3-O-Caffeoylquinic acid methyl ester

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  • Identifiers

    CAS number
    123483-19-2

    Molecular formula
    C17H20O9

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 72.69%
    Vanilla 31.14%
    Milky 26.94%
    Sweet 26.7%
    Caramellic 25.27%
    Savory 21.63%
    Burnt 21.32%
    Creamy 21.0%
    Balsamic 18.87%
    Spicy 18.54%

     

    Flavor
    Bitter 75.73%
    Odorless 40.73%
    Bland 32.88%
    Very mild 27.43%
    Sweet-like 23.95%
    Mild 19.59%
    Ethyl benzoate 19.22%
    Parsley 19.19%
    Cedarleaf 19.15%
    Lovage 19.09%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    7.37 (neutral)

    Molecular weight
    368.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1158°C

    Flash point

    • 252.42 ˚C est.

  • Synonyms

    • Methyl chlorogenate
    • 3-O-Caffeoylquinic acid methyl ester
    • 123483-19-2
    • Methyl 5-o-caffeoylquinate
    • Chlorogenic acid, methyl ester
    • E6GC3KV7JK
    • Chlorogenic methyl ester
    • DTXSID501289036
    • Cyclohexanecarboxylic acid, 3-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)-
    • Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)-
    • Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, methyl ester, (1S-(1alpha,3beta,4alpha,5alpha))-
    • RefChem:42506
    • DTXCID201719666
    • Chlorogenic acid methyl ester
    • Methyl (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylate
    • 29708-87-0
    • CHEMBL416955
    • methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylate
    • UNII-E6GC3KV7JK
    • Chlorogenic acid methylester
    • methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylate
    • methyl-3-O-caffeoylquinate
    • orb1297496
    • SCHEMBL29480625
    • HY-N4168B
    • MZNIJRAPCCELQX-AWOKGZDASA-
    • CHEBI:145094
    • HY-N4168
    • BDBM50343049
    • NSC741645
    • AKOS037514511
    • AKOS040763658
    • EBC-616749
    • FS-7815
    • NSC-741645
    • DA-49620
    • DA-55393
    • FC177959
    • METHYL (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-DIHYDROXYPHENYL)PROP-2-ENOYL]OXY}-1,4,5-TRIHYDROXYCYCLOHEXANE-1-CARBOXYLATE
    • methyl (1S,3R,4R,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate
    • CS-0032297
    • CS-0618388
    • E80658
    • G14242
    • Q27276938
    • (1S,3R,4R,5R)-3-[(E)-3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester
    • CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, METHYL ESTER, (1S-(1.ALPHA.,3.BETA.,4.ALPHA.,5.ALPHA.))-
    • Cyclohexanecarboxylic acid, 3-(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl-Oxy-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)-
    • InChI=1/C17H20O9/c1-25-16(23)17(24)7-12(20)15(22)13(8-17)26-14(21)5-3-9-2-4-10(18)11(19)6-9/h2-6,12-13,15,18-20,22,24H,7-8H2,1H3/b5-3+/t12-,13-,15-,17+/m1/s1
    • Methyl (1S,3R,4R,5R)-3-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylate
    • 123483-19-2

  • Applications

    3-O-Caffeoylquinic acid methyl ester (CAS 123483-19-2) is primarily used as an intermediate in the synthesis of caffeoylquinic acid derivatives and related polyphenolic compounds in chemical, pharmaceutical, and cosmetic R&D. It is investigated as an antioxidant additive in cosmetic/personal care formulations owing to its phenolic structure. It can serve as a stabilizer or antioxidant additive in coatings, inks, and polymer formulations to improve oxidative stability. It is also explored as a research precursor for flavor/fragrance development and for functional materials in coatings and related industrial formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 218.24
    methanol 422.08
    isopropanol 88.43
    water 16.75
    ethyl acetate 24.83
    n-propanol 98.94
    acetone 191.31
    n-butanol 47.79
    acetonitrile 28.38
    DMF 560.9
    toluene 1.75
    isobutanol 22.09
    1,4-dioxane 140.97
    methyl acetate 27.82
    THF 399.39
    2-butanone 46.87
    n-pentanol 16.74
    sec-butanol 40.08
    n-hexane 0.28
    ethylene glycol 305.1
    NMP 189.43
    cyclohexane 0.73
    DMSO 2187.62
    n-butyl acetate 1.82
    n-octanol 7.71
    chloroform 1.37
    n-propyl acetate 4.8
    acetic acid 241.68
    dichloromethane 2.92
    cyclohexanone 30.43
    propylene glycol 195.88
    isopropyl acetate 10.53
    DMAc 401.43
    2-ethoxyethanol 310.05
    isopentanol 17.6
    n-heptane 0.7
    ethyl formate 23.59
    1,2-dichloroethane 5.0
    n-hexanol 6.35
    2-methoxyethanol 841.95
    isobutyl acetate 1.14
    tetrachloromethane 0.35
    n-pentyl acetate 3.61
    transcutol 118.09
    n-heptanol 7.82
    ethylbenzene 0.82
    MIBK 10.83
    2-propoxyethanol 75.98
    tert-butanol 58.92
    MTBE 11.96
    2-butoxyethanol 33.87
    propionic acid 44.17
    o-xylene 1.49
    formic acid 522.96
    diethyl ether 29.78
    m-xylene 1.07
    p-xylene 0.73
    chlorobenzene 0.57
    dimethyl carbonate 43.69
    n-octane 0.55
    formamide 818.3
    cyclopentanone 100.19
    2-pentanone 41.36
    anisole 7.34
    cyclopentyl methyl ether 29.29
    gamma-butyrolactone 112.77
    1-methoxy-2-propanol 357.91
    pyridine 24.53
    3-pentanone 17.97
    furfural 51.27
    n-dodecane 0.33
    diethylene glycol 158.8
    diisopropyl ether 2.68
    tert-amyl alcohol 30.6
    acetylacetone 65.91
    n-hexadecane 0.37
    acetophenone 7.09
    methyl propionate 37.07
    isopentyl acetate 1.49
    trichloroethylene 5.31
    n-nonanol 7.63
    cyclohexanol 19.68
    benzyl alcohol 11.71
    2-ethylhexanol 2.11
    isooctanol 4.66
    dipropyl ether 8.37
    1,2-dichlorobenzene 0.64
    ethyl lactate 14.5
    propylene carbonate 15.28
    n-methylformamide 289.16
    2-pentanol 20.69
    n-pentane 0.52
    1-propoxy-2-propanol 30.83
    1-methoxy-2-propyl acetate 11.01
    2-(2-methoxypropoxy) propanol 27.2
    mesitylene 0.73
    ε-caprolactone 23.76
    p-cymene 0.59
    epichlorohydrin 93.07
    1,1,1-trichloroethane 0.86
    2-aminoethanol 322.74
    morpholine-4-carbaldehyde 228.68
    sulfolane 198.44
    2,2,4-trimethylpentane 0.18
    2-methyltetrahydrofuran 54.07
    n-hexyl acetate 5.41
    isooctane 0.1
    2-(2-butoxyethoxy)ethanol 50.21
    sec-butyl acetate 2.45
    tert-butyl acetate 10.86
    decalin 0.18
    glycerin 402.32
    diglyme 92.6
    acrylic acid 53.83
    isopropyl myristate 2.5
    n-butyric acid 38.73
    acetyl acetate 10.12
    di(2-ethylhexyl) phthalate 3.18
    ethyl propionate 7.38
    nitromethane 372.17
    1,2-diethoxyethane 17.59
    benzonitrile 2.58
    trioctyl phosphate 3.01
    1-bromopropane 1.84
    gamma-valerolactone 175.27
    n-decanol 5.42
    triethyl phosphate 2.68
    4-methyl-2-pentanol 5.62
    propionitrile 10.21
    vinylene carbonate 12.23
    1,1,2-trichlorotrifluoroethane 79.9
    DMS 6.37
    cumene 0.51
    2-octanol 4.58
    2-hexanone 7.12
    octyl acetate 4.26
    limonene 1.11
    1,2-dimethoxyethane 183.49
    ethyl orthosilicate 2.67
    tributyl phosphate 2.32
    diacetone alcohol 50.32
    N,N-dimethylaniline 5.82
    acrylonitrile 17.62
    aniline 8.67
    1,3-propanediol 330.3
    bromobenzene 0.37
    dibromomethane 1.34
    1,1,2,2-tetrachloroethane 5.91
    2-methyl-cyclohexyl acetate 2.24
    tetrabutyl urea 5.91
    diisobutyl methanol 1.82
    2-phenylethanol 4.99
    styrene 0.9
    dioctyl adipate 4.98
    dimethyl sulfate 75.62
    ethyl butyrate 3.17
    methyl lactate 75.69
    butyl lactate 6.8
    diethyl carbonate 2.18
    propanediol butyl ether 31.98
    triethyl orthoformate 3.81
    p-tert-butyltoluene 0.65
    methyl 4-tert-butylbenzoate 10.79
    morpholine 206.35
    tert-butylamine 10.68
    n-dodecanol 3.79
    dimethoxymethane 425.94
    ethylene carbonate 10.7
    cyrene 43.03
    2-ethoxyethyl acetate 10.27
    2-ethylhexyl acetate 1.01
    1,2,4-trichlorobenzene 1.16
    4-methylpyridine 10.9
    dibutyl ether 4.88
    2,6-dimethyl-4-heptanol 1.82
    DEF 64.34
    dimethyl isosorbide 29.83
    tetrachloroethylene 3.93
    eugenol 13.01
    triacetin 10.06
    span 80 19.21
    1,4-butanediol 94.21
    1,1-dichloroethane 1.51
    2-methyl-1-pentanol 6.99
    methyl formate 191.63
    2-methyl-1-butanol 16.28
    n-decane 0.7
    butyronitrile 8.54
    3,7-dimethyl-1-octanol 3.71
    1-chlorooctane 1.58
    1-chlorotetradecane 0.65
    n-nonane 0.64
    undecane 0.47
    tert-butylcyclohexane 0.12
    cyclooctane 0.34
    cyclopentanol 44.64
    tetrahydropyran 46.38
    tert-amyl methyl ether 11.67
    2,5,8-trioxanonane 70.6
    1-hexene 1.04
    2-isopropoxyethanol 79.72
    2,2,2-trifluoroethanol 71.48
    methyl butyrate 8.95

    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