(1R,2R,4E,6R,9S)-6-(Acetyloxy)-2-hydroxy-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene-3,7-dione

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  • Identifiers

    CAS number
    92121-62-5

    Molecular formula
    C17H22O5

    SMILES
    C/C/1=C\[C@H](C(=O)C(=C)[C@H]2CC([C@@H]2[C@H](C1=O)O)(C)C)OC(=O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 50.03%
    Caramellic 48.99%
    Burnt 36.13%
    Odorless 34.86%
    Woody 27.39%
    Mint 26.25%
    Spicy 23.89%
    Tobacco 22.64%
    Nutty 19.49%
    Phenolic 19.47%

     

    Flavor
    Bitter 67.4%
    Maple 23.29%
    Sweet 21.96%
    Fenugreek 21.73%
    Cotton candy 21.13%
    Seedy 21.08%
    Extremely sweet 21.01%
    Odorless 20.78%
    Toffee 20.41%
    Leaves 20.34%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    6.61 (neutral)

    Molecular weight
    306.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    446°C

    Flash point

    • 178.3 ˚C est.

  • Synonyms

    • Naematolon
    • DTXSID801110644
    • 92121-62-5
    • ((1S,4R,5E,8R,9R)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxo-4-bicyclo(7.2.0)undec-5-enyl) acetate
    • (1R,2R,4E,6R,9S)-6-(Acetyloxy)-2-hydroxy-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene-3,7-dione
    • (1R,2R,4E,6R,9S)-6-(Acetyloxy)-2-hydroxy-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene-3,7-dione
    • [(1S,4R,5E,8R,9R)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxo-4-bicyclo[7.2.0]undec-5-enyl] acetate
    • RefChem:905690
    • DTXCID501542264
    • Bicyclo(7.2.0)undec-4-ene-3,7-dione, 6-(acetyloxy)-2-hydroxy-4,11,11-trimethyl-8-methylene-, (1R-(1R*,2R*,4E,6R*,9S*))-
    • 4-Acetyloxy-8-hydroxy-2-methylene-6,10,10-trimethyl-bicyclo(7.2.0)undec-5-ene-3,7-dione
    • CHEMBL477125
    • Bicyclo[7.2.0]undec-4-ene-3,7-dione, 6-(acetyloxy)-2-hydroxy-4,11,11-trimethyl-8-methylene-, (1R,2R,4E,6R,9S)-
    • 92121-62-5

  • Applications

    Chemical name: (1R,2R,4E,6R,9S)-6-(Acetyloxy)-2-hydroxy-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene-3,7-dione; CAS number: 92121-62-5; this bicyclic diketone bearing an acetate group and a hydroxy function is typically evaluated as a building block or intermediate in organic synthesis; potential applications include fragrance ingredients or fixatives in perfumery and cosmetics; it may serve as a precursor in industrial manufacturing of specialty chemicals and formulation components; in polymers/plastics and coatings/inks it can act as a specialty additive or crosslinking/curing agent under suitable conditions; and in medicinal or agrochemical research it may be studied as a chiral building block for further development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 115.29
    methanol 187.1
    isopropanol 102.61
    water 0.47
    ethyl acetate 31.92
    n-propanol 90.46
    acetone 97.31
    n-butanol 77.55
    acetonitrile 26.27
    DMF 218.9
    toluene 36.1
    isobutanol 59.7
    1,4-dioxane 132.83
    methyl acetate 42.59
    THF 329.67
    2-butanone 72.89
    n-pentanol 65.62
    sec-butanol 68.43
    n-hexane 0.62
    ethylene glycol 27.95
    NMP 153.1
    cyclohexane 1.24
    DMSO 210.71
    n-butyl acetate 32.46
    n-octanol 20.43
    chloroform 101.24
    n-propyl acetate 33.25
    acetic acid 85.51
    dichloromethane 80.76
    cyclohexanone 112.17
    propylene glycol 58.66
    isopropyl acetate 29.34
    DMAc 165.05
    2-ethoxyethanol 112.21
    isopentanol 65.83
    n-heptane 0.53
    ethyl formate 35.81
    1,2-dichloroethane 46.52
    n-hexanol 52.48
    2-methoxyethanol 198.4
    isobutyl acetate 28.32
    tetrachloromethane 6.63
    n-pentyl acetate 26.09
    transcutol 121.39
    n-heptanol 29.42
    ethylbenzene 17.01
    MIBK 40.23
    2-propoxyethanol 128.36
    tert-butanol 91.37
    MTBE 22.46
    2-butoxyethanol 73.92
    propionic acid 47.72
    o-xylene 18.96
    formic acid 67.65
    diethyl ether 20.2
    m-xylene 22.57
    p-xylene 23.2
    chlorobenzene 32.83
    dimethyl carbonate 28.72
    n-octane 0.45
    formamide 86.49
    cyclopentanone 164.77
    2-pentanone 54.36
    anisole 43.19
    cyclopentyl methyl ether 56.0
    gamma-butyrolactone 144.11
    1-methoxy-2-propanol 172.22
    pyridine 101.9
    3-pentanone 29.05
    furfural 120.09
    n-dodecane 0.49
    diethylene glycol 120.38
    diisopropyl ether 5.5
    tert-amyl alcohol 59.09
    acetylacetone 72.36
    n-hexadecane 0.58
    acetophenone 55.68
    methyl propionate 36.51
    isopentyl acetate 35.39
    trichloroethylene 109.96
    n-nonanol 19.67
    cyclohexanol 58.61
    benzyl alcohol 78.14
    2-ethylhexanol 21.32
    isooctanol 22.99
    dipropyl ether 11.58
    1,2-dichlorobenzene 28.77
    ethyl lactate 35.01
    propylene carbonate 71.18
    n-methylformamide 89.27
    2-pentanol 39.93
    n-pentane 0.6
    1-propoxy-2-propanol 75.2
    1-methoxy-2-propyl acetate 49.53
    2-(2-methoxypropoxy) propanol 57.46
    mesitylene 10.58
    ε-caprolactone 86.38
    p-cymene 9.48
    epichlorohydrin 170.43
    1,1,1-trichloroethane 28.52
    2-aminoethanol 65.37
    morpholine-4-carbaldehyde 165.62
    sulfolane 160.96
    2,2,4-trimethylpentane 0.74
    2-methyltetrahydrofuran 101.83
    n-hexyl acetate 31.74
    isooctane 0.63
    2-(2-butoxyethoxy)ethanol 73.31
    sec-butyl acetate 22.67
    tert-butyl acetate 34.54
    decalin 1.48
    glycerin 84.24
    diglyme 103.32
    acrylic acid 47.31
    isopropyl myristate 12.36
    n-butyric acid 62.5
    acetyl acetate 26.43
    di(2-ethylhexyl) phthalate 24.6
    ethyl propionate 23.93
    nitromethane 89.42
    1,2-diethoxyethane 30.88
    benzonitrile 48.23
    trioctyl phosphate 16.58
    1-bromopropane 18.84
    gamma-valerolactone 195.94
    n-decanol 13.73
    triethyl phosphate 16.96
    4-methyl-2-pentanol 27.54
    propionitrile 28.28
    vinylene carbonate 62.22
    1,1,2-trichlorotrifluoroethane 113.59
    DMS 31.45
    cumene 11.33
    2-octanol 16.95
    2-hexanone 45.57
    octyl acetate 18.45
    limonene 10.91
    1,2-dimethoxyethane 127.29
    ethyl orthosilicate 16.1
    tributyl phosphate 15.96
    diacetone alcohol 78.82
    N,N-dimethylaniline 34.97
    acrylonitrile 42.3
    aniline 56.91
    1,3-propanediol 102.72
    bromobenzene 28.29
    dibromomethane 45.43
    1,1,2,2-tetrachloroethane 84.41
    2-methyl-cyclohexyl acetate 30.53
    tetrabutyl urea 25.29
    diisobutyl methanol 11.94
    2-phenylethanol 66.93
    styrene 18.67
    dioctyl adipate 24.38
    dimethyl sulfate 52.18
    ethyl butyrate 22.29
    methyl lactate 49.68
    butyl lactate 33.78
    diethyl carbonate 16.91
    propanediol butyl ether 64.37
    triethyl orthoformate 19.63
    p-tert-butyltoluene 9.27
    methyl 4-tert-butylbenzoate 44.67
    morpholine 167.53
    tert-butylamine 26.82
    n-dodecanol 9.33
    dimethoxymethane 128.09
    ethylene carbonate 48.64
    cyrene 89.83
    2-ethoxyethyl acetate 38.42
    2-ethylhexyl acetate 24.79
    1,2,4-trichlorobenzene 40.59
    4-methylpyridine 96.16
    dibutyl ether 9.97
    2,6-dimethyl-4-heptanol 11.94
    DEF 55.64
    dimethyl isosorbide 95.72
    tetrachloroethylene 46.48
    eugenol 56.4
    triacetin 37.36
    span 80 49.88
    1,4-butanediol 53.22
    1,1-dichloroethane 40.53
    2-methyl-1-pentanol 51.9
    methyl formate 75.43
    2-methyl-1-butanol 51.96
    n-decane 0.86
    butyronitrile 35.19
    3,7-dimethyl-1-octanol 19.41
    1-chlorooctane 6.05
    1-chlorotetradecane 2.38
    n-nonane 0.66
    undecane 0.63
    tert-butylcyclohexane 1.23
    cyclooctane 0.51
    cyclopentanol 81.53
    tetrahydropyran 80.51
    tert-amyl methyl ether 19.96
    2,5,8-trioxanonane 76.73
    1-hexene 5.24
    2-isopropoxyethanol 79.04
    2,2,2-trifluoroethanol 32.71
    methyl butyrate 38.88

    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