-O-di-caffeoylquinic acid
    • 1,3-O-dicaffeoyl-quinic acid
    • CHEMBL478574
    • orb1301539
    • 1,3-dicaffeoyl-epi-quinic acid
    • SCHEMBL20886514
    • SCHEMBL29531475
    • HY-N1412R
    • GLXC-05970
    • HMS6018M11
    • HY-N1412
    • MSK40231
    • BDBM50455379
    • s9512
    • 1,3-Dicaffeoylquinic acid (Standard)
    • AKOS016011057
    • CS-6268
    • EBC-615599
    • FD64833
    • AC-34182
    • AS-74956
    • DA-49020
    • SY232472
    • 1,5-Dicaffeoylquinic acid, >=98% (HPLC)
    • 1,5-Dicaffeoylquinic acid, analytical standard
    • F21510
    • 870D463
    • BRD-K53083666-001-01-0
    • 1,5-Dicaffeoylquinic acid1,5-Dicaffeoylquinic acid; Cynarin; Dicaffeoylquininic acid
    • 19870-46-3

  • Applications

    Chemical name: 1,5-O-Trans-Dicaffeoylquinic Acid; CAS number: 19870-46-3. 1,5-O-Trans-Dicaffeoylquinic acid is a polyphenolic ester of quinic acid with two caffeoyl groups and is primarily used as a natural antioxidant and stabilizer in cosmetics and personal care formulations to protect products from oxidative degradation; it is also evaluated as an antioxidant additive in food processing and packaging to retard lipid oxidation; it can serve as an intermediate or starting material for the synthesis of caffeoylquinic acid derivatives used in pharmaceuticals and nutraceuticals; it may function as a stabilizer in polymers and coatings to improve aging resistance; and it is commonly explored as an intermediate in the synthesis of related polyphenol compounds in industrial settings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 448.19
    methanol 384.0
    isopropanol 258.19
    water 4.96
    ethyl acetate 86.67
    n-propanol 251.68
    acetone 830.75
    n-butanol 98.35
    acetonitrile 90.17
    DMF 925.37
    toluene 3.99
    isobutanol 66.04
    1,4-dioxane 439.49
    methyl acetate 151.45
    THF 1607.98
    2-butanone 293.65
    n-pentanol 45.85
    sec-butanol 135.02
    n-hexane 0.43
    ethylene glycol 234.61
    NMP 357.35
    cyclohexane 1.09
    DMSO 4392.59
    n-butyl acetate 6.97
    n-octanol 14.88
    chloroform 7.92
    n-propyl acetate 19.63
    acetic acid 560.93
    dichloromethane 13.59
    cyclohexanone 114.49
    propylene glycol 266.04
    isopropyl acetate 31.75
    DMAc 774.9
    2-ethoxyethanol 477.95
    isopentanol 30.66
    n-heptane 0.63
    ethyl formate 74.68
    1,2-dichloroethane 21.21
    n-hexanol 11.05
    2-methoxyethanol 1146.39
    isobutyl acetate 3.26
    tetrachloromethane 1.0
    n-pentyl acetate 10.58
    transcutol 164.71
    n-heptanol 11.96
    ethylbenzene 1.27
    MIBK 22.29
    2-propoxyethanol 118.42
    tert-butanol 136.76
    MTBE 49.7
    2-butoxyethanol 56.52
    propionic acid 137.62
    o-xylene 2.22
    formic acid 387.65
    diethyl ether 96.02
    m-xylene 1.38
    p-xylene 1.21
    chlorobenzene 1.55
    dimethyl carbonate 79.31
    n-octane 0.49
    formamide 728.91
    cyclopentanone 390.11
    2-pentanone 128.06
    anisole 13.57
    cyclopentyl methyl ether 75.67
    gamma-butyrolactone 353.28
    1-methoxy-2-propanol 506.3
    pyridine 105.56
    3-pentanone 64.44
    furfural 99.19
    n-dodecane 0.39
    diethylene glycol 136.42
    diisopropyl ether 5.4
    tert-amyl alcohol 81.46
    acetylacetone 177.59
    n-hexadecane 0.43
    acetophenone 11.91
    methyl propionate 114.18
    isopentyl acetate 3.48
    trichloroethylene 20.73
    n-nonanol 14.63
    cyclohexanol 41.03
    benzyl alcohol 18.53
    2-ethylhexanol 2.49
    isooctanol 5.37
    dipropyl ether 17.97
    1,2-dichlorobenzene 0.8
    ethyl lactate 19.17
    propylene carbonate 36.6
    n-methylformamide 456.22
    2-pentanol 39.27
    n-pentane 1.0
    1-propoxy-2-propanol 51.98
    1-methoxy-2-propyl acetate 20.25
    2-(2-methoxypropoxy) propanol 34.59
    mesitylene 0.68
    ε-caprolactone 82.12
    p-cymene 0.47
    epichlorohydrin 312.52
    1,1,1-trichloroethane 4.81
    2-aminoethanol 329.57
    morpholine-4-carbaldehyde 356.89
    sulfolane 470.44
    2,2,4-trimethylpentane 0.19
    2-methyltetrahydrofuran 242.68
    n-hexyl acetate 13.37
    isooctane 0.07
    2-(2-butoxyethoxy)ethanol 72.39
    sec-butyl acetate 7.89
    tert-butyl acetate 25.14
    decalin 0.16
    glycerin 348.4
    diglyme 141.26
    acrylic acid 122.55
    isopropyl myristate 4.93
    n-butyric acid 93.16
    acetyl acetate 26.75
    di(2-ethylhexyl) phthalate 2.95
    ethyl propionate 20.88
    nitromethane 894.45
    1,2-diethoxyethane 44.51
    benzonitrile 4.59
    trioctyl phosphate 3.83
    1-bromopropane 8.61
    gamma-valerolactone 507.95
    n-decanol 10.25
    triethyl phosphate 2.83
    4-methyl-2-pentanol 7.05
    propionitrile 32.58
    vinylene carbonate 24.31
    1,1,2-trichlorotrifluoroethane 113.63
    DMS 10.29
    cumene 0.55
    2-octanol 7.56
    2-hexanone 30.52
    octyl acetate 9.78
    limonene 1.03
    1,2-dimethoxyethane 362.6
    ethyl orthosilicate 2.95
    tributyl phosphate 2.9
    diacetone alcohol 85.14
    N,N-dimethylaniline 6.62
    acrylonitrile 43.67
    aniline 22.31
    1,3-propanediol 403.11
    bromobenzene 0.85
    dibromomethane 6.23
    1,1,2,2-tetrachloroethane 20.95
    2-methyl-cyclohexyl acetate 2.98
    tetrabutyl urea 9.1
    diisobutyl methanol 1.64
    2-phenylethanol 6.34
    styrene 1.66
    dioctyl adipate 7.9
    dimethyl sulfate 111.99
    ethyl butyrate 7.48
    methyl lactate 101.76
    butyl lactate 10.68
    diethyl carbonate 3.61
    propanediol butyl ether 48.59
    triethyl orthoformate 6.66
    p-tert-butyltoluene 0.53
    methyl 4-tert-butylbenzoate 10.42
    morpholine 608.17
    tert-butylamine 25.79
    n-dodecanol 7.08
    dimethoxymethane 651.84
    ethylene carbonate 25.85
    cyrene 44.47
    2-ethoxyethyl acetate 25.4
    2-ethylhexyl acetate 1.99
    1,2,4-trichlorobenzene 1.86
    4-methylpyridine 37.9
    dibutyl ether 12.81
    2,6-dimethyl-4-heptanol 1.64
    DEF 119.54
    dimethyl isosorbide 26.87
    tetrachloroethylene 9.89
    eugenol 10.08
    triacetin 13.9
    span 80 26.56
    1,4-butanediol 119.59
    1,1-dichloroethane 11.85
    2-methyl-1-pentanol 14.49
    methyl formate 322.43
    2-methyl-1-butanol 36.17
    n-decane 0.77
    butyronitrile 25.11
    3,7-dimethyl-1-octanol 4.64
    1-chlorooctane 2.76
    1-chlorotetradecane 1.11
    n-nonane 0.69
    undecane 0.53
    tert-butylcyclohexane 0.1
    cyclooctane 0.33
    cyclopentanol 139.2
    tetrahydropyran 209.1
    tert-amyl methyl ether 32.89
    2,5,8-trioxanonane 90.05
    1-hexene 2.47
    2-isopropoxyethanol 136.3
    2,2,2-trifluoroethanol 120.86
    methyl butyrate 27.5

    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