5-O-Caffeoylshikimic acid

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  • Identifiers

    CAS number
    73263-62-4

    Molecular formula
    C16H16O8

    SMILES
    C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 78.15%
    Burnt 22.69%
    Balsamic 22.67%
    Savory 22.64%
    Vanilla 22.4%
    Milky 20.79%
    Phenolic 20.04%
    Spicy 18.54%
    Caramellic 18.38%
    Bitter 17.86%

     

    Flavor
    Bitter 65.33%
    Odorless 47.54%
    Very mild 30.33%
    Bland 28.36%
    Sweet-like 22.65%
    Mild 21.25%
    Nitrile 19.69%
    Fenugreek 19.34%
    Lovage 19.3%
    Yeast 19.25%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    7.45 (neutral)

    Molecular weight
    336.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    709°C

    Melting point expt.

    • 300 °C

    Flash point

    • 290.4 ˚C est.

  • Synonyms

    • 5-O-Caffeoylshikimic acid
    • 73263-62-4
    • 5-caffeoylshikimic acid
    • 5U399BD0RZ
    • (3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
    • DTXSID501312675
    • (3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxy-cyclohexene-1-carboxylic acid
    • 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-
    • (3R,4R,5R)-5-((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy-3,4-dihydroxy-cyclohexene-1-carboxylic acid
    • (3R,4R,5R)-5-((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
    • RefChem:26000
    • DTXCID801742461
    • MEGxp0_000239
    • ACon1_000160
    • (3R,4R,5R)-5-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-3,4-dihydroxycyclohex-1-enecarboxylic acid
    • (3R,4R,5R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
    • 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-
    • AC1NQZ12
    • UNII-5U399BD0RZ
    • (3R,4R,5R)-5-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxy-1-cyclohexene-1-carboxylic Acid
    • 5-CSA
    • CHEBI:2106
    • orb1297486
    • 5-(trans-caffeoyl)shikimic acid
    • 5-[(E)-caffeoyl]shikimic acid
    • SCHEMBL30084864
    • MolPort-001-740-420
    • HY-N8321
    • YCA26362
    • AKOS040760230
    • EBC-615791
    • TRANS-5-O-CAFFEOYLSHIKIMIC ACID
    • NCGC00180823-01
    • NCGC00180823-02
    • TRANS-CAFFEIC ACID 5-O-SHIKIMATE
    • DA-60469
    • MS-25090
    • PD166603
    • CS-0143081
    • E80649
    • Q27105553
    • 1-CYCLOHEXENE-1-CARBOXYLIC ACID, 3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-4,5-DIHYDROXY-, (3R,4R,5R)-
    • 1-CYCLOHEXENE-1-CARBOXYLIC ACID, 5-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (3R,4R,5R)-
    • 73263-62-4

  • Applications

    5-O-Caffeoylshikimic acid (CAS 73263-62-4) is primarily used as a plant-derived building block and a research reagent for the synthesis of complex polyphenolic derivatives. In industry, it is commonly employed as a synthetic precursor for caffeoyl–shikimate esters in pharmaceutical research and in cosmetic/personal-care formulation development. The compound is also explored as an antioxidant and potential stabilizing additive in polymer systems and coatings to improve oxidative durability. Additionally, as a polyphenolic ester, it may be investigated as a fragrance or flavor chemistry precursor in fragrance formulations. Use of this compound is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 305.01
    methanol 516.59
    isopropanol 182.85
    water 26.73
    ethyl acetate 39.66
    n-propanol 172.05
    acetone 359.04
    n-butanol 77.94
    acetonitrile 51.22
    DMF 485.67
    toluene 2.26
    isobutanol 36.63
    1,4-dioxane 228.63
    methyl acetate 52.27
    THF 574.59
    2-butanone 110.4
    n-pentanol 30.6
    sec-butanol 80.08
    n-hexane 0.26
    ethylene glycol 345.77
    NMP 111.65
    cyclohexane 0.65
    DMSO 1854.99
    n-butyl acetate 2.81
    n-octanol 8.7
    chloroform 0.7
    n-propyl acetate 7.69
    acetic acid 254.99
    dichloromethane 1.24
    cyclohexanone 43.18
    propylene glycol 210.14
    isopropyl acetate 15.53
    DMAc 486.35
    2-ethoxyethanol 466.74
    isopentanol 30.2
    n-heptane 0.56
    ethyl formate 35.03
    1,2-dichloroethane 3.81
    n-hexanol 9.21
    2-methoxyethanol 1138.98
    isobutyl acetate 1.2
    tetrachloromethane 0.28
    n-pentyl acetate 4.07
    transcutol 115.38
    n-heptanol 9.16
    ethylbenzene 1.07
    MIBK 14.27
    2-propoxyethanol 88.79
    tert-butanol 142.3
    MTBE 24.03
    2-butoxyethanol 40.24
    propionic acid 59.8
    o-xylene 2.07
    formic acid 475.66
    diethyl ether 42.32
    m-xylene 1.32
    p-xylene 0.99
    chlorobenzene 0.52
    dimethyl carbonate 43.08
    n-octane 0.48
    formamide 1029.92
    cyclopentanone 118.11
    2-pentanone 68.09
    anisole 9.7
    cyclopentyl methyl ether 36.85
    gamma-butyrolactone 110.79
    1-methoxy-2-propanol 398.61
    pyridine 36.52
    3-pentanone 28.74
    furfural 43.95
    n-dodecane 0.36
    diethylene glycol 158.66
    diisopropyl ether 3.52
    tert-amyl alcohol 68.07
    acetylacetone 83.58
    n-hexadecane 0.39
    acetophenone 8.37
    methyl propionate 52.42
    isopentyl acetate 1.96
    trichloroethylene 3.48
    n-nonanol 9.27
    cyclohexanol 31.64
    benzyl alcohol 17.64
    2-ethylhexanol 2.4
    isooctanol 4.74
    dipropyl ether 11.07
    1,2-dichlorobenzene 0.44
    ethyl lactate 13.37
    propylene carbonate 11.6
    n-methylformamide 364.67
    2-pentanol 32.57
    n-pentane 0.45
    1-propoxy-2-propanol 35.36
    1-methoxy-2-propyl acetate 10.84
    2-(2-methoxypropoxy) propanol 27.69
    mesitylene 0.79
    ε-caprolactone 30.09
    p-cymene 0.57
    epichlorohydrin 116.9
    1,1,1-trichloroethane 0.94
    2-aminoethanol 410.54
    morpholine-4-carbaldehyde 200.96
    sulfolane 142.85
    2,2,4-trimethylpentane 0.17
    2-methyltetrahydrofuran 90.13
    n-hexyl acetate 5.82
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 55.36
    sec-butyl acetate 3.53
    tert-butyl acetate 14.36
    decalin 0.18
    glycerin 373.61
    diglyme 104.76
    acrylic acid 59.88
    isopropyl myristate 2.94
    n-butyric acid 49.64
    acetyl acetate 12.7
    di(2-ethylhexyl) phthalate 2.61
    ethyl propionate 9.55
    nitromethane 484.23
    1,2-diethoxyethane 21.84
    benzonitrile 2.76
    trioctyl phosphate 2.75
    1-bromopropane 1.63
    gamma-valerolactone 185.91
    n-decanol 7.13
    triethyl phosphate 2.37
    4-methyl-2-pentanol 7.4
    propionitrile 16.15
    vinylene carbonate 9.0
    1,1,2-trichlorotrifluoroethane 65.05
    DMS 5.48
    cumene 0.55
    2-octanol 5.26
    2-hexanone 12.01
    octyl acetate 4.92
    limonene 0.97
    1,2-dimethoxyethane 260.56
    ethyl orthosilicate 2.46
    tributyl phosphate 2.22
    diacetone alcohol 65.22
    N,N-dimethylaniline 5.83
    acrylonitrile 24.5
    aniline 14.24
    1,3-propanediol 464.0
    bromobenzene 0.3
    dibromomethane 0.59
    1,1,2,2-tetrachloroethane 4.35
    2-methyl-cyclohexyl acetate 2.05
    tetrabutyl urea 6.64
    diisobutyl methanol 1.96
    2-phenylethanol 6.33
    styrene 1.15
    dioctyl adipate 4.68
    dimethyl sulfate 53.91
    ethyl butyrate 3.67
    methyl lactate 71.2
    butyl lactate 6.29
    diethyl carbonate 2.31
    propanediol butyl ether 32.78
    triethyl orthoformate 3.86
    p-tert-butyltoluene 0.64
    methyl 4-tert-butylbenzoate 9.54
    morpholine 336.73
    tert-butylamine 21.22
    n-dodecanol 5.24
    dimethoxymethane 417.98
    ethylene carbonate 9.18
    cyrene 34.8
    2-ethoxyethyl acetate 11.26
    2-ethylhexyl acetate 1.11
    1,2,4-trichlorobenzene 0.87
    4-methylpyridine 15.72
    dibutyl ether 6.17
    2,6-dimethyl-4-heptanol 1.96
    DEF 75.95
    dimethyl isosorbide 24.07
    tetrachloroethylene 2.94
    eugenol 11.11
    triacetin 7.6
    span 80 17.52
    1,4-butanediol 137.25
    1,1-dichloroethane 1.54
    2-methyl-1-pentanol 12.21
    methyl formate 211.01
    2-methyl-1-butanol 27.33
    n-decane 0.67
    butyronitrile 13.12
    3,7-dimethyl-1-octanol 3.51
    1-chlorooctane 1.61
    1-chlorotetradecane 0.74
    n-nonane 0.59
    undecane 0.47
    tert-butylcyclohexane 0.1
    cyclooctane 0.29
    cyclopentanol 71.36
    tetrahydropyran 83.61
    tert-amyl methyl ether 19.18
    2,5,8-trioxanonane 75.15
    1-hexene 1.16
    2-isopropoxyethanol 116.25
    2,2,2-trifluoroethanol 75.23
    methyl butyrate 11.85

    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