2H-3,9a-Methanocyclopent(b)oxocin, octahydro-2,2,6,9-tetramethyl-, (3R,6S,6aR,9S,9aS)-

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  • Identifiers

    CAS number
    20149-50-2

    Molecular formula
    C15H26O

    SMILES
    C[C@H]1CC[C@@H]2C[C@]3([C@@H]1CC[C@@H]3C)OC2(C)C

  • Odor profile

    Herbal 62.57%
    Woody 58.86%
    Green 55.91%
    Spicy 53.96%
    Fresh 53.18%
    Mint 47.69%
    Earthy 43.9%
    Camphoreous 40.3%
    Cooling 37.6%
    Pine 37.47%

    Scent© AI

  • Properties

    XLogP3-AA
    4.0

    pKa est.
    7.48 (neutral)

    Molecular weight
    222.37 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    280°C

    Flash point est.
    118.04 ˚C

  • Synonyms

    • Guaiane oxide
    • Guaioxide
    • 20149-50-2
    • 2H-3,9a-Methanocyclopent[b]oxocin, octahydro-2,2,6,9-tetramethyl-, (3R,6S,6aR,9S,9aS)-
    • DTXSID20885119
    • 2H-3,9a-Methanocyclopent(b)oxocin, octahydro-2,2,6,9-tetramethyl-, (3R,6S,6aR,9S,9aS)-
    • GXMJXGUEPXEOGR-WHPHWUKISA-N
    • DTXCID001024518
    • Q67879908

  • Applications

    2H-3,9a-Methanocyclopent(b)oxocin, octahydro-2,2,6,9-tetramethyl-, (3R,6S,6aR,9S,9aS)-, CAS 20149-50-2, is a hydrophobic, rigid, chiral polycyclic ether typically explored/used in fragrance and personal-care applications as an odor modifier and substantivity aid due to good oxidative stability and persistence in soaps, detergents, candles, and fine fragrances; at trace levels it can be evaluated to fine-tune terpenic/resinous/coniferous facets or impart a dry-warm nuance in woody–amber accords; in foods and beverages it may be assessed only at very low levels as a flavor modifier supporting herbal/resin notes where permitted; additionally it serves as a stereochemically defined scaffold in asymmetric synthesis, an analytical reference/internal standard for GC/GC-MS in essential-oil/natural-product fingerprinting, and in controlled-release research (encapsulation, carriers) for aroma delivery; always confirm the safety dossier, use limits, and applicable local regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 468.69
    methanol 457.55
    isopropanol 498.58
    water 6.25
    ethyl acetate 1010.36
    n-propanol 583.42
    acetone 987.93
    n-butanol 571.1
    acetonitrile 675.19
    DMF 1179.07
    toluene 1419.31
    isobutanol 543.2
    1,4-dioxane 1929.77
    methyl acetate 1020.64
    THF 2669.24
    2-butanone 1062.74
    n-pentanol 412.32
    sec-butanol 504.83
    n-hexane 210.08
    ethylene glycol 162.46
    NMP 1510.07
    cyclohexane 536.86
    DMSO 751.54
    n-butyl acetate 1027.22
    n-octanol 520.14
    chloroform 3975.74
    n-propyl acetate 773.37
    acetic acid 468.41
    dichloromethane 2984.48
    cyclohexanone 2121.25
    propylene glycol 223.19
    isopropyl acetate 857.91
    DMAc 1027.73
    2-ethoxyethanol 601.27
    isopentanol 552.51
    n-heptane 255.25
    ethyl formate 723.66
    1,2-dichloroethane 1526.06
    n-hexanol 677.27
    2-methoxyethanol 828.99
    isobutyl acetate 723.62
    tetrachloromethane 915.48
    n-pentyl acetate 917.68
    transcutol 1203.82
    n-heptanol 483.48
    ethylbenzene 750.76
    MIBK 737.79
    2-propoxyethanol 966.03
    tert-butanol 491.19
    MTBE 739.33
    2-butoxyethanol 713.43
    propionic acid 617.33
    o-xylene 866.73
    formic acid 142.54
    diethyl ether 795.44
    m-xylene 974.77
    p-xylene 983.23
    chlorobenzene 1643.15
    dimethyl carbonate 545.16
    n-octane 139.32
    formamide 232.9
    cyclopentanone 2233.7
    2-pentanone 906.52
    anisole 1024.21
    cyclopentyl methyl ether 1362.2
    gamma-butyrolactone 2322.92
    1-methoxy-2-propanol 695.73
    pyridine 1880.8
    3-pentanone 854.96
    furfural 1908.88
    n-dodecane 122.64
    diethylene glycol 582.81
    diisopropyl ether 450.0
    tert-amyl alcohol 466.42
    acetylacetone 1151.73
    n-hexadecane 143.32
    acetophenone 957.81
    methyl propionate 886.7
    isopentyl acetate 1082.51
    trichloroethylene 2804.43
    n-nonanol 460.35
    cyclohexanol 901.98
    benzyl alcohol 750.33
    2-ethylhexanol 542.64
    isooctanol 433.66
    dipropyl ether 687.58
    1,2-dichlorobenzene 1520.62
    ethyl lactate 421.86
    propylene carbonate 1463.88
    n-methylformamide 600.07
    2-pentanol 445.11
    n-pentane 216.89
    1-propoxy-2-propanol 728.67
    1-methoxy-2-propyl acetate 1005.88
    2-(2-methoxypropoxy) propanol 623.0
    mesitylene 689.6
    ε-caprolactone 1841.88
    p-cymene 579.06
    epichlorohydrin 2052.99
    1,1,1-trichloroethane 1798.75
    2-aminoethanol 291.4
    morpholine-4-carbaldehyde 1686.83
    sulfolane 2055.26
    2,2,4-trimethylpentane 141.39
    2-methyltetrahydrofuran 1753.31
    n-hexyl acetate 1165.04
    isooctane 140.3
    2-(2-butoxyethoxy)ethanol 712.29
    sec-butyl acetate 650.47
    tert-butyl acetate 836.89
    decalin 287.2
    glycerin 305.27
    diglyme 1425.21
    acrylic acid 547.83
    isopropyl myristate 554.54
    n-butyric acid 803.46
    acetyl acetate 862.69
    di(2-ethylhexyl) phthalate 462.04
    ethyl propionate 760.05
    nitromethane 966.14
    1,2-diethoxyethane 775.32
    benzonitrile 1310.77
    trioctyl phosphate 387.69
    1-bromopropane 1061.71
    gamma-valerolactone 2617.32
    n-decanol 341.1
    triethyl phosphate 475.09
    4-methyl-2-pentanol 354.74
    propionitrile 795.49
    vinylene carbonate 1573.36
    1,1,2-trichlorotrifluoroethane 1129.77
    DMS 1074.49
    cumene 555.28
    2-octanol 407.48
    2-hexanone 751.05
    octyl acetate 644.44
    limonene 686.23
    1,2-dimethoxyethane 1185.04
    ethyl orthosilicate 429.34
    tributyl phosphate 442.08
    diacetone alcohol 627.7
    N,N-dimethylaniline 669.37
    acrylonitrile 910.24
    aniline 940.18
    1,3-propanediol 432.51
    bromobenzene 2003.73
    dibromomethane 2060.03
    1,1,2,2-tetrachloroethane 2278.97
    2-methyl-cyclohexyl acetate 810.22
    tetrabutyl urea 525.59
    diisobutyl methanol 384.62
    2-phenylethanol 876.92
    styrene 900.11
    dioctyl adipate 686.58
    dimethyl sulfate 745.34
    ethyl butyrate 788.42
    methyl lactate 451.74
    butyl lactate 599.07
    diethyl carbonate 611.54
    propanediol butyl ether 558.72
    triethyl orthoformate 637.33
    p-tert-butyltoluene 559.79
    methyl 4-tert-butylbenzoate 865.49
    morpholine 1615.44
    tert-butylamine 397.2
    n-dodecanol 272.54
    dimethoxymethane 1029.2
    ethylene carbonate 1356.12
    cyrene 636.98
    2-ethoxyethyl acetate 992.75
    2-ethylhexyl acetate 1000.81
    1,2,4-trichlorobenzene 1607.68
    4-methylpyridine 1850.08
    dibutyl ether 643.77
    2,6-dimethyl-4-heptanol 384.62
    DEF 934.26
    dimethyl isosorbide 1174.77
    tetrachloroethylene 1564.54
    eugenol 727.68
    triacetin 992.77
    span 80 600.68
    1,4-butanediol 237.9
    1,1-dichloroethane 1587.41
    2-methyl-1-pentanol 431.1
    methyl formate 618.04
    2-methyl-1-butanol 543.25
    n-decane 191.87
    butyronitrile 814.13
    3,7-dimethyl-1-octanol 489.59
    1-chlorooctane 528.23
    1-chlorotetradecane 251.01
    n-nonane 195.02
    undecane 146.97
    tert-butylcyclohexane 240.86
    cyclooctane 267.43
    cyclopentanol 938.22
    tetrahydropyran 1749.63
    tert-amyl methyl ether 596.71
    2,5,8-trioxanonane 940.11
    1-hexene 436.54
    2-isopropoxyethanol 502.38
    2,2,2-trifluoroethanol 314.9
    methyl butyrate 918.44

    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
Guaiacwood 1 8016-23-7 Bulnesia sarmienti Lorentz ex Griseb, fam. Zygophyllaceae 2.0%
Patchouli (Indonesia) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.0%
Patchouli (Indonesia) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.1%