2-Cyclohexen-1-one, 2-methyl-5-(2-methyloxiranyl)-

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  • Identifiers

    CAS number
    56423-45-1

    Molecular formula
    C10H14O2

    SMILES
    CC1=CCC(CC1=O)C2(CO2)C

    Retention indicies (RI)

    • Carbowax: 1805.0

  • Odor profile

    Mint 46.16%
    Sweet 45.71%
    Woody 42.95%
    Caramellic 39.78%
    Tobacco 32.47%
    Herbal 31.46%
    Hay 31.1%
    Nutty 29.57%
    Coumarinic 28.65%
    Camphoreous 27.67%

    Scent© AI

  • Properties

    XLogP3-AA
    1.0

    Molecular weight
    166.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    253°C

    Flash point est.
    100.38 ˚C

  • Synonyms

    • 56423-45-1
    • 2-Cyclohexen-1-one, 2-methyl-5-(2-methyloxiranyl)-
    • DTXSID20432788
    • DTXCID30383616
    • AKOS015905531
    • methyl-5-(2-methyloxiran-2-yl)cyclohex-2-en-1-one
    • 2-methyl-5-(2-methyl-2-oxiranyl)-2-cyclohexen-1-one
    • 2-methyl-5-(2-methyl-oxiran-2-yl)-cyclohex-2-en-1-one

  • Applications

    The compound 2-Cyclohexen-1-one, 2-methyl-5-(2-methyloxiranyl)- (CAS 56423-45-1) is primarily used as a multifunctional building block in organic synthesis, leveraging the conjugated enone (Michael acceptor, dienophile) together with a ring-strained epoxide to enable selective assembly strategies such as Michael/1,2-additions, nucleophilic ring-opening, stereocontrolled reductions, cascade sequences, and rearrangements to access polyols, aminoalcohols, lactones, and bicyclic scaffolds; in drug and agrochemical discovery it serves as a versatile intermediate to reach diversified cyclohexanone/terpenoid-like cores, tune polarity and install stereocenters via asymmetric epoxide opening or selective hydrogenation; in methodology research it is commonly employed as a model substrate to benchmark asymmetric catalysis (organocatalysis/transition-metal catalysis) for 1,4-addition, hydroxyamination, and directed epoxide opening, and as a precursor in classic transformations such as Robinson annulation for ring expansion, with occasional use in materials chemistry to introduce reactive epoxy‑enone handles onto oligomers or surfaces at laboratory scale.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 182.05
    methanol 239.32
    isopropanol 136.77
    water 2.63
    ethyl acetate 151.06
    n-propanol 125.59
    acetone 114.69
    n-butanol 111.4
    acetonitrile 202.32
    DMF 117.72
    toluene 116.07
    isobutanol 83.9
    1,4-dioxane 323.75
    methyl acetate 163.4
    THF 194.6
    2-butanone 133.44
    n-pentanol 69.8
    sec-butanol 96.11
    n-hexane 2.53
    ethylene glycol 58.85
    NMP 61.73
    cyclohexane 10.27
    DMSO 101.8
    n-butyl acetate 72.06
    n-octanol 39.43
    chloroform 386.68
    n-propyl acetate 69.11
    acetic acid 130.77
    dichloromethane 320.56
    cyclohexanone 110.64
    propylene glycol 66.27
    isopropyl acetate 88.03
    DMAc 150.66
    2-ethoxyethanol 159.92
    isopentanol 97.1
    n-heptane 3.93
    ethyl formate 96.15
    1,2-dichloroethane 123.53
    n-hexanol 72.59
    2-methoxyethanol 253.48
    isobutyl acetate 49.64
    tetrachloromethane 47.89
    n-pentyl acetate 44.43
    transcutol 436.13
    n-heptanol 39.1
    ethylbenzene 57.64
    MIBK 67.9
    2-propoxyethanol 156.69
    tert-butanol 139.55
    MTBE 93.46
    2-butoxyethanol 94.54
    propionic acid 88.56
    o-xylene 70.06
    formic acid 93.16
    diethyl ether 88.22
    m-xylene 68.0
    p-xylene 83.67
    chlorobenzene 100.69
    dimethyl carbonate 56.5
    n-octane 2.3
    formamide 172.82
    cyclopentanone 98.81
    2-pentanone 85.38
    anisole 140.82
    cyclopentyl methyl ether 63.69
    gamma-butyrolactone 103.9
    1-methoxy-2-propanol 163.69
    pyridine 251.27
    3-pentanone 68.22
    furfural 165.55
    n-dodecane 3.23
    diethylene glycol 139.48
    diisopropyl ether 28.03
    tert-amyl alcohol 86.61
    acetylacetone 115.89
    n-hexadecane 3.73
    acetophenone 109.54
    methyl propionate 96.76
    isopentyl acetate 73.05
    trichloroethylene 261.02
    n-nonanol 39.52
    cyclohexanol 73.72
    benzyl alcohol 116.01
    2-ethylhexanol 42.38
    isooctanol 33.71
    dipropyl ether 36.03
    1,2-dichlorobenzene 86.5
    ethyl lactate 42.96
    propylene carbonate 75.85
    n-methylformamide 104.34
    2-pentanol 66.01
    n-pentane 4.42
    1-propoxy-2-propanol 97.68
    1-methoxy-2-propyl acetate 105.9
    2-(2-methoxypropoxy) propanol 112.15
    mesitylene 37.5
    ε-caprolactone 103.34
    p-cymene 32.27
    epichlorohydrin 174.08
    1,1,1-trichloroethane 142.43
    2-aminoethanol 99.45
    morpholine-4-carbaldehyde 170.95
    sulfolane 79.16
    2,2,4-trimethylpentane 4.08
    2-methyltetrahydrofuran 116.83
    n-hexyl acetate 65.64
    isooctane 4.01
    2-(2-butoxyethoxy)ethanol 147.16
    sec-butyl acetate 59.27
    tert-butyl acetate 77.64
    decalin 7.32
    glycerin 80.68
    diglyme 254.27
    acrylic acid 77.86
    isopropyl myristate 32.87
    n-butyric acid 111.88
    acetyl acetate 110.89
    di(2-ethylhexyl) phthalate 40.29
    ethyl propionate 66.34
    nitromethane 204.13
    1,2-diethoxyethane 117.52
    benzonitrile 137.37
    trioctyl phosphate 23.04
    1-bromopropane 69.78
    gamma-valerolactone 173.47
    n-decanol 29.36
    triethyl phosphate 36.13
    4-methyl-2-pentanol 49.72
    propionitrile 144.7
    vinylene carbonate 95.18
    1,1,2-trichlorotrifluoroethane 131.72
    DMS 71.91
    cumene 37.57
    2-octanol 25.63
    2-hexanone 65.25
    octyl acetate 39.18
    limonene 34.23
    1,2-dimethoxyethane 220.02
    ethyl orthosilicate 35.9
    tributyl phosphate 28.63
    diacetone alcohol 95.79
    N,N-dimethylaniline 80.95
    acrylonitrile 183.53
    aniline 130.7
    1,3-propanediol 142.86
    bromobenzene 106.21
    dibromomethane 187.32
    1,1,2,2-tetrachloroethane 180.1
    2-methyl-cyclohexyl acetate 59.56
    tetrabutyl urea 37.27
    diisobutyl methanol 31.11
    2-phenylethanol 104.38
    styrene 74.62
    dioctyl adipate 48.35
    dimethyl sulfate 53.94
    ethyl butyrate 62.84
    methyl lactate 56.36
    butyl lactate 43.17
    diethyl carbonate 55.1
    propanediol butyl ether 82.85
    triethyl orthoformate 47.4
    p-tert-butyltoluene 30.92
    methyl 4-tert-butylbenzoate 71.97
    morpholine 284.4
    tert-butylamine 75.0
    n-dodecanol 22.5
    dimethoxymethane 137.07
    ethylene carbonate 77.4
    cyrene 81.0
    2-ethoxyethyl acetate 89.03
    2-ethylhexyl acetate 54.5
    1,2,4-trichlorobenzene 102.66
    4-methylpyridine 200.71
    dibutyl ether 38.58
    2,6-dimethyl-4-heptanol 31.11
    DEF 84.49
    dimethyl isosorbide 135.08
    tetrachloroethylene 124.01
    eugenol 83.36
    triacetin 84.24
    span 80 72.94
    1,4-butanediol 54.63
    1,1-dichloroethane 147.04
    2-methyl-1-pentanol 66.36
    methyl formate 69.7
    2-methyl-1-butanol 76.95
    n-decane 4.61
    butyronitrile 126.57
    3,7-dimethyl-1-octanol 47.34
    1-chlorooctane 19.6
    1-chlorotetradecane 10.16
    n-nonane 3.54
    undecane 3.78
    tert-butylcyclohexane 6.78
    cyclooctane 3.78
    cyclopentanol 62.89
    tetrahydropyran 158.66
    tert-amyl methyl ether 55.55
    2,5,8-trioxanonane 188.26
    1-hexene 15.12
    2-isopropoxyethanol 105.46
    2,2,2-trifluoroethanol 57.68
    methyl butyrate 76.66

    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
Chenopodium ambrosioides Chenopodium ambrosioides L., fam. Chenopodiaceae 0.16%