(E,E)-1,8,8-Trimethyl-5-methylene-1,6-cycloundecadiene

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  • Identifiers

    CAS number
    26259-79-0

    Molecular formula
    C15H24

    SMILES
    C/C/1=C/CCC(=C)/C=C\C(CCC1)(C)C

  • Odor profile

    Woody 65.46%
    Citrus 55.53%
    Spicy 50.63%
    Herbal 46.48%
    Terpenic 43.12%
    Lemon 39.73%
    Camphoreous 37.4%
    Dry 36.59%
    Tobacco 35.61%
    Sweet 34.93%

    Scent© AI

  • Properties

    XLogP3-AA
    5.0

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    266°C

    Flash point est.
    104.17 ˚C

  • Synonyms

    • (E,E)-1,8,8-Trimethyl-5-methylene-1,6-cycloundecadiene
    • 26259-79-0
    • gamma-Humulene
    • (1Z,6Z)-1,8,8-trimethyl-5-methylidenecycloundeca-1,6-diene
    • 1,6-Cycloundecadiene, 1,8,8-trimethyl-5-methylene-, (E,E)-
    • 1,6-Cycloundecadiene, 1,8,8-trimethyl-5-methylene-, (1E,6E)-
    • FNXUOGPQAOCFKU-NDFWULPDSA-N
    • AKOS016015977
    • 1,8,8-trimethyl-5-methylene-1 ,6-cycloundecadiene
    • 1,6-Cycloundecadiene,1,8,8-trimethyl-5-methylene-,(1E,6E)-

  • Applications

    The applications of (E,E)-1,8,8-Trimethyl-5-methylene-1,6-cycloundecadiene (CAS 26259-79-0) are primarily research-oriented: a sesquiterpene hydrocarbon found at trace levels in plant essential oils, it is used as a reference/marker compound for GC-MS/GC-FID profiling and phytochemical studies; as a synthetic intermediate and substrate for selective transformations (epoxidation, hydroboration–oxidation, ozonolysis, Diels–Alder, and olefin metathesis) to access oxygenated sesquiterpenoids and macrocyclic frameworks; investigated preclinically for potential bioactivities (antimicrobial/antifungal, anti-inflammatory, insect-repellent); occasionally explored in fragrance and flavor research to impart woody–terpenic–herbal nuances, subject to safety and regulatory evaluation before commercial use; useful in botanical authenticity (chemotaxonomy) and in studying oxidative stability/packaging interactions; recommended storage under inert gas, cool, and protected from light due to susceptibility to autoxidation and isomerization.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 104.81
    methanol 35.56
    isopropanol 122.14
    water 0.02
    ethyl acetate 234.08
    n-propanol 120.44
    acetone 123.16
    n-butanol 171.65
    acetonitrile 53.32
    DMF 80.65
    toluene 315.2
    isobutanol 107.26
    1,4-dioxane 367.62
    methyl acetate 128.7
    THF 689.83
    2-butanone 208.76
    n-pentanol 127.51
    sec-butanol 159.13
    n-hexane 172.85
    ethylene glycol 6.02
    NMP 96.63
    cyclohexane 226.29
    DMSO 95.04
    n-butyl acetate 479.97
    n-octanol 203.66
    chloroform 329.96
    n-propyl acetate 158.5
    acetic acid 33.87
    dichloromethane 267.2
    cyclohexanone 272.13
    propylene glycol 25.9
    isopropyl acetate 212.59
    DMAc 134.63
    2-ethoxyethanol 98.27
    isopentanol 178.33
    n-heptane 366.4
    ethyl formate 62.96
    1,2-dichloroethane 175.04
    n-hexanol 367.23
    2-methoxyethanol 118.17
    isobutyl acetate 161.27
    tetrachloromethane 75.93
    n-pentyl acetate 209.74
    transcutol 656.91
    n-heptanol 175.18
    ethylbenzene 219.87
    MIBK 198.39
    2-propoxyethanol 284.81
    tert-butanol 205.7
    MTBE 350.37
    2-butoxyethanol 176.59
    propionic acid 45.38
    o-xylene 183.25
    formic acid 3.86
    diethyl ether 351.79
    m-xylene 243.13
    p-xylene 225.0
    chlorobenzene 170.9
    dimethyl carbonate 40.71
    n-octane 95.89
    formamide 7.99
    cyclopentanone 237.26
    2-pentanone 221.54
    anisole 243.88
    cyclopentyl methyl ether 358.25
    gamma-butyrolactone 156.34
    1-methoxy-2-propanol 158.91
    pyridine 264.17
    3-pentanone 170.39
    furfural 124.79
    n-dodecane 64.92
    diethylene glycol 82.93
    diisopropyl ether 191.19
    tert-amyl alcohol 200.76
    acetylacetone 174.68
    n-hexadecane 73.91
    acetophenone 168.37
    methyl propionate 136.97
    isopentyl acetate 436.73
    trichloroethylene 267.61
    n-nonanol 199.84
    cyclohexanol 181.32
    benzyl alcohol 107.32
    2-ethylhexanol 366.17
    isooctanol 166.91
    dipropyl ether 604.91
    1,2-dichlorobenzene 146.89
    ethyl lactate 57.88
    propylene carbonate 122.99
    n-methylformamide 23.96
    2-pentanol 170.17
    n-pentane 136.9
    1-propoxy-2-propanol 350.18
    1-methoxy-2-propyl acetate 356.63
    2-(2-methoxypropoxy) propanol 261.57
    mesitylene 176.4
    ε-caprolactone 220.93
    p-cymene 232.81
    epichlorohydrin 246.01
    1,1,1-trichloroethane 231.96
    2-aminoethanol 23.41
    morpholine-4-carbaldehyde 157.07
    sulfolane 157.53
    2,2,4-trimethylpentane 75.33
    2-methyltetrahydrofuran 514.45
    n-hexyl acetate 331.99
    isooctane 78.36
    2-(2-butoxyethoxy)ethanol 314.59
    sec-butyl acetate 172.55
    tert-butyl acetate 271.14
    decalin 120.47
    glycerin 27.72
    diglyme 459.51
    acrylic acid 23.63
    isopropyl myristate 210.87
    n-butyric acid 118.85
    acetyl acetate 115.75
    di(2-ethylhexyl) phthalate 144.74
    ethyl propionate 156.26
    nitromethane 45.94
    1,2-diethoxyethane 505.63
    benzonitrile 131.18
    trioctyl phosphate 105.71
    1-bromopropane 309.69
    gamma-valerolactone 222.95
    n-decanol 162.48
    triethyl phosphate 125.77
    4-methyl-2-pentanol 139.39
    propionitrile 99.65
    vinylene carbonate 86.07
    1,1,2-trichlorotrifluoroethane 90.26
    DMS 144.42
    cumene 161.78
    2-octanol 141.39
    2-hexanone 193.73
    octyl acetate 216.95
    limonene 345.95
    1,2-dimethoxyethane 271.67
    ethyl orthosilicate 142.83
    tributyl phosphate 124.28
    diacetone alcohol 196.04
    N,N-dimethylaniline 187.63
    acrylonitrile 63.29
    aniline 149.58
    1,3-propanediol 55.9
    bromobenzene 234.64
    dibromomethane 252.93
    1,1,2,2-tetrachloroethane 249.17
    2-methyl-cyclohexyl acetate 270.31
    tetrabutyl urea 161.5
    diisobutyl methanol 248.32
    2-phenylethanol 209.62
    styrene 220.5
    dioctyl adipate 223.77
    dimethyl sulfate 44.57
    ethyl butyrate 314.92
    methyl lactate 45.75
    butyl lactate 119.81
    diethyl carbonate 163.82
    propanediol butyl ether 143.08
    triethyl orthoformate 238.45
    p-tert-butyltoluene 244.79
    methyl 4-tert-butylbenzoate 220.15
    morpholine 374.09
    tert-butylamine 187.52
    n-dodecanol 137.2
    dimethoxymethane 155.44
    ethylene carbonate 88.13
    cyrene 124.87
    2-ethoxyethyl acetate 238.56
    2-ethylhexyl acetate 409.65
    1,2,4-trichlorobenzene 165.36
    4-methylpyridine 266.77
    dibutyl ether 400.13
    2,6-dimethyl-4-heptanol 248.32
    DEF 158.05
    dimethyl isosorbide 439.55
    tetrachloroethylene 133.21
    eugenol 154.74
    triacetin 208.18
    span 80 245.22
    1,4-butanediol 22.4
    1,1-dichloroethane 199.85
    2-methyl-1-pentanol 152.15
    methyl formate 19.14
    2-methyl-1-butanol 158.66
    n-decane 107.52
    butyronitrile 161.77
    3,7-dimethyl-1-octanol 254.26
    1-chlorooctane 220.27
    1-chlorotetradecane 111.7
    n-nonane 112.53
    undecane 80.78
    tert-butylcyclohexane 120.24
    cyclooctane 131.04
    cyclopentanol 125.61
    tetrahydropyran 587.21
    tert-amyl methyl ether 292.55
    2,5,8-trioxanonane 360.32
    1-hexene 321.14
    2-isopropoxyethanol 112.27
    2,2,2-trifluoroethanol 8.41
    methyl butyrate 167.47

    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

Botanical

Name CAS Botanical Proportion
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.5%
Cubeb 3 8007-87-2 Piper cubeba L., fam. Piperaceae 1.9%
Cubeb 2 8007-87-2 Piper cubeba L., fam. Piperaceae 4.7%
Cubeb (Sri Lanka) 8007-87-2 Piper cubeba L., fam. Piperaceae 4.2%