2-(3,4-Dihydroxyphenyl)-6-(beta-D-glucopyranosyloxy)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one

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  • Identifiers

    CAS number
    22860-72-6

    Molecular formula
    C22H22O12

    SMILES
    COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 75.1%
    Phenolic 34.23%
    Vanilla 32.97%
    Burnt 26.02%
    Smoky 22.69%
    Milky 22.61%
    Savory 21.92%
    Balsamic 19.34%
    Creamy 18.53%
    Spicy 18.26%

     

    Flavor
    Bitter 77.7%
    Odorless 35.24%
    Bland 34.32%
    Sweet-like 26.68%
    Very mild 20.53%
    Eugenol 20.39%
    Cedarleaf 20.18%
    Parsley 20.07%
    Lovage 19.4%
    Very slight 18.95%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    8.77 (weak base)

    Molecular weight
    478.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3167°C

    Flash point

    • 298.31 ˚C est.

  • Synonyms

    • 22860-72-6
    • DTXSID901120686
    • RefChem:1061006
    • DTXCID501552239
    • 2-(3,4-Dihydroxyphenyl)-6-(beta-D-glucopyranosyloxy)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one
    • Pedaliin
    • 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
    • Glucosyl-6-pedalitin
    • 4H-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-6-beta-D-glucopyranosyl-5 -hydroxy-7-methoxy-
    • PEDALITIN 6-O-GLUCOSIDE
    • pedalitin-6-O-glucoside
    • orb1681186
    • SCHEMBL9063808
    • CHEMBL1272196
    • CHEBI:191737
    • HY-N9588
    • MFCD00210559
    • AKOS040762745
    • DA-66540
    • CS-0201485
    • G88886
    • 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-6-yl beta-D-glucopyranoside
    • 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
    • 2-(3,4-Dihydroxyphenyl)-6-(I(2)-D-glucopyranosyloxy)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one
    • 22860-72-6

  • Applications

    2-(3,4-Dihydroxyphenyl)-6-(beta-D-glucopyranosyloxy)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one (CAS 22860-72-6) is primarily used as an intermediate for the synthesis of glycosylated flavonoids in pharmaceutical and agrochemical research; its glycosylated flavonoid scaffold also serves as a basis for medicinal chemistry studies in lead-derivative development. In cosmetics and personal care, it is often evaluated as a natural antioxidant additive that can be incorporated into formulations with polymer matrices. In coatings and inks, it may function as a natural phenolic stabilizer/antioxidant to improve the light and thermal stability of polymer systems. In early-stage research, it is explored as a building block for semi-synthetic flavonoid derivatives with potential biological activity, under appropriate regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.03
    methanol 5.59
    isopropanol 6.63
    water 0.17
    ethyl acetate 0.66
    n-propanol 9.8
    acetone 3.85
    n-butanol 2.84
    acetonitrile 0.71
    DMF 42.3
    toluene 0.07
    isobutanol 2.15
    1,4-dioxane 8.8
    methyl acetate 1.86
    THF 24.67
    2-butanone 4.26
    n-pentanol 1.17
    sec-butanol 4.33
    n-hexane 0.01
    ethylene glycol 32.28
    NMP 39.75
    cyclohexane 0.02
    DMSO 135.18
    n-butyl acetate 0.21
    n-octanol 0.63
    chloroform 0.05
    n-propyl acetate 0.3
    acetic acid 25.25
    dichloromethane 0.08
    cyclohexanone 3.04
    propylene glycol 33.37
    isopropyl acetate 0.29
    DMAc 51.43
    2-ethoxyethanol 23.56
    isopentanol 0.89
    n-heptane 0.03
    ethyl formate 1.04
    1,2-dichloroethane 0.15
    n-hexanol 0.46
    2-methoxyethanol 72.94
    isobutyl acetate 0.09
    tetrachloromethane 0.02
    n-pentyl acetate 0.49
    transcutol 16.16
    n-heptanol 0.78
    ethylbenzene 0.03
    MIBK 0.29
    2-propoxyethanol 8.37
    tert-butanol 2.43
    MTBE 0.43
    2-butoxyethanol 5.4
    propionic acid 6.8
    o-xylene 0.05
    formic acid 41.83
    diethyl ether 0.74
    m-xylene 0.04
    p-xylene 0.03
    chlorobenzene 0.02
    dimethyl carbonate 1.93
    n-octane 0.02
    formamide 45.5
    cyclopentanone 10.11
    2-pentanone 1.22
    anisole 0.19
    cyclopentyl methyl ether 1.43
    gamma-butyrolactone 13.72
    1-methoxy-2-propanol 32.32
    pyridine 2.74
    3-pentanone 0.88
    furfural 6.54
    n-dodecane 0.01
    diethylene glycol 17.96
    diisopropyl ether 0.06
    tert-amyl alcohol 1.74
    acetylacetone 1.83
    n-hexadecane 0.02
    acetophenone 0.34
    methyl propionate 1.96
    isopentyl acetate 0.16
    trichloroethylene 0.21
    n-nonanol 0.7
    cyclohexanol 1.49
    benzyl alcohol 0.65
    2-ethylhexanol 0.17
    isooctanol 0.42
    dipropyl ether 0.49
    1,2-dichlorobenzene 0.02
    ethyl lactate 1.24
    propylene carbonate 1.35
    n-methylformamide 20.63
    2-pentanol 1.06
    n-pentane 0.02
    1-propoxy-2-propanol 4.26
    1-methoxy-2-propyl acetate 1.08
    2-(2-methoxypropoxy) propanol 3.96
    mesitylene 0.02
    ε-caprolactone 3.49
    p-cymene 0.03
    epichlorohydrin 6.88
    1,1,1-trichloroethane 0.03
    2-aminoethanol 33.46
    morpholine-4-carbaldehyde 36.13
    sulfolane 30.23
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 4.32
    n-hexyl acetate 0.56
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 6.96
    sec-butyl acetate 0.13
    tert-butyl acetate 0.32
    decalin 0.01
    glycerin 70.75
    diglyme 11.79
    acrylic acid 8.96
    isopropyl myristate 0.19
    n-butyric acid 2.73
    acetyl acetate 0.29
    di(2-ethylhexyl) phthalate 0.31
    ethyl propionate 0.3
    nitromethane 23.73
    1,2-diethoxyethane 1.33
    benzonitrile 0.16
    trioctyl phosphate 0.31
    1-bromopropane 0.08
    gamma-valerolactone 31.01
    n-decanol 0.47
    triethyl phosphate 0.23
    4-methyl-2-pentanol 0.22
    propionitrile 0.62
    vinylene carbonate 1.01
    1,1,2-trichlorotrifluoroethane 13.5
    DMS 0.59
    cumene 0.02
    2-octanol 0.42
    2-hexanone 0.49
    octyl acetate 0.42
    limonene 0.06
    1,2-dimethoxyethane 11.09
    ethyl orthosilicate 0.21
    tributyl phosphate 0.26
    diacetone alcohol 3.09
    N,N-dimethylaniline 0.17
    acrylonitrile 1.23
    aniline 0.53
    1,3-propanediol 28.82
    bromobenzene 0.01
    dibromomethane 0.04
    1,1,2,2-tetrachloroethane 0.26
    2-methyl-cyclohexyl acetate 0.2
    tetrabutyl urea 0.69
    diisobutyl methanol 0.1
    2-phenylethanol 0.36
    styrene 0.03
    dioctyl adipate 0.49
    dimethyl sulfate 4.91
    ethyl butyrate 0.24
    methyl lactate 7.42
    butyl lactate 1.32
    diethyl carbonate 0.16
    propanediol butyl ether 6.42
    triethyl orthoformate 0.39
    p-tert-butyltoluene 0.03
    methyl 4-tert-butylbenzoate 0.93
    morpholine 24.99
    tert-butylamine 0.37
    n-dodecanol 0.3
    dimethoxymethane 14.77
    ethylene carbonate 0.8
    cyrene 5.54
    2-ethoxyethyl acetate 1.26
    2-ethylhexyl acetate 0.11
    1,2,4-trichlorobenzene 0.05
    4-methylpyridine 0.73
    dibutyl ether 0.35
    2,6-dimethyl-4-heptanol 0.1
    DEF 3.38
    dimethyl isosorbide 3.75
    tetrachloroethylene 0.18
    eugenol 1.21
    triacetin 1.21
    span 80 3.47
    1,4-butanediol 7.35
    1,1-dichloroethane 0.06
    2-methyl-1-pentanol 0.4
    methyl formate 10.16
    2-methyl-1-butanol 1.23
    n-decane 0.03
    butyronitrile 0.34
    3,7-dimethyl-1-octanol 0.24
    1-chlorooctane 0.09
    1-chlorotetradecane 0.03
    n-nonane 0.03
    undecane 0.02
    tert-butylcyclohexane 0.0
    cyclooctane 0.01
    cyclopentanol 5.44
    tetrahydropyran 3.28
    tert-amyl methyl ether 0.46
    2,5,8-trioxanonane 8.13
    1-hexene 0.04
    2-isopropoxyethanol 5.91
    2,2,2-trifluoroethanol 7.49
    methyl butyrate 0.47

    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