1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene

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  • Identifiers

    CAS number
    92760-25-3

    Molecular formula
    C10H16O

    SMILES
    CC1(C2CCC(O1)(C=C2)C)C

    Retention indicies (RI)

    • DB5: 991.0
    • Carbowax: 1192.33

  • Odor profile

    Herbal 56.53%
    Mint 49.11%
    Fresh 47.08%
    Woody 45.7%
    Spicy 39.95%
    Camphoreous 39.87%
    Pine 33.01%
    Citrus 32.49%
    Cooling 30.74%
    Sweet 30.73%

    Scent© AI

  • Properties

    XLogP3-AA
    1.9

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point

    • 179.00 to 181.00 °C. @ 760.00 mm Hg

    Flash point est.
    55.63 ˚C

  • Synonyms

    • 2,3-Dehydro-1,8-cineole
    • Dehydrocineole
    • 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene
    • Dehydro-1,8-cineol
    • Dehydro-1,8-cineole
    • 66113-06-2
    • 1,8-Dehydrocineole
    • 1,8-cineole dehydro
    • Dehydro-1,8-cyneole
    • Dehydro-1.8-cineole
    • 2,3-Dehydro-1,8-cineol
    • 2,3-dihydro-1,8-cineole
    • 1,8-Epoxy-p-menth-2-ene
    • 92760-25-3
    • SCHEMBL23358702
    • DTXSID80335140
    • CHEBI:167365
    • LOOYOTLEOHYYOV-UHFFFAOYSA-N
    • 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene #
    • Q67879829

  • Applications

    1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-ene (CAS 92760-25-3) is leveraged as a bicyclic, terpene-like building block with a reactive C=C bond for preparing fragrance and flavor derivatives (e.g., selective conversion to isobornyl-type alcohols/ketones/esters), as a hydrophobic intermediate in pharma and agrochemical discovery, and as a functional component in polymer materials where copolymerization or grafting can impart rigidity, gloss, and thermal stability to UV-curable coatings, inks, and adhesives; in fundamental research, its oxabicyclic framework and olefin serve as model substrates for hydrofunctionalization, acid-catalyzed ring opening, epoxidation–ring-opening, and photoinduced cationic transformations to probe stereoselectivity and kinetics, and in some fragrance systems the bulky scaffold can act as a slow-release odor carrier to reduce volatility and prolong longevity; users should verify safety data, purity, and regulatory status (e.g., IFRA/REACH) for their specific application.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 243.45
    methanol 296.55
    isopropanol 165.97
    water 6.43
    ethyl acetate 301.21
    n-propanol 214.63
    acetone 206.15
    n-butanol 191.5
    acetonitrile 252.79
    DMF 230.19
    toluene 267.06
    isobutanol 155.56
    1,4-dioxane 497.62
    methyl acetate 279.64
    THF 512.03
    2-butanone 230.74
    n-pentanol 123.24
    sec-butanol 160.0
    n-hexane 75.93
    ethylene glycol 83.56
    NMP 337.27
    cyclohexane 125.03
    DMSO 174.51
    n-butyl acetate 244.73
    n-octanol 151.9
    chloroform 848.68
    n-propyl acetate 125.19
    acetic acid 213.49
    dichloromethane 651.34
    cyclohexanone 317.04
    propylene glycol 93.48
    isopropyl acetate 172.62
    DMAc 257.82
    2-ethoxyethanol 171.12
    isopentanol 149.78
    n-heptane 70.37
    ethyl formate 150.52
    1,2-dichloroethane 315.44
    n-hexanol 278.09
    2-methoxyethanol 282.23
    isobutyl acetate 103.25
    tetrachloromethane 195.54
    n-pentyl acetate 163.88
    transcutol 706.73
    n-heptanol 138.2
    ethylbenzene 104.79
    MIBK 132.92
    2-propoxyethanol 379.67
    tert-butanol 170.62
    MTBE 207.89
    2-butoxyethanol 199.23
    propionic acid 198.88
    o-xylene 160.15
    formic acid 116.07
    diethyl ether 315.24
    m-xylene 179.35
    p-xylene 123.89
    chlorobenzene 264.9
    dimethyl carbonate 116.86
    n-octane 29.67
    formamide 126.8
    cyclopentanone 331.38
    2-pentanone 189.79
    anisole 172.55
    cyclopentyl methyl ether 301.83
    gamma-butyrolactone 412.75
    1-methoxy-2-propanol 226.72
    pyridine 309.02
    3-pentanone 198.71
    furfural 312.86
    n-dodecane 25.16
    diethylene glycol 262.0
    diisopropyl ether 112.35
    tert-amyl alcohol 154.54
    acetylacetone 214.77
    n-hexadecane 28.57
    acetophenone 142.74
    methyl propionate 250.09
    isopentyl acetate 208.01
    trichloroethylene 538.99
    n-nonanol 132.87
    cyclohexanol 195.93
    benzyl alcohol 120.43
    2-ethylhexanol 160.17
    isooctanol 103.79
    dipropyl ether 201.18
    1,2-dichlorobenzene 220.03
    ethyl lactate 82.82
    propylene carbonate 236.15
    n-methylformamide 180.69
    2-pentanol 138.83
    n-pentane 79.24
    1-propoxy-2-propanol 259.19
    1-methoxy-2-propyl acetate 266.13
    2-(2-methoxypropoxy) propanol 192.09
    mesitylene 117.42
    ε-caprolactone 331.86
    p-cymene 99.85
    epichlorohydrin 389.99
    1,1,1-trichloroethane 340.72
    2-aminoethanol 135.91
    morpholine-4-carbaldehyde 356.91
    sulfolane 313.12
    2,2,4-trimethylpentane 38.11
    2-methyltetrahydrofuran 398.14
    n-hexyl acetate 248.22
    isooctane 30.9
    2-(2-butoxyethoxy)ethanol 256.67
    sec-butyl acetate 106.89
    tert-butyl acetate 161.99
    decalin 53.09
    glycerin 125.37
    diglyme 405.98
    acrylic acid 168.85
    isopropyl myristate 109.57
    n-butyric acid 215.34
    acetyl acetate 207.21
    di(2-ethylhexyl) phthalate 98.99
    ethyl propionate 136.69
    nitromethane 297.3
    1,2-diethoxyethane 278.57
    benzonitrile 178.99
    trioctyl phosphate 73.93
    1-bromopropane 262.32
    gamma-valerolactone 425.5
    n-decanol 98.19
    triethyl phosphate 97.34
    4-methyl-2-pentanol 91.35
    propionitrile 210.19
    vinylene carbonate 232.16
    1,1,2-trichlorotrifluoroethane 241.8
    DMS 193.71
    cumene 84.87
    2-octanol 94.0
    2-hexanone 126.92
    octyl acetate 132.25
    limonene 135.2
    1,2-dimethoxyethane 246.62
    ethyl orthosilicate 99.19
    tributyl phosphate 96.88
    diacetone alcohol 145.14
    N,N-dimethylaniline 123.63
    acrylonitrile 216.51
    aniline 229.02
    1,3-propanediol 156.8
    bromobenzene 299.44
    dibromomethane 444.86
    1,1,2,2-tetrachloroethane 423.44
    2-methyl-cyclohexyl acetate 145.11
    tetrabutyl urea 105.75
    diisobutyl methanol 87.5
    2-phenylethanol 182.7
    styrene 118.58
    dioctyl adipate 127.13
    dimethyl sulfate 141.06
    ethyl butyrate 157.92
    methyl lactate 115.86
    butyl lactate 115.89
    diethyl carbonate 117.77
    propanediol butyl ether 164.98
    triethyl orthoformate 136.49
    p-tert-butyltoluene 100.85
    methyl 4-tert-butylbenzoate 161.21
    morpholine 449.83
    tert-butylamine 142.13
    n-dodecanol 76.13
    dimethoxymethane 267.23
    ethylene carbonate 212.82
    cyrene 132.17
    2-ethoxyethyl acetate 245.71
    2-ethylhexyl acetate 193.65
    1,2,4-trichlorobenzene 252.81
    4-methylpyridine 306.28
    dibutyl ether 163.57
    2,6-dimethyl-4-heptanol 87.5
    DEF 206.07
    dimethyl isosorbide 291.23
    tetrachloroethylene 308.52
    eugenol 149.08
    triacetin 212.09
    span 80 165.13
    1,4-butanediol 65.73
    1,1-dichloroethane 344.36
    2-methyl-1-pentanol 114.14
    methyl formate 149.83
    2-methyl-1-butanol 157.72
    n-decane 40.91
    butyronitrile 189.8
    3,7-dimethyl-1-octanol 139.69
    1-chlorooctane 121.32
    1-chlorotetradecane 58.12
    n-nonane 41.01
    undecane 31.15
    tert-butylcyclohexane 48.49
    cyclooctane 60.0
    cyclopentanol 185.93
    tetrahydropyran 411.19
    tert-amyl methyl ether 181.3
    2,5,8-trioxanonane 291.48
    1-hexene 130.96
    2-isopropoxyethanol 130.52
    2,2,2-trifluoroethanol 107.04
    methyl butyrate 136.14

    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
Achillea wilhelmsii (Egypt) Achillea wilhelmsii C. Koch (A. santolina Auct. Mult.), fam. Asteraceae 0.5%
Achillea wilhelmsii (Turkey) Achillea wilhelmsii C. Koch (A. santolina Auct. Mult.), fam. Asteraceae 0.3%
Cardamom (Costa Rica) 8000-66-6 Elettaria cardamomum (L.) Maton, fam. Zingiberaceae 0.02%
Narcissus tazetta absolute 2 8023-75-4 Narcissus tazetta L., fam. Amaryllidaceae 0.1%
Pistacia lentiscus (Spain) 1a leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.03%
Artemisia persica (India) Artemisia persica Boiss., fam. Asteraceae (Compositae) 0.7%
Achillea biebersteinii (Turkey) 1 Achillea biebersteinii Afan., fam. Asteraceae (Compositae) 0.22%
Gingergrass (India) 5 Cymbopogon martini Stapf., var. sofia, fam. Poaceae (Gramineae) 0.05%
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Artemisia gmelini (Himalaya) Artemisia gmelinii Web. ex Stechm., fam. Asteracae (Compositae) 0.69%
Artemisia afra Willd. (Kenia) Artemisia afra Willd., fam. Asteraceae (Compositae) 0.06%
Artemisia umbelliformis (Italy) Artemisia umbelliformis Lam., fam. Asteraceae (Compositae) 0.01%
Artemisia campestris (Italy) 1 Artemisia campestris L. ssp. borealis (Pallas), H.M. Hall et Clements 5.2%
Artemisia genipi (Italy) Artemisia genipi Weber, fam. Asteraceae (Compositae) 0.01%
Artemisia petrosa (Italy) Artemisia petrosa Baumg. ssp. eriantha Ten., fam. Asteraceae (Compositae) 0.01%
Artemisia vallesiaca (Italy) Artemisia vallesiaca All., fam. Asteraceae (Compositae) 0.1%
Wormwood (Mugwort) (Italy) 2 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 0.01%
Artemisia chamaemelifolia (Italy) Artemisia chamaemelifolia Vill., fam. Asteraceae (Compositae) 0.1%
Artemisia glacialis (Italy) Artemisia glacialis L., fam. Asteraceae (Compositae) 0.1%
Artemisia campestris (Italy) 2 Artemisia campestris L. ssp. campestris, fam. Asteraceae (Compositae) 0.3%
Artemisia alba (Italy) 84775-75-7 Artemisia alba Turra, fam. Asteraceae (Compositae) 0.01%
Artemisia abrotanum (Italy) Artemisia abrotanum L., fam. Asteraceae (Compositae) 0.01%
Annual wormwood (Italy) Artemisia annua L., fam. Asteraceae (Compositae) 0.1%
Artemisia verlotiorum (Italy) Artemisia verlotiorum Lamotte, fam. Asteraceae (Compositae) 1.1%
Armoise (Italy) 8008-93-3 Artemisia vulgaris L., fam. Asteraceae (Compositae) 0.01%
Inula viscosa (Turkey) Inula viscosa (L.) Aiton (Dittrichia viscosa (L.) Greuter), fam.Asteraceae 0.3%
Bay, West Indian (Guadeloupe) 1b 8015-73-4 Pimenta racemosa var. racemosa (P. Miller) J.W. Moore, fam. Myrtaceae 0.1%
Hexalobus monopetalus leaf Hexalobus monopetalus (A. Rich) Engl., fam. Annonaceae 0.01%
Lime (Mexican, West Indian, Key) 5 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.04%
Lime (Mexican, West Indian, Key) (Peru) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.21%
Lime (Mexican, West Indian, Key) (Ivory Coast) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.27%
Lime (Mexican, West Indian, Key) 7 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.25%
Laurel leaf 1 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.2%
Olibanum, Frankincense (Turkey) 8016-36-2 Boswellia carterii Birdwood, fam. Burseraceae 0.1%
Mullilam leaf (India) Zanthoxylum rhetsa D.C. syn. Z. limonella (Dennst.) Alston, fam. Rutaceae 0.01%
Bay, West Indian (Guadeloupe) 2a 8015-73-4 Pimenta racemosa var. racemosa (P. Miller) J.W. Moore, fam. Myrtaceae 0.31%
Bay, West Indian (Guadeloupe) 2b 8015-73-4 Pimenta racemosa var. racemosa (P. Miller) J.W. Moore, fam. Myrtaceae 0.06%
Balsamite/Costmary (Iran) Chrysanthemum balsamita L., fam. Asteraceae (Compositae) 0.8%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.2%
Laurel leaf (Czechia) 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Laurel leaf (Turkey) 2a hydrodistilled 8006-78-8 Laurus nobilis L., fam. Lauraceae 1.0%
Laurel leaf (Turkey) 2b steamdistilled 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.5%
Laurel leaf (Turkey) 2c CO2-extracted 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.05%
Thymus lotocephallus (Portugal) flower Thymus lotocephallus G. Lopez & R. Morales, fam. Lamiaceae (Labiatae) 0.3%
Yarrow (India) 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.05%
Cymbopogon olivieri (Iran) Cymbopogon olivieri (Boiss.) Bor, fam. Poaceae (Gramineae) 0.2%
Annual wormwood (India) 2 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.2%
Thymus fedtschenkoi var. handelii (Turkey) Thymus fedtschenkoi var. handelii, fam. Lamiaceae (Labiatae) 0.3%
Thymus pubescens (Iran) 2 Thymus pubescens Boiss. et Kotschy ex Celak, fam. Lamiaceae (Labiatae) 0.35%