2-Cyclohexen-1-one, 3,5,5-trimethyl-4-methylene-

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    20548-00-9

    Molecular formula
    C10H14O

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

  • Odor profile

    Woody 73.22%
    Sweet 65.6%
    Fruity 64.84%
    Tobacco 61.5%
    Mint 60.49%
    Camphoreous 49.95%
    Herbal 45.04%
    Spicy 42.43%
    Green 41.61%
    Tea 37.92%

    Scent© AI

  • Properties

    XLogP3-AA
    1.7

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    232°C

    Flash point est.
    78.0 ˚C

  • Synonyms

    • 4-Methyleneisophorone
    • 2-cyclohexen-1-one, 3,5,5-trimethyl-4-methylene-
    • Methyleneisophorone
    • D5MU2X8KSH
    • 20548-00-9
    • UNII-D5MU2X8KSH
    • Isophorone-4-methylene
    • 3,5,5-trimethyl-4-methylenecyclohex-2-en-1-one
    • 4-Methylene-3,5,5-trimethyl-2-cyclohexen-1-one
    • 3,5,5-Trimethyl-4-methylene-1-cyclohexanon-2-ene
    • DTXSID10348889
    • 3,5,5-trimethyl-4-methylidenecyclohex-2-en-1-one
    • 3,5,5-Trimethyl-4-methylenecyclohex-2-enone
    • 4-methylene-3,5,5-trimethylcyclohex-2-enone
    • SCHEMBL11607730
    • DTXCID90299961
    • Q67879615

  • Applications

    2-Cyclohexen-1-one, 3,5,5-trimethyl-4-methylene- (CAS 20548-00-9) is a highly activated exocyclic-methylene enone used mainly as a versatile synthetic intermediate: a strong Michael acceptor and dienophile to build bicyclic/terpenoid frameworks; a key precursor to ionone/methylionone-type and damascone fragrance ingredients and woody/amber odorants via Diels–Alder, aldol/Knövenagel, metathesis or epoxidation followed by downstream transformations; a starting point for derivatives applied in aroma chemicals and specialty intermediates for coatings and performance additives; and a benchmark substrate in asymmetric catalysis and methodology development (1,4-additions, Robinson annulation, selective reductions/oxidations), leveraging the combined reactivity of the activated carbonyl and exocyclic double bond to enable selective functionalization and streamlined routes.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 594.42
    methanol 721.25
    isopropanol 494.78
    water 3.65
    ethyl acetate 578.28
    n-propanol 524.95
    acetone 528.51
    n-butanol 467.53
    acetonitrile 722.7
    DMF 680.22
    toluene 455.07
    isobutanol 353.84
    1,4-dioxane 1292.35
    methyl acetate 521.08
    THF 1640.95
    2-butanone 491.42
    n-pentanol 280.06
    sec-butanol 399.25
    n-hexane 151.65
    ethylene glycol 94.45
    NMP 636.72
    cyclohexane 186.39
    DMSO 360.34
    n-butyl acetate 376.69
    n-octanol 213.91
    chloroform 1275.04
    n-propyl acetate 246.22
    acetic acid 392.34
    dichloromethane 972.9
    cyclohexanone 689.71
    propylene glycol 123.1
    isopropyl acetate 339.82
    DMAc 415.02
    2-ethoxyethanol 318.53
    isopentanol 362.57
    n-heptane 98.32
    ethyl formate 302.25
    1,2-dichloroethane 587.89
    n-hexanol 561.43
    2-methoxyethanol 627.43
    isobutyl acetate 159.52
    tetrachloromethane 263.08
    n-pentyl acetate 216.7
    transcutol 1040.25
    n-heptanol 210.11
    ethylbenzene 210.0
    MIBK 293.38
    2-propoxyethanol 672.93
    tert-butanol 584.51
    MTBE 506.87
    2-butoxyethanol 283.9
    propionic acid 342.5
    o-xylene 237.11
    formic acid 188.31
    diethyl ether 697.41
    m-xylene 332.35
    p-xylene 245.04
    chlorobenzene 419.95
    dimethyl carbonate 200.2
    n-octane 34.95
    formamide 237.07
    cyclopentanone 812.05
    2-pentanone 472.42
    anisole 354.55
    cyclopentyl methyl ether 775.61
    gamma-butyrolactone 914.02
    1-methoxy-2-propanol 547.33
    pyridine 648.68
    3-pentanone 363.14
    furfural 592.31
    n-dodecane 23.18
    diethylene glycol 400.87
    diisopropyl ether 233.58
    tert-amyl alcohol 413.45
    acetylacetone 414.1
    n-hexadecane 27.01
    acetophenone 246.02
    methyl propionate 416.58
    isopentyl acetate 312.13
    trichloroethylene 961.57
    n-nonanol 181.4
    cyclohexanol 459.54
    benzyl alcohol 229.61
    2-ethylhexanol 265.77
    isooctanol 156.44
    dipropyl ether 311.92
    1,2-dichlorobenzene 323.53
    ethyl lactate 125.17
    propylene carbonate 410.84
    n-methylformamide 423.25
    2-pentanol 367.12
    n-pentane 135.95
    1-propoxy-2-propanol 423.09
    1-methoxy-2-propyl acetate 411.31
    2-(2-methoxypropoxy) propanol 249.16
    mesitylene 197.65
    ε-caprolactone 574.21
    p-cymene 121.47
    epichlorohydrin 936.22
    1,1,1-trichloroethane 694.47
    2-aminoethanol 215.67
    morpholine-4-carbaldehyde 673.67
    sulfolane 640.01
    2,2,4-trimethylpentane 52.61
    2-methyltetrahydrofuran 1084.67
    n-hexyl acetate 350.75
    isooctane 51.39
    2-(2-butoxyethoxy)ethanol 365.01
    sec-butyl acetate 198.14
    tert-butyl acetate 360.2
    decalin 78.49
    glycerin 163.66
    diglyme 593.54
    acrylic acid 262.83
    isopropyl myristate 131.97
    n-butyric acid 433.03
    acetyl acetate 314.1
    di(2-ethylhexyl) phthalate 107.91
    ethyl propionate 265.92
    nitromethane 634.97
    1,2-diethoxyethane 398.61
    benzonitrile 348.44
    trioctyl phosphate 86.25
    1-bromopropane 496.04
    gamma-valerolactone 902.46
    n-decanol 131.36
    triethyl phosphate 115.24
    4-methyl-2-pentanol 213.06
    propionitrile 550.54
    vinylene carbonate 382.79
    1,1,2-trichlorotrifluoroethane 388.39
    DMS 271.36
    cumene 139.97
    2-octanol 145.52
    2-hexanone 271.7
    octyl acetate 162.28
    limonene 178.92
    1,2-dimethoxyethane 522.61
    ethyl orthosilicate 116.84
    tributyl phosphate 106.75
    diacetone alcohol 371.24
    N,N-dimethylaniline 223.24
    acrylonitrile 532.98
    aniline 410.21
    1,3-propanediol 319.83
    bromobenzene 427.87
    dibromomethane 700.2
    1,1,2,2-tetrachloroethane 755.87
    2-methyl-cyclohexyl acetate 196.74
    tetrabutyl urea 129.47
    diisobutyl methanol 139.55
    2-phenylethanol 330.98
    styrene 227.32
    dioctyl adipate 146.21
    dimethyl sulfate 246.83
    ethyl butyrate 239.38
    methyl lactate 188.45
    butyl lactate 148.83
    diethyl carbonate 165.01
    propanediol butyl ether 227.54
    triethyl orthoformate 173.77
    p-tert-butyltoluene 130.5
    methyl 4-tert-butylbenzoate 229.98
    morpholine 1316.7
    tert-butylamine 413.75
    n-dodecanol 96.07
    dimethoxymethane 576.41
    ethylene carbonate 341.8
    cyrene 206.34
    2-ethoxyethyl acetate 287.2
    2-ethylhexyl acetate 250.27
    1,2,4-trichlorobenzene 352.61
    4-methylpyridine 678.5
    dibutyl ether 241.78
    2,6-dimethyl-4-heptanol 139.55
    DEF 430.13
    dimethyl isosorbide 437.66
    tetrachloroethylene 483.21
    eugenol 215.19
    triacetin 223.8
    span 80 226.09
    1,4-butanediol 109.67
    1,1-dichloroethane 749.06
    2-methyl-1-pentanol 230.58
    methyl formate 328.89
    2-methyl-1-butanol 336.79
    n-decane 42.98
    butyronitrile 535.96
    3,7-dimethyl-1-octanol 207.27
    1-chlorooctane 155.51
    1-chlorotetradecane 61.03
    n-nonane 43.45
    undecane 30.75
    tert-butylcyclohexane 77.02
    cyclooctane 68.32
    cyclopentanol 478.36
    tetrahydropyran 1230.01
    tert-amyl methyl ether 382.11
    2,5,8-trioxanonane 380.45
    1-hexene 319.79
    2-isopropoxyethanol 237.83
    2,2,2-trifluoroethanol 165.83
    methyl butyrate 277.61

    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 0.1%
Saffron 2 8022-19-3 Crocus sativus L., fam. Iridaceae 0.01%