3-Thujopsanone

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  • Identifiers

    CAS number
    25966-79-4

    Molecular formula
    C15H24O

    SMILES
    C[C@H]1[C@@H]2C[C@]23[C@@](CCCC3(C)C)(CC1=O)C

    Retention indicies (RI)

    • DB5: 1650.0

  • Odor profile

    Woody 89.26%
    Amber 63.07%
    Cedar 58.42%
    Dry 55.35%
    Musk 48.78%
    Vetiver 41.53%
    Tobacco 39.87%
    Earthy 38.51%
    Spicy 35.13%
    Animal 34.42%

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  • Properties

    XLogP3-AA
    4.2

    Molecular weight
    220.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    315°C

    Flash point est.
    110.3 ˚C

  • Synonyms

    • 3-Thujopsanone
    • (-)-Thujopsanone
    • 25966-79-4
    • EINECS 247-381-1
    • Cyclopropa[d]naphthalen-3(1H)-one, octahydro-2,4a,8,8-tetramethyl-, (1aS,2S,4aS,8aS)-
    • DTXSID70885321
    • Cyclopropa(d)naphthalen-3(1H)-one, octahydro-2,4a,8,8-tetramethyl-, (1aS,2S,4aS,8aS)-
    • DTXSID101027941
    • SCHEMBL20024360
    • DTXCID701024707
    • DTXCID701513508
    • Q67879579
    • (1AS-(1aalpha,2alpha,4abeta,8aR*))-octahydro-2,4a,8,8-tetramethylcyclopropa(d)naphthalen-3(1H)-one

  • Applications

    3-Thujopsanone (CAS 25966-79-4) is a relatively rare bicyclic terpenoid ketone that occurs at trace levels in certain conifer essential oils; in practice it is used mainly as a reference standard and a specialty odorant. Typical applications include: (1) a fragrance ingredient imparting dry cedar/pine-resin nuances that reinforce woody, resinous, herbal, and forest-air accords; (2) an analytical reference in GC-MS for identification, retention-index tracking, and terpenoid profiling of Cupressaceae oils to support batch quality control, provenance studies, and adulteration screening; (3) a bicyclic ketone scaffold for organic reactivity studies (selective reductions, Baeyer-Villiger to lactones, oxime/hydrazone formation, epimerization) and as a synthetic building block toward new terpenoid derivatives; (4) a test compound in in vitro bioactivity screens (antimicrobial, insect deterrent/repellent, antifungal) to clarify the contribution of minor constituents to the natural preservative performance of certain essential oils; (5) a model odorant in sensory/olfactometry research and smell machine-learning datasets for panel calibration or algorithm training. In practical use it is typically dosed at very low levels or employed as a marker; note its susceptibility to oxidation and volatility—store tightly closed, cool, protected from light, preferably under inert gas—and comply with safety and labeling requirements for terpenoid ketones.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 107.16
    methanol 123.5
    isopropanol 102.56
    water 2.21
    ethyl acetate 201.18
    n-propanol 102.08
    acetone 313.43
    n-butanol 91.58
    acetonitrile 263.28
    DMF 381.47
    toluene 262.27
    isobutanol 74.37
    1,4-dioxane 397.92
    methyl acetate 209.59
    THF 730.58
    2-butanone 216.94
    n-pentanol 46.9
    sec-butanol 62.57
    n-hexane 7.18
    ethylene glycol 39.65
    NMP 320.33
    cyclohexane 26.92
    DMSO 160.46
    n-butyl acetate 125.82
    n-octanol 40.94
    chloroform 628.92
    n-propyl acetate 104.41
    acetic acid 118.49
    dichloromethane 539.61
    cyclohexanone 374.17
    propylene glycol 41.65
    isopropyl acetate 159.26
    DMAc 225.67
    2-ethoxyethanol 89.8
    isopentanol 74.13
    n-heptane 10.29
    ethyl formate 127.48
    1,2-dichloroethane 281.04
    n-hexanol 79.77
    2-methoxyethanol 182.38
    isobutyl acetate 82.78
    tetrachloromethane 111.94
    n-pentyl acetate 93.3
    transcutol 186.46
    n-heptanol 51.52
    ethylbenzene 93.18
    MIBK 143.56
    2-propoxyethanol 188.76
    tert-butanol 106.45
    MTBE 110.09
    2-butoxyethanol 105.57
    propionic acid 107.5
    o-xylene 141.88
    formic acid 50.78
    diethyl ether 128.41
    m-xylene 178.78
    p-xylene 128.54
    chlorobenzene 282.93
    dimethyl carbonate 135.02
    n-octane 4.84
    formamide 107.77
    cyclopentanone 564.92
    2-pentanone 194.5
    anisole 185.66
    cyclopentyl methyl ether 228.38
    gamma-butyrolactone 560.57
    1-methoxy-2-propanol 168.79
    pyridine 413.65
    3-pentanone 150.97
    furfural 424.96
    n-dodecane 4.49
    diethylene glycol 137.89
    diisopropyl ether 52.39
    tert-amyl alcohol 62.25
    acetylacetone 303.67
    n-hexadecane 5.48
    acetophenone 169.14
    methyl propionate 173.71
    isopentyl acetate 129.37
    trichloroethylene 562.08
    n-nonanol 41.15
    cyclohexanol 100.44
    benzyl alcohol 119.69
    2-ethylhexanol 52.1
    isooctanol 43.2
    dipropyl ether 67.92
    1,2-dichlorobenzene 248.13
    ethyl lactate 58.98
    propylene carbonate 264.23
    n-methylformamide 194.68
    2-pentanol 59.54
    n-pentane 11.16
    1-propoxy-2-propanol 118.74
    1-methoxy-2-propyl acetate 178.76
    2-(2-methoxypropoxy) propanol 93.1
    mesitylene 103.38
    ε-caprolactone 274.91
    p-cymene 59.93
    epichlorohydrin 520.39
    1,1,1-trichloroethane 322.69
    2-aminoethanol 67.75
    morpholine-4-carbaldehyde 360.15
    sulfolane 408.38
    2,2,4-trimethylpentane 7.42
    2-methyltetrahydrofuran 303.78
    n-hexyl acetate 118.68
    isooctane 8.44
    2-(2-butoxyethoxy)ethanol 109.55
    sec-butyl acetate 83.24
    tert-butyl acetate 163.63
    decalin 15.34
    glycerin 65.52
    diglyme 240.53
    acrylic acid 111.19
    isopropyl myristate 53.21
    n-butyric acid 137.43
    acetyl acetate 196.42
    di(2-ethylhexyl) phthalate 60.63
    ethyl propionate 109.58
    nitromethane 326.03
    1,2-diethoxyethane 98.54
    benzonitrile 224.12
    trioctyl phosphate 42.14
    1-bromopropane 140.66
    gamma-valerolactone 545.38
    n-decanol 30.8
    triethyl phosphate 56.53
    4-methyl-2-pentanol 46.82
    propionitrile 196.53
    vinylene carbonate 292.14
    1,1,2-trichlorotrifluoroethane 228.28
    DMS 159.92
    cumene 58.89
    2-octanol 33.45
    2-hexanone 100.76
    octyl acetate 63.05
    limonene 68.72
    1,2-dimethoxyethane 186.59
    ethyl orthosilicate 54.63
    tributyl phosphate 46.01
    diacetone alcohol 144.8
    N,N-dimethylaniline 103.76
    acrylonitrile 266.69
    aniline 198.37
    1,3-propanediol 101.52
    bromobenzene 318.36
    dibromomethane 308.0
    1,1,2,2-tetrachloroethane 358.37
    2-methyl-cyclohexyl acetate 99.44
    tetrabutyl urea 60.18
    diisobutyl methanol 40.13
    2-phenylethanol 152.33
    styrene 112.24
    dioctyl adipate 71.87
    dimethyl sulfate 183.42
    ethyl butyrate 102.73
    methyl lactate 91.53
    butyl lactate 72.61
    diethyl carbonate 74.64
    propanediol butyl ether 71.19
    triethyl orthoformate 75.39
    p-tert-butyltoluene 62.09
    methyl 4-tert-butylbenzoate 140.73
    morpholine 332.5
    tert-butylamine 66.64
    n-dodecanol 23.48
    dimethoxymethane 279.32
    ethylene carbonate 235.15
    cyrene 115.56
    2-ethoxyethyl acetate 149.07
    2-ethylhexyl acetate 100.63
    1,2,4-trichlorobenzene 272.93
    4-methylpyridine 377.28
    dibutyl ether 45.9
    2,6-dimethyl-4-heptanol 40.13
    DEF 158.46
    dimethyl isosorbide 207.44
    tetrachloroethylene 250.07
    eugenol 126.12
    triacetin 135.23
    span 80 82.94
    1,4-butanediol 35.77
    1,1-dichloroethane 297.7
    2-methyl-1-pentanol 42.64
    methyl formate 178.23
    2-methyl-1-butanol 60.26
    n-decane 7.64
    butyronitrile 155.27
    3,7-dimethyl-1-octanol 44.92
    1-chlorooctane 34.92
    1-chlorotetradecane 15.46
    n-nonane 6.32
    undecane 5.75
    tert-butylcyclohexane 12.8
    cyclooctane 10.52
    cyclopentanol 137.05
    tetrahydropyran 283.78
    tert-amyl methyl ether 71.57
    2,5,8-trioxanonane 152.11
    1-hexene 28.55
    2-isopropoxyethanol 71.94
    2,2,2-trifluoroethanol 88.68
    methyl butyrate 125.13

    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
Cedarwood, Mulanje Widdringtonia whytei Rendle, fam. Cupressaceae 5.0%
Cedarwood Texas 1 Juniperus mexicana L., fam. Cupressaceae 15.5%
Cedarwood Virginia 2 8000-27-9 Juniperus virginiana L., fam. Cupressaceae 13.3%