(4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E,3E)-3-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypenta-1,3-dienyl]cyclohex-2-en-1-one

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  • Identifiers

    CAS number
    145153-00-0

    Molecular formula
    C21H32O8

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

    Safety labels

  • Odor profile

    Fragrance
    Woody 39.5%
    Sweet 36.18%
    Odorless 32.52%
    Spicy 29.66%
    Floral 27.3%
    Mint 26.65%
    Fruity 26.09%
    Warm 21.29%
    Dry 20.52%
    Cooling 20.11%

     

    Flavor
    Bitter 68.14%
    Odorless 20.91%
    Sweet-like 20.88%
    Fruity 20.38%
    Cedarleaf 20.04%
    Leaves 19.56%
    Parsley 19.04%
    Seedy 19.03%
    Ripe apricot 18.99%
    Cotton candy 18.94%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.2

    pKa est.
    6.3 (neutral)

    Molecular weight
    412.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2204°C

    Flash point

    • 240.57 ˚C est.

  • Synonyms

    • 145153-00-0
    • (4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E,3E)-3-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypenta-1,3-dienyl]cyclohex-2-en-1-one
    • Compound NP-020336
    • DTXSID101106745
    • AKOS040738044
    • (4S)-4-[(1E,3E)-5-(I(2)-D-Glucopyranosyloxy)-3-methyl-1,3-pentadien-1-yl]-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one
    • 145153-00-0

  • Applications

    The compound (4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E,3E)-3-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypenta-1,3-dienyl]cyclohex-2-en-1-one (CAS 145153-00-0) is mainly used as an intermediate in the synthesis of glycosylated terpenoid derivatives, providing a chiral sugar-containing framework for natural product–inspired libraries. It may also be evaluated as a fragrance and flavor precursor, where glycoside conjugates can serve as odorant precursors or profragrances. In cosmetics and personal care, it can function as a starting material for glycoside-derived actives or as a scaffold for sugar-terpene conjugates, subject to regulatory and formulation constraints. In pharmaceutical research, it offers a potential chiral building block for synthetic routes to natural product analogs and medicinal chemistry programs. In academic and process-development settings, it supports glycosylation studies and stereochemical investigations as a reference compound for method development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 26.15
    methanol 90.93
    isopropanol 5.62
    water 2.27
    ethyl acetate 2.96
    n-propanol 10.65
    acetone 16.36
    n-butanol 7.23
    acetonitrile 3.12
    DMF 94.64
    toluene 1.65
    isobutanol 3.14
    1,4-dioxane 27.23
    methyl acetate 3.08
    THF 68.87
    2-butanone 6.14
    n-pentanol 4.4
    sec-butanol 3.67
    n-hexane 0.15
    ethylene glycol 16.75
    NMP 51.21
    cyclohexane 0.41
    DMSO 269.62
    n-butyl acetate 0.71
    n-octanol 2.95
    chloroform 1.97
    n-propyl acetate 1.23
    acetic acid 42.64
    dichloromethane 2.55
    cyclohexanone 11.78
    propylene glycol 15.97
    isopropyl acetate 1.91
    DMAc 79.78
    2-ethoxyethanol 42.79
    isopentanol 3.22
    n-heptane 0.24
    ethyl formate 3.73
    1,2-dichloroethane 2.23
    n-hexanol 2.43
    2-methoxyethanol 100.41
    isobutyl acetate 0.67
    tetrachloromethane 0.45
    n-pentyl acetate 1.95
    transcutol 41.53
    n-heptanol 3.46
    ethylbenzene 0.78
    MIBK 3.29
    2-propoxyethanol 21.04
    tert-butanol 3.88
    MTBE 1.73
    2-butoxyethanol 14.06
    propionic acid 6.03
    o-xylene 1.24
    formic acid 83.92
    diethyl ether 4.03
    m-xylene 1.19
    p-xylene 0.77
    chlorobenzene 0.77
    dimethyl carbonate 6.05
    n-octane 0.17
    formamide 78.9
    cyclopentanone 23.27
    2-pentanone 6.15
    anisole 3.26
    cyclopentyl methyl ether 8.91
    gamma-butyrolactone 18.47
    1-methoxy-2-propanol 44.92
    pyridine 9.95
    3-pentanone 3.94
    furfural 18.54
    n-dodecane 0.09
    diethylene glycol 31.97
    diisopropyl ether 0.65
    tert-amyl alcohol 2.99
    acetylacetone 12.29
    n-hexadecane 0.1
    acetophenone 4.09
    methyl propionate 5.09
    isopentyl acetate 0.81
    trichloroethylene 3.94
    n-nonanol 3.05
    cyclohexanol 4.38
    benzyl alcohol 5.92
    2-ethylhexanol 1.01
    isooctanol 2.23
    dipropyl ether 1.92
    1,2-dichlorobenzene 0.76
    ethyl lactate 3.26
    propylene carbonate 4.44
    n-methylformamide 36.74
    2-pentanol 2.47
    n-pentane 0.21
    1-propoxy-2-propanol 8.43
    1-methoxy-2-propyl acetate 4.0
    2-(2-methoxypropoxy) propanol 10.32
    mesitylene 0.68
    ε-caprolactone 8.7
    p-cymene 0.46
    epichlorohydrin 20.83
    1,1,1-trichloroethane 0.64
    2-aminoethanol 28.0
    morpholine-4-carbaldehyde 58.85
    sulfolane 48.45
    2,2,4-trimethylpentane 0.08
    2-methyltetrahydrofuran 10.39
    n-hexyl acetate 2.78
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 17.31
    sec-butyl acetate 0.78
    tert-butyl acetate 2.58
    decalin 0.13
    glycerin 43.57
    diglyme 31.51
    acrylic acid 10.38
    isopropyl myristate 0.85
    n-butyric acid 6.08
    acetyl acetate 2.73
    di(2-ethylhexyl) phthalate 2.04
    ethyl propionate 1.52
    nitromethane 41.13
    1,2-diethoxyethane 5.4
    benzonitrile 1.75
    trioctyl phosphate 1.34
    1-bromopropane 0.93
    gamma-valerolactone 46.91
    n-decanol 1.82
    triethyl phosphate 1.12
    4-methyl-2-pentanol 1.25
    propionitrile 1.8
    vinylene carbonate 4.89
    1,1,2-trichlorotrifluoroethane 23.71
    DMS 2.46
    cumene 0.5
    2-octanol 1.62
    2-hexanone 2.56
    octyl acetate 1.54
    limonene 0.76
    1,2-dimethoxyethane 32.86
    ethyl orthosilicate 1.18
    tributyl phosphate 1.04
    diacetone alcohol 10.44
    N,N-dimethylaniline 3.04
    acrylonitrile 3.32
    aniline 3.89
    1,3-propanediol 33.66
    bromobenzene 0.55
    dibromomethane 1.41
    1,1,2,2-tetrachloroethane 3.48
    2-methyl-cyclohexyl acetate 1.47
    tetrabutyl urea 2.37
    diisobutyl methanol 0.67
    2-phenylethanol 3.42
    styrene 0.79
    dioctyl adipate 2.07
    dimethyl sulfate 12.96
    ethyl butyrate 1.04
    methyl lactate 10.76
    butyl lactate 3.22
    diethyl carbonate 0.64
    propanediol butyl ether 14.3
    triethyl orthoformate 1.43
    p-tert-butyltoluene 0.49
    methyl 4-tert-butylbenzoate 5.88
    morpholine 38.13
    tert-butylamine 1.09
    n-dodecanol 1.09
    dimethoxymethane 53.02
    ethylene carbonate 3.44
    cyrene 17.95
    2-ethoxyethyl acetate 4.74
    2-ethylhexyl acetate 0.61
    1,2,4-trichlorobenzene 1.22
    4-methylpyridine 5.09
    dibutyl ether 1.33
    2,6-dimethyl-4-heptanol 0.67
    DEF 12.84
    dimethyl isosorbide 14.68
    tetrachloroethylene 2.98
    eugenol 7.17
    triacetin 4.61
    span 80 8.44
    1,4-butanediol 10.74
    1,1-dichloroethane 0.75
    2-methyl-1-pentanol 2.42
    methyl formate 23.12
    2-methyl-1-butanol 3.12
    n-decane 0.21
    butyronitrile 2.04
    3,7-dimethyl-1-octanol 1.59
    1-chlorooctane 0.72
    1-chlorotetradecane 0.22
    n-nonane 0.19
    undecane 0.13
    tert-butylcyclohexane 0.09
    cyclooctane 0.21
    cyclopentanol 6.55
    tetrahydropyran 10.29
    tert-amyl methyl ether 2.01
    2,5,8-trioxanonane 22.25
    1-hexene 0.47
    2-isopropoxyethanol 14.32
    2,2,2-trifluoroethanol 11.37
    methyl butyrate 2.05

    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