3,8,8-Trimethyl-4-oxatricyclo[5.1.0.03,5]octane

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  • Identifiers

    CAS number
    2225-98-1

    Molecular formula
    C10H16O

    SMILES
    CC1(C2C1CC3(C(C2)O3)C)C

    Retention indicies (RI)

    • Carbowax: 1438.0

  • Odor profile

    Fragrance
    Woody 75.91%
    Herbal 55.42%
    Fresh 48.83%
    Spicy 47.17%
    Earthy 46.5%
    Green 46.33%
    Camphoreous 45.63%
    Pine 43.92%
    Sweet 41.03%
    Mint 39.84%

     

    Flavor
    Herbal 51.49%
    Woody 51.41%
    Green 49.67%
    Earthy 49.07%
    Sweet 45.21%
    Camphor 44.59%
    Pine 41.28%
    Minty 34.76%
    Spicy 34.64%
    Earth 34.62%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    7.77 (neutral)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    187°C

    Flash point

    • 48.63 ˚C est.

  • Synonyms

    • 2225-98-1
    • 3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane
    • 3,4-epoxycarane
    • 3,8,8-Trimethyl-4-oxatricyclo[5.1.0.0,3,5]octane
    • 3-carene oxide
    • 3,8,8-Trimethyl-4-oxatricyclo(5.1.0.03,5)octane
    • NSC96745
    • EINECS 218-753-0
    • SCHEMBL1261773
    • (1alpha,3beta,5beta,7alpha)-3,8,8-Trimethyl-4-oxatricyclo(5.1.0.03,5)octane
    • DTXSID201241384
    • 21218-11-1
    • CAA22598
    • EINECS 244-280-4
    • EINECS 252-664-8
    • NSC 96745
    • NSC-96745
    • NS00042324
    • EN300-248203
    • G40187
    • 3,8,8-trimethyl-4-oxatricyclo[5.1.0.0?,?]octane
    • Z1509024943
    • (1alpha,3alpha,5alpha,7alpha)-3,8,8-Trimethyl-4-oxatricyclo(5.1.0.03,5)octane
    • 4-Oxatricyclo[5.1.0.0(3,5)-]octane, 3,8,8-trimethyl-, (1.alpha.,3.alpha.,5.alpha.,7.alpha.)-
    • 4-Oxatricyclo[5.1.0.0(3,5)-]octane, 3,8,8-trimethyl-, (1.alpha.,3.beta.,5.beta.,7.alpha.)-

  • Applications

    3,8,8-Trimethyl-4-oxatricyclo[5.1.0.03,5]octane (CAS 2225-98-1) is a highly reactive pinane-type monoterpene epoxide, thus used primarily as a versatile intermediate in fragrance/aroma chemistry and terpenoid synthesis: under acid catalysis it undergoes Meinwald-type rearrangements to camphoraceous aldehydes/ketones (e.g., campholenic aldehyde) that serve as precursors to pine-, eucalyptus- and camphor-like notes; via selective ring-opening, hydrolysis or hydrogenation it furnishes terpenoid alcohols (terpineol, borneol/isoborneol) and related derivatives for resin and aroma applications; it also serves as a convenient model substrate for developing asymmetric catalysts for epoxide ring-opening, annulation and rearrangement reactions, and is widely used in mechanistic studies and in upgrading renewable turpentine/essential-oil feedstocks; at industrial scale it functions as a flexible building block toward fragrance ingredients, pinane-based pharmaceutical/agrochemical intermediates and other fine chemicals, where its inherent stereochemical bias helps control odor, bioactivity and material properties.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 331.76
    methanol 331.01
    isopropanol 316.81
    water 4.27
    ethyl acetate 367.43
    n-propanol 316.76
    acetone 423.65
    n-butanol 250.36
    acetonitrile 341.36
    DMF 390.44
    toluene 156.4
    isobutanol 237.77
    1,4-dioxane 526.21
    methyl acetate 412.5
    THF 634.05
    2-butanone 390.49
    n-pentanol 164.8
    sec-butanol 224.32
    n-hexane 28.15
    ethylene glycol 143.91
    NMP 181.3
    cyclohexane 37.59
    DMSO 284.29
    n-butyl acetate 225.19
    n-octanol 142.94
    chloroform 716.7
    n-propyl acetate 186.37
    acetic acid 161.25
    dichloromethane 508.36
    cyclohexanone 274.78
    propylene glycol 190.95
    isopropyl acetate 257.43
    DMAc 326.66
    2-ethoxyethanol 331.06
    isopentanol 207.93
    n-heptane 29.67
    ethyl formate 204.29
    1,2-dichloroethane 296.3
    n-hexanol 257.88
    2-methoxyethanol 517.49
    isobutyl acetate 152.23
    tetrachloromethane 126.02
    n-pentyl acetate 149.59
    transcutol 670.57
    n-heptanol 130.0
    ethylbenzene 103.22
    MIBK 207.37
    2-propoxyethanol 552.19
    tert-butanol 289.36
    MTBE 292.47
    2-butoxyethanol 266.17
    propionic acid 206.2
    o-xylene 105.38
    formic acid 95.83
    diethyl ether 298.55
    m-xylene 132.37
    p-xylene 130.73
    chlorobenzene 195.78
    dimethyl carbonate 183.34
    n-octane 17.46
    formamide 150.64
    cyclopentanone 381.46
    2-pentanone 297.96
    anisole 216.96
    cyclopentyl methyl ether 254.39
    gamma-butyrolactone 385.79
    1-methoxy-2-propanol 445.72
    pyridine 302.92
    3-pentanone 237.29
    furfural 298.44
    n-dodecane 18.38
    diethylene glycol 429.44
    diisopropyl ether 114.17
    tert-amyl alcohol 196.9
    acetylacetone 344.07
    n-hexadecane 20.56
    acetophenone 167.88
    methyl propionate 318.1
    isopentyl acetate 215.75
    trichloroethylene 506.29
    n-nonanol 126.64
    cyclohexanol 156.44
    benzyl alcohol 159.06
    2-ethylhexanol 124.23
    isooctanol 100.92
    dipropyl ether 173.21
    1,2-dichlorobenzene 173.37
    ethyl lactate 145.03
    propylene carbonate 209.78
    n-methylformamide 254.54
    2-pentanol 180.58
    n-pentane 33.02
    1-propoxy-2-propanol 353.33
    1-methoxy-2-propyl acetate 338.14
    2-(2-methoxypropoxy) propanol 209.35
    mesitylene 86.79
    ε-caprolactone 255.22
    p-cymene 75.84
    epichlorohydrin 475.6
    1,1,1-trichloroethane 313.92
    2-aminoethanol 226.35
    morpholine-4-carbaldehyde 352.92
    sulfolane 272.28
    2,2,4-trimethylpentane 20.76
    2-methyltetrahydrofuran 352.7
    n-hexyl acetate 217.87
    isooctane 22.37
    2-(2-butoxyethoxy)ethanol 285.57
    sec-butyl acetate 144.59
    tert-butyl acetate 237.68
    decalin 26.68
    glycerin 220.25
    diglyme 494.19
    acrylic acid 169.33
    isopropyl myristate 96.88
    n-butyric acid 227.04
    acetyl acetate 228.3
    di(2-ethylhexyl) phthalate 81.29
    ethyl propionate 202.1
    nitromethane 386.17
    1,2-diethoxyethane 263.46
    benzonitrile 184.83
    trioctyl phosphate 66.37
    1-bromopropane 216.14
    gamma-valerolactone 466.6
    n-decanol 97.9
    triethyl phosphate 92.06
    4-methyl-2-pentanol 137.6
    propionitrile 304.35
    vinylene carbonate 217.46
    1,1,2-trichlorotrifluoroethane 308.43
    DMS 220.8
    cumene 81.76
    2-octanol 91.65
    2-hexanone 191.96
    octyl acetate 112.39
    limonene 84.87
    1,2-dimethoxyethane 450.26
    ethyl orthosilicate 90.96
    tributyl phosphate 80.2
    diacetone alcohol 246.87
    N,N-dimethylaniline 134.27
    acrylonitrile 324.35
    aniline 175.35
    1,3-propanediol 269.06
    bromobenzene 200.24
    dibromomethane 340.7
    1,1,2,2-tetrachloroethane 418.45
    2-methyl-cyclohexyl acetate 129.87
    tetrabutyl urea 92.44
    diisobutyl methanol 99.56
    2-phenylethanol 198.42
    styrene 111.35
    dioctyl adipate 101.8
    dimethyl sulfate 192.14
    ethyl butyrate 162.54
    methyl lactate 207.64
    butyl lactate 143.83
    diethyl carbonate 125.1
    propanediol butyl ether 240.3
    triethyl orthoformate 131.32
    p-tert-butyltoluene 78.57
    methyl 4-tert-butylbenzoate 152.12
    morpholine 484.55
    tert-butylamine 193.11
    n-dodecanol 76.97
    dimethoxymethane 426.85
    ethylene carbonate 197.91
    cyrene 153.48
    2-ethoxyethyl acetate 242.81
    2-ethylhexyl acetate 163.95
    1,2,4-trichlorobenzene 197.54
    4-methylpyridine 273.11
    dibutyl ether 139.26
    2,6-dimethyl-4-heptanol 99.56
    DEF 217.82
    dimethyl isosorbide 267.25
    tetrachloroethylene 262.56
    eugenol 158.56
    triacetin 211.1
    span 80 160.44
    1,4-butanediol 134.33
    1,1-dichloroethane 380.45
    2-methyl-1-pentanol 126.19
    methyl formate 226.14
    2-methyl-1-butanol 180.22
    n-decane 27.61
    butyronitrile 254.09
    3,7-dimethyl-1-octanol 132.89
    1-chlorooctane 91.53
    1-chlorotetradecane 40.7
    n-nonane 25.44
    undecane 22.0
    tert-butylcyclohexane 28.91
    cyclooctane 19.77
    cyclopentanol 183.57
    tetrahydropyran 378.28
    tert-amyl methyl ether 178.2
    2,5,8-trioxanonane 296.87
    1-hexene 89.57
    2-isopropoxyethanol 249.2
    2,2,2-trifluoroethanol 118.12
    methyl butyrate 215.28

    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
Caraway seed (Yugoslavia) 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.03%