2H-3,9a-Methano-1-benzoxepin, octahydro-2,2,5a,9-tetramethyl-

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  • Identifiers

    CAS number
    5956-09-2

    Molecular formula
    C15H26O

    SMILES
    C[C@@H]1CCC[C@@]2([C@]13C[C@@H](CC2)C(O3)(C)C)C

    Retention indicies (RI)

    • Carbowax: 1698.0

  • Odor profile

    Green 66.95%
    Woody 66.53%
    Herbal 51.41%
    Fresh 48.88%
    Earthy 48.36%
    Spicy 44.02%
    Camphoreous 43.47%
    Mint 40.33%
    Pine 39.93%
    Dry 37.73%

    Scent© AI

  • Properties

    XLogP3-AA
    3.9

    Molecular weight
    222.37 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    277°C

    Flash point est.
    135.82 ˚C

  • Synonyms

    • Dihydro-beta-agarofuran
    • Deoxybaimuxinol
    • Dihydroagarofuran
    • trans-Dihydroagarofuran
    • beta-Agarofuran, dihydro-
    • 5956-09-2
    • 2H-3,9a-Methano-1-benzoxepin, octahydro-2,2,5a,9-tetramethyl-
    • Octahydro-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin
    • (1S,2R,6S,9R)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecane
    • (3R,5aS,9R,9aS)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepine
    • SCHEMBL2400604
    • CHEBI:71547
    • Q27139701

  • Applications

    2H-3,9a-Methano-1-benzoxepin, octahydro-2,2,5a,9-tetramethyl-, CAS 5956-09-2, is often explored and applied as a specialty fragrance ingredient because its hydrophobic oxygenated bicyclic scaffold affords relative thermo-oxidative robustness, enabling woody-amber-resinous facets in fine fragrances, personal care and air care, acting as a fixative to support longevity and diffusion; it also serves as a GC-MS reference/standard for method development (including chiral separations), as a substrate for derivatizing odorants via selective oxidation, hydrogenation or acetalization in terpenoid chemistry, and as a candidate for encapsulation (polymer microcapsules or cyclodextrin complexes) to achieve controlled scent release in detergents, fabric softeners and home fragrances; at a technical level it is useful for physicochemical profiling (logP, vapor pressure, partition coefficients), solvent-surfactant compatibility assessments in formulation, stability/compliance evaluations against IFRA and REACH with sensitization testing, and as a model compound for olfactory modeling, QSAR training and route optimization toward greener, bio-based manufacture.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 270.26
    methanol 270.05
    isopropanol 277.83
    water 4.35
    ethyl acetate 645.54
    n-propanol 330.72
    acetone 667.89
    n-butanol 330.14
    acetonitrile 453.96
    DMF 871.65
    toluene 951.43
    isobutanol 302.03
    1,4-dioxane 1139.78
    methyl acetate 657.72
    THF 1624.51
    2-butanone 700.91
    n-pentanol 240.38
    sec-butanol 275.86
    n-hexane 120.07
    ethylene glycol 94.96
    NMP 997.26
    cyclohexane 275.77
    DMSO 466.86
    n-butyl acetate 702.42
    n-octanol 325.23
    chloroform 2258.5
    n-propyl acetate 509.07
    acetic acid 261.26
    dichloromethane 1732.22
    cyclohexanone 1331.25
    propylene glycol 125.61
    isopropyl acetate 565.63
    DMAc 776.62
    2-ethoxyethanol 361.87
    isopentanol 315.66
    n-heptane 150.98
    ethyl formate 461.2
    1,2-dichloroethane 918.54
    n-hexanol 420.95
    2-methoxyethanol 502.3
    isobutyl acetate 482.67
    tetrachloromethane 574.87
    n-pentyl acetate 610.11
    transcutol 806.88
    n-heptanol 314.6
    ethylbenzene 548.06
    MIBK 502.95
    2-propoxyethanol 629.08
    tert-butanol 301.67
    MTBE 469.55
    2-butoxyethanol 468.81
    propionic acid 353.84
    o-xylene 633.22
    formic acid 82.27
    diethyl ether 495.46
    m-xylene 738.14
    p-xylene 711.85
    chlorobenzene 1021.63
    dimethyl carbonate 388.35
    n-octane 85.16
    formamide 151.05
    cyclopentanone 1457.12
    2-pentanone 594.74
    anisole 726.74
    cyclopentyl methyl ether 866.3
    gamma-butyrolactone 1426.28
    1-methoxy-2-propanol 429.31
    pyridine 1146.17
    3-pentanone 587.12
    furfural 1212.4
    n-dodecane 77.87
    diethylene glycol 380.25
    diisopropyl ether 294.27
    tert-amyl alcohol 278.28
    acetylacetone 815.22
    n-hexadecane 91.09
    acetophenone 684.24
    methyl propionate 590.98
    isopentyl acetate 742.79
    trichloroethylene 1792.52
    n-nonanol 291.44
    cyclohexanol 503.93
    benzyl alcohol 481.05
    2-ethylhexanol 340.7
    isooctanol 278.94
    dipropyl ether 457.31
    1,2-dichlorobenzene 1008.51
    ethyl lactate 287.91
    propylene carbonate 891.42
    n-methylformamide 412.9
    2-pentanol 254.16
    n-pentane 122.93
    1-propoxy-2-propanol 490.78
    1-methoxy-2-propyl acetate 731.09
    2-(2-methoxypropoxy) propanol 428.62
    mesitylene 538.1
    ε-caprolactone 1116.94
    p-cymene 416.15
    epichlorohydrin 1273.87
    1,1,1-trichloroethane 1120.66
    2-aminoethanol 170.32
    morpholine-4-carbaldehyde 1163.39
    sulfolane 1223.68
    2,2,4-trimethylpentane 90.15
    2-methyltetrahydrofuran 1027.3
    n-hexyl acetate 755.83
    isooctane 92.44
    2-(2-butoxyethoxy)ethanol 485.17
    sec-butyl acetate 443.19
    tert-butyl acetate 591.59
    decalin 182.52
    glycerin 178.58
    diglyme 972.84
    acrylic acid 326.88
    isopropyl myristate 377.49
    n-butyric acid 478.64
    acetyl acetate 584.79
    di(2-ethylhexyl) phthalate 313.35
    ethyl propionate 531.37
    nitromethane 618.46
    1,2-diethoxyethane 509.23
    benzonitrile 849.87
    trioctyl phosphate 263.74
    1-bromopropane 640.9
    gamma-valerolactone 1676.1
    n-decanol 222.37
    triethyl phosphate 343.9
    4-methyl-2-pentanol 222.84
    propionitrile 508.83
    vinylene carbonate 978.79
    1,1,2-trichlorotrifluoroethane 694.28
    DMS 762.93
    cumene 418.78
    2-octanol 263.35
    2-hexanone 510.16
    octyl acetate 429.74
    limonene 459.0
    1,2-dimethoxyethane 789.52
    ethyl orthosilicate 313.16
    tributyl phosphate 311.16
    diacetone alcohol 431.63
    N,N-dimethylaniline 517.12
    acrylonitrile 609.49
    aniline 601.25
    1,3-propanediol 254.23
    bromobenzene 1277.22
    dibromomethane 1201.22
    1,1,2,2-tetrachloroethane 1415.83
    2-methyl-cyclohexyl acetate 552.47
    tetrabutyl urea 366.98
    diisobutyl methanol 265.11
    2-phenylethanol 573.1
    styrene 618.4
    dioctyl adipate 452.13
    dimethyl sulfate 527.96
    ethyl butyrate 545.59
    methyl lactate 302.02
    butyl lactate 414.55
    diethyl carbonate 440.29
    propanediol butyl ether 359.95
    triethyl orthoformate 443.75
    p-tert-butyltoluene 409.35
    methyl 4-tert-butylbenzoate 618.03
    morpholine 975.64
    tert-butylamine 250.01
    n-dodecanol 181.36
    dimethoxymethane 719.48
    ethylene carbonate 837.17
    cyrene 427.84
    2-ethoxyethyl acetate 683.65
    2-ethylhexyl acetate 688.21
    1,2,4-trichlorobenzene 1049.46
    4-methylpyridine 1179.54
    dibutyl ether 404.43
    2,6-dimethyl-4-heptanol 265.11
    DEF 645.91
    dimethyl isosorbide 813.4
    tetrachloroethylene 999.97
    eugenol 534.69
    triacetin 687.55
    span 80 393.33
    1,4-butanediol 141.52
    1,1-dichloroethane 976.21
    2-methyl-1-pentanol 250.88
    methyl formate 413.74
    2-methyl-1-butanol 304.87
    n-decane 121.41
    butyronitrile 519.22
    3,7-dimethyl-1-octanol 320.09
    1-chlorooctane 333.34
    1-chlorotetradecane 163.81
    n-nonane 119.27
    undecane 93.87
    tert-butylcyclohexane 161.3
    cyclooctane 155.0
    cyclopentanol 523.18
    tetrahydropyran 1031.55
    tert-amyl methyl ether 392.99
    2,5,8-trioxanonane 657.22
    1-hexene 265.51
    2-isopropoxyethanol 316.13
    2,2,2-trifluoroethanol 192.17
    methyl butyrate 615.46

    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
Amyris 1 8015-65-4 Amyris balsamifera L., fam. Rutaceae 0.8%
Pelargonium reniforme Pelargonium reniforme Curt., fam. Geraniaceae 0.01%
Prostanthera staurophylla Prostanthera staurophylla F. Muell., fam. Lamiaceae (Labiatae) 0.5%
Vetiver (Haiti) 84238-29-9 Vetiveria zizanioides Stapf, fam. Poaceae (Gramineae) 0.5%
Celery seed (India) 5 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 0.1%
Eucalyptus resinifera (Cuba) Eucalyptus resinifera Smith, fam. Myrtaceae 0.3%
Corymbia maculata (Cuba) Corymbia maculata (Hook.) K.D. Hill & L.A.S. Johnson, fam. Myrtaceae 0.3%