2,6,6-Trimethyl-2-vinyltetrahydropyran

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  • Identifiers

    CAS number
    7392-19-0

    Molecular formula
    C10H18O

    SMILES
    CC1(CCCC(O1)(C)C=C)C

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1109.0

  • Odor profile

    Herbal 82.33%
    Citrus 70.17%
    Floral 69.94%
    Sweet 69.22%
    Fresh 68.79%
    Woody 67.28%
    Mint 62.29%
    Spicy 56.12%
    Camphoreous 55.49%
    Terpenic 51.54%

    Scent© AI

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    9.29 (weak base)

    Molecular weight
    154.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    163°C

    Flash point est.
    40.69 ˚C

    Solubility expt.

    • Insoluble in water; Soluble in fat
    • soluble (in ethanol)

  • Synonyms

    • 7392-19-0
    • LIMETOL
    • 2-ethenyl-2,6,6-trimethyloxane
    • 2,6,6-Trimethyl-2-vinyltetrahydropyran
    • Linaloyl oxide
    • 2,2,6-Trimethyl-6-vinyltetrahydropyran
    • Bois de rose oxide
    • 2H-Pyran, 2-ethenyltetrahydro-2,6,6-trimethyl-
    • 13837-56-4
    • 2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyran
    • GERANIC OXIDE
    • FEMA No. 3735
    • 2H-Pyran, tetrahydro-2,2,6-trimethyl-6-vinyl-
    • Tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran
    • 2-Ethenyltetrahydro-2,6,6-trimethyl-2H-pyran
    • Linalool 3,7-oxide
    • 2,6,6-Trimethyl-2-ethenyltetrahydropyran
    • 2,6,6-Trimethyl-2-ethenyltetrahydro-2H-pyran
    • EINECS 230-983-3
    • EINECS 237-550-8
    • 2H-Pyran,2-ethenyltetrahydro-2,6,6-trimethyl-
    • V3824Q785M
    • 2-VINYLTETRAHYDRO-2,6,6-TRIMETHYL-2H-PYRAN
    • 2,6,6-Trimethoxy-2-vinyltetrahydropyran
    • 2,2,6-Trimethyl-6-ethenyl-tetrahydropyran
    • DTXSID8051338
    • CHEBI:132848
    • 2,6,6-Trimethyl-2-vinyl-tetrahydropyrane
    • Dehydroxylinalool oxide A
    • 2,2,6-TRIMETHYL-6-VINYLTETRAHYDROPYRANE
    • (1)-Tetrahydro-2,6,6-trimethyl-2-vinyl-2H-pyran
    • 2,6,6-TRIMETHYL-2-VINYLTETRAHYDRO-2H-PYRAN
    • PYRAN, TETRAHYDRO-2,2,6-TRIMETHYL-6-VINYL-
    • 2,6,6-TRIMETHYL-6-VINYLTETRAHYDROPYRAN [FHFI]
    • (+/-)-2,6,6-TRIMETHYL-2-VINYLTETRAHYDROPYRAN
    • 2,6,6-TRIMETHYL-2-VINYLTETRAHYDROPYRAN, (+/-)-
    • Geranic_oxide
    • UNII-V3824Q785M
    • FEMA 3735
    • 2,2,6-Trimethyl-6-vinyl-tetrahydropyran
    • SCHEMBL583643
    • (+-)-tetrahydro-2,6,6-trimethyl-2-vinyl-2H-pyran
    • DTXCID3029940
    • HAA39219
    • AKOS006281378
    • 2-vinyl-2,6,6-trimethyl tetrahydropyran
    • DB-239415
    • NS00019922
    • NS00086244
    • 2,6,6-Trimethyl-2-ethenyltetrahydro-2-pyran
    • 2,6,6-TRIMETHYL-6-VINYLTETRAHYDROPYRAN
    • 2-Ethenyltetrahydro-2,6,6-trimethylpyran, 9CI
    • Q27291478
    • 13226-34-1
    • 237-550-8

  • Applications

    2,6,6-Trimethyl-2-vinyltetrahydropyran (CAS 7392-19-0) is an organic building block featuring a saturated tetrahydropyran ring and a reactive vinyl handle, making it useful as an intermediate to access terpenoid, lactone and fragrance-related derivatives via hydroboration–oxidation, epoxidation, ozonolysis, olefin metathesis or cross-coupling; it is also explored as a mono-/co-monomer for functional polymers through radical polymerization or thiol–ene chemistry to install bulky ether rings that tune Tg, hydrophobicity, barrier and solvent resistance, and enable acid-triggered ring opening in photoresponsive materials, coatings and UV-curable inks; additionally, it serves as a model substrate for studies of acid-catalyzed ring opening/rearrangement and for optimizing selective functionalization at the vinyl moiety.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 625.09
    methanol 711.9
    isopropanol 612.53
    water 4.22
    ethyl acetate 630.86
    n-propanol 673.01
    acetone 482.15
    n-butanol 767.8
    acetonitrile 388.26
    DMF 540.97
    toluene 629.54
    isobutanol 631.72
    1,4-dioxane 977.1
    methyl acetate 581.37
    THF 1276.0
    2-butanone 638.51
    n-pentanol 524.68
    sec-butanol 754.44
    n-hexane 626.57
    ethylene glycol 156.75
    NMP 741.33
    cyclohexane 522.34
    DMSO 388.95
    n-butyl acetate 615.81
    n-octanol 643.98
    chloroform 1544.25
    n-propyl acetate 337.48
    acetic acid 329.33
    dichloromethane 1100.62
    cyclohexanone 967.26
    propylene glycol 265.93
    isopropyl acetate 471.08
    DMAc 703.54
    2-ethoxyethanol 471.26
    isopentanol 727.79
    n-heptane 465.33
    ethyl formate 326.88
    1,2-dichloroethane 647.07
    n-hexanol 1284.28
    2-methoxyethanol 661.76
    isobutyl acetate 301.9
    tetrachloromethane 476.47
    n-pentyl acetate 481.28
    transcutol 1356.2
    n-heptanol 550.29
    ethylbenzene 351.05
    MIBK 449.25
    2-propoxyethanol 1064.28
    tert-butanol 840.97
    MTBE 1001.77
    2-butoxyethanol 541.06
    propionic acid 457.81
    o-xylene 475.6
    formic acid 126.08
    diethyl ether 1019.47
    m-xylene 514.88
    p-xylene 419.25
    chlorobenzene 546.76
    dimethyl carbonate 208.39
    n-octane 166.9
    formamide 103.73
    cyclopentanone 777.67
    2-pentanone 596.98
    anisole 425.83
    cyclopentyl methyl ether 1032.64
    gamma-butyrolactone 753.23
    1-methoxy-2-propanol 682.3
    pyridine 553.07
    3-pentanone 577.19
    furfural 571.42
    n-dodecane 119.86
    diethylene glycol 569.23
    diisopropyl ether 458.9
    tert-amyl alcohol 908.3
    acetylacetone 488.31
    n-hexadecane 132.14
    acetophenone 332.67
    methyl propionate 551.06
    isopentyl acetate 572.15
    trichloroethylene 967.53
    n-nonanol 524.29
    cyclohexanol 863.79
    benzyl alcohol 322.62
    2-ethylhexanol 766.57
    isooctanol 428.06
    dipropyl ether 708.56
    1,2-dichlorobenzene 467.89
    ethyl lactate 214.44
    propylene carbonate 495.18
    n-methylformamide 285.06
    2-pentanol 704.41
    n-pentane 519.62
    1-propoxy-2-propanol 823.54
    1-methoxy-2-propyl acetate 602.01
    2-(2-methoxypropoxy) propanol 476.35
    mesitylene 360.42
    ε-caprolactone 868.41
    p-cymene 311.07
    epichlorohydrin 799.55
    1,1,1-trichloroethane 903.58
    2-aminoethanol 297.85
    morpholine-4-carbaldehyde 754.97
    sulfolane 775.38
    2,2,4-trimethylpentane 256.85
    2-methyltetrahydrofuran 1233.33
    n-hexyl acetate 792.71
    isooctane 198.81
    2-(2-butoxyethoxy)ethanol 639.3
    sec-butyl acetate 315.87
    tert-butyl acetate 542.8
    decalin 276.44
    glycerin 326.74
    diglyme 874.73
    acrylic acid 305.33
    isopropyl myristate 308.52
    n-butyric acid 598.03
    acetyl acetate 362.22
    di(2-ethylhexyl) phthalate 242.96
    ethyl propionate 363.29
    nitromethane 397.8
    1,2-diethoxyethane 596.72
    benzonitrile 401.25
    trioctyl phosphate 212.67
    1-bromopropane 784.44
    gamma-valerolactone 886.13
    n-decanol 376.79
    triethyl phosphate 215.17
    4-methyl-2-pentanol 447.39
    propionitrile 514.58
    vinylene carbonate 428.55
    1,1,2-trichlorotrifluoroethane 550.03
    DMS 401.96
    cumene 294.96
    2-octanol 435.23
    2-hexanone 434.25
    octyl acetate 383.33
    limonene 510.2
    1,2-dimethoxyethane 723.33
    ethyl orthosilicate 237.24
    tributyl phosphate 251.22
    diacetone alcohol 535.75
    N,N-dimethylaniline 355.77
    acrylonitrile 408.22
    aniline 493.07
    1,3-propanediol 368.27
    bromobenzene 615.42
    dibromomethane 923.03
    1,1,2,2-tetrachloroethane 998.81
    2-methyl-cyclohexyl acetate 406.52
    tetrabutyl urea 287.1
    diisobutyl methanol 358.21
    2-phenylethanol 492.55
    styrene 352.34
    dioctyl adipate 314.76
    dimethyl sulfate 288.99
    ethyl butyrate 381.77
    methyl lactate 271.03
    butyl lactate 341.91
    diethyl carbonate 243.32
    propanediol butyl ether 512.67
    triethyl orthoformate 321.95
    p-tert-butyltoluene 317.71
    methyl 4-tert-butylbenzoate 420.47
    morpholine 983.19
    tert-butylamine 769.71
    n-dodecanol 285.32
    dimethoxymethane 549.57
    ethylene carbonate 402.01
    cyrene 318.29
    2-ethoxyethyl acetate 497.01
    2-ethylhexyl acetate 542.45
    1,2,4-trichlorobenzene 531.0
    4-methylpyridine 738.14
    dibutyl ether 629.89
    2,6-dimethyl-4-heptanol 358.21
    DEF 635.38
    dimethyl isosorbide 667.76
    tetrachloroethylene 684.02
    eugenol 339.17
    triacetin 492.09
    span 80 472.34
    1,4-butanediol 198.68
    1,1-dichloroethane 866.1
    2-methyl-1-pentanol 547.39
    methyl formate 229.0
    2-methyl-1-butanol 788.27
    n-decane 208.1
    butyronitrile 544.55
    3,7-dimethyl-1-octanol 596.15
    1-chlorooctane 506.53
    1-chlorotetradecane 206.81
    n-nonane 235.33
    undecane 151.92
    tert-butylcyclohexane 310.16
    cyclooctane 284.35
    cyclopentanol 666.24
    tetrahydropyran 1197.19
    tert-amyl methyl ether 900.13
    2,5,8-trioxanonane 616.64
    1-hexene 803.49
    2-isopropoxyethanol 419.03
    2,2,2-trifluoroethanol 151.79
    methyl butyrate 409.08

    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
Pistacia lentiscus (Spain) 1a leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.02%
Geranium (China, Yunnan) 6 8000-46-2 Pelargonium graveolens L'Herit. ex Aiton, fam. Geraniaceae 0.34%
Bitter orange leaf (Petitgrain) (Spain) 2 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.01%
Lime (Mexican, West Indian, Key) 5 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.22%
Lime (Mexican, West Indian, Key) (Cuba) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.5%
Lime (Persian) (Cuba) 90063-52-8 Citrus latifolia Tanaka, fam. Rutaceae 0.6%