6-Oxabicyclo(3.2.1)oct-3-ene, 4,7,7-trimethyl-

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  • Identifiers

    CAS number
    2437-97-0

    Molecular formula
    C10H16O

    SMILES
    CC1=CCC2CC1OC2(C)C

  • Odor profile

    Herbal 84.86%
    Mint 75.0%
    Green 68.04%
    Fresh 66.08%
    Camphoreous 64.92%
    Cooling 59.69%
    Sweet 59.32%
    Woody 58.32%
    Spicy 55.71%
    Terpenic 50.83%

    Scent© AI

  • Properties

    XLogP3-AA
    1.7

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    190°C

    Flash point est.
    55.27 ˚C

  • Synonyms

    • Pinol
    • 4,7,7-trimethyl-6-oxabicyclo[3.2.1]oct-3-ene
    • 2437-97-0
    • xi-Pinol
    • p-Menth-1-ene, 6,8-epoxy-
    • EINECS 219-446-4
    • NSC 407159
    • 6-Oxabicyclo[3.2.1]oct-3-ene, 4,7,7-trimethyl-
    • AI3-22990
    • DTXSID90871443
    • 4,7,7-Trimethyl-6-oxabicyclo(3.2.1)oct-3-ene
    • 6-Oxabicyclo(3.2.1)oct-3-ene, 4,7,7-trimethyl-
    • dl-4,7,7-Trimethyl-6-oxabicyclo(3.2.1)oct-3-ene
    • p-Menth-1-ene,8-epoxy-
    • SCHEMBL221186
    • 6,8-Epoxymenth-1-ene (Pinol)
    • DTXCID20819111
    • CHEBI:171932
    • NSC407159
    • p-Menth-1-ene, 6,8-epoxy-(8CI)
    • NSC-407159
    • NS00047646
    • 6-Oxabicyclo[3.2.1]oct-3-ene,7,7-trimethyl-
    • 4,7,7-trimethyl-6-oxabicyclo[3,2,1)oct-3-ene
    • 219-446-4

  • Applications

    6-Oxabicyclo(3.2.1)oct-3-ene, 4,7,7-trimethyl- (CAS 2437-97-0) is an energy-rich bicyclic monoterpenoid scaffold featuring an ether bridge and an endocyclic double bond, commonly employed as a synthetic intermediate and chiral building block; its rigid, low-polarity framework lends itself to selective transformations such as epoxidation, hydroboration, ozonolysis, allylic functionalization, and ene-type reactions, enabling access to derivative families explored in fragrance R&D (tuning camphoraceous/eucalyptus, woody, and herbal notes), in pharmaceutical and agrochemical lead discovery, and in materials chemistry for creating functional monomers and crosslinked networks; it is also used as an analytical reference and mechanistic model to probe stereochemical control, reaction selectivity, and terpene-like rearrangements, while practical deployment depends on enantiomeric form, purity, safety practices, and sector regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 696.37
    methanol 831.03
    isopropanol 654.16
    water 13.9
    ethyl acetate 827.96
    n-propanol 676.53
    acetone 833.43
    n-butanol 656.7
    acetonitrile 817.61
    DMF 880.08
    toluene 613.41
    isobutanol 586.53
    1,4-dioxane 1291.7
    methyl acetate 845.86
    THF 1319.94
    2-butanone 825.95
    n-pentanol 435.6
    sec-butanol 609.52
    n-hexane 168.34
    ethylene glycol 266.22
    NMP 582.38
    cyclohexane 196.76
    DMSO 547.46
    n-butyl acetate 491.71
    n-octanol 438.15
    chloroform 2667.91
    n-propyl acetate 414.74
    acetic acid 400.46
    dichloromethane 1957.18
    cyclohexanone 811.52
    propylene glycol 381.23
    isopropyl acetate 581.62
    DMAc 830.08
    2-ethoxyethanol 669.66
    isopentanol 577.07
    n-heptane 125.89
    ethyl formate 440.46
    1,2-dichloroethane 917.67
    n-hexanol 641.01
    2-methoxyethanol 960.39
    isobutyl acetate 328.36
    tetrachloromethane 626.23
    n-pentyl acetate 409.44
    transcutol 1596.49
    n-heptanol 388.45
    ethylbenzene 365.1
    MIBK 501.11
    2-propoxyethanol 993.78
    tert-butanol 693.93
    MTBE 708.44
    2-butoxyethanol 615.89
    propionic acid 496.67
    o-xylene 445.55
    formic acid 211.5
    diethyl ether 756.63
    m-xylene 481.37
    p-xylene 479.3
    chlorobenzene 681.14
    dimethyl carbonate 372.05
    n-octane 75.42
    formamide 314.57
    cyclopentanone 859.42
    2-pentanone 666.06
    anisole 696.66
    cyclopentyl methyl ether 724.97
    gamma-butyrolactone 852.67
    1-methoxy-2-propanol 847.76
    pyridine 815.69
    3-pentanone 593.22
    furfural 872.49
    n-dodecane 75.94
    diethylene glycol 669.2
    diisopropyl ether 325.53
    tert-amyl alcohol 551.5
    acetylacetone 752.58
    n-hexadecane 85.34
    acetophenone 531.09
    methyl propionate 641.85
    isopentyl acetate 477.19
    trichloroethylene 1606.14
    n-nonanol 377.83
    cyclohexanol 531.87
    benzyl alcohol 467.66
    2-ethylhexanol 367.85
    isooctanol 311.63
    dipropyl ether 435.96
    1,2-dichlorobenzene 648.93
    ethyl lactate 275.0
    propylene carbonate 540.63
    n-methylformamide 503.78
    2-pentanol 495.36
    n-pentane 173.21
    1-propoxy-2-propanol 686.27
    1-methoxy-2-propyl acetate 611.53
    2-(2-methoxypropoxy) propanol 519.94
    mesitylene 336.0
    ε-caprolactone 730.4
    p-cymene 256.15
    epichlorohydrin 1114.61
    1,1,1-trichloroethane 1191.54
    2-aminoethanol 464.06
    morpholine-4-carbaldehyde 894.18
    sulfolane 697.16
    2,2,4-trimethylpentane 105.22
    2-methyltetrahydrofuran 940.87
    n-hexyl acetate 643.96
    isooctane 97.06
    2-(2-butoxyethoxy)ethanol 674.91
    sec-butyl acetate 370.68
    tert-butyl acetate 567.34
    decalin 139.13
    glycerin 420.21
    diglyme 1143.29
    acrylic acid 421.3
    isopropyl myristate 289.99
    n-butyric acid 582.85
    acetyl acetate 565.64
    di(2-ethylhexyl) phthalate 230.34
    ethyl propionate 444.38
    nitromethane 802.58
    1,2-diethoxyethane 634.58
    benzonitrile 594.31
    trioctyl phosphate 177.93
    1-bromopropane 737.25
    gamma-valerolactone 1096.41
    n-decanol 279.63
    triethyl phosphate 221.94
    4-methyl-2-pentanol 362.86
    propionitrile 697.63
    vinylene carbonate 580.67
    1,1,2-trichlorotrifluoroethane 771.73
    DMS 522.28
    cumene 290.33
    2-octanol 298.8
    2-hexanone 454.3
    octyl acetate 341.79
    limonene 310.07
    1,2-dimethoxyethane 958.57
    ethyl orthosilicate 228.38
    tributyl phosphate 209.44
    diacetone alcohol 529.71
    N,N-dimethylaniline 445.39
    acrylonitrile 740.63
    aniline 626.51
    1,3-propanediol 524.46
    bromobenzene 765.82
    dibromomethane 1285.71
    1,1,2,2-tetrachloroethane 1360.04
    2-methyl-cyclohexyl acetate 330.29
    tetrabutyl urea 249.29
    diisobutyl methanol 252.75
    2-phenylethanol 501.13
    styrene 415.43
    dioctyl adipate 312.82
    dimethyl sulfate 441.81
    ethyl butyrate 384.53
    methyl lactate 375.65
    butyl lactate 315.02
    diethyl carbonate 290.31
    propanediol butyl ether 524.35
    triethyl orthoformate 305.57
    p-tert-butyltoluene 261.27
    methyl 4-tert-butylbenzoate 482.95
    morpholine 1140.86
    tert-butylamine 536.62
    n-dodecanol 216.76
    dimethoxymethane 829.57
    ethylene carbonate 504.99
    cyrene 357.4
    2-ethoxyethyl acetate 566.24
    2-ethylhexyl acetate 386.6
    1,2,4-trichlorobenzene 698.35
    4-methylpyridine 889.43
    dibutyl ether 439.23
    2,6-dimethyl-4-heptanol 252.75
    DEF 583.16
    dimethyl isosorbide 667.0
    tetrachloroethylene 950.68
    eugenol 466.94
    triacetin 566.04
    span 80 425.42
    1,4-butanediol 269.95
    1,1-dichloroethane 1239.15
    2-methyl-1-pentanol 398.54
    methyl formate 420.44
    2-methyl-1-butanol 549.91
    n-decane 115.79
    butyronitrile 660.09
    3,7-dimethyl-1-octanol 392.0
    1-chlorooctane 334.5
    1-chlorotetradecane 159.86
    n-nonane 111.75
    undecane 90.68
    tert-butylcyclohexane 145.83
    cyclooctane 108.3
    cyclopentanol 556.22
    tetrahydropyran 940.61
    tert-amyl methyl ether 532.56
    2,5,8-trioxanonane 756.12
    1-hexene 372.04
    2-isopropoxyethanol 511.14
    2,2,2-trifluoroethanol 273.84
    methyl butyrate 480.2

    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
Mace 2 8007-12-3 Myristica fragrans Houtt., fam. Myristicaceae 0.01%
Nutmeg (India) 2 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.01%
Pinus pinaster (Portugal) 1 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Rhus coriaria Rhus coriaria L., fam. Anarcadiaceae 0.01%
St. John's wort (India) 84082-80-4 Hypericum perforatum L., fam. Guttiferae (Hypericaceae) 0.01%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.05%
Carrot umbel (Poland) 8015-88-1 Daucus carota L. ssp. carota, fam. Apiaceae (Umbelliferae) 0.3%