Kaempferol 3-gentiobioside

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  • Identifiers

    CAS number
    22149-35-5

    Molecular formula
    C27H30O16

    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)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 78.54%
    Vanilla 26.78%
    Phenolic 24.59%
    Sweet 24.44%
    Savory 21.31%
    Milky 20.13%
    Bitter 19.36%
    Burnt 18.45%
    Smoky 17.69%
    Creamy 16.65%

     

    Flavor
    Bitter 72.97%
    Odorless 37.32%
    Bland 33.43%
    Sweet-like 28.53%
    Very mild 20.89%
    Cedarleaf 20.05%
    Very slight 19.42%
    Eugenol 19.3%
    Parsley 19.25%
    Lovage 18.88%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -1.4

    pKa est.
    7.69 (neutral)

    Molecular weight
    610.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    5851°C

    Flash point

    • 313.23 ˚C est.

  • Synonyms

    • Kaempferol 3-gentiobioside
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-one
    • RefChem:924046
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-((2S,5S)-3,4,5-trihydroxy-6-(((2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-one
    • Kaempferol 3-O-gentiobioside
    • 22149-35-5
    • kaempferol-3-gentiobioside
    • kaempferol 3-O-beta-gentiobioside
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
    • Kaempferol3-O-gentiobioside
    • Kaempferol-3-O-gentiobioside
    • Aempferol 3-O-gentiobioside
    • kaempferol 3-beta-gentiobioside
    • orb1299126
    • SCHEMBL30819172
    • ACon1_002321
    • HY-N1510R
    • CHEBI:136785
    • DTXSID501309020
    • HY-N1510
    • AKOS027460738
    • EBC-616225
    • OK74480
    • Kaempferol 3-O-gentiobioside (Standard)
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
    • DA-54587
    • MS-30701
    • CS-0017053
    • kaempferol beta-D-glucosyl-(1->6)-beta-D-glucoside
    • BRD-K41678615-001-01-4
    • kaempferol beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside
    • 3-[(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-beta-D-glucosyl-beta-D-glucoside
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucosyl-(1->6)-beta-D-glucoside
    • 22149-35-5

  • Applications

    Kaempferol 3-gentiobioside (CAS 22149-35-5) is commonly evaluated for its antioxidant activity and may serve as a natural polyphenol ingredient in cosmetic and personal-care formulations, helping protect the skin and support formulation stability. In research settings it can function as an intermediate or starting material for the synthesis of flavonoid glycoside derivatives and is used to study bioactivity and structure–activity relationships. It may occur in plant-derived extracts used in food processing or as a functional component of nutraceuticals, contributing to the antioxidant profile of finished products. In analytical chemistry, it is used as a reference compound or analyte for LC-MS profiling of flavonoid glycosides. In materials and coatings, it can act as a stabilizing additive in polymers, coatings, and inks to enhance oxidative stability or serve as a polyphenol-based functional component.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.22
    methanol 10.6
    isopropanol 1.2
    water 0.11
    ethyl acetate 0.11
    n-propanol 2.78
    acetone 0.84
    n-butanol 0.9
    acetonitrile 0.16
    DMF 16.03
    toluene 0.05
    isobutanol 0.57
    1,4-dioxane 3.6
    methyl acetate 0.38
    THF 6.1
    2-butanone 0.91
    n-pentanol 0.47
    sec-butanol 0.92
    n-hexane 0.0
    ethylene glycol 12.77
    NMP 16.47
    cyclohexane 0.01
    DMSO 31.22
    n-butyl acetate 0.07
    n-octanol 0.31
    chloroform 0.04
    n-propyl acetate 0.08
    acetic acid 7.27
    dichloromethane 0.07
    cyclohexanone 1.0
    propylene glycol 14.86
    isopropyl acetate 0.06
    DMAc 13.9
    2-ethoxyethanol 7.49
    isopentanol 0.27
    n-heptane 0.01
    ethyl formate 0.38
    1,2-dichloroethane 0.08
    n-hexanol 0.19
    2-methoxyethanol 25.48
    isobutyl acetate 0.03
    tetrachloromethane 0.01
    n-pentyl acetate 0.22
    transcutol 9.38
    n-heptanol 0.37
    ethylbenzene 0.01
    MIBK 0.08
    2-propoxyethanol 3.41
    tert-butanol 0.32
    MTBE 0.1
    2-butoxyethanol 2.92
    propionic acid 1.75
    o-xylene 0.03
    formic acid 19.58
    diethyl ether 0.22
    m-xylene 0.02
    p-xylene 0.01
    chlorobenzene 0.01
    dimethyl carbonate 0.48
    n-octane 0.01
    formamide 14.75
    cyclopentanone 2.39
    2-pentanone 0.31
    anisole 0.08
    cyclopentyl methyl ether 0.4
    gamma-butyrolactone 2.84
    1-methoxy-2-propanol 9.77
    pyridine 1.1
    3-pentanone 0.23
    furfural 2.59
    n-dodecane 0.0
    diethylene glycol 7.15
    diisopropyl ether 0.02
    tert-amyl alcohol 0.34
    acetylacetone 0.4
    n-hexadecane 0.01
    acetophenone 0.12
    methyl propionate 0.4
    isopentyl acetate 0.05
    trichloroethylene 0.11
    n-nonanol 0.32
    cyclohexanol 0.41
    benzyl alcohol 0.31
    2-ethylhexanol 0.06
    isooctanol 0.18
    dipropyl ether 0.13
    1,2-dichlorobenzene 0.01
    ethyl lactate 0.42
    propylene carbonate 0.4
    n-methylformamide 7.99
    2-pentanol 0.24
    n-pentane 0.01
    1-propoxy-2-propanol 1.55
    1-methoxy-2-propyl acetate 0.34
    2-(2-methoxypropoxy) propanol 1.98
    mesitylene 0.01
    ε-caprolactone 1.06
    p-cymene 0.01
    epichlorohydrin 2.15
    1,1,1-trichloroethane 0.01
    2-aminoethanol 13.14
    morpholine-4-carbaldehyde 16.95
    sulfolane 8.39
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 1.02
    n-hexyl acetate 0.25
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.8
    sec-butyl acetate 0.04
    tert-butyl acetate 0.06
    decalin 0.0
    glycerin 32.53
    diglyme 5.38
    acrylic acid 3.02
    isopropyl myristate 0.06
    n-butyric acid 0.74
    acetyl acetate 0.05
    di(2-ethylhexyl) phthalate 0.15
    ethyl propionate 0.07
    nitromethane 4.81
    1,2-diethoxyethane 0.54
    benzonitrile 0.07
    trioctyl phosphate 0.13
    1-bromopropane 0.04
    gamma-valerolactone 11.29
    n-decanol 0.2
    triethyl phosphate 0.06
    4-methyl-2-pentanol 0.06
    propionitrile 0.16
    vinylene carbonate 0.4
    1,1,2-trichlorotrifluoroethane 5.88
    DMS 0.2
    cumene 0.01
    2-octanol 0.17
    2-hexanone 0.16
    octyl acetate 0.17
    limonene 0.02
    1,2-dimethoxyethane 3.4
    ethyl orthosilicate 0.05
    tributyl phosphate 0.09
    diacetone alcohol 0.72
    N,N-dimethylaniline 0.07
    acrylonitrile 0.36
    aniline 0.22
    1,3-propanediol 9.96
    bromobenzene 0.01
    dibromomethane 0.03
    1,1,2,2-tetrachloroethane 0.13
    2-methyl-cyclohexyl acetate 0.06
    tetrabutyl urea 0.26
    diisobutyl methanol 0.03
    2-phenylethanol 0.14
    styrene 0.01
    dioctyl adipate 0.19
    dimethyl sulfate 1.22
    ethyl butyrate 0.07
    methyl lactate 2.33
    butyl lactate 0.66
    diethyl carbonate 0.04
    propanediol butyl ether 4.68
    triethyl orthoformate 0.11
    p-tert-butyltoluene 0.01
    methyl 4-tert-butylbenzoate 0.4
    morpholine 8.81
    tert-butylamine 0.07
    n-dodecanol 0.11
    dimethoxymethane 4.69
    ethylene carbonate 0.26
    cyrene 3.07
    2-ethoxyethyl acetate 0.64
    2-ethylhexyl acetate 0.04
    1,2,4-trichlorobenzene 0.02
    4-methylpyridine 0.31
    dibutyl ether 0.11
    2,6-dimethyl-4-heptanol 0.03
    DEF 0.95
    dimethyl isosorbide 1.63
    tetrachloroethylene 0.09
    eugenol 0.62
    triacetin 0.54
    span 80 2.22
    1,4-butanediol 2.78
    1,1-dichloroethane 0.03
    2-methyl-1-pentanol 0.17
    methyl formate 3.92
    2-methyl-1-butanol 0.39
    n-decane 0.01
    butyronitrile 0.11
    3,7-dimethyl-1-octanol 0.1
    1-chlorooctane 0.04
    1-chlorotetradecane 0.01
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 1.14
    tetrahydropyran 0.93
    tert-amyl methyl ether 0.12
    2,5,8-trioxanonane 3.8
    1-hexene 0.01
    2-isopropoxyethanol 1.83
    2,2,2-trifluoroethanol 1.78
    methyl butyrate 0.13

    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