2,2,6-Trimethylcyclohexane-1,4-dione

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  • Identifiers

    CAS number
    20547-99-3

    Molecular formula
    C9H14O2

    SMILES
    CC1CC(=O)CC(C1=O)(C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Sweet 49.89%
    Tobacco 48.84%
    Mint 46.72%
    Camphoreous 46.25%
    Caramellic 38.04%
    Herbal 37.64%
    Woody 37.35%
    Citrus 35.39%
    Burnt 34.65%
    Tea 33.27%

    Scent© AI

  • Properties

    XLogP3-AA
    0.9

    Molecular weight
    154.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    266°C

    Flash point est.
    85.59 ˚C

  • Synonyms

    • 20547-99-3
    • 2,2,6-trimethylcyclohexane-1,4-dione
    • 2,2,6-TRIMETHYL-1,4-CYCLOHEXANEDIONE
    • 1,4-Cyclohexanedione, 2,2,6-trimethyl-
    • 2,2,6-trimethyl-cyclohexane-1,4-dione
    • xi-2,2,6-Trimethyl-1,4-cyclohexanedione
    • 1125-20-8
    • DTXSID70942726
    • 2,6,6-Trimethyl-1,4-cyclohexanedione
    • SCHEMBL1720186
    • CHEBI:180432
    • DTXCID201371117
    • MFCD14708262
    • 3,5,5-Trimethyl-1,4-cyclohexadione
    • AKOS015842161
    • 2,6,6-Trimethyl-1,4-cyclohexa-dione
    • 3,5,5-Trimethyl-1,4-cyclohexanedione
    • AS-63676
    • Cyclohexan-1,4-dione, 2,2,6-trimethyl
    • DB-302047
    • CS-0498236
    • NS00010665
    • F11628
    • 990-180-5

  • Applications

    2,2,6-Trimethylcyclohexane-1,4-dione (CAS 20547-99-3) is a bulky 1,4-diketone used primarily as a key intermediate in fine and performance chemical synthesis; most notably, it sits on the isophorone → this 1,4-dione → 2,3,5-trimethylhydroquinone route that furnishes the essential precursor to alpha-tocopherol (vitamin E); beyond that, it serves as a versatile building block for Paal–Knorr cyclizations to sterically hindered furans/pyrroles/thiophenes, for transformations toward substituted hydroquinones/benzoquinones used as antioxidants and UV stabilizers, and for Michael/aldol couplings and selective reductions/hydrogenations in the preparation of pharmaceutical, agrochemical, and pigment intermediates; in research, it is frequently employed as a model substrate to probe aerobic oxidation catalysis, carbonyl reductions, and keto–enol equilibria, as well as a starting point for constructing bulky aromatic frameworks and functional organic materials.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 822.95
    methanol 1405.95
    isopropanol 559.83
    water 31.94
    ethyl acetate 648.12
    n-propanol 580.79
    acetone 813.66
    n-butanol 511.6
    acetonitrile 1074.82
    DMF 947.64
    toluene 390.54
    isobutanol 445.03
    1,4-dioxane 1056.24
    methyl acetate 636.7
    THF 1371.49
    2-butanone 592.71
    n-pentanol 307.5
    sec-butanol 439.22
    n-hexane 99.72
    ethylene glycol 215.49
    NMP 887.96
    cyclohexane 119.91
    DMSO 543.03
    n-butyl acetate 421.13
    n-octanol 217.67
    chloroform 1756.27
    n-propyl acetate 337.31
    acetic acid 1169.35
    dichloromethane 1440.59
    cyclohexanone 849.16
    propylene glycol 181.92
    isopropyl acetate 416.98
    DMAc 614.65
    2-ethoxyethanol 452.78
    isopentanol 414.46
    n-heptane 58.38
    ethyl formate 527.16
    1,2-dichloroethane 743.48
    n-hexanol 469.7
    2-methoxyethanol 846.21
    isobutyl acetate 219.06
    tetrachloromethane 378.06
    n-pentyl acetate 269.74
    transcutol 1111.77
    n-heptanol 202.4
    ethylbenzene 213.72
    MIBK 350.29
    2-propoxyethanol 673.27
    tert-butanol 609.47
    MTBE 471.29
    2-butoxyethanol 320.14
    propionic acid 610.88
    o-xylene 256.82
    formic acid 707.06
    diethyl ether 620.44
    m-xylene 321.83
    p-xylene 278.83
    chlorobenzene 486.19
    dimethyl carbonate 250.04
    n-octane 23.45
    formamide 641.79
    cyclopentanone 963.62
    2-pentanone 536.49
    anisole 380.93
    cyclopentyl methyl ether 660.72
    gamma-butyrolactone 1208.54
    1-methoxy-2-propanol 563.29
    pyridine 665.24
    3-pentanone 415.83
    furfural 958.33
    n-dodecane 18.32
    diethylene glycol 502.61
    diisopropyl ether 218.0
    tert-amyl alcohol 457.0
    acetylacetone 563.01
    n-hexadecane 21.1
    acetophenone 336.9
    methyl propionate 473.86
    isopentyl acetate 368.25
    trichloroethylene 1447.82
    n-nonanol 175.56
    cyclohexanol 487.96
    benzyl alcohol 292.58
    2-ethylhexanol 225.31
    isooctanol 155.67
    dipropyl ether 274.71
    1,2-dichlorobenzene 451.09
    ethyl lactate 162.04
    propylene carbonate 625.08
    n-methylformamide 720.07
    2-pentanol 347.2
    n-pentane 94.45
    1-propoxy-2-propanol 390.31
    1-methoxy-2-propyl acetate 403.58
    2-(2-methoxypropoxy) propanol 250.78
    mesitylene 197.65
    ε-caprolactone 725.22
    p-cymene 132.08
    epichlorohydrin 1119.58
    1,1,1-trichloroethane 908.17
    2-aminoethanol 356.65
    morpholine-4-carbaldehyde 871.94
    sulfolane 912.95
    2,2,4-trimethylpentane 46.0
    2-methyltetrahydrofuran 902.33
    n-hexyl acetate 426.43
    isooctane 38.51
    2-(2-butoxyethoxy)ethanol 355.71
    sec-butyl acetate 244.04
    tert-butyl acetate 434.7
    decalin 64.66
    glycerin 281.88
    diglyme 656.33
    acrylic acid 561.89
    isopropyl myristate 133.35
    n-butyric acid 713.21
    acetyl acetate 492.95
    di(2-ethylhexyl) phthalate 127.39
    ethyl propionate 303.14
    nitromethane 1485.86
    1,2-diethoxyethane 395.6
    benzonitrile 489.73
    trioctyl phosphate 98.95
    1-bromopropane 485.64
    gamma-valerolactone 1082.74
    n-decanol 117.06
    triethyl phosphate 139.26
    4-methyl-2-pentanol 203.31
    propionitrile 650.08
    vinylene carbonate 611.73
    1,1,2-trichlorotrifluoroethane 664.19
    DMS 339.73
    cumene 153.06
    2-octanol 145.92
    2-hexanone 330.51
    octyl acetate 166.26
    limonene 180.4
    1,2-dimethoxyethane 681.06
    ethyl orthosilicate 141.16
    tributyl phosphate 129.02
    diacetone alcohol 386.93
    N,N-dimethylaniline 256.79
    acrylonitrile 741.77
    aniline 409.09
    1,3-propanediol 480.91
    bromobenzene 466.57
    dibromomethane 935.45
    1,1,2,2-tetrachloroethane 1031.14
    2-methyl-cyclohexyl acetate 231.32
    tetrabutyl urea 148.08
    diisobutyl methanol 126.89
    2-phenylethanol 329.0
    styrene 230.04
    dioctyl adipate 168.02
    dimethyl sulfate 354.99
    ethyl butyrate 283.91
    methyl lactate 222.18
    butyl lactate 196.79
    diethyl carbonate 201.52
    propanediol butyl ether 268.72
    triethyl orthoformate 196.58
    p-tert-butyltoluene 135.61
    methyl 4-tert-butylbenzoate 276.54
    morpholine 1022.5
    tert-butylamine 384.11
    n-dodecanol 84.94
    dimethoxymethane 674.97
    ethylene carbonate 509.26
    cyrene 258.56
    2-ethoxyethyl acetate 353.05
    2-ethylhexyl acetate 282.18
    1,2,4-trichlorobenzene 493.23
    4-methylpyridine 732.71
    dibutyl ether 214.91
    2,6-dimethyl-4-heptanol 126.89
    DEF 522.79
    dimethyl isosorbide 447.62
    tetrachloroethylene 770.52
    eugenol 251.83
    triacetin 301.52
    span 80 218.76
    1,4-butanediol 195.35
    1,1-dichloroethane 894.14
    2-methyl-1-pentanol 275.19
    methyl formate 661.62
    2-methyl-1-butanol 394.39
    n-decane 34.29
    butyronitrile 625.26
    3,7-dimethyl-1-octanol 189.66
    1-chlorooctane 140.42
    1-chlorotetradecane 51.33
    n-nonane 33.78
    undecane 24.08
    tert-butylcyclohexane 61.11
    cyclooctane 46.77
    cyclopentanol 507.4
    tetrahydropyran 869.04
    tert-amyl methyl ether 353.22
    2,5,8-trioxanonane 393.89
    1-hexene 256.32
    2-isopropoxyethanol 311.32
    2,2,2-trifluoroethanol 484.29
    methyl butyrate 376.67

    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
Saffron 1 8022-19-3 Crocus sativus L., fam. Iridaceae 1.5%
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.49%
Artemisia judaica (Egypt) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 1.53%
Artemisia judaica (Egypt) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.61%
Saffron 2 8022-19-3 Crocus sativus L., fam. Iridaceae 1.82%
Nicotiana rustica flower Nicotiana rustica L, subgenus Rustica, var. brasilia, fam. Solanaceae 0.7%
Acacia confusa flower (China) Acacia confusa Merr., fam. Mimosaceae (Leguminosae) 0.85%
Tansy (Japan) 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 2.0%
Carob bean powder 2b roasted 9000-40-2 Ceratonia siliqua L., fam. Leguminoseae 0.01%