2,2,5-Trimethyl-4-cyclohepten-1-one

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  • Identifiers

    CAS number
    19822-67-4

    Molecular formula
    C10H16O

    SMILES
    CC1=CCC(C(=O)CC1)(C)C

    Retention indicies (RI)

    • DB5: 1155.0

  • Odor profile

    Herbal 71.95%
    Mint 70.0%
    Camphoreous 57.24%
    Tobacco 44.81%
    Citrus 43.4%
    Ketonic 39.63%
    Fresh 37.06%
    Cooling 35.03%
    Woody 34.72%
    Spicy 33.06%

    Scent© AI

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    8.9 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    220°C

    Flash point est.
    76.3 ˚C

  • Synonyms

    • Karahanaenone
    • 2,2,5-Trimethyl-4-cyclohepten-1-one
    • 19822-67-4
    • 2,2,5-trimethylcyclohept-4-en-1-one
    • EINECS 243-351-7
    • SCHEMBL7632538
    • DTXSID20173543
    • 2,2,5-trimethyl-cyclohept-4-en-1-one
    • NS00026449

  • Applications

    2,2,5-Trimethyl-4-cyclohepten-1-one (CAS 19822-67-4) is a versatile seven-membered enone used primarily as a synthetic building block to access bicyclic/terpenoid-like frameworks and functionalized ketone derivatives; in pharmaceutical and agrochemical discovery it serves as an intermediate enabling Michael (1,4) additions, Diels-Alder reactions, and redox manipulations for rapid library generation; in fragrance research, the compound and its saturated/oxygenated derivatives are explored as precursors for tuning woody/resinous/amber facets and improving odor longevity in bases; in analytical chemistry it can act as a reference standard and aid GC/LC-MS method development on cyclic enones, as well as mechanistic studies (Michael kinetics, epoxidation, photochemistry); additionally, its conjugated carbonyl makes it useful in reactive materials (thiol-/aza-Michael crosslinkable networks and coatings) and as a teaching model to illustrate 1,4 vs 1,2 addition.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 986.68
    methanol 962.62
    isopropanol 1062.34
    water 6.3
    ethyl acetate 1152.64
    n-propanol 1000.45
    acetone 1130.71
    n-butanol 831.17
    acetonitrile 1082.01
    DMF 1586.51
    toluene 659.08
    isobutanol 828.24
    1,4-dioxane 1548.19
    methyl acetate 1248.36
    THF 1358.86
    2-butanone 1253.54
    n-pentanol 553.32
    sec-butanol 981.5
    n-hexane 172.57
    ethylene glycol 230.81
    NMP 809.19
    cyclohexane 167.36
    DMSO 698.7
    n-butyl acetate 692.58
    n-octanol 488.7
    chloroform 2751.5
    n-propyl acetate 574.11
    acetic acid 515.06
    dichloromethane 1948.39
    cyclohexanone 1126.79
    propylene glycol 407.92
    isopropyl acetate 714.2
    DMAc 1223.35
    2-ethoxyethanol 746.46
    isopentanol 750.63
    n-heptane 106.4
    ethyl formate 628.87
    1,2-dichloroethane 1115.03
    n-hexanol 763.64
    2-methoxyethanol 1086.32
    isobutyl acetate 443.43
    tetrachloromethane 612.08
    n-pentyl acetate 512.78
    transcutol 1766.79
    n-heptanol 483.31
    ethylbenzene 458.84
    MIBK 635.91
    2-propoxyethanol 1068.7
    tert-butanol 1116.29
    MTBE 1049.18
    2-butoxyethanol 737.48
    propionic acid 711.77
    o-xylene 474.26
    formic acid 214.35
    diethyl ether 892.52
    m-xylene 497.4
    p-xylene 626.75
    chlorobenzene 780.35
    dimethyl carbonate 387.08
    n-octane 67.86
    formamide 354.96
    cyclopentanone 1172.43
    2-pentanone 896.42
    anisole 871.02
    cyclopentyl methyl ether 738.02
    gamma-butyrolactone 1141.77
    1-methoxy-2-propanol 1000.33
    pyridine 1137.87
    3-pentanone 742.49
    furfural 1175.75
    n-dodecane 58.08
    diethylene glycol 634.69
    diisopropyl ether 345.27
    tert-amyl alcohol 937.77
    acetylacetone 938.5
    n-hexadecane 66.22
    acetophenone 657.58
    methyl propionate 799.1
    isopentyl acetate 647.69
    trichloroethylene 2154.45
    n-nonanol 419.19
    cyclohexanol 633.84
    benzyl alcohol 556.46
    2-ethylhexanol 469.96
    isooctanol 403.52
    dipropyl ether 449.05
    1,2-dichlorobenzene 736.88
    ethyl lactate 320.01
    propylene carbonate 756.95
    n-methylformamide 731.98
    2-pentanol 683.58
    n-pentane 143.9
    1-propoxy-2-propanol 762.75
    1-methoxy-2-propyl acetate 670.25
    2-(2-methoxypropoxy) propanol 563.07
    mesitylene 345.99
    ε-caprolactone 955.1
    p-cymene 270.4
    epichlorohydrin 1348.23
    1,1,1-trichloroethane 1582.97
    2-aminoethanol 519.8
    morpholine-4-carbaldehyde 1210.81
    sulfolane 951.02
    2,2,4-trimethylpentane 99.05
    2-methyltetrahydrofuran 1083.58
    n-hexyl acetate 767.86
    isooctane 93.75
    2-(2-butoxyethoxy)ethanol 773.34
    sec-butyl acetate 493.46
    tert-butyl acetate 731.68
    decalin 139.28
    glycerin 417.46
    diglyme 1292.0
    acrylic acid 556.21
    isopropyl myristate 305.57
    n-butyric acid 843.1
    acetyl acetate 615.84
    di(2-ethylhexyl) phthalate 250.0
    ethyl propionate 564.29
    nitromethane 1078.41
    1,2-diethoxyethane 743.21
    benzonitrile 761.43
    trioctyl phosphate 195.55
    1-bromopropane 852.63
    gamma-valerolactone 1472.79
    n-decanol 301.56
    triethyl phosphate 242.13
    4-methyl-2-pentanol 446.89
    propionitrile 998.81
    vinylene carbonate 773.95
    1,1,2-trichlorotrifluoroethane 924.82
    DMS 571.32
    cumene 353.14
    2-octanol 370.42
    2-hexanone 656.12
    octyl acetate 374.77
    limonene 341.41
    1,2-dimethoxyethane 1173.53
    ethyl orthosilicate 249.03
    tributyl phosphate 224.51
    diacetone alcohol 734.97
    N,N-dimethylaniline 545.88
    acrylonitrile 1095.75
    aniline 664.36
    1,3-propanediol 634.09
    bromobenzene 844.96
    dibromomethane 1322.62
    1,1,2,2-tetrachloroethane 1723.07
    2-methyl-cyclohexyl acetate 394.47
    tetrabutyl urea 268.31
    diisobutyl methanol 288.93
    2-phenylethanol 596.7
    styrene 537.92
    dioctyl adipate 346.44
    dimethyl sulfate 507.82
    ethyl butyrate 505.87
    methyl lactate 418.47
    butyl lactate 386.29
    diethyl carbonate 349.14
    propanediol butyl ether 631.9
    triethyl orthoformate 353.25
    p-tert-butyltoluene 283.94
    methyl 4-tert-butylbenzoate 570.98
    morpholine 1430.45
    tert-butylamine 796.82
    n-dodecanol 228.25
    dimethoxymethane 900.15
    ethylene carbonate 619.23
    cyrene 433.57
    2-ethoxyethyl acetate 660.13
    2-ethylhexyl acetate 493.69
    1,2,4-trichlorobenzene 789.38
    4-methylpyridine 1263.31
    dibutyl ether 478.55
    2,6-dimethyl-4-heptanol 288.93
    DEF 895.75
    dimethyl isosorbide 734.77
    tetrachloroethylene 1127.1
    eugenol 557.31
    triacetin 574.26
    span 80 516.58
    1,4-butanediol 306.49
    1,1-dichloroethane 1609.06
    2-methyl-1-pentanol 523.58
    methyl formate 570.12
    2-methyl-1-butanol 729.66
    n-decane 95.31
    butyronitrile 934.72
    3,7-dimethyl-1-octanol 436.48
    1-chlorooctane 338.83
    1-chlorotetradecane 143.83
    n-nonane 95.28
    undecane 71.26
    tert-butylcyclohexane 154.54
    cyclooctane 75.99
    cyclopentanol 676.48
    tetrahydropyran 1138.94
    tert-amyl methyl ether 709.76
    2,5,8-trioxanonane 793.57
    1-hexene 484.51
    2-isopropoxyethanol 634.17
    2,2,2-trifluoroethanol 299.82
    methyl butyrate 707.9

    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
Cypress 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.7%