4,12,12-Trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane

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  • Identifiers

    CAS number
    13877-94-6

    Molecular formula
    C15H24O

    SMILES
    CC1(CC2C1CCC3(C(O3)CCC2=C)C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Woody 83.22%
    Amber 49.33%
    Sweet 49.28%
    Cedar 48.65%
    Spicy 48.42%
    Dry 47.01%
    Fresh 41.95%
    Tobacco 38.61%
    Camphoreous 37.15%
    Earthy 36.41%

     

    Flavor
    Woody 68.46%
    Sweet 63.64%
    Spicy 49.66%
    Spice 41.25%
    Wood 41.12%
    Dry 40.06%
    Earthy 38.95%
    Herbal 37.64%
    Fresh 37.2%
    Camphor 36.57%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    7.05 (neutral)

    Molecular weight
    220.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    290°C

    Melting point expt.

    • 63.5 - 64 °C

    Flash point

    • 102.41 ˚C est.

  • Synonyms

    • Caryophyllene epoxide
    • 13877-94-6
    • 17627-43-9
    • Caryophylene oxide
    • 4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane
    • 5-Oxatricyclo[8.2.0.04,6]dodecane, 4,12,12-trimethyl-9-methylene-
    • Caryophyllene alpha-oxide
    • DTXSID50859585
    • 4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane
    • 4,5-epoxy-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undecane
    • 5-Oxatricyclo(8.2.0.04,6)dodecane, 4,12,12-trimethyl-9-methylene-
    • 4,12,12-TRIMETHYL-9-METHYLIDENE-5-OXATRICYCLO[8.2.0.0?,?]DODECANE
    • 4,5-Epoxy-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undecane
    • 4,12,12-Trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane
    • 4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0~4,6~]dodecane
    • b-Caryophyllene Epoxide
    • 5-Oxatricyclo[8.2.0.0(4,6)-]dodecane, 4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-
    • Isocaryophyllene, oxide
    • .beta.-Caryophyllene epoxide
    • (-)-.beta.-Caryophyllene oxide
    • 5-Oxatricyclo[8.2.0.04,6]dodecane,4,12,12-trimethyl-9-methylene-
    • Caryophyllene oxyde
    • EINECS 237-642-8
    • EINECS 241-609-3
    • Caryophyllene a-oxide
    • SCHEMBL1532444
    • DTXCID60210426
    • 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane, (1R,4R,6R,10S)-
    • CHEBI:156179
    • (-)-5-Oxatricyclo[8.2.0.0(4,6)]dodecane,4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-
    • BBL034003
    • STL372857
    • AKOS024282622
    • (10S,1R,4R,6R)-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.0<4,6>]dodeca ne
    • SY011401
    • VS-12369
    • DB-060569
    • NS00012081
    • NS00101167
    • Q67879768
    • 4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane
    • 241-609-3

  • Applications

    4,12,12-Trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane (CAS 13877-94-6) is primarily considered a synthetic intermediate in the preparation of specialty fragrance components and odor-active compounds; it may be used in perfumery as a fragrance ingredient or fixative, in cosmetics/personal care as a scent additive, and in household products as a fragrance contributor; in industrial manufacturing it serves as an intermediate for building blocks in aroma-related chemical syntheses, and in polymers/plastics it may function as a scaffold or functional additive for select polymer systems and coatings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 258.93
    methanol 199.75
    isopropanol 232.43
    water 0.98
    ethyl acetate 273.32
    n-propanol 221.58
    acetone 266.46
    n-butanol 225.18
    acetonitrile 242.32
    DMF 231.73
    toluene 287.96
    isobutanol 172.84
    1,4-dioxane 595.99
    methyl acetate 250.5
    THF 780.65
    2-butanone 268.14
    n-pentanol 158.76
    sec-butanol 166.54
    n-hexane 27.67
    ethylene glycol 52.26
    NMP 203.77
    cyclohexane 71.69
    DMSO 176.1
    n-butyl acetate 297.12
    n-octanol 129.16
    chloroform 807.36
    n-propyl acetate 212.08
    acetic acid 183.98
    dichloromethane 603.47
    cyclohexanone 359.4
    propylene glycol 90.7
    isopropyl acetate 237.36
    DMAc 235.29
    2-ethoxyethanol 234.95
    isopentanol 202.84
    n-heptane 41.76
    ethyl formate 185.72
    1,2-dichloroethane 281.91
    n-hexanol 241.58
    2-methoxyethanol 340.02
    isobutyl acetate 197.89
    tetrachloromethane 127.24
    n-pentyl acetate 199.32
    transcutol 886.93
    n-heptanol 133.67
    ethylbenzene 149.37
    MIBK 202.4
    2-propoxyethanol 384.1
    tert-butanol 220.67
    MTBE 236.85
    2-butoxyethanol 246.9
    propionic acid 153.08
    o-xylene 162.26
    formic acid 61.15
    diethyl ether 245.66
    m-xylene 201.36
    p-xylene 203.1
    chlorobenzene 271.37
    dimethyl carbonate 115.57
    n-octane 17.69
    formamide 101.02
    cyclopentanone 387.6
    2-pentanone 232.5
    anisole 267.99
    cyclopentyl methyl ether 282.09
    gamma-butyrolactone 373.85
    1-methoxy-2-propanol 290.87
    pyridine 423.87
    3-pentanone 178.88
    furfural 361.05
    n-dodecane 17.42
    diethylene glycol 268.5
    diisopropyl ether 109.65
    tert-amyl alcohol 155.76
    acetylacetone 298.43
    n-hexadecane 20.36
    acetophenone 231.43
    methyl propionate 195.52
    isopentyl acetate 313.9
    trichloroethylene 540.49
    n-nonanol 121.07
    cyclohexanol 189.75
    benzyl alcohol 203.78
    2-ethylhexanol 156.01
    isooctanol 114.66
    dipropyl ether 195.27
    1,2-dichlorobenzene 240.82
    ethyl lactate 114.1
    propylene carbonate 264.59
    n-methylformamide 136.87
    2-pentanol 156.71
    n-pentane 34.56
    1-propoxy-2-propanol 299.89
    1-methoxy-2-propyl acetate 354.99
    2-(2-methoxypropoxy) propanol 253.9
    mesitylene 129.31
    ε-caprolactone 328.1
    p-cymene 127.23
    epichlorohydrin 459.61
    1,1,1-trichloroethane 288.52
    2-aminoethanol 110.84
    morpholine-4-carbaldehyde 356.85
    sulfolane 271.67
    2,2,4-trimethylpentane 23.48
    2-methyltetrahydrofuran 422.31
    n-hexyl acetate 264.14
    isooctane 25.56
    2-(2-butoxyethoxy)ethanol 328.79
    sec-butyl acetate 184.89
    tert-butyl acetate 241.98
    decalin 40.86
    glycerin 113.74
    diglyme 582.77
    acrylic acid 127.94
    isopropyl myristate 125.96
    n-butyric acid 224.95
    acetyl acetate 219.54
    di(2-ethylhexyl) phthalate 129.26
    ethyl propionate 180.73
    nitromethane 257.43
    1,2-diethoxyethane 344.17
    benzonitrile 286.28
    trioctyl phosphate 93.09
    1-bromopropane 214.11
    gamma-valerolactone 543.63
    n-decanol 91.52
    triethyl phosphate 112.97
    4-methyl-2-pentanol 130.38
    propionitrile 228.38
    vinylene carbonate 282.06
    1,1,2-trichlorotrifluoroethane 281.89
    DMS 212.4
    cumene 111.71
    2-octanol 91.37
    2-hexanone 209.96
    octyl acetate 143.38
    limonene 144.44
    1,2-dimethoxyethane 413.42
    ethyl orthosilicate 114.27
    tributyl phosphate 107.85
    diacetone alcohol 209.96
    N,N-dimethylaniline 166.48
    acrylonitrile 233.77
    aniline 233.96
    1,3-propanediol 191.75
    bromobenzene 295.91
    dibromomethane 398.46
    1,1,2,2-tetrachloroethane 424.49
    2-methyl-cyclohexyl acetate 214.87
    tetrabutyl urea 125.21
    diisobutyl methanol 118.67
    2-phenylethanol 250.91
    styrene 173.74
    dioctyl adipate 166.46
    dimethyl sulfate 121.48
    ethyl butyrate 217.52
    methyl lactate 120.23
    butyl lactate 170.37
    diethyl carbonate 164.41
    propanediol butyl ether 217.98
    triethyl orthoformate 187.9
    p-tert-butyltoluene 126.16
    methyl 4-tert-butylbenzoate 194.85
    morpholine 539.92
    tert-butylamine 166.96
    n-dodecanol 73.64
    dimethoxymethane 286.3
    ethylene carbonate 250.48
    cyrene 199.39
    2-ethoxyethyl acetate 286.06
    2-ethylhexyl acetate 255.25
    1,2,4-trichlorobenzene 266.15
    4-methylpyridine 409.5
    dibutyl ether 165.6
    2,6-dimethyl-4-heptanol 118.67
    DEF 199.6
    dimethyl isosorbide 391.19
    tetrachloroethylene 265.95
    eugenol 197.43
    triacetin 260.87
    span 80 222.67
    1,4-butanediol 82.91
    1,1-dichloroethane 321.93
    2-methyl-1-pentanol 149.95
    methyl formate 121.42
    2-methyl-1-butanol 163.55
    n-decane 27.78
    butyronitrile 257.0
    3,7-dimethyl-1-octanol 152.65
    1-chlorooctane 90.29
    1-chlorotetradecane 44.16
    n-nonane 24.53
    undecane 21.35
    tert-butylcyclohexane 36.23
    cyclooctane 30.37
    cyclopentanol 193.94
    tetrahydropyran 496.45
    tert-amyl methyl ether 158.81
    2,5,8-trioxanonane 372.12
    1-hexene 94.64
    2-isopropoxyethanol 191.22
    2,2,2-trifluoroethanol 81.64
    methyl butyrate 212.97

    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