Spiro(bicyclo(3.1.1)heptane-3,1'-(2)cyclohexen)-4'-one, 2,6,6-trimethyl-, (1S,1'S,2S,5R)-

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  • Identifiers

    CAS number
    133636-82-5

    Molecular formula
    C15H22O

    SMILES
    C[C@H]1[C@@H]2C[C@@H](C2(C)C)C[C@]13CCC(=O)C=C3

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Woody 83.6%
    Cedar 49.74%
    Dry 42.7%
    Amber 41.9%
    Spicy 40.59%
    Fresh 39.38%
    Herbal 38.6%
    Camphoreous 38.09%
    Balsamic 34.6%
    Pine 34.15%

     

    Flavor
    Woody 41.92%
    Herbal 36.64%
    Minty 36.0%
    Spicy 35.24%
    Spice 34.62%
    Camphor 33.76%
    Fresh 28.09%
    Sweet 27.79%
    Mint 27.36%
    Balsam 26.27%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.8

    pKa est.
    7.84 (neutral)

    Molecular weight
    218.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    319°C

    Flash point

    • 111.52 ˚C est.

  • Synonyms

    • EC 430-460-1
    • (+)-(1S,2S,3S,5R)-2,6,6-Trimethylbicyclo(3.1.1)heptane-3-spiro-1'-(cyclohex-2'-en-4'-one)
    • Spiro(bicyclo(3.1.1)heptane-3,1'-(2)cyclohexen)-4'-one, 2,6,6-trimethyl-, (1S,1'S,2S,5R)-
    • Spiro[bicyclo[3.1.1]heptane-3,1'-[2]cyclohexen]-4'-one, 2,6,6-trimethyl-, (1S,1'S,2S,5R)-
    • (+)-(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-3-spiro-1'-(cyclohex-2'-en-4'-one)
    • RefChem:888718
    • 133636-82-5
    • YBDPZJGWLRHCHO-WJNVRWDZSA-N
    • DTXSID1051480
    • SCHEMBL16447635
    • NS00024302
    • (1S,1'S,2S,5R)-2,6,6-Trimethylspiro[bicyclo[3.1.1]heptane-3,1'-cyclohexan]-2'-en-4'-one
    • (1S,2S,3S,5R)-2,6,6-Trimethylspiro[bicyclo[3.1.1]heptane-3,1'-cyclohexane]-2'-en-4'-one
    • 133636-82-5

  • Applications

    Spiro(bicyclo(3.1.1)heptane-3,1'-(2)cyclohexen)-4'-one, 2,6,6-trimethyl-, (1S,1'S,2S,5R)- (CAS 133636-82-5) is a rigid chiral spirocyclic ketone that is commonly evaluated as an intermediate and building block in complex organic synthesis. It serves as a chiral scaffold in pharmaceutical and agrochemical synthesis, enabling asymmetric transformations and the construction of stereochemically defined frameworks. It may function as a precursor to further functionalization to access advanced intermediates, natural-product mimics, and specialty polymers or coatings. The enone functionality offers opportunities for selective conjugate additions and cycloadditions, supporting applications in fine chemicals, cosmetics ingredients as a chiral precursor, and performance materials after further derivatization. Overall, industries that work with chiral synthons, high-purity intermediates, and rigid scaffolds—pharmaceuticals, agrochemicals, specialty polymers, and cosmetics—may consider this compound within their synthetic toolkit, subject to regulatory constraints and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 285.52
    methanol 241.57
    isopropanol 265.95
    water 1.64
    ethyl acetate 598.26
    n-propanol 276.9
    acetone 678.4
    n-butanol 237.11
    acetonitrile 480.23
    DMF 659.54
    toluene 562.98
    isobutanol 175.33
    1,4-dioxane 952.55
    methyl acetate 516.71
    THF 1254.14
    2-butanone 548.29
    n-pentanol 88.99
    sec-butanol 129.99
    n-hexane 11.56
    ethylene glycol 61.81
    NMP 253.0
    cyclohexane 44.87
    DMSO 283.19
    n-butyl acetate 252.12
    n-octanol 65.23
    chloroform 1218.54
    n-propyl acetate 208.47
    acetic acid 151.98
    dichloromethane 881.37
    cyclohexanone 545.57
    propylene glycol 85.38
    isopropyl acetate 371.66
    DMAc 375.23
    2-ethoxyethanol 200.5
    isopentanol 189.17
    n-heptane 12.67
    ethyl formate 250.37
    1,2-dichloroethane 554.12
    n-hexanol 169.05
    2-methoxyethanol 453.36
    isobutyl acetate 149.95
    tetrachloromethane 152.23
    n-pentyl acetate 154.46
    transcutol 1059.92
    n-heptanol 82.71
    ethylbenzene 172.1
    MIBK 271.33
    2-propoxyethanol 392.76
    tert-butanol 244.35
    MTBE 309.46
    2-butoxyethanol 197.4
    propionic acid 190.2
    o-xylene 251.08
    formic acid 74.88
    diethyl ether 394.8
    m-xylene 352.89
    p-xylene 220.01
    chlorobenzene 445.64
    dimethyl carbonate 264.18
    n-octane 6.21
    formamide 183.66
    cyclopentanone 779.68
    2-pentanone 439.92
    anisole 334.88
    cyclopentyl methyl ether 430.95
    gamma-butyrolactone 708.5
    1-methoxy-2-propanol 405.93
    pyridine 672.88
    3-pentanone 349.37
    furfural 533.6
    n-dodecane 5.53
    diethylene glycol 294.68
    diisopropyl ether 129.41
    tert-amyl alcohol 133.81
    acetylacetone 514.98
    n-hexadecane 6.77
    acetophenone 250.97
    methyl propionate 463.75
    isopentyl acetate 235.02
    trichloroethylene 1056.14
    n-nonanol 65.25
    cyclohexanol 192.01
    benzyl alcohol 202.27
    2-ethylhexanol 88.83
    isooctanol 71.4
    dipropyl ether 137.09
    1,2-dichlorobenzene 346.02
    ethyl lactate 109.18
    propylene carbonate 355.13
    n-methylformamide 389.51
    2-pentanol 141.61
    n-pentane 20.46
    1-propoxy-2-propanol 268.92
    1-methoxy-2-propyl acetate 396.31
    2-(2-methoxypropoxy) propanol 198.39
    mesitylene 192.97
    ε-caprolactone 436.14
    p-cymene 85.43
    epichlorohydrin 864.28
    1,1,1-trichloroethane 555.2
    2-aminoethanol 133.69
    morpholine-4-carbaldehyde 478.05
    sulfolane 416.57
    2,2,4-trimethylpentane 12.31
    2-methyltetrahydrofuran 549.99
    n-hexyl acetate 205.97
    isooctane 14.62
    2-(2-butoxyethoxy)ethanol 270.07
    sec-butyl acetate 177.11
    tert-butyl acetate 332.3
    decalin 22.52
    glycerin 118.34
    diglyme 523.21
    acrylic acid 162.83
    isopropyl myristate 83.45
    n-butyric acid 291.7
    acetyl acetate 334.29
    di(2-ethylhexyl) phthalate 81.41
    ethyl propionate 225.67
    nitromethane 455.45
    1,2-diethoxyethane 349.62
    benzonitrile 324.04
    trioctyl phosphate 57.4
    1-bromopropane 307.09
    gamma-valerolactone 839.66
    n-decanol 49.81
    triethyl phosphate 90.56
    4-methyl-2-pentanol 108.03
    propionitrile 418.58
    vinylene carbonate 403.37
    1,1,2-trichlorotrifluoroethane 342.78
    DMS 275.36
    cumene 103.87
    2-octanol 50.87
    2-hexanone 185.41
    octyl acetate 99.47
    limonene 93.15
    1,2-dimethoxyethane 384.68
    ethyl orthosilicate 87.93
    tributyl phosphate 71.9
    diacetone alcohol 290.23
    N,N-dimethylaniline 168.94
    acrylonitrile 489.82
    aniline 439.77
    1,3-propanediol 225.7
    bromobenzene 469.3
    dibromomethane 545.41
    1,1,2,2-tetrachloroethane 709.23
    2-methyl-cyclohexyl acetate 134.59
    tetrabutyl urea 82.36
    diisobutyl methanol 72.37
    2-phenylethanol 236.89
    styrene 197.73
    dioctyl adipate 106.27
    dimethyl sulfate 251.6
    ethyl butyrate 183.05
    methyl lactate 200.68
    butyl lactate 137.49
    diethyl carbonate 138.39
    propanediol butyl ether 180.22
    triethyl orthoformate 128.29
    p-tert-butyltoluene 88.79
    methyl 4-tert-butylbenzoate 195.87
    morpholine 835.88
    tert-butylamine 152.59
    n-dodecanol 38.52
    dimethoxymethane 616.17
    ethylene carbonate 343.87
    cyrene 157.96
    2-ethoxyethyl acetate 303.87
    2-ethylhexyl acetate 174.69
    1,2,4-trichlorobenzene 379.27
    4-methylpyridine 680.02
    dibutyl ether 99.05
    2,6-dimethyl-4-heptanol 72.37
    DEF 313.53
    dimethyl isosorbide 329.44
    tetrachloroethylene 424.12
    eugenol 181.56
    triacetin 237.98
    span 80 146.7
    1,4-butanediol 58.12
    1,1-dichloroethane 636.38
    2-methyl-1-pentanol 83.65
    methyl formate 301.96
    2-methyl-1-butanol 138.08
    n-decane 9.39
    butyronitrile 351.54
    3,7-dimethyl-1-octanol 85.02
    1-chlorooctane 50.96
    1-chlorotetradecane 20.84
    n-nonane 8.31
    undecane 7.06
    tert-butylcyclohexane 20.22
    cyclooctane 17.81
    cyclopentanol 196.47
    tetrahydropyran 735.19
    tert-amyl methyl ether 169.61
    2,5,8-trioxanonane 307.52
    1-hexene 56.13
    2-isopropoxyethanol 148.49
    2,2,2-trifluoroethanol 108.29
    methyl butyrate 235.53

    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