Picras-3-ene-2,16-dione, 13,20-epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-, (1beta,11beta,12alpha,15beta)-

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  • Identifiers

    CAS number
    152369-48-7

    Molecular formula
    C25H32O9

    SMILES
    CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)C=C(C)C)(OC5)C)O)O)C)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 47.94%
    Sweet 37.4%
    Mint 28.04%
    Spicy 26.85%
    Caramellic 26.29%
    Woody 22.86%
    Cooling 21.12%
    Burnt 20.63%
    Vanilla 17.63%
    Roasted 17.24%

     

    Flavor
    Bitter 85.96%
    Cedarleaf 21.49%
    Bland 21.36%
    Sweet-like 21.12%
    Lovage 19.63%
    Leaves 19.58%
    Parsley 19.35%
    Odorless 19.31%
    Ripe apricot 19.28%
    Fenugreek 19.07%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    4.66 (weak acid)

    Molecular weight
    476.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    721°C

    Flash point

    • 222.47 ˚C est.

  • Synonyms

    • Gutolactone
    • 152369-48-7
    • CHEBI:65989
    • DTXSID90934486
    • Picras-3-ene-2,16-dione, 13,20-epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-, (1beta,11beta,12alpha,15beta)-
    • RefChem:929256
    • DTXCID201767796
    • ((1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo(12.5.0.01,6.02,17.08,13)nonadec-9-en-3-yl) 3-methylbut-2-enoate
    • Gurolactone
    • (+)-Gurolactone
    • Q27134490
    • (1beta,11beta,12alpha,13beta,15beta)-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-15-yl 3-methylbut-2-enoate
    • (1beta,11beta,12alpha,15beta)-13,20-Epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)picras-3-ene-2,16-dione
    • 13,20-Epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)picras-3-ene-2,16-dione (1beta,11beta,12alpha,15beta)-
    • 1beta,11beta,12alpha-Trihydroxy-2,16-dioxo-13beta-13,20-epoxypicras-3-en-15beta-yl 3-methylbut-2-enoate
    • 152369-48-7

  • Applications

    Picras-3-ene-2,16-dione, 13,20-epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-, (1beta,11beta,12alpha,15beta)- (CAS number: 152369-48-7) is a multifunctional, stereochemically rich intermediate used as a building block in organic synthesis. It is commonly evaluated as a precursor for the preparation of complex natural product derivatives and related target compounds. In industry, potential applications include fragrance/perfumery as a fragrance intermediate or odorant precursor; cosmetics/personal care as a chiral ingredient for formulation development; pharmaceuticals or agrochemicals research as a synthetic scaffold; polymers/plastics as a reactive building block for functionalized materials; and coatings/inks as a specialty additive. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 47.34
    methanol 144.53
    isopropanol 23.25
    water 0.71
    ethyl acetate 35.85
    n-propanol 35.96
    acetone 96.28
    n-butanol 23.51
    acetonitrile 37.82
    DMF 231.14
    toluene 10.58
    isobutanol 15.68
    1,4-dioxane 95.71
    methyl acetate 44.62
    THF 221.35
    2-butanone 48.9
    n-pentanol 13.8
    sec-butanol 11.69
    n-hexane 0.33
    ethylene glycol 38.81
    NMP 281.61
    cyclohexane 0.82
    DMSO 359.89
    n-butyl acetate 16.23
    n-octanol 4.35
    chloroform 74.79
    n-propyl acetate 17.07
    acetic acid 332.96
    dichloromethane 66.83
    cyclohexanone 86.03
    propylene glycol 29.66
    isopropyl acetate 17.68
    DMAc 169.94
    2-ethoxyethanol 72.75
    isopentanol 12.06
    n-heptane 0.3
    ethyl formate 47.24
    1,2-dichloroethane 40.32
    n-hexanol 12.1
    2-methoxyethanol 183.89
    isobutyl acetate 8.39
    tetrachloromethane 8.63
    n-pentyl acetate 13.41
    transcutol 45.05
    n-heptanol 7.67
    ethylbenzene 3.21
    MIBK 15.77
    2-propoxyethanol 80.09
    tert-butanol 12.58
    MTBE 4.9
    2-butoxyethanol 36.25
    propionic acid 60.71
    o-xylene 5.15
    formic acid 212.15
    diethyl ether 15.03
    m-xylene 5.25
    p-xylene 4.17
    chlorobenzene 15.74
    dimethyl carbonate 57.85
    n-octane 0.15
    formamide 220.74
    cyclopentanone 171.39
    2-pentanone 39.39
    anisole 10.78
    cyclopentyl methyl ether 32.85
    gamma-butyrolactone 231.87
    1-methoxy-2-propanol 90.17
    pyridine 72.9
    3-pentanone 26.09
    furfural 145.15
    n-dodecane 0.12
    diethylene glycol 92.56
    diisopropyl ether 2.2
    tert-amyl alcohol 7.94
    acetylacetone 64.26
    n-hexadecane 0.14
    acetophenone 19.61
    methyl propionate 48.12
    isopentyl acetate 11.74
    trichloroethylene 95.72
    n-nonanol 4.91
    cyclohexanol 14.67
    benzyl alcohol 20.98
    2-ethylhexanol 4.58
    isooctanol 5.02
    dipropyl ether 6.29
    1,2-dichlorobenzene 13.3
    ethyl lactate 19.63
    propylene carbonate 73.16
    n-methylformamide 174.17
    2-pentanol 7.99
    n-pentane 0.5
    1-propoxy-2-propanol 32.69
    1-methoxy-2-propyl acetate 31.0
    2-(2-methoxypropoxy) propanol 20.73
    mesitylene 2.35
    ε-caprolactone 81.78
    p-cymene 2.25
    epichlorohydrin 178.29
    1,1,1-trichloroethane 22.53
    2-aminoethanol 52.41
    morpholine-4-carbaldehyde 217.94
    sulfolane 272.41
    2,2,4-trimethylpentane 0.17
    2-methyltetrahydrofuran 52.83
    n-hexyl acetate 12.55
    isooctane 0.13
    2-(2-butoxyethoxy)ethanol 29.74
    sec-butyl acetate 8.16
    tert-butyl acetate 13.43
    decalin 0.36
    glycerin 83.33
    diglyme 52.74
    acrylic acid 94.88
    isopropyl myristate 3.58
    n-butyric acid 69.8
    acetyl acetate 40.06
    di(2-ethylhexyl) phthalate 8.59
    ethyl propionate 14.7
    nitromethane 323.11
    1,2-diethoxyethane 12.24
    benzonitrile 21.05
    trioctyl phosphate 6.09
    1-bromopropane 11.99
    gamma-valerolactone 272.93
    n-decanol 3.06
    triethyl phosphate 7.31
    4-methyl-2-pentanol 4.41
    propionitrile 24.65
    vinylene carbonate 83.36
    1,1,2-trichlorotrifluoroethane 155.66
    DMS 20.7
    cumene 2.0
    2-octanol 3.31
    2-hexanone 17.76
    octyl acetate 6.52
    limonene 2.95
    1,2-dimethoxyethane 70.41
    ethyl orthosilicate 5.92
    tributyl phosphate 5.62
    diacetone alcohol 30.9
    N,N-dimethylaniline 7.81
    acrylonitrile 50.53
    aniline 22.98
    1,3-propanediol 76.28
    bromobenzene 12.3
    dibromomethane 34.78
    1,1,2,2-tetrachloroethane 61.59
    2-methyl-cyclohexyl acetate 11.01
    tetrabutyl urea 8.91
    diisobutyl methanol 2.28
    2-phenylethanol 20.84
    styrene 4.07
    dioctyl adipate 8.59
    dimethyl sulfate 101.8
    ethyl butyrate 11.07
    methyl lactate 61.35
    butyl lactate 16.46
    diethyl carbonate 8.29
    propanediol butyl ether 25.01
    triethyl orthoformate 8.4
    p-tert-butyltoluene 1.97
    methyl 4-tert-butylbenzoate 17.74
    morpholine 115.66
    tert-butylamine 3.46
    n-dodecanol 1.84
    dimethoxymethane 135.92
    ethylene carbonate 66.07
    cyrene 51.63
    2-ethoxyethyl acetate 27.67
    2-ethylhexyl acetate 8.92
    1,2,4-trichlorobenzene 20.3
    4-methylpyridine 45.14
    dibutyl ether 2.55
    2,6-dimethyl-4-heptanol 2.28
    DEF 50.23
    dimethyl isosorbide 42.13
    tetrachloroethylene 47.04
    eugenol 20.82
    triacetin 20.39
    span 80 19.99
    1,4-butanediol 26.22
    1,1-dichloroethane 26.76
    2-methyl-1-pentanol 7.96
    methyl formate 146.79
    2-methyl-1-butanol 11.74
    n-decane 0.24
    butyronitrile 19.78
    3,7-dimethyl-1-octanol 3.32
    1-chlorooctane 1.61
    1-chlorotetradecane 0.55
    n-nonane 0.2
    undecane 0.17
    tert-butylcyclohexane 0.23
    cyclooctane 0.28
    cyclopentanol 32.89
    tetrahydropyran 41.39
    tert-amyl methyl ether 5.0
    2,5,8-trioxanonane 33.3
    1-hexene 1.75
    2-isopropoxyethanol 30.25
    2,2,2-trifluoroethanol 113.15
    methyl butyrate 21.11

    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