Taxifolin 3-O-beta-D-glucopyranoside

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  • Identifiers

    CAS number
    27297-45-6

    Molecular formula
    C21H22O12

    SMILES
    C1=CC(=C(C=C1[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 80.69%
    Phenolic 28.38%
    Vanilla 26.48%
    Savory 21.18%
    Burnt 20.82%
    Milky 18.96%
    Smoky 18.89%
    Sweet 18.71%
    Bitter 17.94%
    Spicy 17.0%

     

    Flavor
    Bitter 77.18%
    Odorless 35.52%
    Bland 32.73%
    Sweet-like 27.57%
    Very mild 21.02%
    Cedarleaf 20.13%
    Eugenol 19.29%
    Parsley 19.26%
    Lovage 19.08%
    Nitrile 18.98%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    7.63 (neutral)

    Molecular weight
    466.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3311°C

    Flash point

    • 288.26 ˚C est.

  • Synonyms

    • Taxifolin-3-glucoside
    • 27297-45-6
    • Dihydroquercetin 3-glucoside
    • Dihydroquercetin-3 o-glucoside
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-
    • Glucopyranoside, taxifolin-3, beta-d
    • Taxifolin 3-O-beta-D-glucopyranoside
    • 9Y2629204W
    • 2R,3R-Dihydroquercetin 3-O-beta-D-glucoside
    • DTXSID80181740
    • Flavanone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucopyranoside
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-2,3-dihydro-5,7-dihydroxy-, (2R-trans)-
    • RefChem:1099405
    • DTXCID20104231
    • (2R,3R)-Glucodistylin
    • (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
    • UNII-9Y2629204W
    • (2R,3R)-(+/-)-Taxifolin 3-glucoside
    • taxifolin-3-O-glycoside
    • dihydroquercetin-3-glucoside
    • orb1680470
    • CHEMBL2332678
    • Taxifolin 3-O-|A-D-glucopyranoside
    • AKOS040763321
    • (2R,3R)-(+)-TAXIFOLIN 3-GLUCOSIDE
    • GLUCOPYRANOSIDE, TAXIFOLIN-3, .BETA.-D
    • TAXIFOLIN 3-O-.BETA.-D-GLUCOPYRANOSIDE
    • (2R,3R)-taxifolin-3'-O-beta-D-pyranglucoside
    • Q27273370
    • 2R,3R-DIHYDROQUERCETIN 3-O-.BETA.-D-GLUCOSIDE
    • FLAVANONE, 3,3',4',5,7-PENTAHYDROXY-, 3-.BETA.-D-GLUCOPYRANOSIDE
    • (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
    • (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) oxan-2-yl]oxy-2,3-dihydrochromen-4-one
    • (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-4-one
    • (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl beta-D-glucopyranoside
    • 4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-5,7-DIHYDROXY-, (2R,3R)-
    • 4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-5,7-DIHYDROXY-, (2R-TRANS)-
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(|A-D-glucopyranosyloxy)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-
    • NCGC00385598-01!(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
    • 27297-45-6

  • Applications

    Taxifolin 3-O-beta-D-glucopyranoside (CAS 27297-45-6) is a glucoside form of the flavonoid taxifolin, commonly regarded as a natural product intermediate and antioxidant in formulation work. In cosmetics and personal care, it can function as an antioxidant ingredient and stabilizer to help formulations resist oxidative degradation; in polymer, coatings, and inks, it is evaluated as a natural antioxidant stabilizer or additive to improve aging resistance. It is also used as an intermediate in flavonoid synthesis for pharmaceutical and natural product research, and may serve as a starting material or precursor for derivative development. In agriculture and related research it is explored for bioactive properties as a natural plant-defense compound, and in household products it can act as a natural antioxidant additive. These applications are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 34.17
    methanol 87.4
    isopropanol 10.07
    water 1.24
    ethyl acetate 5.72
    n-propanol 23.05
    acetone 42.42
    n-butanol 9.24
    acetonitrile 8.32
    DMF 247.95
    toluene 0.4
    isobutanol 4.29
    1,4-dioxane 27.05
    methyl acetate 8.18
    THF 47.69
    2-butanone 17.42
    n-pentanol 2.65
    sec-butanol 5.89
    n-hexane 0.02
    ethylene glycol 118.01
    NMP 116.35
    cyclohexane 0.08
    DMSO 699.78
    n-butyl acetate 0.86
    n-octanol 2.09
    chloroform 0.33
    n-propyl acetate 1.41
    acetic acid 123.0
    dichloromethane 0.54
    cyclohexanone 13.63
    propylene glycol 100.47
    isopropyl acetate 2.06
    DMAc 162.32
    2-ethoxyethanol 103.4
    isopentanol 2.95
    n-heptane 0.08
    ethyl formate 10.79
    1,2-dichloroethane 1.1
    n-hexanol 1.25
    2-methoxyethanol 350.75
    isobutyl acetate 0.34
    tetrachloromethane 0.09
    n-pentyl acetate 1.55
    transcutol 58.55
    n-heptanol 2.11
    ethylbenzene 0.11
    MIBK 2.21
    2-propoxyethanol 35.04
    tert-butanol 4.81
    MTBE 1.26
    2-butoxyethanol 16.46
    propionic acid 21.61
    o-xylene 0.27
    formic acid 245.14
    diethyl ether 3.76
    m-xylene 0.21
    p-xylene 0.11
    chlorobenzene 0.15
    dimethyl carbonate 12.02
    n-octane 0.06
    formamide 267.13
    cyclopentanone 33.39
    2-pentanone 9.9
    anisole 1.03
    cyclopentyl methyl ether 4.13
    gamma-butyrolactone 40.38
    1-methoxy-2-propanol 130.41
    pyridine 8.91
    3-pentanone 4.98
    furfural 29.4
    n-dodecane 0.05
    diethylene glycol 81.12
    diisopropyl ether 0.29
    tert-amyl alcohol 3.22
    acetylacetone 21.87
    n-hexadecane 0.06
    acetophenone 1.62
    methyl propionate 11.71
    isopentyl acetate 0.59
    trichloroethylene 1.44
    n-nonanol 2.09
    cyclohexanol 2.94
    benzyl alcohol 2.66
    2-ethylhexanol 0.54
    isooctanol 1.2
    dipropyl ether 1.69
    1,2-dichlorobenzene 0.13
    ethyl lactate 7.02
    propylene carbonate 6.29
    n-methylformamide 139.62
    2-pentanol 2.46
    n-pentane 0.06
    1-propoxy-2-propanol 14.94
    1-methoxy-2-propyl acetate 5.81
    2-(2-methoxypropoxy) propanol 14.03
    mesitylene 0.12
    ε-caprolactone 10.53
    p-cymene 0.13
    epichlorohydrin 25.58
    1,1,1-trichloroethane 0.19
    2-aminoethanol 118.34
    morpholine-4-carbaldehyde 122.68
    sulfolane 97.36
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 7.85
    n-hexyl acetate 1.98
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 23.7
    sec-butyl acetate 0.56
    tert-butyl acetate 1.99
    decalin 0.02
    glycerin 237.26
    diglyme 42.43
    acrylic acid 33.29
    isopropyl myristate 0.76
    n-butyric acid 13.82
    acetyl acetate 3.01
    di(2-ethylhexyl) phthalate 1.26
    ethyl propionate 1.9
    nitromethane 178.67
    1,2-diethoxyethane 5.07
    benzonitrile 0.92
    trioctyl phosphate 1.23
    1-bromopropane 0.4
    gamma-valerolactone 111.9
    n-decanol 1.48
    triethyl phosphate 1.03
    4-methyl-2-pentanol 0.77
    propionitrile 3.67
    vinylene carbonate 6.41
    1,1,2-trichlorotrifluoroethane 46.95
    DMS 2.54
    cumene 0.06
    2-octanol 1.04
    2-hexanone 1.83
    octyl acetate 1.57
    limonene 0.26
    1,2-dimethoxyethane 49.11
    ethyl orthosilicate 0.87
    tributyl phosphate 0.99
    diacetone alcohol 14.81
    N,N-dimethylaniline 0.78
    acrylonitrile 8.71
    aniline 2.2
    1,3-propanediol 111.14
    bromobenzene 0.08
    dibromomethane 0.26
    1,1,2,2-tetrachloroethane 1.3
    2-methyl-cyclohexyl acetate 0.78
    tetrabutyl urea 2.64
    diisobutyl methanol 0.39
    2-phenylethanol 1.42
    styrene 0.13
    dioctyl adipate 2.04
    dimethyl sulfate 26.16
    ethyl butyrate 1.34
    methyl lactate 40.74
    butyl lactate 4.58
    diethyl carbonate 0.87
    propanediol butyl ether 21.46
    triethyl orthoformate 1.64
    p-tert-butyltoluene 0.13
    methyl 4-tert-butylbenzoate 3.89
    morpholine 54.4
    tert-butylamine 0.75
    n-dodecanol 0.98
    dimethoxymethane 98.96
    ethylene carbonate 4.74
    cyrene 20.89
    2-ethoxyethyl acetate 4.9
    2-ethylhexyl acetate 0.37
    1,2,4-trichlorobenzene 0.27
    4-methylpyridine 3.26
    dibutyl ether 1.1
    2,6-dimethyl-4-heptanol 0.39
    DEF 18.95
    dimethyl isosorbide 16.45
    tetrachloroethylene 0.98
    eugenol 5.46
    triacetin 5.23
    span 80 11.42
    1,4-butanediol 24.11
    1,1-dichloroethane 0.34
    2-methyl-1-pentanol 1.07
    methyl formate 86.88
    2-methyl-1-butanol 3.16
    n-decane 0.1
    butyronitrile 2.44
    3,7-dimethyl-1-octanol 0.9
    1-chlorooctane 0.33
    1-chlorotetradecane 0.13
    n-nonane 0.09
    undecane 0.07
    tert-butylcyclohexane 0.01
    cyclooctane 0.04
    cyclopentanol 7.04
    tetrahydropyran 7.37
    tert-amyl methyl ether 1.39
    2,5,8-trioxanonane 31.14
    1-hexene 0.08
    2-isopropoxyethanol 21.18
    2,2,2-trifluoroethanol 29.51
    methyl butyrate 2.94

    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