Daphnetin-8-glucoside

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  • Identifiers

    CAS number
    20853-56-9

    Molecular formula
    C15H16O9

    SMILES
    C1=CC(=C(C2=C1C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O

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  • Odor profile

    Fragrance
    Odorless 75.74%
    Vanilla 31.18%
    Sweet 23.98%
    Caramellic 23.45%
    Milky 23.27%
    Phenolic 22.52%
    Burnt 22.38%
    Savory 21.79%
    Creamy 19.51%
    Bitter 17.69%

     

    Flavor
    Bitter 72.19%
    Odorless 36.11%
    Bland 29.56%
    Sweet-like 27.47%
    Very mild 22.25%
    Sweet 21.33%
    Eugenol 20.11%
    Very slight 19.98%
    Cedarleaf 19.9%
    Naphthalic 19.89%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    6.89 (neutral)

    Molecular weight
    340.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2040°C

    Flash point

    • 275.08 ˚C est.

  • Synonyms

    • Daphnetin-8-glucoside
    • 20853-56-9
    • 7-hydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
    • DTXSID40174971
    • 2H-1-Benzopyran-2-one, 8-(beta-D-glucopyranosyloxy)-7-hydroxy-
    • 7-hydroxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-2-one
    • RefChem:130928
    • DTXCID9097462
    • 8-?(?-?D-?Glucopyranosyloxy)?-?7-?Hydroxy-2H-?1-?Benzopyran-?2-?One
    • Daphnetin 8-glucoside
    • D7S6VL7JTH
    • 8-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one
    • XD163785
    • 7-Hydroxy-2-oxo-2H-1-benzopyran-8-yl beta-D-glucopyranoside
    • 8-(| cent-D-Glucopyranosyloxy)-7-Hydroxy-2H-1-Benzopyran-2-One
    • 20853-56-9

  • Applications

    Daphnetin-8-glucoside is primarily viewed as an intermediate in the synthesis of glycoside derivatives of daphnetin and is studied in organic chemistry to develop glycosylated coumarin frameworks. It also serves as a substrate for glycosidase enzymes in biochemical research and as a tool to study glycosidic hydrolysis. In analytical contexts, it can be used as a reference standard for HPLC/LC-MS methods when identifying coumarin glycosides or related metabolites. In cosmetic and personal-care development, it may be considered as a precursor or foundational scaffold for glycoside coumarin compounds explored for fragrance-related or formulation-stability studies, and in pharmaceutical research as a building block for glycoside derivatives of coumarin, subject to regulatory limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.55
    methanol 8.89
    isopropanol 7.09
    water 2.55
    ethyl acetate 0.71
    n-propanol 6.0
    acetone 2.82
    n-butanol 3.59
    acetonitrile 0.94
    DMF 57.49
    toluene 0.22
    isobutanol 2.08
    1,4-dioxane 6.24
    methyl acetate 1.26
    THF 14.82
    2-butanone 2.28
    n-pentanol 1.32
    sec-butanol 4.44
    n-hexane 0.03
    ethylene glycol 54.03
    NMP 52.76
    cyclohexane 0.1
    DMSO 178.04
    n-butyl acetate 0.43
    n-octanol 1.13
    chloroform 0.01
    n-propyl acetate 0.4
    acetic acid 19.79
    dichloromethane 0.03
    cyclohexanone 3.47
    propylene glycol 35.68
    isopropyl acetate 0.55
    DMAc 75.16
    2-ethoxyethanol 27.6
    isopentanol 1.98
    n-heptane 0.18
    ethyl formate 0.82
    1,2-dichloroethane 0.1
    n-hexanol 1.17
    2-methoxyethanol 82.76
    isobutyl acetate 0.14
    tetrachloromethane 0.01
    n-pentyl acetate 0.68
    transcutol 36.56
    n-heptanol 1.67
    ethylbenzene 0.1
    MIBK 0.71
    2-propoxyethanol 13.21
    tert-butanol 5.45
    MTBE 0.88
    2-butoxyethanol 8.55
    propionic acid 5.5
    o-xylene 0.27
    formic acid 73.11
    diethyl ether 0.93
    m-xylene 0.18
    p-xylene 0.12
    chlorobenzene 0.04
    dimethyl carbonate 2.75
    n-octane 0.11
    formamide 95.1
    cyclopentanone 7.27
    2-pentanone 1.42
    anisole 0.43
    cyclopentyl methyl ether 2.81
    gamma-butyrolactone 9.58
    1-methoxy-2-propanol 44.69
    pyridine 2.52
    3-pentanone 1.15
    furfural 6.83
    n-dodecane 0.07
    diethylene glycol 36.03
    diisopropyl ether 0.25
    tert-amyl alcohol 3.83
    acetylacetone 2.73
    n-hexadecane 0.08
    acetophenone 0.85
    methyl propionate 2.04
    isopentyl acetate 0.43
    trichloroethylene 0.09
    n-nonanol 1.28
    cyclohexanol 3.39
    benzyl alcohol 1.29
    2-ethylhexanol 0.62
    isooctanol 1.06
    dipropyl ether 1.43
    1,2-dichlorobenzene 0.04
    ethyl lactate 2.31
    propylene carbonate 1.66
    n-methylformamide 22.29
    2-pentanol 2.09
    n-pentane 0.05
    1-propoxy-2-propanol 8.23
    1-methoxy-2-propyl acetate 2.4
    2-(2-methoxypropoxy) propanol 8.7
    mesitylene 0.13
    ε-caprolactone 3.65
    p-cymene 0.2
    epichlorohydrin 3.57
    1,1,1-trichloroethane 0.02
    2-aminoethanol 42.87
    morpholine-4-carbaldehyde 44.9
    sulfolane 32.77
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 3.85
    n-hexyl acetate 0.88
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 13.92
    sec-butyl acetate 0.24
    tert-butyl acetate 0.86
    decalin 0.03
    glycerin 106.9
    diglyme 21.85
    acrylic acid 8.32
    isopropyl myristate 0.46
    n-butyric acid 3.24
    acetyl acetate 0.43
    di(2-ethylhexyl) phthalate 0.76
    ethyl propionate 0.45
    nitromethane 19.1
    1,2-diethoxyethane 2.53
    benzonitrile 0.34
    trioctyl phosphate 0.76
    1-bromopropane 0.06
    gamma-valerolactone 22.2
    n-decanol 1.03
    triethyl phosphate 0.65
    4-methyl-2-pentanol 0.73
    propionitrile 0.65
    vinylene carbonate 1.21
    1,1,2-trichlorotrifluoroethane 10.34
    DMS 1.08
    cumene 0.08
    2-octanol 0.9
    2-hexanone 0.55
    octyl acetate 0.8
    limonene 0.34
    1,2-dimethoxyethane 13.07
    ethyl orthosilicate 0.63
    tributyl phosphate 0.62
    diacetone alcohol 7.38
    N,N-dimethylaniline 0.64
    acrylonitrile 1.35
    aniline 1.15
    1,3-propanediol 39.14
    bromobenzene 0.02
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.14
    2-methyl-cyclohexyl acetate 0.61
    tetrabutyl urea 1.97
    diisobutyl methanol 0.56
    2-phenylethanol 1.1
    styrene 0.08
    dioctyl adipate 1.03
    dimethyl sulfate 7.36
    ethyl butyrate 0.57
    methyl lactate 11.91
    butyl lactate 2.09
    diethyl carbonate 0.41
    propanediol butyl ether 9.87
    triethyl orthoformate 0.97
    p-tert-butyltoluene 0.22
    methyl 4-tert-butylbenzoate 2.76
    morpholine 17.21
    tert-butylamine 1.11
    n-dodecanol 0.77
    dimethoxymethane 16.89
    ethylene carbonate 0.99
    cyrene 10.43
    2-ethoxyethyl acetate 1.74
    2-ethylhexyl acetate 0.3
    1,2,4-trichlorobenzene 0.1
    4-methylpyridine 1.03
    dibutyl ether 0.76
    2,6-dimethyl-4-heptanol 0.56
    DEF 5.99
    dimethyl isosorbide 8.98
    tetrachloroethylene 0.14
    eugenol 3.21
    triacetin 2.3
    span 80 6.61
    1,4-butanediol 11.58
    1,1-dichloroethane 0.02
    2-methyl-1-pentanol 0.8
    methyl formate 8.67
    2-methyl-1-butanol 1.95
    n-decane 0.13
    butyronitrile 0.47
    3,7-dimethyl-1-octanol 0.69
    1-chlorooctane 0.22
    1-chlorotetradecane 0.11
    n-nonane 0.11
    undecane 0.09
    tert-butylcyclohexane 0.02
    cyclooctane 0.06
    cyclopentanol 5.8
    tetrahydropyran 2.93
    tert-amyl methyl ether 1.15
    2,5,8-trioxanonane 18.31
    1-hexene 0.07
    2-isopropoxyethanol 8.45
    2,2,2-trifluoroethanol 8.71
    methyl butyrate 0.65

    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