2,6,6-Trimethyl-2-cyclohexen-1-one

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  • Identifiers

    CAS number
    20013-73-4

    Molecular formula
    C9H14O

    SMILES
    CC1=CCCC(C1=O)(C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1376.0

  • Odor profile

    Herbal 67.96%
    Mint 67.91%
    Camphoreous 61.92%
    Tobacco 51.77%
    Sweet 43.01%
    Citrus 39.68%
    Woody 36.41%
    Ketonic 34.86%
    Musty 32.65%
    Cooling 32.65%

    Scent© AI

  • Properties

    XLogP3-AA
    2.2

    Molecular weight
    138.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    187°C

    Flash point est.
    61.72 ˚C

  • Synonyms

    • 2,6,6-Trimethyl-2-cyclohexen-1-one
    • 2,6,6-Trimethylcyclohex-2-en-1-one
    • 20013-73-4
    • 2,6,6-trimethyl-2-cyclohexenone
    • 2-Cyclohexen-1-one, 2,6,6-trimethyl-
    • EINECS 243-465-7
    • UNII-077U78EJL5
    • 077U78EJL5
    • DTXSID10173830
    • 2,2,6-TRIMETHYLCYCLOHEX-5-ENONE
    • SCHEMBL2996151
    • DTXCID3096321
    • 2,6,6- Trimethyl-2-cyclohexenon
    • 2,6,6-trimethyl-cyclohex-2-enone
    • BCP25842
    • AKOS040767336
    • 2,6,6-trimethyl-cyclohex-2-en-1-one
    • DB-239557
    • NS00021814
    • Q27236270
    • 2,6,6-Trimethyl-1-Cyclohex-2-Enone; 2-Cyclohexen-1-one, 2,6,6-trimethyl-
    • 2,6,6-Trimethyl-2-cyclohexen-1-one; 2-Cyclohexen-1-one, 2,6,6-trimethyl-; 2,6,6-Trimethyl-2-cyclohexen-1-one; 2,2,6-Trimethylcyclohex-5-enone; 2,6,6-Trimethyl-2-cyclohexenone
    • 243-465-7

  • Applications

    2,6,6-Trimethyl-2-cyclohexen-1-one (CAS 20013-73-4) is a reactive cyclic enone used mainly as an intermediate in fragrance synthesis (ionones, damascones and violet-like derivatives), in APIs, and in carotenoid/retinoid pathways; it serves as a prototypical Michael acceptor in Michael addition, aldol, Robinson annulation, and Diels-Alder reactions to build terpenoid/polycyclic frameworks; it is also explored as a precursor in agrochemicals and materials additives (UV absorbers, photoinitiator motifs, resin modifiers) and as a model substrate in mechanistic studies and asymmetric catalysis development.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 765.74
    methanol 1157.25
    isopropanol 531.13
    water 7.74
    ethyl acetate 653.77
    n-propanol 581.54
    acetone 580.99
    n-butanol 599.99
    acetonitrile 782.79
    DMF 612.21
    toluene 466.41
    isobutanol 456.55
    1,4-dioxane 1074.84
    methyl acetate 559.37
    THF 1162.17
    2-butanone 549.09
    n-pentanol 400.67
    sec-butanol 430.69
    n-hexane 185.78
    ethylene glycol 133.95
    NMP 566.78
    cyclohexane 182.02
    DMSO 363.39
    n-butyl acetate 640.7
    n-octanol 331.69
    chloroform 1933.96
    n-propyl acetate 388.39
    acetic acid 616.92
    dichloromethane 1513.47
    cyclohexanone 775.85
    propylene glycol 136.93
    isopropyl acetate 438.21
    DMAc 412.58
    2-ethoxyethanol 505.48
    isopentanol 546.1
    n-heptane 121.27
    ethyl formate 460.02
    1,2-dichloroethane 832.84
    n-hexanol 625.98
    2-methoxyethanol 731.23
    isobutyl acetate 279.01
    tetrachloromethane 528.07
    n-pentyl acetate 420.93
    transcutol 1642.04
    n-heptanol 351.98
    ethylbenzene 289.68
    MIBK 412.78
    2-propoxyethanol 761.25
    tert-butanol 618.5
    MTBE 615.49
    2-butoxyethanol 507.97
    propionic acid 429.98
    o-xylene 318.08
    formic acid 341.07
    diethyl ether 782.93
    m-xylene 386.5
    p-xylene 364.85
    chlorobenzene 599.27
    dimethyl carbonate 202.12
    n-octane 54.3
    formamide 384.94
    cyclopentanone 775.62
    2-pentanone 545.09
    anisole 485.16
    cyclopentyl methyl ether 603.89
    gamma-butyrolactone 867.4
    1-methoxy-2-propanol 505.78
    pyridine 739.17
    3-pentanone 413.51
    furfural 812.35
    n-dodecane 37.38
    diethylene glycol 458.08
    diisopropyl ether 327.4
    tert-amyl alcohol 519.31
    acetylacetone 478.76
    n-hexadecane 42.67
    acetophenone 394.41
    methyl propionate 414.73
    isopentyl acetate 558.63
    trichloroethylene 1461.51
    n-nonanol 280.01
    cyclohexanol 453.06
    benzyl alcohol 336.82
    2-ethylhexanol 367.94
    isooctanol 281.11
    dipropyl ether 422.55
    1,2-dichlorobenzene 574.9
    ethyl lactate 170.78
    propylene carbonate 523.05
    n-methylformamide 460.84
    2-pentanol 409.83
    n-pentane 158.99
    1-propoxy-2-propanol 523.68
    1-methoxy-2-propyl acetate 488.24
    2-(2-methoxypropoxy) propanol 380.59
    mesitylene 270.22
    ε-caprolactone 654.83
    p-cymene 220.81
    epichlorohydrin 1019.76
    1,1,1-trichloroethane 1045.04
    2-aminoethanol 305.6
    morpholine-4-carbaldehyde 720.59
    sulfolane 683.52
    2,2,4-trimethylpentane 91.4
    2-methyltetrahydrofuran 789.77
    n-hexyl acetate 584.06
    isooctane 95.51
    2-(2-butoxyethoxy)ethanol 557.16
    sec-butyl acetate 294.62
    tert-butyl acetate 485.09
    decalin 117.8
    glycerin 198.95
    diglyme 906.41
    acrylic acid 372.08
    isopropyl myristate 198.22
    n-butyric acid 640.02
    acetyl acetate 391.0
    di(2-ethylhexyl) phthalate 183.69
    ethyl propionate 342.67
    nitromethane 812.08
    1,2-diethoxyethane 707.29
    benzonitrile 573.32
    trioctyl phosphate 133.87
    1-bromopropane 606.95
    gamma-valerolactone 943.61
    n-decanol 191.73
    triethyl phosphate 177.13
    4-methyl-2-pentanol 295.76
    propionitrile 625.39
    vinylene carbonate 527.03
    1,1,2-trichlorotrifluoroethane 563.71
    DMS 359.47
    cumene 229.97
    2-octanol 241.29
    2-hexanone 417.36
    octyl acetate 245.19
    limonene 267.2
    1,2-dimethoxyethane 750.24
    ethyl orthosilicate 197.23
    tributyl phosphate 176.03
    diacetone alcohol 427.52
    N,N-dimethylaniline 330.13
    acrylonitrile 622.34
    aniline 434.86
    1,3-propanediol 436.92
    bromobenzene 632.0
    dibromomethane 1052.42
    1,1,2,2-tetrachloroethane 1100.84
    2-methyl-cyclohexyl acetate 309.17
    tetrabutyl urea 186.8
    diisobutyl methanol 236.79
    2-phenylethanol 424.65
    styrene 331.43
    dioctyl adipate 232.85
    dimethyl sulfate 250.19
    ethyl butyrate 388.56
    methyl lactate 185.07
    butyl lactate 271.57
    diethyl carbonate 264.05
    propanediol butyl ether 369.67
    triethyl orthoformate 281.54
    p-tert-butyltoluene 222.1
    methyl 4-tert-butylbenzoate 357.84
    morpholine 1010.04
    tert-butylamine 506.46
    n-dodecanol 137.9
    dimethoxymethane 528.68
    ethylene carbonate 451.46
    cyrene 277.59
    2-ethoxyethyl acetate 495.48
    2-ethylhexyl acetate 450.85
    1,2,4-trichlorobenzene 579.54
    4-methylpyridine 794.39
    dibutyl ether 380.13
    2,6-dimethyl-4-heptanol 236.79
    DEF 506.8
    dimethyl isosorbide 553.06
    tetrachloroethylene 904.56
    eugenol 349.92
    triacetin 360.46
    span 80 325.16
    1,4-butanediol 190.74
    1,1-dichloroethane 969.12
    2-methyl-1-pentanol 398.66
    methyl formate 380.01
    2-methyl-1-butanol 474.8
    n-decane 70.06
    butyronitrile 716.96
    3,7-dimethyl-1-octanol 307.41
    1-chlorooctane 234.86
    1-chlorotetradecane 88.35
    n-nonane 70.51
    undecane 49.18
    tert-butylcyclohexane 126.76
    cyclooctane 83.19
    cyclopentanol 412.3
    tetrahydropyran 888.19
    tert-amyl methyl ether 449.09
    2,5,8-trioxanonane 558.13
    1-hexene 385.35
    2-isopropoxyethanol 377.83
    2,2,2-trifluoroethanol 257.87
    methyl butyrate 410.23

    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
Cistus (Spain) 2 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 0.3%
Artemisia judaica (Israel) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 4.8%