(4E,7E)-1,5,9,9-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

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  • Identifiers

    CAS number
    19888-33-6

    Molecular formula
    C15H24O

    SMILES
    C/C/1=C/CCC2(C(O2)CC(/C=C\C1)(C)C)C

    Retention indicies (RI)

    • DB5: 1598.75
    • Carbowax: 2008.5

  • Odor profile

    Woody 64.75%
    Herbal 61.04%
    Spicy 50.43%
    Citrus 43.96%
    Fresh 36.82%
    Mint 35.53%
    Earthy 35.31%
    Amber 33.58%
    Dry 32.33%
    Tobacco 31.9%

    Scent© AI

  • Properties

    XLogP3-AA
    3.9

    Molecular weight
    220.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    277°C

    Flash point est.
    151.71 ˚C

  • Synonyms

    • 19888-33-6
    • (4E,7E)-1,5,9,9-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene
    • (4Z,7Z)-1,5,9,9-TETRAMETHYL-12-OXABICYCLO[9.1.0]DODECA-4,7-DIENE
    • humuleneoxide,1,5,9,9-tetramethyl-12-oxabicyclododeca-4,7-diene

  • Applications

    (4E,7E)-1,5,9,9-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene (CAS 19888-33-6) is a terpenoid-like bicyclic ether often explored as a reference material and synthetic intermediate in fragrance research to probe how a hydrophobic bicyclic scaffold and E,E double bonds influence odor character, oxidative stability, and volatility; in organic synthesis it serves as a rigid, carbon-rich framework for selective functional transformations (e.g., epoxidation/hydroxylation, addition reactions, and controlled hydrogenation) to access oxygenated terpenoid derivatives or pharma/agrochemical intermediates, while supporting mechanistic, kinetic, and stereocontrol studies; it is also used as a GC/GC–MS analytical standard to calibrate retention indices and detector responses for bicyclic ethers, as a test article for material compatibility and scent longevity in consumer matrices, and as a molecular model for studying permeability, solvent affinity, and intermolecular interactions in materials and surface science, with all uses subject to safety/toxicity assessment and regulatory compliance.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 77.98
    methanol 55.53
    isopropanol 74.05
    water 0.27
    ethyl acetate 109.89
    n-propanol 84.31
    acetone 90.96
    n-butanol 88.36
    acetonitrile 75.98
    DMF 81.89
    toluene 130.11
    isobutanol 77.35
    1,4-dioxane 222.22
    methyl acetate 105.58
    THF 269.08
    2-butanone 126.34
    n-pentanol 94.62
    sec-butanol 86.8
    n-hexane 44.17
    ethylene glycol 17.6
    NMP 129.6
    cyclohexane 68.46
    DMSO 87.89
    n-butyl acetate 164.12
    n-octanol 109.17
    chloroform 352.67
    n-propyl acetate 113.08
    acetic acid 64.64
    dichloromethane 240.22
    cyclohexanone 171.24
    propylene glycol 42.75
    isopropyl acetate 97.34
    DMAc 143.86
    2-ethoxyethanol 108.91
    isopentanol 90.27
    n-heptane 56.18
    ethyl formate 65.41
    1,2-dichloroethane 119.41
    n-hexanol 150.15
    2-methoxyethanol 108.18
    isobutyl acetate 116.31
    tetrachloromethane 57.83
    n-pentyl acetate 118.21
    transcutol 379.33
    n-heptanol 95.36
    ethylbenzene 106.97
    MIBK 97.5
    2-propoxyethanol 190.44
    tert-butanol 88.07
    MTBE 107.3
    2-butoxyethanol 142.23
    propionic acid 67.64
    o-xylene 107.69
    formic acid 16.42
    diethyl ether 109.17
    m-xylene 105.82
    p-xylene 138.58
    chlorobenzene 121.41
    dimethyl carbonate 46.0
    n-octane 25.72
    formamide 25.5
    cyclopentanone 156.95
    2-pentanone 104.03
    anisole 143.58
    cyclopentyl methyl ether 145.43
    gamma-butyrolactone 146.37
    1-methoxy-2-propanol 113.23
    pyridine 171.98
    3-pentanone 102.87
    furfural 142.95
    n-dodecane 26.13
    diethylene glycol 116.37
    diisopropyl ether 63.48
    tert-amyl alcohol 90.89
    acetylacetone 110.69
    n-hexadecane 29.09
    acetophenone 137.59
    methyl propionate 90.33
    isopentyl acetate 174.77
    trichloroethylene 230.26
    n-nonanol 105.0
    cyclohexanol 105.43
    benzyl alcohol 110.23
    2-ethylhexanol 123.77
    isooctanol 86.34
    dipropyl ether 132.73
    1,2-dichlorobenzene 122.81
    ethyl lactate 73.51
    propylene carbonate 117.63
    n-methylformamide 41.75
    2-pentanol 77.8
    n-pentane 36.53
    1-propoxy-2-propanol 171.37
    1-methoxy-2-propyl acetate 167.43
    2-(2-methoxypropoxy) propanol 170.86
    mesitylene 79.41
    ε-caprolactone 168.85
    p-cymene 96.54
    epichlorohydrin 180.66
    1,1,1-trichloroethane 140.39
    2-aminoethanol 42.9
    morpholine-4-carbaldehyde 177.74
    sulfolane 146.11
    2,2,4-trimethylpentane 27.82
    2-methyltetrahydrofuran 209.5
    n-hexyl acetate 180.91
    isooctane 22.74
    2-(2-butoxyethoxy)ethanol 194.85
    sec-butyl acetate 107.76
    tert-butyl acetate 109.02
    decalin 52.78
    glycerin 45.6
    diglyme 281.57
    acrylic acid 55.26
    isopropyl myristate 101.05
    n-butyric acid 90.63
    acetyl acetate 86.88
    di(2-ethylhexyl) phthalate 103.2
    ethyl propionate 100.75
    nitromethane 79.92
    1,2-diethoxyethane 176.89
    benzonitrile 132.61
    trioctyl phosphate 73.39
    1-bromopropane 114.82
    gamma-valerolactone 201.75
    n-decanol 83.34
    triethyl phosphate 86.44
    4-methyl-2-pentanol 67.71
    propionitrile 86.83
    vinylene carbonate 112.52
    1,1,2-trichlorotrifluoroethane 142.67
    DMS 131.38
    cumene 87.93
    2-octanol 73.99
    2-hexanone 125.09
    octyl acetate 115.43
    limonene 118.04
    1,2-dimethoxyethane 188.47
    ethyl orthosilicate 87.15
    tributyl phosphate 82.65
    diacetone alcohol 105.26
    N,N-dimethylaniline 111.86
    acrylonitrile 82.6
    aniline 101.07
    1,3-propanediol 58.37
    bromobenzene 138.78
    dibromomethane 183.23
    1,1,2,2-tetrachloroethane 208.86
    2-methyl-cyclohexyl acetate 162.66
    tetrabutyl urea 103.38
    diisobutyl methanol 79.77
    2-phenylethanol 141.14
    styrene 110.71
    dioctyl adipate 125.81
    dimethyl sulfate 58.78
    ethyl butyrate 134.07
    methyl lactate 60.06
    butyl lactate 109.6
    diethyl carbonate 103.3
    propanediol butyl ether 137.69
    triethyl orthoformate 120.51
    p-tert-butyltoluene 91.64
    methyl 4-tert-butylbenzoate 137.16
    morpholine 217.26
    tert-butylamine 71.81
    n-dodecanol 70.63
    dimethoxymethane 95.94
    ethylene carbonate 101.66
    cyrene 141.9
    2-ethoxyethyl acetate 152.08
    2-ethylhexyl acetate 160.82
    1,2,4-trichlorobenzene 150.37
    4-methylpyridine 166.23
    dibutyl ether 123.19
    2,6-dimethyl-4-heptanol 79.77
    DEF 104.14
    dimethyl isosorbide 247.78
    tetrachloroethylene 130.94
    eugenol 135.39
    triacetin 180.87
    span 80 164.4
    1,4-butanediol 40.43
    1,1-dichloroethane 131.98
    2-methyl-1-pentanol 102.81
    methyl formate 35.0
    2-methyl-1-butanol 90.36
    n-decane 38.37
    butyronitrile 94.42
    3,7-dimethyl-1-octanol 109.33
    1-chlorooctane 86.62
    1-chlorotetradecane 48.69
    n-nonane 35.01
    undecane 30.98
    tert-butylcyclohexane 44.19
    cyclooctane 37.9
    cyclopentanol 98.25
    tetrahydropyran 218.72
    tert-amyl methyl ether 101.17
    2,5,8-trioxanonane 219.31
    1-hexene 92.88
    2-isopropoxyethanol 106.03
    2,2,2-trifluoroethanol 28.54
    methyl butyrate 116.33

    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
Hop (Nugget cultivar) (USA) 8007-04-3 Humulus lupulus L., cultivar Nugget, fam. Cannabaceae 0.03%
Hop (Cascade cultivar) (USA) 8007-04-3 Humulus lupulus L., cultivar Cascade, fam. Cannabaceae 0.05%
Hop (Galena cultivar) (USA) 8007-04-3 Humulus lupulus L., cultivar Galena, fam. Cannabaceae 0.04%
Hop (Styrian cultivar) (USA) 8007-04-3 Humulus lupulus L., cultivar Styrian, fam. Cannabaceae 0.16%
Hop (Willamette cultivar) (USA) 8007-04-3 Humulus lupulus L., cultivar Willamette, fam. Cannabaceae 0.02%
Aframomum melegueta Aframomum melegueta (Roscoe) K. Schum., fam. Zingiberaceae 1.3%
Aframomum sulcatum Aframomum sulcatum (Oliv. and Hanb.) K. Schum., fam. Zingiberaceae 1.0%
Zingiber zerumbet (Vietnam) 1 rhizome Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 3.8%
Juniper leaf (France) 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.01%
Phoebe 1 Phoebe porosa Mez. (syn. Oreodaphne porosa Nees et Mart.), fam. Lauraceae 0.6%
Nepeta cataria (Argentina) 84929-35-1 Nepeta cataria L., fam. Lamiaceae (Labiatae) 1.63%
Boronia megastigma 91771-36-7 Boronia megastigma Nees., fam. Rutaceae 0.03%
Sage, dalmatian (Cuba) 8022-56-8 Salvia officinalis L., fam. Lamiaceae (Labiatae) 2.21%
Eupatorium capillifolium (Cuba) Eupatorium capillifolium (Lam.) Small, fam. Asteraceae (Compositae) 1.58%
Salvia aramiensis (Turkey) Salvia aramiensis Rech. fil., fam. Lamiaceae (Labiatae) 0.05%
Tejpat leaf Cinnamomum tamala (Ham.) Nees et Eberm., fam. Lauraceae 0.1%
Savory, summer (Iran) 1 8016-68-0 Satureja hortensis L., fam. Lamiaceae (Labiatae) 0.2%
Orthodon dianthera (Vietnam) Orthodon dianthera Maxim. (Mosla dianthera Maxim.), fam. Lamiaceae 1.4%
Cinnamon fruit (India) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.5%
Pepper, black (India) 6b free volatiles 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Cassinia laevis flower Cassinia laevis R.Br., fam. Asteraceae (Compositae) 0.2%
Cassinia laevis leaf Cassinia laevis R.Br., fam. Asteraceae (Compositae) 0.9%
Myrtle leaf (Turkey) 2 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.2%
Yarrow (India) 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.1%
Annual wormwood (India) 2 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.4%
Cinnamomum tamala leaf (Pakistan) Cinnamomum tamala (Ham.) Nees et Eberm., fam. Lauraceae 0.1%
Myrceugenia alpigena (Brazil) Myrceugenia alpigena (DC.) Landrum, fam. Myrtaceae 0.4%
Myrceugenia miersiana (Brazil) Myrceugenia miersiana (Gardner) D. Legrand et Kausel, fam. Myrtaceae 1.3%
Myrceugenia myrcioides (Brazil) Myrceugenia myrcioides (Cambess.) O. Berg, fam. Myrtaceae 2.2%
Salvia aucheri (Turkey) 1a var. aucheri Salvia aucheri Benth. var. aucheri, fam. Lamiaceae (Labiatae) 0.05%