8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-one

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  • Identifiers

    CAS number
    28449-87-8

    Molecular formula
    C10H14O2

    SMILES
    CC1(C2CCC(=C)C1C(=O)O2)C

    Safety labels

  • Odor profile

    Fragrance
    Mint 62.5%
    Herbal 54.7%
    Woody 49.52%
    Camphoreous 48.26%
    Spicy 47.32%
    Tobacco 46.63%
    Sweet 41.06%
    Cooling 30.92%
    Green 30.7%
    Phenolic 28.34%

     

    Flavor
    Bitter 46.31%
    Minty 41.36%
    Fruity 28.76%
    Woody 26.91%
    Herbal 25.51%
    Tobacco 23.95%
    Spice 22.68%
    Camphor 21.9%
    Red fruit 21.3%
    Ripe apricot 21.25%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    9.09 (weak base)

    Molecular weight
    166.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    270°C

    Flash point

    • 89.91 ˚C est.

  • Synonyms

    • 8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-one
    • 28449-87-8
    • 8,8-Dimethyl-2-methylene-6-oxabicyclo(3.2.1)octan-7-one
    • RefChem:311557
    • Karahana lactone
    • 8,8-dimethyl-2-methylidene-6-oxabicyclo[3.2.1]octan-7-one
    • CHEBI:195779
    • DTXSID601203352
    • 28449-87-8

  • Applications

    8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octan-7-one (CAS 28449-87-8) is used as an intermediate in organic synthesis and is commonly evaluated for fragrance materials and odorants; it may be employed in cosmetics and personal care as a fragrance-building block; in industrial manufacturing it can serve as a precursor for complex synthetic routes; it may function as a specialty monomer or intermediate for polymers and plastics; and it has potential use in coatings and inks as a reactive specialty chemical.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 356.5
    methanol 635.59
    isopropanol 284.72
    water 13.21
    ethyl acetate 399.15
    n-propanol 305.35
    acetone 449.51
    n-butanol 256.38
    acetonitrile 549.01
    DMF 567.9
    toluene 265.39
    isobutanol 217.1
    1,4-dioxane 915.97
    methyl acetate 394.12
    THF 1225.11
    2-butanone 333.66
    n-pentanol 174.0
    sec-butanol 215.5
    n-hexane 18.61
    ethylene glycol 128.54
    NMP 506.74
    cyclohexane 40.01
    DMSO 401.71
    n-butyl acetate 252.0
    n-octanol 119.1
    chloroform 1543.37
    n-propyl acetate 196.71
    acetic acid 564.04
    dichloromethane 1243.43
    cyclohexanone 501.47
    propylene glycol 121.58
    isopropyl acetate 259.85
    DMAc 291.65
    2-ethoxyethanol 292.67
    isopentanol 229.73
    n-heptane 16.74
    ethyl formate 312.75
    1,2-dichloroethane 618.07
    n-hexanol 242.15
    2-methoxyethanol 562.02
    isobutyl acetate 134.48
    tetrachloromethane 197.95
    n-pentyl acetate 165.97
    transcutol 880.18
    n-heptanol 120.72
    ethylbenzene 103.1
    MIBK 231.23
    2-propoxyethanol 469.63
    tert-butanol 300.04
    MTBE 228.79
    2-butoxyethanol 237.3
    propionic acid 321.56
    o-xylene 135.2
    formic acid 404.22
    diethyl ether 314.81
    m-xylene 208.27
    p-xylene 135.56
    chlorobenzene 399.61
    dimethyl carbonate 203.65
    n-octane 7.82
    formamide 470.47
    cyclopentanone 654.79
    2-pentanone 308.72
    anisole 241.49
    cyclopentyl methyl ether 422.84
    gamma-butyrolactone 913.28
    1-methoxy-2-propanol 408.65
    pyridine 587.37
    3-pentanone 209.05
    furfural 685.46
    n-dodecane 8.58
    diethylene glycol 405.0
    diisopropyl ether 106.24
    tert-amyl alcohol 200.28
    acetylacetone 391.67
    n-hexadecane 9.9
    acetophenone 199.72
    methyl propionate 307.16
    isopentyl acetate 224.97
    trichloroethylene 1227.0
    n-nonanol 102.81
    cyclohexanol 274.22
    benzyl alcohol 193.81
    2-ethylhexanol 118.02
    isooctanol 98.54
    dipropyl ether 126.32
    1,2-dichlorobenzene 347.65
    ethyl lactate 115.69
    propylene carbonate 460.85
    n-methylformamide 489.23
    2-pentanol 180.39
    n-pentane 25.04
    1-propoxy-2-propanol 277.17
    1-methoxy-2-propyl acetate 302.99
    2-(2-methoxypropoxy) propanol 204.17
    mesitylene 119.25
    ε-caprolactone 467.01
    p-cymene 68.47
    epichlorohydrin 963.4
    1,1,1-trichloroethane 608.5
    2-aminoethanol 215.36
    morpholine-4-carbaldehyde 597.11
    sulfolane 640.35
    2,2,4-trimethylpentane 17.05
    2-methyltetrahydrofuran 613.45
    n-hexyl acetate 249.48
    isooctane 17.51
    2-(2-butoxyethoxy)ethanol 297.96
    sec-butyl acetate 142.54
    tert-butyl acetate 265.69
    decalin 21.65
    glycerin 198.71
    diglyme 506.4
    acrylic acid 327.45
    isopropyl myristate 88.24
    n-butyric acid 389.75
    acetyl acetate 293.35
    di(2-ethylhexyl) phthalate 91.86
    ethyl propionate 182.21
    nitromethane 830.66
    1,2-diethoxyethane 268.57
    benzonitrile 344.16
    trioctyl phosphate 69.33
    1-bromopropane 299.38
    gamma-valerolactone 774.84
    n-decanol 74.4
    triethyl phosphate 90.47
    4-methyl-2-pentanol 130.11
    propionitrile 361.09
    vinylene carbonate 465.83
    1,1,2-trichlorotrifluoroethane 464.79
    DMS 253.16
    cumene 77.64
    2-octanol 83.97
    2-hexanone 177.85
    octyl acetate 108.89
    limonene 83.97
    1,2-dimethoxyethane 427.84
    ethyl orthosilicate 87.45
    tributyl phosphate 90.77
    diacetone alcohol 260.02
    N,N-dimethylaniline 144.46
    acrylonitrile 469.79
    aniline 289.99
    1,3-propanediol 305.29
    bromobenzene 405.25
    dibromomethane 762.9
    1,1,2,2-tetrachloroethane 807.08
    2-methyl-cyclohexyl acetate 142.42
    tetrabutyl urea 102.12
    diisobutyl methanol 75.87
    2-phenylethanol 235.07
    styrene 126.03
    dioctyl adipate 114.42
    dimethyl sulfate 274.94
    ethyl butyrate 152.63
    methyl lactate 162.1
    butyl lactate 138.49
    diethyl carbonate 123.01
    propanediol butyl ether 201.13
    triethyl orthoformate 121.2
    p-tert-butyltoluene 67.76
    methyl 4-tert-butylbenzoate 191.71
    morpholine 827.58
    tert-butylamine 186.78
    n-dodecanol 55.19
    dimethoxymethane 517.1
    ethylene carbonate 397.83
    cyrene 198.03
    2-ethoxyethyl acetate 251.55
    2-ethylhexyl acetate 161.32
    1,2,4-trichlorobenzene 373.39
    4-methylpyridine 507.04
    dibutyl ether 108.44
    2,6-dimethyl-4-heptanol 75.87
    DEF 272.1
    dimethyl isosorbide 364.69
    tetrachloroethylene 538.63
    eugenol 194.73
    triacetin 201.23
    span 80 172.89
    1,4-butanediol 114.73
    1,1-dichloroethane 672.68
    2-methyl-1-pentanol 150.1
    methyl formate 450.85
    2-methyl-1-butanol 203.6
    n-decane 13.55
    butyronitrile 343.9
    3,7-dimethyl-1-octanol 119.83
    1-chlorooctane 70.8
    1-chlorotetradecane 28.58
    n-nonane 11.82
    undecane 10.44
    tert-butylcyclohexane 20.49
    cyclooctane 15.46
    cyclopentanol 315.76
    tetrahydropyran 649.42
    tert-amyl methyl ether 160.88
    2,5,8-trioxanonane 331.86
    1-hexene 78.2
    2-isopropoxyethanol 198.4
    2,2,2-trifluoroethanol 280.34
    methyl butyrate 217.31

    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