(E,E)-1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene

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  • Identifiers

    CAS number
    116-04-1

    Molecular formula
    C15H24

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

    Retention indicies (RI)

    • DB5: 1440.0

  • Odor profile

    Woody 63.8%
    Citrus 61.17%
    Spicy 53.93%
    Herbal 53.25%
    Terpenic 44.42%
    Lemon 42.51%
    Dry 35.58%
    Fresh 34.86%
    Camphoreous 34.68%
    Mint 32.7%

    Scent© AI

  • Properties

    XLogP3-AA
    4.8

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    260°C

    Flash point est.
    102.97 ˚C

  • Synonyms

    • beta-Humulene
    • .beta.-Humulene
    • 116-04-1
    • (E,E)-1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene
    • (4E,8E)-beta-humulene
    • UNII-KK0W1K5Z3S
    • KK0W1K5Z3S
    • (1E,5E)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene
    • 1,5-Cycloundecadiene, 1,4,4-trimethyl-8-methylene-, (1E,5E)-
    • (1E,5E)-1,4,4-trimethyl-8-methylenecycloundeca-1,5-diene
    • 1,5-Cycloundecadiene, 1,4,4-trimethyl-8-methylene-, (E,E)-
    • (1E,5E)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene (4E,8E)-humula-4,8,11-triene
    • beta -Humulene
    • .BETA.-HUMULENE [MI]
    • CHEBI:49312
    • HAVYZKHVTLAPDZ-PPGMXFKZSA-N
    • DTXSID101019015
    • (4E,8E)-humula-4,8,11-triene
    • LMPR0103110005
    • beta-Humulene, technical, >=90% (GC)
    • 1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene #
    • Q27121617

  • Applications

    (E,E)-1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene (CAS 116-04-1) is a sesquiterpene hydrocarbon (C15H24) with a woody, herbal, mildly spicy odor found in various essential oils (e.g., hops, clove, basil, cannabis) and used as a fragrance/flavor ingredient in perfumery, personal care products, and food and beverage formulations (notably hop-like notes); it also serves as an analytical reference/standard in GC-MS profiling of essential oils and aromas; in materials and synthetic chemistry its 11-membered terpene scaffold is a versatile feedstock/building block to access new sesquiterpene derivatives, oxidized/epoxidized products, and to probe stereoselective transformations; in agriculture and chemical ecology the compound and mixtures containing it are investigated as insect attractants/repellents and semiochemicals that modulate pest behavior; in biomedical research it is studied in vitro and in vivo for anti-inflammatory, antimicrobial, antioxidant, immunomodulatory, and antiproliferative potential, motivating formulation strategies (e.g., encapsulation, carrier systems) to improve stability, solubility, and controlled release; additionally, its volatility and distinctive scent make it useful for microencapsulation or slow-release delivery in consumer products and as a sensory marker in shelf-life/aging assessments.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 97.05
    methanol 32.54
    isopropanol 115.66
    water 0.02
    ethyl acetate 220.61
    n-propanol 113.3
    acetone 122.11
    n-butanol 160.4
    acetonitrile 52.05
    DMF 81.24
    toluene 299.28
    isobutanol 103.29
    1,4-dioxane 346.23
    methyl acetate 124.53
    THF 675.09
    2-butanone 207.63
    n-pentanol 121.19
    sec-butanol 151.61
    n-hexane 173.22
    ethylene glycol 5.99
    NMP 103.73
    cyclohexane 220.48
    DMSO 94.91
    n-butyl acetate 454.94
    n-octanol 199.83
    chloroform 316.47
    n-propyl acetate 154.67
    acetic acid 34.33
    dichloromethane 255.47
    cyclohexanone 272.47
    propylene glycol 25.54
    isopropyl acetate 205.73
    DMAc 135.04
    2-ethoxyethanol 95.44
    isopentanol 172.11
    n-heptane 376.26
    ethyl formate 63.05
    1,2-dichloroethane 169.32
    n-hexanol 352.81
    2-methoxyethanol 112.68
    isobutyl acetate 160.25
    tetrachloromethane 71.92
    n-pentyl acetate 204.09
    transcutol 630.18
    n-heptanol 172.21
    ethylbenzene 214.28
    MIBK 200.24
    2-propoxyethanol 273.57
    tert-butanol 198.59
    MTBE 335.25
    2-butoxyethanol 175.2
    propionic acid 45.32
    o-xylene 179.4
    formic acid 3.85
    diethyl ether 323.73
    m-xylene 239.94
    p-xylene 223.14
    chlorobenzene 167.88
    dimethyl carbonate 41.15
    n-octane 96.17
    formamide 7.76
    cyclopentanone 245.71
    2-pentanone 215.63
    anisole 241.47
    cyclopentyl methyl ether 363.7
    gamma-butyrolactone 161.47
    1-methoxy-2-propanol 153.78
    pyridine 254.09
    3-pentanone 168.48
    furfural 128.5
    n-dodecane 66.58
    diethylene glycol 81.7
    diisopropyl ether 183.7
    tert-amyl alcohol 195.15
    acetylacetone 177.1
    n-hexadecane 75.64
    acetophenone 171.82
    methyl propionate 132.96
    isopentyl acetate 427.97
    trichloroethylene 263.03
    n-nonanol 197.21
    cyclohexanol 179.8
    benzyl alcohol 107.32
    2-ethylhexanol 366.22
    isooctanol 165.36
    dipropyl ether 598.69
    1,2-dichlorobenzene 145.27
    ethyl lactate 59.45
    propylene carbonate 128.11
    n-methylformamide 23.64
    2-pentanol 163.02
    n-pentane 134.09
    1-propoxy-2-propanol 341.14
    1-methoxy-2-propyl acetate 350.39
    2-(2-methoxypropoxy) propanol 261.37
    mesitylene 175.61
    ε-caprolactone 223.08
    p-cymene 234.54
    epichlorohydrin 247.19
    1,1,1-trichloroethane 226.54
    2-aminoethanol 22.44
    morpholine-4-carbaldehyde 160.25
    sulfolane 165.41
    2,2,4-trimethylpentane 77.13
    2-methyltetrahydrofuran 507.66
    n-hexyl acetate 324.92
    isooctane 80.0
    2-(2-butoxyethoxy)ethanol 311.59
    sec-butyl acetate 170.45
    tert-butyl acetate 268.55
    decalin 122.49
    glycerin 27.78
    diglyme 458.31
    acrylic acid 24.44
    isopropyl myristate 211.97
    n-butyric acid 116.16
    acetyl acetate 114.02
    di(2-ethylhexyl) phthalate 145.24
    ethyl propionate 154.38
    nitromethane 47.1
    1,2-diethoxyethane 475.68
    benzonitrile 131.29
    trioctyl phosphate 107.33
    1-bromopropane 296.23
    gamma-valerolactone 226.92
    n-decanol 160.33
    triethyl phosphate 128.71
    4-methyl-2-pentanol 137.85
    propionitrile 94.92
    vinylene carbonate 88.86
    1,1,2-trichlorotrifluoroethane 93.8
    DMS 144.08
    cumene 160.39
    2-octanol 138.07
    2-hexanone 194.19
    octyl acetate 216.74
    limonene 356.32
    1,2-dimethoxyethane 264.85
    ethyl orthosilicate 144.01
    tributyl phosphate 125.48
    diacetone alcohol 198.77
    N,N-dimethylaniline 187.75
    acrylonitrile 61.47
    aniline 145.52
    1,3-propanediol 53.31
    bromobenzene 229.43
    dibromomethane 240.7
    1,1,2,2-tetrachloroethane 246.33
    2-methyl-cyclohexyl acetate 276.8
    tetrabutyl urea 162.3
    diisobutyl methanol 252.84
    2-phenylethanol 205.82
    styrene 213.71
    dioctyl adipate 223.8
    dimethyl sulfate 45.31
    ethyl butyrate 312.73
    methyl lactate 46.45
    butyl lactate 120.85
    diethyl carbonate 164.19
    propanediol butyl ether 143.24
    triethyl orthoformate 239.29
    p-tert-butyltoluene 245.89
    methyl 4-tert-butylbenzoate 224.19
    morpholine 350.64
    tert-butylamine 180.56
    n-dodecanol 136.23
    dimethoxymethane 149.62
    ethylene carbonate 90.63
    cyrene 130.94
    2-ethoxyethyl acetate 230.52
    2-ethylhexyl acetate 398.81
    1,2,4-trichlorobenzene 166.0
    4-methylpyridine 258.19
    dibutyl ether 393.18
    2,6-dimethyl-4-heptanol 252.84
    DEF 156.22
    dimethyl isosorbide 446.44
    tetrachloroethylene 130.48
    eugenol 157.47
    triacetin 210.27
    span 80 247.87
    1,4-butanediol 22.26
    1,1-dichloroethane 190.46
    2-methyl-1-pentanol 147.62
    methyl formate 19.48
    2-methyl-1-butanol 152.55
    n-decane 108.77
    butyronitrile 153.93
    3,7-dimethyl-1-octanol 254.84
    1-chlorooctane 220.62
    1-chlorotetradecane 113.04
    n-nonane 113.6
    undecane 82.2
    tert-butylcyclohexane 122.91
    cyclooctane 132.46
    cyclopentanol 128.81
    tetrahydropyran 560.56
    tert-amyl methyl ether 286.29
    2,5,8-trioxanonane 360.89
    1-hexene 312.02
    2-isopropoxyethanol 111.92
    2,2,2-trifluoroethanol 8.61
    methyl butyrate 166.49

    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
Pimento (Allspice) 1 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 0.1%
Minthostachys spicata Minthostachys spicata (Benth.) Epl., fam Lamiaceae (Labiatae) 1.1%
Aristolochia impudica leaf Aristolochia impudica J. Ortega, fam. Aristolochiaceae 0.02%
Amorpha fruticosa fruit Amorpha fruticosa L., fam. Papilionaceae 0.9%
Baccharis uncinella (Brazil) Baccharis uncinella DC., fam. Asteraceae (Compositae) 0.1%
Coespeletia thyrsiformis leaf (Venezuela) Coespeletia thyrsiformis (A.C. Smith) Cuatr., fam. Asteraceae 1.3%