2,6-Dimethylocta-2,5,7-trien-4-one

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  • Identifiers

    CAS number
    33746-72-4

    Molecular formula
    C10H14O

    SMILES
    CC(=CC(=O)C=C(C)C=C)C

    Retention indicies (RI)

    • DB5: 1243.0
    • Carbowax: 1651.0

  • Odor profile

    Herbal 61.87%
    Mint 58.8%
    Sweet 57.93%
    Green 56.12%
    Spicy 51.82%
    Fruity 41.91%
    Pungent 40.64%
    Woody 39.9%
    Vegetable 38.11%
    Camphoreous 37.69%

    Scent© AI

  • Properties

    XLogP3-AA
    3.3

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    211°C

    Flash point est.
    74.54 ˚C

  • Synonyms

    • 2,6-DIMETHYLOCTA-2,5,7-TRIEN-4-ONE
    • 33746-72-4
    • (e)-ocimenone
    • 2,5,7-Octatrien-4-one, 2,6-dimethyl-
    • 502-33-0
    • DTXSID601296412
    • IBA74672
    • 2,6-Dimethyl-2,5,7-octatrien-4-one

  • Applications

    2,6-Dimethylocta-2,5,7-trien-4-one (CAS 33746-72-4) is used primarily as an intermediate and research reagent in organic synthesis: as a conjugated enone it serves as a dienophile and Michael acceptor in selective addition chemistry, participates in Diels-Alder reactions, 1,4-conjugate additions with nucleophiles (e.g., cuprates), and controlled redox to access allylic alcohols or saturated ketones, as well as Nazarov-type cyclizations to build cyclopentenone frameworks; its polyene backbone also makes it a useful building block toward terpenoid/norisoprenoid scaffolds and precursors to related aroma compounds, and a reference/standard when developing and calibrating analytical methods (GC-MS, LC-MS, UV-Vis) and in spectroscopic, kinetic, and photochemical studies of enone systems; it may appear as a step in routes to functional polyenes or UV-absorbing organic materials, but its applications are largely confined to R&D rather than consumer products.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 304.89
    methanol 333.97
    isopropanol 272.65
    water 1.23
    ethyl acetate 194.12
    n-propanol 267.97
    acetone 249.23
    n-butanol 301.6
    acetonitrile 202.09
    DMF 365.02
    toluene 151.55
    isobutanol 227.75
    1,4-dioxane 442.87
    methyl acetate 186.73
    THF 644.44
    2-butanone 238.0
    n-pentanol 208.06
    sec-butanol 296.79
    n-hexane 216.96
    ethylene glycol 54.4
    NMP 396.59
    cyclohexane 234.35
    DMSO 185.82
    n-butyl acetate 238.54
    n-octanol 200.35
    chloroform 653.62
    n-propyl acetate 136.0
    acetic acid 234.01
    dichloromethane 349.31
    cyclohexanone 414.84
    propylene glycol 119.49
    isopropyl acetate 131.01
    DMAc 311.19
    2-ethoxyethanol 163.59
    isopentanol 249.08
    n-heptane 133.35
    ethyl formate 143.4
    1,2-dichloroethane 209.09
    n-hexanol 431.93
    2-methoxyethanol 283.43
    isobutyl acetate 112.57
    tetrachloromethane 117.8
    n-pentyl acetate 136.37
    transcutol 516.74
    n-heptanol 171.22
    ethylbenzene 131.88
    MIBK 152.94
    2-propoxyethanol 367.46
    tert-butanol 369.59
    MTBE 264.63
    2-butoxyethanol 189.63
    propionic acid 195.3
    o-xylene 126.49
    formic acid 69.35
    diethyl ether 240.16
    m-xylene 135.94
    p-xylene 164.54
    chlorobenzene 197.28
    dimethyl carbonate 79.42
    n-octane 46.96
    formamide 71.89
    cyclopentanone 374.12
    2-pentanone 209.82
    anisole 189.29
    cyclopentyl methyl ether 312.36
    gamma-butyrolactone 352.17
    1-methoxy-2-propanol 255.22
    pyridine 288.47
    3-pentanone 159.76
    furfural 304.57
    n-dodecane 36.78
    diethylene glycol 195.23
    diisopropyl ether 101.32
    tert-amyl alcohol 340.58
    acetylacetone 185.21
    n-hexadecane 40.25
    acetophenone 161.45
    methyl propionate 154.77
    isopentyl acetate 226.57
    trichloroethylene 430.74
    n-nonanol 178.94
    cyclohexanol 347.08
    benzyl alcohol 158.33
    2-ethylhexanol 244.62
    isooctanol 134.06
    dipropyl ether 219.49
    1,2-dichlorobenzene 184.3
    ethyl lactate 100.71
    propylene carbonate 260.13
    n-methylformamide 145.36
    2-pentanol 243.71
    n-pentane 146.61
    1-propoxy-2-propanol 303.81
    1-methoxy-2-propyl acetate 201.41
    2-(2-methoxypropoxy) propanol 219.69
    mesitylene 99.66
    ε-caprolactone 319.88
    p-cymene 110.04
    epichlorohydrin 332.22
    1,1,1-trichloroethane 307.47
    2-aminoethanol 132.94
    morpholine-4-carbaldehyde 335.16
    sulfolane 353.1
    2,2,4-trimethylpentane 66.13
    2-methyltetrahydrofuran 473.12
    n-hexyl acetate 259.32
    isooctane 53.4
    2-(2-butoxyethoxy)ethanol 273.03
    sec-butyl acetate 112.11
    tert-butyl acetate 169.32
    decalin 98.0
    glycerin 123.61
    diglyme 363.82
    acrylic acid 152.13
    isopropyl myristate 121.54
    n-butyric acid 299.49
    acetyl acetate 131.0
    di(2-ethylhexyl) phthalate 117.54
    ethyl propionate 133.97
    nitromethane 238.6
    1,2-diethoxyethane 202.71
    benzonitrile 196.75
    trioctyl phosphate 90.7
    1-bromopropane 212.71
    gamma-valerolactone 417.23
    n-decanol 137.85
    triethyl phosphate 108.13
    4-methyl-2-pentanol 141.4
    propionitrile 192.74
    vinylene carbonate 215.0
    1,1,2-trichlorotrifluoroethane 266.82
    DMS 158.13
    cumene 107.76
    2-octanol 135.16
    2-hexanone 175.49
    octyl acetate 155.14
    limonene 167.92
    1,2-dimethoxyethane 333.32
    ethyl orthosilicate 110.99
    tributyl phosphate 109.06
    diacetone alcohol 206.08
    N,N-dimethylaniline 159.58
    acrylonitrile 177.43
    aniline 181.34
    1,3-propanediol 180.45
    bromobenzene 183.92
    dibromomethane 299.71
    1,1,2,2-tetrachloroethane 420.61
    2-methyl-cyclohexyl acetate 178.78
    tetrabutyl urea 138.8
    diisobutyl methanol 138.4
    2-phenylethanol 204.06
    styrene 137.22
    dioctyl adipate 158.75
    dimethyl sulfate 104.07
    ethyl butyrate 169.29
    methyl lactate 105.61
    butyl lactate 140.42
    diethyl carbonate 136.95
    propanediol butyl ether 207.84
    triethyl orthoformate 145.31
    p-tert-butyltoluene 109.64
    methyl 4-tert-butylbenzoate 186.83
    morpholine 494.55
    tert-butylamine 288.07
    n-dodecanol 110.19
    dimethoxymethane 206.68
    ethylene carbonate 187.04
    cyrene 182.95
    2-ethoxyethyl acetate 145.76
    2-ethylhexyl acetate 182.22
    1,2,4-trichlorobenzene 207.48
    4-methylpyridine 306.0
    dibutyl ether 190.38
    2,6-dimethyl-4-heptanol 138.4
    DEF 212.19
    dimethyl isosorbide 332.48
    tetrachloroethylene 247.38
    eugenol 179.74
    triacetin 185.74
    span 80 245.33
    1,4-butanediol 79.58
    1,1-dichloroethane 278.55
    2-methyl-1-pentanol 211.83
    methyl formate 121.13
    2-methyl-1-butanol 250.22
    n-decane 56.79
    butyronitrile 252.64
    3,7-dimethyl-1-octanol 185.68
    1-chlorooctane 138.32
    1-chlorotetradecane 70.59
    n-nonane 60.47
    undecane 44.68
    tert-butylcyclohexane 92.02
    cyclooctane 83.27
    cyclopentanol 300.55
    tetrahydropyran 522.97
    tert-amyl methyl ether 221.11
    2,5,8-trioxanonane 274.17
    1-hexene 292.37
    2-isopropoxyethanol 134.91
    2,2,2-trifluoroethanol 80.18
    methyl butyrate 182.44

    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
Tagetes (USA) 1 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 5.5%
Tagetes 1 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 1.0%
Tagetes 2 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 5.3%
Tagetes (Argentina) 1 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 30.0%
Tagetes argentina 3 (Argentina) Tagetes argentina Cabrera, fam. Asteraceae (Compositae) 38.3%
Tagetes laxa (Argentina) Tagetes laxa Cabrera, fam. Asteraceae (Compositae) 33.2%
Tagetes terniflora (Argentina) Tagetes terniflora H.B.K., fam. Asteraceae (Compositae) 5.5%
Tagetes (India) 5 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 3.5%
Tagetes (India) 4 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 15.0%
Tagetes (Turkey) 8016-84-0 Tagetes minuta L. (T. glandulifera Schrank), fam. Asteraceae (Compositae) 15.35%
Tagetes (Egypt) 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 1.13%
Tagetes (USA) 2 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.5%
Tagetes (Rwanda) 1 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 5.0%
Tagetes (France) 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 3.7%
Tagetes (Cameroon) 1a leaf 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 16.9%
Tagetes (Cameroon) 1b flower 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 1.8%
Tagetes (Zimbabwe) 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 7.0%
Rosemary (Brazil) 2 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Tagetes (Argentina) 3 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 5.0%
Tagetes 4 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 4.01%
Tagetes (Italy) 1a 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 2.24%
Tagetes (Italy) 1b 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.65%
Tagetes (India) 6a whole plant 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 1.7%
Tagetes (India) 6b leaf 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 1.3%
Tagetes (India) 6c flower 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 6.9%
Tagetes maxima (Bolivia) Tagetes maxima Kuntze, fam. Asteraceae (Compositae) 17.7%