(4S)-4-((1E)-4-(beta-D-Glucopyranosyloxy)-3-oxo-1-buten-1-yl)-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

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  • Identifiers

    CAS number
    189344-54-5

    Molecular formula
    C19H28O9

    SMILES
    CC1=CC(=O)CC([C@]1(/C=C/C(=O)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)(C)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 47.06%
    Odorless 37.52%
    Woody 34.24%
    Caramellic 27.56%
    Spicy 22.36%
    Mint 21.71%
    Vanilla 21.27%
    Milky 20.6%
    Creamy 20.02%
    Savory 18.63%

     

    Flavor
    Bitter 63.23%
    Odorless 27.47%
    Fruity 24.78%
    Very mild 23.73%
    Sweet-like 22.91%
    Bland 21.37%
    Cotton candy 19.94%
    Seedy 19.89%
    Extremely sweet 19.64%
    Toffee 19.48%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.7

    pKa est.
    6.0 (neutral)

    Molecular weight
    400.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2382°C

    Flash point

    • 236.61 ˚C est.

  • Synonyms

    • DTXSID601111927
    • 189344-54-5
    • (4S)-4-((1E)-4-(beta-D-Glucopyranosyloxy)-3-oxo-1-buten-1-yl)-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one
    • RefChem:906154
    • DTXCID401543538
    • Corchoionoside B
    • (3E)-4-[(1S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-2-oxobut-3-en-1-yl beta-D-glucopyranoside
    • (4S)-4-[(1E)-4-(I(2)-D-Glucopyranosyloxy)-3-oxo-1-buten-1-yl]-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one
    • 189344-54-5

  • Applications

    The chemical (4S)-4-((1E)-4-(beta-D-Glucopyranosyloxy)-3-oxo-1-buten-1-yl)-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one (CAS 189344-54-5) can function as a fragrance intermediate or odorant precursor, a cosmetic formulation intermediate, and a chiral building block in pharmaceutical research; it is also employed as an intermediate in the synthesis of agrochemicals and may be explored as a flavor/aroma precursor for food applications, depending on regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.51
    methanol 107.25
    isopropanol 5.43
    water 9.74
    ethyl acetate 8.23
    n-propanol 9.46
    acetone 24.72
    n-butanol 6.8
    acetonitrile 8.67
    DMF 233.78
    toluene 1.92
    isobutanol 2.86
    1,4-dioxane 32.43
    methyl acetate 7.46
    THF 61.27
    2-butanone 8.81
    n-pentanol 3.36
    sec-butanol 3.4
    n-hexane 0.18
    ethylene glycol 51.21
    NMP 150.56
    cyclohexane 0.49
    DMSO 583.34
    n-butyl acetate 1.33
    n-octanol 2.42
    chloroform 2.66
    n-propyl acetate 2.43
    acetic acid 89.6
    dichloromethane 5.34
    cyclohexanone 13.63
    propylene glycol 32.29
    isopropyl acetate 4.0
    DMAc 156.83
    2-ethoxyethanol 59.88
    isopentanol 2.85
    n-heptane 0.37
    ethyl formate 7.75
    1,2-dichloroethane 4.45
    n-hexanol 2.07
    2-methoxyethanol 176.29
    isobutyl acetate 0.94
    tetrachloromethane 0.51
    n-pentyl acetate 2.34
    transcutol 51.68
    n-heptanol 2.77
    ethylbenzene 0.85
    MIBK 4.09
    2-propoxyethanol 30.6
    tert-butanol 3.95
    MTBE 2.02
    2-butoxyethanol 14.13
    propionic acid 13.07
    o-xylene 1.54
    formic acid 282.75
    diethyl ether 5.77
    m-xylene 1.36
    p-xylene 0.85
    chlorobenzene 1.04
    dimethyl carbonate 20.94
    n-octane 0.23
    formamide 265.78
    cyclopentanone 33.37
    2-pentanone 9.57
    anisole 4.29
    cyclopentyl methyl ether 12.05
    gamma-butyrolactone 46.76
    1-methoxy-2-propanol 77.24
    pyridine 14.13
    3-pentanone 6.53
    furfural 43.4
    n-dodecane 0.11
    diethylene glycol 61.87
    diisopropyl ether 0.97
    tert-amyl alcohol 2.84
    acetylacetone 24.06
    n-hexadecane 0.13
    acetophenone 5.9
    methyl propionate 14.47
    isopentyl acetate 1.08
    trichloroethylene 7.51
    n-nonanol 2.39
    cyclohexanol 4.91
    benzyl alcohol 5.85
    2-ethylhexanol 0.96
    isooctanol 1.72
    dipropyl ether 3.24
    1,2-dichlorobenzene 1.13
    ethyl lactate 6.84
    propylene carbonate 11.31
    n-methylformamide 104.11
    2-pentanol 2.85
    n-pentane 0.26
    1-propoxy-2-propanol 11.86
    1-methoxy-2-propyl acetate 7.64
    2-(2-methoxypropoxy) propanol 11.09
    mesitylene 0.83
    ε-caprolactone 14.13
    p-cymene 0.54
    epichlorohydrin 38.34
    1,1,1-trichloroethane 1.11
    2-aminoethanol 51.49
    morpholine-4-carbaldehyde 132.17
    sulfolane 122.85
    2,2,4-trimethylpentane 0.09
    2-methyltetrahydrofuran 12.11
    n-hexyl acetate 3.07
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 19.04
    sec-butyl acetate 1.45
    tert-butyl acetate 4.19
    decalin 0.15
    glycerin 112.47
    diglyme 39.9
    acrylic acid 26.48
    isopropyl myristate 0.92
    n-butyric acid 11.87
    acetyl acetate 7.32
    di(2-ethylhexyl) phthalate 1.8
    ethyl propionate 3.89
    nitromethane 128.94
    1,2-diethoxyethane 7.02
    benzonitrile 2.4
    trioctyl phosphate 1.28
    1-bromopropane 1.3
    gamma-valerolactone 79.24
    n-decanol 1.53
    triethyl phosphate 1.92
    4-methyl-2-pentanol 1.31
    propionitrile 3.64
    vinylene carbonate 12.05
    1,1,2-trichlorotrifluoroethane 50.07
    DMS 4.49
    cumene 0.51
    2-octanol 1.41
    2-hexanone 2.98
    octyl acetate 1.7
    limonene 0.85
    1,2-dimethoxyethane 46.61
    ethyl orthosilicate 1.81
    tributyl phosphate 1.11
    diacetone alcohol 16.75
    N,N-dimethylaniline 3.93
    acrylonitrile 8.53
    aniline 5.25
    1,3-propanediol 49.63
    bromobenzene 0.84
    dibromomethane 2.22
    1,1,2,2-tetrachloroethane 5.38
    2-methyl-cyclohexyl acetate 1.66
    tetrabutyl urea 2.63
    diisobutyl methanol 0.71
    2-phenylethanol 3.29
    styrene 0.95
    dioctyl adipate 2.15
    dimethyl sulfate 50.94
    ethyl butyrate 2.21
    methyl lactate 30.73
    butyl lactate 3.66
    diethyl carbonate 1.48
    propanediol butyl ether 14.39
    triethyl orthoformate 2.45
    p-tert-butyltoluene 0.56
    methyl 4-tert-butylbenzoate 6.83
    morpholine 45.57
    tert-butylamine 1.06
    n-dodecanol 0.97
    dimethoxymethane 112.08
    ethylene carbonate 7.97
    cyrene 26.49
    2-ethoxyethyl acetate 6.3
    2-ethylhexyl acetate 0.81
    1,2,4-trichlorobenzene 1.77
    4-methylpyridine 7.78
    dibutyl ether 1.58
    2,6-dimethyl-4-heptanol 0.71
    DEF 26.98
    dimethyl isosorbide 21.04
    tetrachloroethylene 4.14
    eugenol 8.23
    triacetin 6.58
    span 80 8.8
    1,4-butanediol 14.47
    1,1-dichloroethane 1.37
    2-methyl-1-pentanol 1.66
    methyl formate 73.35
    2-methyl-1-butanol 2.78
    n-decane 0.26
    butyronitrile 3.33
    3,7-dimethyl-1-octanol 1.21
    1-chlorooctane 0.69
    1-chlorotetradecane 0.22
    n-nonane 0.25
    undecane 0.16
    tert-butylcyclohexane 0.09
    cyclooctane 0.27
    cyclopentanol 8.12
    tetrahydropyran 9.8
    tert-amyl methyl ether 2.45
    2,5,8-trioxanonane 27.24
    1-hexene 0.52
    2-isopropoxyethanol 18.38
    2,2,2-trifluoroethanol 34.31
    methyl butyrate 4.41

    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