3-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

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  • Identifiers

    CAS number
    79-89-0

    Molecular formula
    C14H22O

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

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Woody 85.68%
    Floral 84.23%
    Violet 63.84%
    Orris 62.71%
    Powdery 60.75%
    Berry 50.13%
    Sweet 49.87%
    Fruity 45.72%
    Raspberry 45.15%
    Dry 44.36%

    Scent© AI

  • Properties

    XLogP3-AA
    3.3

    Molecular weight
    206.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    260°C

    Flash point est.
    107.76 ˚C

    Solubility expt.

    • Practically insoluble to insoluble
    • Soluble (in ethanol)

  • Synonyms

    • 79-89-0
    • 3-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one
    • 3-Buten-2-one, 3-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-
    • DTXSID0052544
    • 3-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one
    • Isomethyl-?-ionone
    • DTXCID7031117
    • NSSHGPBKKVJJMM-UHFFFAOYSA-N
    • AAA07989
    • NS00012706
    • NS00075619
    • 4-(2,6,6-trimethylcyclohex-1-en-1-yl)-3-methylbut-3-en-2-one

  • Applications

    Gamma-ionone (3-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one, CAS 79-89-0) is a key fragrance ingredient with violet/orris, powdery, woody and ripe-fruity facets, used widely in fine fragrances, soaps, detergents, body washes, hair care, deodorants and scented candles; it is also employed as a flavoring to impart raspberry, tea and tobacco nuances in foods and beverages (within applicable regulatory/IFRA limits), as an intermediate and building block for the synthesis of retinoids and carotenoids (e.g., β-carotene, vitamin A) and other terpenoid derivatives, and as an analytical standard/marker in GC–MS for aroma research, quality control, aroma-release modeling/encapsulation and odor–odor interaction studies; in consumer formulations it further helps mask off-notes, boost diffusion and improve longevity thanks to its relatively good stability under mildly alkaline/oxidative conditions.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 463.49
    methanol 328.13
    isopropanol 560.45
    water 0.38
    ethyl acetate 793.67
    n-propanol 495.87
    acetone 787.83
    n-butanol 509.99
    acetonitrile 665.97
    DMF 1086.01
    toluene 846.53
    isobutanol 430.97
    1,4-dioxane 1417.28
    methyl acetate 768.73
    THF 1880.39
    2-butanone 960.63
    n-pentanol 307.29
    sec-butanol 514.06
    n-hexane 131.45
    ethylene glycol 45.44
    NMP 891.04
    cyclohexane 233.67
    DMSO 382.77
    n-butyl acetate 766.42
    n-octanol 298.85
    chloroform 2080.84
    n-propyl acetate 426.23
    acetic acid 213.61
    dichloromethane 1738.22
    cyclohexanone 1221.44
    propylene glycol 115.05
    isopropyl acetate 536.32
    DMAc 874.38
    2-ethoxyethanol 296.89
    isopentanol 492.58
    n-heptane 107.61
    ethyl formate 387.59
    1,2-dichloroethane 958.82
    n-hexanol 638.72
    2-methoxyethanol 530.51
    isobutyl acetate 316.62
    tetrachloromethane 369.66
    n-pentyl acetate 419.65
    transcutol 1271.96
    n-heptanol 294.4
    ethylbenzene 455.87
    MIBK 464.65
    2-propoxyethanol 664.79
    tert-butanol 777.43
    MTBE 881.21
    2-butoxyethanol 388.65
    propionic acid 278.16
    o-xylene 498.88
    formic acid 48.58
    diethyl ether 764.4
    m-xylene 590.48
    p-xylene 583.49
    chlorobenzene 755.67
    dimethyl carbonate 234.19
    n-octane 50.38
    formamide 116.11
    cyclopentanone 1366.29
    2-pentanone 739.23
    anisole 663.15
    cyclopentyl methyl ether 885.14
    gamma-butyrolactone 1149.85
    1-methoxy-2-propanol 561.75
    pyridine 1031.35
    3-pentanone 593.89
    furfural 824.65
    n-dodecane 38.44
    diethylene glycol 292.28
    diisopropyl ether 278.32
    tert-amyl alcohol 582.71
    acetylacetone 653.48
    n-hexadecane 45.72
    acetophenone 506.14
    methyl propionate 577.37
    isopentyl acetate 669.44
    trichloroethylene 1808.4
    n-nonanol 263.7
    cyclohexanol 553.03
    benzyl alcohol 402.42
    2-ethylhexanol 399.43
    isooctanol 243.41
    dipropyl ether 466.02
    1,2-dichlorobenzene 632.78
    ethyl lactate 183.14
    propylene carbonate 677.99
    n-methylformamide 330.77
    2-pentanol 397.63
    n-pentane 119.81
    1-propoxy-2-propanol 559.45
    1-methoxy-2-propyl acetate 632.97
    2-(2-methoxypropoxy) propanol 408.72
    mesitylene 357.58
    ε-caprolactone 967.87
    p-cymene 287.17
    epichlorohydrin 1333.89
    1,1,1-trichloroethane 1200.53
    2-aminoethanol 140.3
    morpholine-4-carbaldehyde 993.54
    sulfolane 903.1
    2,2,4-trimethylpentane 73.26
    2-methyltetrahydrofuran 1434.66
    n-hexyl acetate 626.1
    isooctane 62.39
    2-(2-butoxyethoxy)ethanol 510.0
    sec-butyl acetate 345.73
    tert-butyl acetate 588.98
    decalin 126.25
    glycerin 121.77
    diglyme 813.28
    acrylic acid 202.19
    isopropyl myristate 270.15
    n-butyric acid 502.16
    acetyl acetate 418.53
    di(2-ethylhexyl) phthalate 234.57
    ethyl propionate 397.2
    nitromethane 507.15
    1,2-diethoxyethane 659.67
    benzonitrile 612.6
    trioctyl phosphate 174.19
    1-bromopropane 798.92
    gamma-valerolactone 1360.14
    n-decanol 198.46
    triethyl phosphate 212.23
    4-methyl-2-pentanol 264.67
    propionitrile 689.45
    vinylene carbonate 609.02
    1,1,2-trichlorotrifluoroethane 534.6
    DMS 442.12
    cumene 296.06
    2-octanol 227.47
    2-hexanone 471.08
    octyl acetate 328.56
    limonene 389.8
    1,2-dimethoxyethane 700.22
    ethyl orthosilicate 212.6
    tributyl phosphate 206.64
    diacetone alcohol 513.48
    N,N-dimethylaniline 444.3
    acrylonitrile 607.82
    aniline 627.49
    1,3-propanediol 244.7
    bromobenzene 905.56
    dibromomethane 1215.67
    1,1,2,2-tetrachloroethane 1347.69
    2-methyl-cyclohexyl acetate 426.49
    tetrabutyl urea 257.08
    diisobutyl methanol 226.09
    2-phenylethanol 501.22
    styrene 497.63
    dioctyl adipate 335.15
    dimethyl sulfate 307.71
    ethyl butyrate 492.59
    methyl lactate 209.03
    butyl lactate 294.23
    diethyl carbonate 319.96
    propanediol butyl ether 350.67
    triethyl orthoformate 319.23
    p-tert-butyltoluene 300.59
    methyl 4-tert-butylbenzoate 455.53
    morpholine 1435.52
    tert-butylamine 603.73
    n-dodecanol 155.01
    dimethoxymethane 699.2
    ethylene carbonate 502.67
    cyrene 358.61
    2-ethoxyethyl acetate 512.47
    2-ethylhexyl acetate 546.19
    1,2,4-trichlorobenzene 727.0
    4-methylpyridine 1266.82
    dibutyl ether 410.93
    2,6-dimethyl-4-heptanol 226.09
    DEF 687.52
    dimethyl isosorbide 759.24
    tetrachloroethylene 787.49
    eugenol 386.98
    triacetin 473.11
    span 80 386.68
    1,4-butanediol 90.64
    1,1-dichloroethane 1253.88
    2-methyl-1-pentanol 338.82
    methyl formate 278.26
    2-methyl-1-butanol 460.99
    n-decane 67.59
    butyronitrile 732.74
    3,7-dimethyl-1-octanol 314.46
    1-chlorooctane 263.39
    1-chlorotetradecane 109.18
    n-nonane 66.7
    undecane 49.11
    tert-butylcyclohexane 122.04
    cyclooctane 86.34
    cyclopentanol 543.97
    tetrahydropyran 1535.56
    tert-amyl methyl ether 569.22
    2,5,8-trioxanonane 569.16
    1-hexene 400.14
    2-isopropoxyethanol 276.07
    2,2,2-trifluoroethanol 86.29
    methyl butyrate 496.06

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction / Specification
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 5.4 % Category 7A
Rinse-off products applied to the hair with some hand contact
 61 %
Category 2
Products applied to the axillae
 1.6 % Category 7B
Leave-on products applied to the hair with some hand contact
 61 %
Category 3
Products applied to the face/body using fingertips
 32 % Category 8
Products with significant anogenital exposure
 3.2 %
Category 4
Products related to fine fragrance
 30 % Category 9
Products with body and hand exposure, primarily rinse off
 59 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 7.6 % Category 10A
Household care products with mostly hand contact
 100 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 7.6 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 100 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 7.6 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 100 %
Category 5D
Baby Creams, baby Oils and baby talc
 7.6 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 100 %
Category 6
Products with oral and lip exposure
 18 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Specification
Pseudo methyl ionones (CAS numbers 26651-96-7, 72968-25-3, 1117-41-5) should not be used as fragrance ingredient as such. A level of up to 2% of Pseudo methyl ionones as an impurity in Methyl ionones is accepted.

Botanical

Name CAS Botanical Proportion
Boldo leaf Boldea fragrans Juss. (Peumus boldus Mol.) 0.05%