2,2,6-Trimethyl-1-oxaspiro(2.5)oct-5-ene

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  • Identifiers

    CAS number
    4584-23-0

    Molecular formula
    C10H16O

    SMILES
    CC1=CCC2(CC1)C(O2)(C)C

    Retention indicies (RI)

    • Carbowax: 1474.0

  • Odor profile

    Fragrance
    Herbal 69.66%
    Woody 68.47%
    Green 66.97%
    Fresh 56.32%
    Sweet 56.14%
    Mint 53.05%
    Spicy 51.28%
    Camphoreous 50.59%
    Citrus 50.12%
    Terpenic 45.55%

     

    Flavor
    Herbal 50.09%
    Woody 48.12%
    Green 44.08%
    Earthy 42.11%
    Camphor 36.51%
    Spicy 36.26%
    Mint 29.33%
    Pine 27.68%
    Wood 27.58%
    Minty 27.16%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    7.99 (neutral)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    179°C

    Flash point

    • 53.05 ˚C est.

  • Synonyms

    • Terpinolene oxide
    • 2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene
    • 4584-23-0
    • 4,8-Terpinolene epoxide
    • 1-Oxaspiro[2.5]oct-5-ene, 2,2,6-trimethyl-
    • 2,2,6-Trimethyl-1-oxaspiro(2.5)oct-5-ene
    • EINECS 224-968-0
    • DTXSID70884091
    • 1-Oxaspiro(2.5)oct-5-ene, 2,2,6-trimethyl-
    • Terpinolene monoxide
    • Terpinolen-4,8-epoxide
    • S7N6ZFD48V
    • SCHEMBL10348473
    • CHEBI:171945
    • DTXCID701023561
    • NS00048785
    • 2,2,6-trimethyl-1-oxa-spiro[2.5]oct-5-ene
    • 224-968-0

  • Applications

    2,2,6-Trimethyl-1-oxaspiro(2.5)oct-5-ene (CAS 4584-23-0) is a rigid oxygen-containing spirocyclic olefin used primarily as a specialty intermediate: a compact building block to introduce spirocyclic geometry, steric bulk, and hydrophobicity in organic synthesis; a platform for lead generation in medicinal and agrochemical research; a precursor whose alkene/ether functions enable selective derivatization (e.g., controlled ring opening, polarity tuning, or installation of new functional groups) to access libraries of analogs; and a structural unit that, when incorporated into polymers, coatings, adhesives, UV-curable or 3D-printable systems, can raise glass-transition temperature, hardness, and dimensional stability; its derivatives are also explored in fragrance chemistry as scaffolds for spiro-ethers/ketals to modulate odor character, volatility, and substantivity; additionally, it serves as a reference compound and mechanistic probe in method development (e.g., chromatographic handling of spiro motifs, kinetics of ether ring opening, or additions to the C=C bond); actual suitability depends on purity grade, scale, regulatory context, and the specific safety profile of the material.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 384.38
    methanol 383.59
    isopropanol 334.39
    water 3.09
    ethyl acetate 269.01
    n-propanol 302.86
    acetone 208.24
    n-butanol 285.73
    acetonitrile 304.93
    DMF 184.09
    toluene 224.6
    isobutanol 200.92
    1,4-dioxane 662.01
    methyl acetate 255.88
    THF 478.88
    2-butanone 235.62
    n-pentanol 186.83
    sec-butanol 255.37
    n-hexane 51.17
    ethylene glycol 93.02
    NMP 132.18
    cyclohexane 98.25
    DMSO 144.43
    n-butyl acetate 155.47
    n-octanol 143.28
    chloroform 736.74
    n-propyl acetate 119.71
    acetic acid 172.85
    dichloromethane 517.14
    cyclohexanone 211.06
    propylene glycol 138.86
    isopropyl acetate 161.57
    DMAc 234.43
    2-ethoxyethanol 272.16
    isopentanol 209.53
    n-heptane 49.83
    ethyl formate 139.77
    1,2-dichloroethane 206.12
    n-hexanol 241.4
    2-methoxyethanol 395.64
    isobutyl acetate 92.47
    tetrachloromethane 142.19
    n-pentyl acetate 111.49
    transcutol 714.49
    n-heptanol 131.51
    ethylbenzene 125.21
    MIBK 125.19
    2-propoxyethanol 369.73
    tert-butanol 302.69
    MTBE 255.99
    2-butoxyethanol 203.88
    propionic acid 162.6
    o-xylene 139.22
    formic acid 95.65
    diethyl ether 316.73
    m-xylene 145.45
    p-xylene 163.27
    chlorobenzene 174.1
    dimethyl carbonate 87.37
    n-octane 21.09
    formamide 159.14
    cyclopentanone 185.56
    2-pentanone 175.47
    anisole 236.12
    cyclopentyl methyl ether 202.1
    gamma-butyrolactone 183.42
    1-methoxy-2-propanol 323.84
    pyridine 372.49
    3-pentanone 153.69
    furfural 213.82
    n-dodecane 20.47
    diethylene glycol 263.46
    diisopropyl ether 104.42
    tert-amyl alcohol 216.35
    acetylacetone 169.85
    n-hexadecane 23.08
    acetophenone 165.07
    methyl propionate 191.15
    isopentyl acetate 149.2
    trichloroethylene 377.53
    n-nonanol 135.66
    cyclohexanol 199.29
    benzyl alcohol 175.76
    2-ethylhexanol 129.87
    isooctanol 93.48
    dipropyl ether 171.98
    1,2-dichlorobenzene 152.19
    ethyl lactate 76.49
    propylene carbonate 123.99
    n-methylformamide 150.27
    2-pentanol 193.67
    n-pentane 65.7
    1-propoxy-2-propanol 257.54
    1-methoxy-2-propyl acetate 207.47
    2-(2-methoxypropoxy) propanol 208.64
    mesitylene 89.43
    ε-caprolactone 203.97
    p-cymene 84.5
    epichlorohydrin 271.82
    1,1,1-trichloroethane 255.47
    2-aminoethanol 184.11
    morpholine-4-carbaldehyde 294.5
    sulfolane 131.13
    2,2,4-trimethylpentane 28.86
    2-methyltetrahydrofuran 327.54
    n-hexyl acetate 181.85
    isooctane 24.56
    2-(2-butoxyethoxy)ethanol 272.92
    sec-butyl acetate 104.1
    tert-butyl acetate 141.45
    decalin 45.21
    glycerin 138.28
    diglyme 423.04
    acrylic acid 126.11
    isopropyl myristate 84.58
    n-butyric acid 191.15
    acetyl acetate 165.03
    di(2-ethylhexyl) phthalate 85.06
    ethyl propionate 127.44
    nitromethane 227.28
    1,2-diethoxyethane 274.24
    benzonitrile 190.58
    trioctyl phosphate 56.24
    1-bromopropane 200.42
    gamma-valerolactone 291.68
    n-decanol 99.12
    triethyl phosphate 77.44
    4-methyl-2-pentanol 118.62
    propionitrile 263.34
    vinylene carbonate 145.16
    1,1,2-trichlorotrifluoroethane 219.83
    DMS 144.04
    cumene 86.72
    2-octanol 84.61
    2-hexanone 139.66
    octyl acetate 103.0
    limonene 104.68
    1,2-dimethoxyethane 372.4
    ethyl orthosilicate 79.49
    tributyl phosphate 65.32
    diacetone alcohol 152.56
    N,N-dimethylaniline 151.95
    acrylonitrile 252.89
    aniline 230.58
    1,3-propanediol 216.86
    bromobenzene 192.97
    dibromomethane 374.35
    1,1,2,2-tetrachloroethane 327.27
    2-methyl-cyclohexyl acetate 124.18
    tetrabutyl urea 78.26
    diisobutyl methanol 83.36
    2-phenylethanol 191.15
    styrene 144.1
    dioctyl adipate 102.92
    dimethyl sulfate 79.74
    ethyl butyrate 131.19
    methyl lactate 104.42
    butyl lactate 89.87
    diethyl carbonate 105.44
    propanediol butyl ether 183.63
    triethyl orthoformate 114.69
    p-tert-butyltoluene 83.75
    methyl 4-tert-butylbenzoate 131.14
    morpholine 637.54
    tert-butylamine 230.87
    n-dodecanol 75.51
    dimethoxymethane 246.88
    ethylene carbonate 128.25
    cyrene 122.63
    2-ethoxyethyl acetate 182.43
    2-ethylhexyl acetate 127.08
    1,2,4-trichlorobenzene 181.36
    4-methylpyridine 301.86
    dibutyl ether 134.02
    2,6-dimethyl-4-heptanol 83.36
    DEF 166.89
    dimethyl isosorbide 247.24
    tetrachloroethylene 214.47
    eugenol 132.96
    triacetin 169.27
    span 80 172.79
    1,4-butanediol 98.13
    1,1-dichloroethane 282.09
    2-methyl-1-pentanol 147.46
    methyl formate 92.61
    2-methyl-1-butanol 184.55
    n-decane 33.29
    butyronitrile 245.79
    3,7-dimethyl-1-octanol 128.09
    1-chlorooctane 86.98
    1-chlorotetradecane 41.6
    n-nonane 30.53
    undecane 25.47
    tert-butylcyclohexane 39.65
    cyclooctane 39.09
    cyclopentanol 175.28
    tetrahydropyran 476.79
    tert-amyl methyl ether 178.85
    2,5,8-trioxanonane 311.89
    1-hexene 121.62
    2-isopropoxyethanol 192.89
    2,2,2-trifluoroethanol 73.35
    methyl butyrate 131.81

    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
Swangi (Citrus hystrix) leaf (Thailand) 2b Citrus hystrix DC (Swangi), fam. Rutaceae 0.01%
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Rosemary (Japan) 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.03%
Seafennel (Turkey) 2 89997-98-8 Crithmum maritimum L., fam. Apiaceae (Umbelliferae) 0.01%