Apigenin 7-O-glucuronide

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  • Identifiers

    CAS number
    29741-09-1

    Molecular formula
    C21H18O11

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 75.14%
    Phenolic 31.83%
    Vanilla 22.93%
    Savory 21.72%
    Bitter 21.66%
    Burnt 20.92%
    Milky 19.82%
    Balsamic 18.24%
    Sweet 17.94%
    Creamy 17.16%

     

    Flavor
    Bitter 83.13%
    Odorless 37.96%
    Bland 30.93%
    Sweet-like 24.41%
    Very mild 21.33%
    Mild 20.28%
    Cedarleaf 20.18%
    Lovage 19.66%
    Nitrile 19.41%
    Parsley 19.38%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    6.25 (neutral)

    Molecular weight
    446.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2374°C

    Flash point

    • 298.28 ˚C est.

  • Synonyms

    • Apigenin 7-O-glucuronide
    • RefChem:558403
    • 29741-09-1
    • Apigenin 7-glucuronide
    • Apigenin-7-glucuronide
    • Scutellarin A
    • Apigenin 7-O-beta-D-glucuronide
    • apigenin-7-O-beta-D-glucuronide
    • MFCD23699539
    • (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid
    • 2CQ5KB3CH0
    • CHEMBL254213
    • Apigenin 7-O-b-glucuronide
    • Apigenin 7-O-.beta.-D-glucuronide
    • beta-D-Glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl
    • (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
    • APIGENIN-7-O-GLUCRONIDE
    • (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
    • Apigenin 7-beta-glucuronide
    • Apigenin-7-O-beta-D-glucuronoside
    • Apigenin-7-O-beta-D-glucuronic acid
    • Apigenin 7-O-beta-D-glucuronopyranoside
    • UNII-2CQ5KB3CH0
    • apigenin-7-o-glucuronic acid
    • MEGxp0_000795
    • orb1301309
    • SCHEMBL2400851
    • SCHEMBL29542179
    • ACon1_001025
    • apigenin 7-O-beta-D-glucurnoide
    • apigenin-7-O-beta-D-glucoronide
    • HY-N1454R
    • DTXSID10183893
    • CHEBI:181620
    • Apigenin-7-glucuronide (Standard)
    • apigenin-7-O-betaD-glucuronic acid
    • HY-N1454
    • BDBM50241345
    • AKOS016011643
    • EBC-469159
    • MA74543
    • apigenin-7-O-beta-D-glucuronopyranoside
    • NCGC00169746-01
    • (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid
    • BS-49735
    • CS-0016900
    • NS00097544
    • F17702
    • Apigenin 7-glucuronide, >=95% (LC/MS-ELSD)
    • Apigenin 7-O-glucuronide, primary pharmaceutical reference standard
    • |A-D-Glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl
    • 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranuronosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-
    • 5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranosiduronic acid
    • BENZOPYRAN-7-YL, .BETA.-D- (8CI) 5-HYDROXY-2-(4-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL .BETA.-D-GLUCOPYRANOSIDURONIC ACID
    • beta-D-Glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl)
    • GLUCOPYRANOSIDURONIC ACID, 5-HYDROXY-2-(P-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL, .BETA.-D-
    • 29741-09-1

  • Applications

    Apigenin 7-O-glucuronide (CAS 29741-09-1) is primarily used in analytical and research contexts as a reference standard and a surrogate metabolite for flavonoid glucuronides. In bioanalysis, it serves as a reference compound in LC-MS/MS methods to quantify apigenin-related conjugates and in pharmacokinetic studies to characterize glucuronidation pathways. It is also used in natural product chemistry and enzymatic glycosylation research as a model substrate for flavonoid glucuronidation and for studying glycosyltransferase activity. In cosmetics and personal care research, it is evaluated for formulation work due to its water-soluble nature and potential antioxidant-related applications, subject to regulatory constraints. Additionally, it may function as an intermediate or synthetic building block in flavonoid chemistry for derivative synthesis and method development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.12
    methanol 0.34
    isopropanol 0.15
    water 0.03
    ethyl acetate 0.02
    n-propanol 0.33
    acetone 0.08
    n-butanol 0.13
    acetonitrile 0.01
    DMF 6.8
    toluene 0.01
    isobutanol 0.1
    1,4-dioxane 0.32
    methyl acetate 0.05
    THF 0.66
    2-butanone 0.16
    n-pentanol 0.06
    sec-butanol 0.21
    n-hexane 0.0
    ethylene glycol 3.67
    NMP 7.74
    cyclohexane 0.0
    DMSO 23.01
    n-butyl acetate 0.02
    n-octanol 0.05
    chloroform 0.0
    n-propyl acetate 0.01
    acetic acid 0.68
    dichloromethane 0.0
    cyclohexanone 0.17
    propylene glycol 6.03
    isopropyl acetate 0.01
    DMAc 8.84
    2-ethoxyethanol 2.67
    isopentanol 0.07
    n-heptane 0.0
    ethyl formate 0.03
    1,2-dichloroethane 0.0
    n-hexanol 0.03
    2-methoxyethanol 10.22
    isobutyl acetate 0.01
    tetrachloromethane 0.0
    n-pentyl acetate 0.03
    transcutol 4.99
    n-heptanol 0.07
    ethylbenzene 0.0
    MIBK 0.03
    2-propoxyethanol 1.49
    tert-butanol 0.1
    MTBE 0.03
    2-butoxyethanol 1.1
    propionic acid 0.33
    o-xylene 0.01
    formic acid 3.43
    diethyl ether 0.03
    m-xylene 0.01
    p-xylene 0.0
    chlorobenzene 0.0
    dimethyl carbonate 0.12
    n-octane 0.0
    formamide 3.4
    cyclopentanone 0.4
    2-pentanone 0.07
    anisole 0.01
    cyclopentyl methyl ether 0.09
    gamma-butyrolactone 0.46
    1-methoxy-2-propanol 5.87
    pyridine 0.11
    3-pentanone 0.06
    furfural 0.54
    n-dodecane 0.0
    diethylene glycol 4.54
    diisopropyl ether 0.01
    tert-amyl alcohol 0.14
    acetylacetone 0.11
    n-hexadecane 0.0
    acetophenone 0.03
    methyl propionate 0.09
    isopentyl acetate 0.01
    trichloroethylene 0.0
    n-nonanol 0.06
    cyclohexanol 0.09
    benzyl alcohol 0.05
    2-ethylhexanol 0.02
    isooctanol 0.04
    dipropyl ether 0.06
    1,2-dichlorobenzene 0.0
    ethyl lactate 0.18
    propylene carbonate 0.06
    n-methylformamide 1.62
    2-pentanol 0.07
    n-pentane 0.0
    1-propoxy-2-propanol 0.85
    1-methoxy-2-propyl acetate 0.14
    2-(2-methoxypropoxy) propanol 1.38
    mesitylene 0.0
    ε-caprolactone 0.17
    p-cymene 0.0
    epichlorohydrin 0.18
    1,1,1-trichloroethane 0.0
    2-aminoethanol 4.09
    morpholine-4-carbaldehyde 6.52
    sulfolane 3.63
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.13
    n-hexyl acetate 0.04
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 2.06
    sec-butyl acetate 0.01
    tert-butyl acetate 0.03
    decalin 0.0
    glycerin 28.67
    diglyme 3.25
    acrylic acid 0.62
    isopropyl myristate 0.01
    n-butyric acid 0.12
    acetyl acetate 0.01
    di(2-ethylhexyl) phthalate 0.04
    ethyl propionate 0.02
    nitromethane 0.74
    1,2-diethoxyethane 0.12
    benzonitrile 0.01
    trioctyl phosphate 0.03
    1-bromopropane 0.0
    gamma-valerolactone 2.86
    n-decanol 0.04
    triethyl phosphate 0.04
    4-methyl-2-pentanol 0.02
    propionitrile 0.02
    vinylene carbonate 0.05
    1,1,2-trichlorotrifluoroethane 1.27
    DMS 0.04
    cumene 0.0
    2-octanol 0.04
    2-hexanone 0.03
    octyl acetate 0.03
    limonene 0.01
    1,2-dimethoxyethane 1.34
    ethyl orthosilicate 0.04
    tributyl phosphate 0.03
    diacetone alcohol 0.44
    N,N-dimethylaniline 0.02
    acrylonitrile 0.05
    aniline 0.03
    1,3-propanediol 2.42
    bromobenzene 0.0
    dibromomethane 0.0
    1,1,2,2-tetrachloroethane 0.01
    2-methyl-cyclohexyl acetate 0.02
    tetrabutyl urea 0.1
    diisobutyl methanol 0.01
    2-phenylethanol 0.03
    styrene 0.0
    dioctyl adipate 0.05
    dimethyl sulfate 0.51
    ethyl butyrate 0.03
    methyl lactate 1.18
    butyl lactate 0.2
    diethyl carbonate 0.02
    propanediol butyl ether 1.67
    triethyl orthoformate 0.06
    p-tert-butyltoluene 0.0
    methyl 4-tert-butylbenzoate 0.17
    morpholine 1.01
    tert-butylamine 0.02
    n-dodecanol 0.02
    dimethoxymethane 1.3
    ethylene carbonate 0.03
    cyrene 1.65
    2-ethoxyethyl acetate 0.08
    2-ethylhexyl acetate 0.01
    1,2,4-trichlorobenzene 0.0
    4-methylpyridine 0.04
    dibutyl ether 0.03
    2,6-dimethyl-4-heptanol 0.01
    DEF 0.28
    dimethyl isosorbide 1.23
    tetrachloroethylene 0.01
    eugenol 0.29
    triacetin 0.15
    span 80 0.82
    1,4-butanediol 0.59
    1,1-dichloroethane 0.0
    2-methyl-1-pentanol 0.04
    methyl formate 0.51
    2-methyl-1-butanol 0.1
    n-decane 0.0
    butyronitrile 0.01
    3,7-dimethyl-1-octanol 0.02
    1-chlorooctane 0.01
    1-chlorotetradecane 0.0
    n-nonane 0.0
    undecane 0.0
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.23
    tetrahydropyran 0.1
    tert-amyl methyl ether 0.05
    2,5,8-trioxanonane 2.58
    1-hexene 0.0
    2-isopropoxyethanol 0.61
    2,2,2-trifluoroethanol 0.29
    methyl butyrate 0.03

    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