2,4,4-Trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    98910-85-1

    Molecular formula
    C13H18O2

    SMILES
    CC1=C(C(CCC1=O)(C)C)/C=C/C(=O)C

  • Odor profile

    Woody 76.49%
    Floral 60.54%
    Fruity 60.09%
    Berry 46.06%
    Tobacco 45.7%
    Sweet 44.68%
    Dry 44.0%
    Caramellic 42.46%
    Raspberry 42.2%
    Orris 40.34%

    Scent© AI

  • Properties

    XLogP3-AA
    1.8

    Molecular weight
    206.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    309°C

    Flash point est.
    128.9 ˚C

  • Synonyms

    • 4-Oxo-beta-ionone
    • 29790-29-2
    • 4-Oxo-b-ionone
    • 2,4,4-Trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one
    • (E)-2,4,4-Trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one
    • 27185-77-9
    • 2,4,4-trimethyl-3-[(E)-3-oxobut-1-enyl]cyclohex-2-en-1-one
    • EINECS 248-307-0
    • 3-Oxo-b-ionone
    • EINECS 249-851-1
    • 3-Oxo-.beta.-ionone
    • 3-Keto-.beta.-ionone
    • (E)-3-oxo-beta-ionone
    • SCHEMBL8390312
    • CHEBI:211741
    • 2-Cyclohexen-1-one, 2,4,4-trimethyl-3-(3-oxo-1-butenyl)-
    • DTXSID701017762
    • NS00085207
    • Q67879619
    • 2,4,4-Trimethyl-3-(3-oxo-1-butenyl)-2-cyclohexen-1-one
    • (E)-2,4,4-Trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one
    • 2,4,4-Trimethyl-3-[(1E)-3-oxo-1-butenyl]-2-cyclohexen-1-one
    • 2,4,4-trimethyl-3-[(E)-3-oxo-but-1-enyl]-cyclohex-2-en-1-one
    • 2-Cyclohexen-1-one, 2,4,4-trimethyl-3-(3-oxo-1-buten-1-yl)-

  • Applications

    In applied organic chemistry, 2,4,4-Trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one is a strongly conjugated enone on an isophorone-like scaffold that serves as a prototypical Michael acceptor and versatile synthetic building block, making it valuable as an intermediate for pharmaceuticals, agrochemicals, functional dyes/fine chemicals, and materials precursors; it enables tandem Michael–aldol sequences, aza‑Michael additions, selective 1,4‑reductions, and cyclizations to hetero/bicyclic frameworks, and is widely used as a benchmark substrate to evaluate catalytic systems (organocatalysis, transition‑metal, and photoredox) for nucleophilic conjugate additions; in materials science, after derivatization it can act as a precursor to oligomers/monomers for high‑performance coatings and resins (tuning UV absorption and hardness) or as an intermediate to UV absorbers/stabilizers and color modifiers; in analytics and safety assessment, its UV‑Vis chromophore and Michael reactivity make it useful as a standard/spike in LC–MS/GC–MS of α,β‑unsaturated ketones, a model for kinetic/mechanistic studies of conjugate addition, and an early toxicology alert probe (e.g., glutathione reactivity) during formulation discovery.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 127.17
    methanol 192.38
    isopropanol 94.29
    water 0.74
    ethyl acetate 168.19
    n-propanol 106.0
    acetone 174.58
    n-butanol 102.67
    acetonitrile 190.05
    DMF 400.33
    toluene 196.34
    isobutanol 71.1
    1,4-dioxane 426.57
    methyl acetate 187.98
    THF 444.2
    2-butanone 175.82
    n-pentanol 64.44
    sec-butanol 79.43
    n-hexane 7.22
    ethylene glycol 24.11
    NMP 373.23
    cyclohexane 17.53
    DMSO 166.34
    n-butyl acetate 117.8
    n-octanol 41.98
    chloroform 549.72
    n-propyl acetate 90.06
    acetic acid 103.75
    dichloromethane 478.64
    cyclohexanone 254.44
    propylene glycol 34.42
    isopropyl acetate 100.91
    DMAc 320.61
    2-ethoxyethanol 99.27
    isopentanol 88.16
    n-heptane 4.78
    ethyl formate 109.23
    1,2-dichloroethane 221.47
    n-hexanol 97.59
    2-methoxyethanol 189.27
    isobutyl acetate 63.8
    tetrachloromethane 70.65
    n-pentyl acetate 67.47
    transcutol 406.63
    n-heptanol 41.86
    ethylbenzene 89.88
    MIBK 86.78
    2-propoxyethanol 178.77
    tert-butanol 125.11
    MTBE 101.2
    2-butoxyethanol 89.35
    propionic acid 87.51
    o-xylene 101.27
    formic acid 55.74
    diethyl ether 112.72
    m-xylene 124.52
    p-xylene 111.29
    chlorobenzene 196.87
    dimethyl carbonate 80.37
    n-octane 2.69
    formamide 103.51
    cyclopentanone 319.85
    2-pentanone 131.3
    anisole 181.37
    cyclopentyl methyl ether 159.81
    gamma-butyrolactone 336.5
    1-methoxy-2-propanol 146.65
    pyridine 288.79
    3-pentanone 111.38
    furfural 297.76
    n-dodecane 2.73
    diethylene glycol 123.76
    diisopropyl ether 32.37
    tert-amyl alcohol 90.7
    acetylacetone 163.48
    n-hexadecane 3.26
    acetophenone 148.22
    methyl propionate 143.44
    isopentyl acetate 109.12
    trichloroethylene 470.05
    n-nonanol 39.34
    cyclohexanol 96.72
    benzyl alcohol 119.47
    2-ethylhexanol 56.6
    isooctanol 34.52
    dipropyl ether 58.13
    1,2-dichlorobenzene 170.71
    ethyl lactate 50.78
    propylene carbonate 193.53
    n-methylformamide 165.36
    2-pentanol 55.7
    n-pentane 6.75
    1-propoxy-2-propanol 108.57
    1-methoxy-2-propyl acetate 142.68
    2-(2-methoxypropoxy) propanol 106.29
    mesitylene 60.76
    ε-caprolactone 226.89
    p-cymene 43.5
    epichlorohydrin 369.28
    1,1,1-trichloroethane 231.57
    2-aminoethanol 57.17
    morpholine-4-carbaldehyde 358.28
    sulfolane 282.27
    2,2,4-trimethylpentane 5.91
    2-methyltetrahydrofuran 273.13
    n-hexyl acetate 104.66
    isooctane 4.73
    2-(2-butoxyethoxy)ethanol 130.01
    sec-butyl acetate 73.24
    tert-butyl acetate 105.6
    decalin 13.31
    glycerin 53.79
    diglyme 255.62
    acrylic acid 81.63
    isopropyl myristate 39.86
    n-butyric acid 115.21
    acetyl acetate 116.7
    di(2-ethylhexyl) phthalate 54.08
    ethyl propionate 94.74
    nitromethane 212.61
    1,2-diethoxyethane 126.43
    benzonitrile 166.98
    trioctyl phosphate 34.11
    1-bromopropane 128.79
    gamma-valerolactone 371.7
    n-decanol 28.0
    triethyl phosphate 56.42
    4-methyl-2-pentanol 40.72
    propionitrile 149.87
    vinylene carbonate 199.02
    1,1,2-trichlorotrifluoroethane 186.55
    DMS 116.5
    cumene 54.75
    2-octanol 27.82
    2-hexanone 94.68
    octyl acetate 52.06
    limonene 52.2
    1,2-dimethoxyethane 225.4
    ethyl orthosilicate 55.29
    tributyl phosphate 42.42
    diacetone alcohol 119.03
    N,N-dimethylaniline 115.82
    acrylonitrile 176.75
    aniline 173.93
    1,3-propanediol 87.3
    bromobenzene 204.05
    dibromomethane 282.45
    1,1,2,2-tetrachloroethane 345.11
    2-methyl-cyclohexyl acetate 89.66
    tetrabutyl urea 56.18
    diisobutyl methanol 32.55
    2-phenylethanol 132.0
    styrene 109.25
    dioctyl adipate 65.11
    dimethyl sulfate 113.28
    ethyl butyrate 90.24
    methyl lactate 68.92
    butyl lactate 59.27
    diethyl carbonate 72.81
    propanediol butyl ether 81.07
    triethyl orthoformate 66.94
    p-tert-butyltoluene 43.42
    methyl 4-tert-butylbenzoate 103.95
    morpholine 410.75
    tert-butylamine 77.1
    n-dodecanol 20.78
    dimethoxymethane 214.43
    ethylene carbonate 154.85
    cyrene 121.65
    2-ethoxyethyl acetate 114.31
    2-ethylhexyl acetate 92.37
    1,2,4-trichlorobenzene 201.77
    4-methylpyridine 347.29
    dibutyl ether 46.36
    2,6-dimethyl-4-heptanol 32.55
    DEF 159.18
    dimethyl isosorbide 225.0
    tetrachloroethylene 212.87
    eugenol 107.46
    triacetin 107.22
    span 80 81.2
    1,4-butanediol 30.75
    1,1-dichloroethane 240.25
    2-methyl-1-pentanol 65.73
    methyl formate 131.87
    2-methyl-1-butanol 78.75
    n-decane 4.66
    butyronitrile 146.78
    3,7-dimethyl-1-octanol 44.19
    1-chlorooctane 27.22
    1-chlorotetradecane 10.94
    n-nonane 3.96
    undecane 3.43
    tert-butylcyclohexane 11.94
    cyclooctane 5.38
    cyclopentanol 100.3
    tetrahydropyran 281.44
    tert-amyl methyl ether 79.23
    2,5,8-trioxanonane 175.39
    1-hexene 37.7
    2-isopropoxyethanol 75.96
    2,2,2-trifluoroethanol 47.05
    methyl butyrate 114.89

    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
Freesia, Living Flower Headspace Freesia refracta L. 5.4%
Osmanthus absolute 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 0.1%
Osmanthus headspace (living flowers) 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 1.9%
Osmanthus headspace (flowers) (China) 2 68917-05-5 Osmanthus fragrans (Thunb.) Lour., var. thunbergii Makino, fam. Oleaceae 0.1%
Leea guineensis (Cameroon) 1b leaf Leea guineensis G. Don, fam. Leeaceae 0.7%