1-O-(9,16,17-Trihydroxy-18-oxokauran-18-yl)hexopyranose

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  • Identifiers

    CAS number
    63558-43-0

    Molecular formula
    C26H42O10

    SMILES
    CC1(CCCC2(C1CCC34C2(CCC(C3)C(C4)(CO)O)O)C)C(=O)OC5C(C(C(C(O5)CO)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 56.86%
    Woody 37.31%
    Cooling 32.48%
    Sweet 30.63%
    Balsamic 27.57%
    Mint 26.66%
    Spicy 24.61%
    Camphoreous 21.93%
    Amber 21.72%
    Clean 21.19%

     

    Flavor
    Bitter 66.55%
    Sweet 33.04%
    Odorless 32.05%
    Fatty 31.66%
    Sweet-like 28.41%
    Bland 24.19%
    Cedarleaf 21.79%
    Patchouli 21.47%
    Soil 21.43%
    Cauliflower 21.24%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    5.05 (weak acid)

    Molecular weight
    514.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    914°C

    Melting point expt.

    • 184 - 187 °C

    Flash point

    • 296.23 ˚C est.

  • Synonyms

    • 63558-43-0
    • DTXSID301150643
    • 1-O-(9,16,17-Trihydroxy-18-oxokauran-18-yl)hexopyranose
    • Kauran-18-oic acid, 9,16,17-trihydroxy-, I(2)-D-glucopyranosyl ester, (4I+/-)-
    • 63558-43-0

  • Applications

    1-O-(9,16,17-Trihydroxy-18-oxokauran-18-yl)hexopyranose (CAS 63558-43-0) is a glycoside diterpenoid that is typically used as an intermediate or starting point for the synthesis of kaurane-type glycoside derivatives in natural product synthesis and medicinal chemistry. In pharmaceutical and biological research, it is evaluated as a scaffold for structure–activity relationship (SAR) studies and lead optimization at the laboratory scale. In agriculture, the compound may serve as a model lead for plant defense mechanisms and related derivative research aimed at developing agrochemical agents. In cosmetics and personal care, it can be considered as a research ingredient for glycoside diterpenoid chemistry or as a template for formulation studies based on glycosides. In industrial chemical technology, it can function as a chiral building block or precursor for more complex glycosides and related glycosylation research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.59
    methanol 59.01
    isopropanol 1.37
    water 1.11
    ethyl acetate 2.54
    n-propanol 2.4
    acetone 6.92
    n-butanol 1.09
    acetonitrile 1.75
    DMF 51.79
    toluene 0.48
    isobutanol 0.69
    1,4-dioxane 13.7
    methyl acetate 2.52
    THF 25.37
    2-butanone 2.67
    n-pentanol 0.63
    sec-butanol 0.56
    n-hexane 0.02
    ethylene glycol 17.25
    NMP 40.4
    cyclohexane 0.06
    DMSO 91.73
    n-butyl acetate 0.86
    n-octanol 0.71
    chloroform 2.29
    n-propyl acetate 0.81
    acetic acid 54.7
    dichloromethane 2.27
    cyclohexanone 4.56
    propylene glycol 7.39
    isopropyl acetate 1.52
    DMAc 30.96
    2-ethoxyethanol 12.97
    isopentanol 0.57
    n-heptane 0.04
    ethyl formate 3.37
    1,2-dichloroethane 1.35
    n-hexanol 0.72
    2-methoxyethanol 47.38
    isobutyl acetate 0.38
    tetrachloromethane 0.41
    n-pentyl acetate 1.5
    transcutol 16.84
    n-heptanol 1.08
    ethylbenzene 0.2
    MIBK 1.19
    2-propoxyethanol 12.79
    tert-butanol 0.73
    MTBE 0.47
    2-butoxyethanol 7.68
    propionic acid 4.13
    o-xylene 0.36
    formic acid 105.67
    diethyl ether 1.24
    m-xylene 0.39
    p-xylene 0.19
    chlorobenzene 0.47
    dimethyl carbonate 7.6
    n-octane 0.03
    formamide 76.25
    cyclopentanone 11.93
    2-pentanone 2.35
    anisole 1.0
    cyclopentyl methyl ether 3.09
    gamma-butyrolactone 18.85
    1-methoxy-2-propanol 17.47
    pyridine 5.41
    3-pentanone 1.59
    furfural 20.11
    n-dodecane 0.02
    diethylene glycol 24.53
    diisopropyl ether 0.23
    tert-amyl alcohol 0.45
    acetylacetone 8.28
    n-hexadecane 0.02
    acetophenone 1.61
    methyl propionate 3.77
    isopentyl acetate 0.69
    trichloroethylene 3.78
    n-nonanol 0.76
    cyclohexanol 0.78
    benzyl alcohol 1.87
    2-ethylhexanol 0.29
    isooctanol 0.61
    dipropyl ether 0.7
    1,2-dichlorobenzene 0.51
    ethyl lactate 2.16
    propylene carbonate 6.02
    n-methylformamide 28.31
    2-pentanol 0.43
    n-pentane 0.04
    1-propoxy-2-propanol 4.89
    1-methoxy-2-propyl acetate 4.6
    2-(2-methoxypropoxy) propanol 3.96
    mesitylene 0.23
    ε-caprolactone 5.11
    p-cymene 0.18
    epichlorohydrin 14.74
    1,1,1-trichloroethane 0.58
    2-aminoethanol 14.77
    morpholine-4-carbaldehyde 50.55
    sulfolane 38.4
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 3.14
    n-hexyl acetate 1.49
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 7.08
    sec-butyl acetate 0.46
    tert-butyl acetate 1.58
    decalin 0.03
    glycerin 32.77
    diglyme 15.32
    acrylic acid 10.23
    isopropyl myristate 0.35
    n-butyric acid 4.29
    acetyl acetate 3.68
    di(2-ethylhexyl) phthalate 0.84
    ethyl propionate 0.96
    nitromethane 55.66
    1,2-diethoxyethane 2.31
    benzonitrile 1.02
    trioctyl phosphate 0.6
    1-bromopropane 0.31
    gamma-valerolactone 40.92
    n-decanol 0.42
    triethyl phosphate 0.63
    4-methyl-2-pentanol 0.3
    propionitrile 0.83
    vinylene carbonate 7.25
    1,1,2-trichlorotrifluoroethane 26.31
    DMS 2.63
    cumene 0.13
    2-octanol 0.42
    2-hexanone 0.78
    octyl acetate 0.7
    limonene 0.24
    1,2-dimethoxyethane 11.08
    ethyl orthosilicate 0.55
    tributyl phosphate 0.49
    diacetone alcohol 4.45
    N,N-dimethylaniline 0.85
    acrylonitrile 2.25
    aniline 1.51
    1,3-propanediol 12.05
    bromobenzene 0.33
    dibromomethane 0.93
    1,1,2,2-tetrachloroethane 2.53
    2-methyl-cyclohexyl acetate 0.69
    tetrabutyl urea 0.83
    diisobutyl methanol 0.19
    2-phenylethanol 1.99
    styrene 0.21
    dioctyl adipate 0.83
    dimethyl sulfate 16.88
    ethyl butyrate 0.75
    methyl lactate 11.19
    butyl lactate 2.38
    diethyl carbonate 0.56
    propanediol butyl ether 7.17
    triethyl orthoformate 0.85
    p-tert-butyltoluene 0.2
    methyl 4-tert-butylbenzoate 3.39
    morpholine 14.74
    tert-butylamine 0.2
    n-dodecanol 0.23
    dimethoxymethane 30.87
    ethylene carbonate 4.54
    cyrene 8.83
    2-ethoxyethyl acetate 4.93
    2-ethylhexyl acetate 0.47
    1,2,4-trichlorobenzene 0.84
    4-methylpyridine 2.49
    dibutyl ether 0.35
    2,6-dimethyl-4-heptanol 0.19
    DEF 5.02
    dimethyl isosorbide 8.01
    tetrachloroethylene 2.56
    eugenol 3.94
    triacetin 3.9
    span 80 3.99
    1,4-butanediol 3.18
    1,1-dichloroethane 0.6
    2-methyl-1-pentanol 0.33
    methyl formate 25.76
    2-methyl-1-butanol 0.49
    n-decane 0.04
    butyronitrile 0.68
    3,7-dimethyl-1-octanol 0.37
    1-chlorooctane 0.17
    1-chlorotetradecane 0.05
    n-nonane 0.03
    undecane 0.02
    tert-butylcyclohexane 0.02
    cyclooctane 0.03
    cyclopentanol 1.64
    tetrahydropyran 2.6
    tert-amyl methyl ether 0.46
    2,5,8-trioxanonane 8.82
    1-hexene 0.08
    2-isopropoxyethanol 3.92
    2,2,2-trifluoroethanol 17.88
    methyl butyrate 1.23

    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