(1alpha,2beta,4beta,6alpha)-2,2,7-Trimethyl-3-oxatricyclo(4.1.1.02,4)octane

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  • Identifiers

    CAS number
    32162-27-9

    Molecular formula
    C10H16O

    SMILES
    C[C@]12[C@H]3C[C@H](C3(C)C)C[C@H]1O2

    Safety labels

    Flammable
    Flammable

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Herbal 70.24%
    Green 69.09%
    Fresh 65.35%
    Sweet 65.27%
    Camphoreous 62.37%
    Woody 62.17%
    Mint 60.21%
    Pine 59.73%
    Cooling 56.07%
    Terpenic 48.85%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    7.66 (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 est.
    44.1 ˚C

  • Synonyms

    • (+-)-alpha-Pinene oxide
    • EINECS 250-938-1
    • EC 250-938-1
    • EINECS 238-617-4
    • 32162-27-9
    • 3-Oxatricyclo(4.1.1.0(sup 2,4))octane, 2,7,7-trimethyl-, d-
    • NQFUSWIGRKFAHK-OORONAJNSA-N
    • AKOS032437793
    • (1alpha,2beta,4beta,6alpha)-2,2,7-Trimethyl-3-oxatricyclo(4.1.1.02,4)octane
    • (1S-(1alpha,2alpha,4alpha,6alpha))-2,2,7-Trimethyl-3-oxatricyclo(4.1.1.02,4)octane
    • NS00123844

  • Applications

    A rigid, terpenoid-like bicyclic ether, (1alpha,2beta,4beta,6alpha)-2,2,7-Trimethyl-3-oxatricyclo(4.1.1.02,4)octane (CAS 32162-27-9) is used mainly as a stereodefined intermediate and chiral building block in organic synthesis (selective functionalizations, ring-opening/rearrangements of strained ethers, and derivatization toward camphor/pinane scaffolds), as an analytical reference for GC–MS and essential-oil profiling, as a model substrate to probe kinetics and mechanisms under acidic, oxidative, or photochemical conditions, and it is occasionally evaluated in fragrance/flavor R&D as a camphoraceous–herbal–pine note or modulator subject to safety and regulatory review; its high-strain rigid framework also serves as a starting point for exploratory medicinal/agrochemical chemistry and laboratory-scale materials-property studies.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 284.7
    methanol 353.31
    isopropanol 214.17
    water 11.6
    ethyl acetate 256.51
    n-propanol 230.04
    acetone 257.84
    n-butanol 200.05
    acetonitrile 329.91
    DMF 214.57
    toluene 181.92
    isobutanol 157.17
    1,4-dioxane 475.23
    methyl acetate 249.52
    THF 602.15
    2-butanone 208.51
    n-pentanol 117.21
    sec-butanol 149.27
    n-hexane 36.98
    ethylene glycol 108.12
    NMP 177.75
    cyclohexane 73.5
    DMSO 155.37
    n-butyl acetate 184.68
    n-octanol 95.8
    chloroform 801.89
    n-propyl acetate 133.79
    acetic acid 242.2
    dichloromethane 611.49
    cyclohexanone 252.97
    propylene glycol 103.57
    isopropyl acetate 186.97
    DMAc 164.12
    2-ethoxyethanol 184.32
    isopentanol 153.6
    n-heptane 39.89
    ethyl formate 157.62
    1,2-dichloroethane 290.01
    n-hexanol 211.41
    2-methoxyethanol 315.17
    isobutyl acetate 108.87
    tetrachloromethane 184.36
    n-pentyl acetate 123.18
    transcutol 539.54
    n-heptanol 110.33
    ethylbenzene 85.44
    MIBK 151.17
    2-propoxyethanol 339.72
    tert-butanol 190.01
    MTBE 184.02
    2-butoxyethanol 187.97
    propionic acid 182.62
    o-xylene 112.01
    formic acid 167.32
    diethyl ether 263.42
    m-xylene 140.78
    p-xylene 114.26
    chlorobenzene 206.77
    dimethyl carbonate 130.1
    n-octane 16.83
    formamide 216.46
    cyclopentanone 308.01
    2-pentanone 192.39
    anisole 156.23
    cyclopentyl methyl ether 261.58
    gamma-butyrolactone 348.04
    1-methoxy-2-propanol 248.99
    pyridine 307.06
    3-pentanone 157.42
    furfural 286.85
    n-dodecane 15.29
    diethylene glycol 274.88
    diisopropyl ether 106.41
    tert-amyl alcohol 130.3
    acetylacetone 220.09
    n-hexadecane 17.36
    acetophenone 122.95
    methyl propionate 195.24
    isopentyl acetate 172.2
    trichloroethylene 500.42
    n-nonanol 88.79
    cyclohexanol 157.19
    benzyl alcohol 113.02
    2-ethylhexanol 110.91
    isooctanol 86.32
    dipropyl ether 150.1
    1,2-dichlorobenzene 190.65
    ethyl lactate 87.82
    propylene carbonate 199.49
    n-methylformamide 194.59
    2-pentanol 137.68
    n-pentane 49.72
    1-propoxy-2-propanol 225.5
    1-methoxy-2-propyl acetate 233.8
    2-(2-methoxypropoxy) propanol 156.75
    mesitylene 97.85
    ε-caprolactone 241.15
    p-cymene 74.14
    epichlorohydrin 381.56
    1,1,1-trichloroethane 334.56
    2-aminoethanol 156.5
    morpholine-4-carbaldehyde 271.13
    sulfolane 230.17
    2,2,4-trimethylpentane 25.14
    2-methyltetrahydrofuran 324.16
    n-hexyl acetate 169.73
    isooctane 27.77
    2-(2-butoxyethoxy)ethanol 214.73
    sec-butyl acetate 109.39
    tert-butyl acetate 178.23
    decalin 33.09
    glycerin 148.7
    diglyme 363.24
    acrylic acid 170.73
    isopropyl myristate 79.67
    n-butyric acid 201.81
    acetyl acetate 205.39
    di(2-ethylhexyl) phthalate 70.59
    ethyl propionate 133.43
    nitromethane 350.27
    1,2-diethoxyethane 228.23
    benzonitrile 163.82
    trioctyl phosphate 56.11
    1-bromopropane 208.15
    gamma-valerolactone 362.5
    n-decanol 67.98
    triethyl phosphate 78.82
    4-methyl-2-pentanol 103.42
    propionitrile 235.26
    vinylene carbonate 216.02
    1,1,2-trichlorotrifluoroethane 228.49
    DMS 160.47
    cumene 68.86
    2-octanol 68.54
    2-hexanone 123.01
    octyl acetate 91.4
    limonene 87.82
    1,2-dimethoxyethane 264.69
    ethyl orthosilicate 80.52
    tributyl phosphate 67.01
    diacetone alcohol 160.48
    N,N-dimethylaniline 99.84
    acrylonitrile 249.42
    aniline 186.48
    1,3-propanediol 201.35
    bromobenzene 219.04
    dibromomethane 403.72
    1,1,2,2-tetrachloroethane 371.02
    2-methyl-cyclohexyl acetate 117.97
    tetrabutyl urea 70.07
    diisobutyl methanol 81.26
    2-phenylethanol 160.2
    styrene 93.1
    dioctyl adipate 89.56
    dimethyl sulfate 123.92
    ethyl butyrate 139.38
    methyl lactate 122.52
    butyl lactate 102.95
    diethyl carbonate 107.06
    propanediol butyl ether 140.79
    triethyl orthoformate 120.54
    p-tert-butyltoluene 75.43
    methyl 4-tert-butylbenzoate 130.2
    morpholine 405.2
    tert-butylamine 153.9
    n-dodecanol 54.0
    dimethoxymethane 274.51
    ethylene carbonate 194.52
    cyrene 116.33
    2-ethoxyethyl acetate 184.39
    2-ethylhexyl acetate 139.63
    1,2,4-trichlorobenzene 199.48
    4-methylpyridine 237.46
    dibutyl ether 112.64
    2,6-dimethyl-4-heptanol 81.26
    DEF 152.1
    dimethyl isosorbide 236.28
    tetrachloroethylene 283.85
    eugenol 128.28
    triacetin 162.63
    span 80 125.15
    1,4-butanediol 83.33
    1,1-dichloroethane 336.61
    2-methyl-1-pentanol 94.72
    methyl formate 171.41
    2-methyl-1-butanol 133.96
    n-decane 24.59
    butyronitrile 217.26
    3,7-dimethyl-1-octanol 99.25
    1-chlorooctane 71.62
    1-chlorotetradecane 34.87
    n-nonane 22.72
    undecane 18.86
    tert-butylcyclohexane 30.74
    cyclooctane 33.89
    cyclopentanol 177.06
    tetrahydropyran 368.38
    tert-amyl methyl ether 130.65
    2,5,8-trioxanonane 241.83
    1-hexene 86.72
    2-isopropoxyethanol 135.66
    2,2,2-trifluoroethanol 139.08
    methyl butyrate 139.5

    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
Pinus pinaster (Portugal) 1 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%