2-Methoxy-3-methyl-2-cyclopentenone

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  • Identifiers

    CAS number
    14189-85-6

    Molecular formula
    C7H10O2

    SMILES
    CC1=C(C(=O)CC1)OC

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 77.08%
    Sweet 53.95%
    Burnt 50.94%
    Nutty 47.9%
    Roasted 42.21%
    Coffee 38.04%
    Mint 33.07%
    Buttery 32.06%
    Musty 31.21%
    Ketonic 30.43%

     

    Flavor
    Fruity 65.97%
    Caramel 63.62%
    Sweet 57.68%
    Tobacco 44.38%
    Maple 37.73%
    Sugar 32.59%
    Phenolic 30.2%
    Spicy 28.44%
    Woody 28.26%
    Minty 27.71%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    7.23 (neutral)

    Molecular weight
    126.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    216°C

    Flash point

    • 55.78 ˚C est.

  • Synonyms

    • 14189-85-6
    • 2-Cyclopenten-1-one, 2-methoxy-3-methyl-
    • 2-Methoxy-3-methyl-2-cyclopentenone
    • 2-methoxy-3-methyl-2-cyclopenten-1-one
    • EINECS 238-042-9
    • NSC 177460
    • NSC-177460
    • DTXSID5065724
    • KK59159647
    • RefChem:474196
    • DTXCID9034604
    • 2-Methoxy-3-methylcyclopent-2-en-1-one
    • Cyclotene monomethyl ether
    • UNII-KK59159647
    • NSC177460
    • SCHEMBL10454572
    • 2-methoxy-3-methyl-cyclopentenone
    • 2-Cyclopenten-1-one,2-methoxy-3-methyl-
    • DS-004049
    • NS00024604
    • Q27282298
    • 14189-85-6

  • Applications

    2-Methoxy-3-methyl-2-cyclopentenone (CAS 14189-85-6) is primarily used as a reactive intermediate in organic synthesis, enabling Michael-type additions and cycloaddition routes to access diverse cyclic frameworks; in fragrance and flavor contexts it may be evaluated as an aroma-building block or fragrance intermediate; it also serves as an intermediate for pharmaceutical and agrochemical synthesis, providing a versatile enone scaffold for constructing bioactive molecules; in polymers and coatings it can function as a functional monomer or crosslinking component due to its enone functionality, supporting specialty polymers and coating formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3049.97
    methanol 5130.65
    isopropanol 1771.12
    water 140.17
    ethyl acetate 1899.57
    n-propanol 2162.04
    acetone 2080.73
    n-butanol 1972.31
    acetonitrile 3729.19
    DMF 1755.99
    toluene 737.4
    isobutanol 1477.3
    1,4-dioxane 3392.2
    methyl acetate 1721.03
    THF 2862.0
    2-butanone 1363.16
    n-pentanol 1319.35
    sec-butanol 1408.66
    n-hexane 231.14
    ethylene glycol 1014.79
    NMP 1209.46
    cyclohexane 386.11
    DMSO 1557.62
    n-butyl acetate 840.26
    n-octanol 468.7
    chloroform 5390.59
    n-propyl acetate 960.93
    acetic acid 4092.15
    dichloromethane 5630.75
    cyclohexanone 1643.92
    propylene glycol 588.61
    isopropyl acetate 894.09
    DMAc 813.33
    2-ethoxyethanol 2486.97
    isopentanol 1402.18
    n-heptane 148.64
    ethyl formate 1612.62
    1,2-dichloroethane 2859.11
    n-hexanol 852.26
    2-methoxyethanol 3760.41
    isobutyl acetate 512.65
    tetrachloromethane 1441.75
    n-pentyl acetate 608.01
    transcutol 3236.38
    n-heptanol 432.27
    ethylbenzene 423.88
    MIBK 788.08
    2-propoxyethanol 1539.77
    tert-butanol 1826.71
    MTBE 1249.36
    2-butoxyethanol 851.43
    propionic acid 1664.58
    o-xylene 440.67
    formic acid 3063.75
    diethyl ether 2217.2
    m-xylene 486.95
    p-xylene 540.28
    chlorobenzene 1156.22
    dimethyl carbonate 564.76
    n-octane 68.67
    formamide 3412.26
    cyclopentanone 1779.97
    2-pentanone 1273.08
    anisole 941.74
    cyclopentyl methyl ether 1353.69
    gamma-butyrolactone 2336.58
    1-methoxy-2-propanol 1716.02
    pyridine 1986.24
    3-pentanone 914.36
    furfural 2147.25
    n-dodecane 47.53
    diethylene glycol 1487.62
    diisopropyl ether 543.35
    tert-amyl alcohol 1247.94
    acetylacetone 1140.74
    n-hexadecane 53.86
    acetophenone 691.57
    methyl propionate 1156.91
    isopentyl acetate 686.14
    trichloroethylene 4637.87
    n-nonanol 398.3
    cyclohexanol 1280.87
    benzyl alcohol 875.11
    2-ethylhexanol 461.04
    isooctanol 365.83
    dipropyl ether 609.57
    1,2-dichlorobenzene 1069.39
    ethyl lactate 386.09
    propylene carbonate 1182.28
    n-methylformamide 2118.75
    2-pentanol 1137.83
    n-pentane 265.51
    1-propoxy-2-propanol 814.56
    1-methoxy-2-propyl acetate 677.04
    2-(2-methoxypropoxy) propanol 543.25
    mesitylene 332.72
    ε-caprolactone 1523.84
    p-cymene 243.67
    epichlorohydrin 3042.06
    1,1,1-trichloroethane 2668.24
    2-aminoethanol 1539.23
    morpholine-4-carbaldehyde 1834.86
    sulfolane 1765.42
    2,2,4-trimethylpentane 132.34
    2-methyltetrahydrofuran 2111.92
    n-hexyl acetate 823.53
    isooctane 113.27
    2-(2-butoxyethoxy)ethanol 866.96
    sec-butyl acetate 565.26
    tert-butyl acetate 941.16
    decalin 145.71
    glycerin 930.86
    diglyme 1797.09
    acrylic acid 1630.58
    isopropyl myristate 268.2
    n-butyric acid 2171.55
    acetyl acetate 1116.9
    di(2-ethylhexyl) phthalate 232.36
    ethyl propionate 802.61
    nitromethane 4669.24
    1,2-diethoxyethane 1212.06
    benzonitrile 1216.22
    trioctyl phosphate 180.46
    1-bromopropane 1417.68
    gamma-valerolactone 2270.95
    n-decanol 265.43
    triethyl phosphate 266.64
    4-methyl-2-pentanol 561.92
    propionitrile 2013.51
    vinylene carbonate 1291.09
    1,1,2-trichlorotrifluoroethane 1757.18
    DMS 632.97
    cumene 302.91
    2-octanol 338.61
    2-hexanone 790.38
    octyl acetate 337.4
    limonene 331.89
    1,2-dimethoxyethane 2505.6
    ethyl orthosilicate 270.24
    tributyl phosphate 239.92
    diacetone alcohol 902.57
    N,N-dimethylaniline 518.97
    acrylonitrile 2244.91
    aniline 973.74
    1,3-propanediol 2290.69
    bromobenzene 1167.69
    dibromomethane 3224.88
    1,1,2,2-tetrachloroethane 2839.93
    2-methyl-cyclohexyl acetate 411.22
    tetrabutyl urea 282.46
    diisobutyl methanol 301.76
    2-phenylethanol 635.95
    styrene 563.62
    dioctyl adipate 339.1
    dimethyl sulfate 614.95
    ethyl butyrate 605.21
    methyl lactate 474.56
    butyl lactate 376.29
    diethyl carbonate 427.23
    propanediol butyl ether 616.59
    triethyl orthoformate 408.16
    p-tert-butyltoluene 234.66
    methyl 4-tert-butylbenzoate 501.32
    morpholine 3352.24
    tert-butylamine 1161.24
    n-dodecanol 194.74
    dimethoxymethane 1818.38
    ethylene carbonate 1161.79
    cyrene 523.6
    2-ethoxyethyl acetate 840.89
    2-ethylhexyl acetate 503.9
    1,2,4-trichlorobenzene 1074.62
    4-methylpyridine 1587.02
    dibutyl ether 566.56
    2,6-dimethyl-4-heptanol 301.76
    DEF 1159.34
    dimethyl isosorbide 883.32
    tetrachloroethylene 2736.79
    eugenol 541.71
    triacetin 554.26
    span 80 448.33
    1,4-butanediol 959.43
    1,1-dichloroethane 2788.07
    2-methyl-1-pentanol 940.66
    methyl formate 1922.99
    2-methyl-1-butanol 1297.02
    n-decane 86.22
    butyronitrile 1926.91
    3,7-dimethyl-1-octanol 435.68
    1-chlorooctane 319.48
    1-chlorotetradecane 116.25
    n-nonane 88.92
    undecane 60.44
    tert-butylcyclohexane 144.44
    cyclooctane 131.51
    cyclopentanol 1321.22
    tetrahydropyran 2373.58
    tert-amyl methyl ether 873.74
    2,5,8-trioxanonane 995.19
    1-hexene 606.91
    2-isopropoxyethanol 1352.4
    2,2,2-trifluoroethanol 1562.11
    methyl butyrate 1030.05

    Scent© AI

1 4

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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