Kaempferol 3-O-glucuronide

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  • Identifiers

    CAS number
    22688-78-4

    Molecular formula
    C21H18O12

    SMILES
    C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 79.4%
    Phenolic 32.11%
    Savory 22.34%
    Burnt 22.02%
    Vanilla 20.79%
    Bitter 20.11%
    Milky 19.63%
    Balsamic 16.34%
    Smoky 16.31%
    Creamy 15.71%

     

    Flavor
    Bitter 82.23%
    Odorless 40.01%
    Bland 32.29%
    Sweet-like 24.83%
    Very mild 21.96%
    Mild 20.84%
    Cedarleaf 20.11%
    Lovage 19.52%
    Parsley 19.5%
    Nitrile 19.3%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    6.72 (neutral)

    Molecular weight
    462.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2873°C

    Flash point

    • 309.77 ˚C est.

  • Synonyms

    • Kaempferol 3-O-glucuronide
    • CHEBI:75721
    • kaempferol 3-O-beta-D-glucoronopyranoside
    • kaempferol 3-O-beta-D-glucopyranosiduronic acid
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranosiduronic acid
    • RefChem:792617
    • 22688-78-4
    • Kaempferol 3-glucuronide
    • Kaempferol-O-glucuronide
    • Kaempferol 3-O-|A-D-glucuronide
    • Kaempferol 3-O-beta-D-glucuronide
    • Kaempferol-3-beta-O-glucuronide
    • Kaempferol 3-O-beta-D-glucuronopyranoside
    • (2S,3S,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosiduronic acid
    • Kaempferol-3-beta-D-glucuronide
    • kaempferol glucuronide
    • Kaempferol3-glucuronide
    • Glucuronyl-3-kaempferol
    • EGG5MC7LNS
    • kaempferol-3-O-glucoronide
    • kaempferol 3-glucuronic acid
    • (2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
    • Kaempferol 3-beta-glucuronide
    • MEGxp0_000322
    • orb1297316
    • SCHEMBL1280014
    • kaempferol 3-O-beta-glucuronide
    • Kaempherol 3-O-beta-glucuronide
    • SCHEMBL30286833
    • ACon1_000499
    • DTXSID90415745
    • kaempferol-3-o-beta-d-glucuronide
    • GLXC-17201
    • Kaempferol 3-O-??-D-glucuronide
    • HY-N7176
    • AKOS032946053
    • kaempferol-3-O-beta-D-glucuronic acid
    • EBC-618552
    • MK08974
    • (2S,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
    • DA-54589
    • MS-28488
    • CS-0103798
    • BRD-K13548766-001-01-0
    • Q27145499
    • Kaempferol 3-O-beta-D-glucuronide, >=97.0% (HPLC)
    • (2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl-beta-D-glucopyranosiduronic acid
    • beta-D-Glucopyranosiduronic acid, 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl
    • Glucopyranosiduronic acid, 5,7-dihydroxy-2-(p-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl, beta-D-
    • 22688-78-4

  • Applications

    Kaempferol 3-O-glucuronide (CAS 22688-78-4) is a plant-derived flavonoid glucuronide that is commonly evaluated for antioxidant activity in cosmetic and personal-care formulations; it is also used in analytical chemistry as a reference standard or analytical target for LC-MS and related methods to study flavonoid metabolism. In pharmaceutical and biomedical research, it is studied as a metabolite related to kaempferol biotransformation and as a tool compound for metabolism investigations. In plant sciences and agriculture, it serves as a glucuronide conjugate useful for investigating plant metabolism and defense responses. In formulation development for polymers or coatings, it may be explored as a natural antioxidant additive or stabilizer candidate, though use in specific products is subject to formulation limits and regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.49
    methanol 4.64
    isopropanol 8.8
    water 0.08
    ethyl acetate 0.56
    n-propanol 13.35
    acetone 5.91
    n-butanol 3.53
    acetonitrile 0.74
    DMF 56.89
    toluene 0.11
    isobutanol 3.57
    1,4-dioxane 5.25
    methyl acetate 1.82
    THF 16.64
    2-butanone 6.9
    n-pentanol 1.83
    sec-butanol 6.92
    n-hexane 0.02
    ethylene glycol 42.74
    NMP 51.6
    cyclohexane 0.03
    DMSO 208.6
    n-butyl acetate 0.3
    n-octanol 0.54
    chloroform 0.02
    n-propyl acetate 0.39
    acetic acid 17.83
    dichloromethane 0.03
    cyclohexanone 3.74
    propylene glycol 62.4
    isopropyl acetate 0.32
    DMAc 69.96
    2-ethoxyethanol 29.84
    isopentanol 1.23
    n-heptane 0.04
    ethyl formate 0.8
    1,2-dichloroethane 0.09
    n-hexanol 0.69
    2-methoxyethanol 77.25
    isobutyl acetate 0.1
    tetrachloromethane 0.01
    n-pentyl acetate 0.4
    transcutol 20.72
    n-heptanol 0.76
    ethylbenzene 0.04
    MIBK 0.5
    2-propoxyethanol 12.55
    tert-butanol 3.93
    MTBE 0.56
    2-butoxyethanol 6.17
    propionic acid 8.28
    o-xylene 0.09
    formic acid 29.87
    diethyl ether 0.83
    m-xylene 0.06
    p-xylene 0.05
    chlorobenzene 0.02
    dimethyl carbonate 1.54
    n-octane 0.02
    formamide 36.59
    cyclopentanone 11.2
    2-pentanone 2.0
    anisole 0.21
    cyclopentyl methyl ether 1.53
    gamma-butyrolactone 11.29
    1-methoxy-2-propanol 50.1
    pyridine 2.51
    3-pentanone 1.44
    furfural 5.69
    n-dodecane 0.01
    diethylene glycol 25.04
    diisopropyl ether 0.09
    tert-amyl alcohol 2.91
    acetylacetone 2.07
    n-hexadecane 0.02
    acetophenone 0.38
    methyl propionate 2.21
    isopentyl acetate 0.22
    trichloroethylene 0.1
    n-nonanol 0.62
    cyclohexanol 1.86
    benzyl alcohol 0.79
    2-ethylhexanol 0.22
    isooctanol 0.42
    dipropyl ether 0.7
    1,2-dichlorobenzene 0.01
    ethyl lactate 1.78
    propylene carbonate 1.01
    n-methylformamide 23.78
    2-pentanol 1.64
    n-pentane 0.03
    1-propoxy-2-propanol 7.34
    1-methoxy-2-propyl acetate 1.57
    2-(2-methoxypropoxy) propanol 5.1
    mesitylene 0.03
    ε-caprolactone 3.32
    p-cymene 0.04
    epichlorohydrin 4.91
    1,1,1-trichloroethane 0.02
    2-aminoethanol 50.51
    morpholine-4-carbaldehyde 35.57
    sulfolane 36.37
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 3.68
    n-hexyl acetate 0.43
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 9.0
    sec-butyl acetate 0.15
    tert-butyl acetate 0.42
    decalin 0.01
    glycerin 114.25
    diglyme 12.02
    acrylic acid 10.05
    isopropyl myristate 0.18
    n-butyric acid 2.46
    acetyl acetate 0.19
    di(2-ethylhexyl) phthalate 0.31
    ethyl propionate 0.34
    nitromethane 17.15
    1,2-diethoxyethane 1.43
    benzonitrile 0.16
    trioctyl phosphate 0.31
    1-bromopropane 0.08
    gamma-valerolactone 33.37
    n-decanol 0.46
    triethyl phosphate 0.21
    4-methyl-2-pentanol 0.34
    propionitrile 0.8
    vinylene carbonate 0.71
    1,1,2-trichlorotrifluoroethane 10.28
    DMS 0.48
    cumene 0.02
    2-octanol 0.38
    2-hexanone 0.82
    octyl acetate 0.38
    limonene 0.08
    1,2-dimethoxyethane 10.95
    ethyl orthosilicate 0.2
    tributyl phosphate 0.26
    diacetone alcohol 5.15
    N,N-dimethylaniline 0.23
    acrylonitrile 1.51
    aniline 0.56
    1,3-propanediol 30.62
    bromobenzene 0.01
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.15
    2-methyl-cyclohexyl acetate 0.24
    tetrabutyl urea 0.84
    diisobutyl methanol 0.13
    2-phenylethanol 0.42
    styrene 0.04
    dioctyl adipate 0.45
    dimethyl sulfate 3.9
    ethyl butyrate 0.31
    methyl lactate 9.76
    butyl lactate 1.54
    diethyl carbonate 0.16
    propanediol butyl ether 8.3
    triethyl orthoformate 0.42
    p-tert-butyltoluene 0.04
    methyl 4-tert-butylbenzoate 0.95
    morpholine 17.35
    tert-butylamine 0.57
    n-dodecanol 0.31
    dimethoxymethane 14.9
    ethylene carbonate 0.57
    cyrene 7.86
    2-ethoxyethyl acetate 1.03
    2-ethylhexyl acetate 0.14
    1,2,4-trichlorobenzene 0.03
    4-methylpyridine 0.73
    dibutyl ether 0.33
    2,6-dimethyl-4-heptanol 0.13
    DEF 3.77
    dimethyl isosorbide 5.56
    tetrachloroethylene 0.1
    eugenol 1.39
    triacetin 1.06
    span 80 4.24
    1,4-butanediol 10.2
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 0.66
    methyl formate 9.1
    2-methyl-1-butanol 1.87
    n-decane 0.03
    butyronitrile 0.39
    3,7-dimethyl-1-octanol 0.25
    1-chlorooctane 0.06
    1-chlorotetradecane 0.03
    n-nonane 0.03
    undecane 0.02
    tert-butylcyclohexane 0.0
    cyclooctane 0.01
    cyclopentanol 6.31
    tetrahydropyran 2.73
    tert-amyl methyl ether 0.64
    2,5,8-trioxanonane 9.44
    1-hexene 0.07
    2-isopropoxyethanol 7.97
    2,2,2-trifluoroethanol 4.49
    methyl butyrate 0.57

    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