6-Methyl-5-methylene-2-heptanone

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  • Identifiers

    CAS number
    498-51-1

    Molecular formula
    C9H16O

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

  • Odor profile

    Fruity 63.61%
    Herbal 60.25%
    Woody 51.2%
    Mint 43.31%
    Ketonic 42.83%
    Fresh 39.82%
    Spicy 37.23%
    Dry 33.8%
    Camphoreous 31.65%
    Floral 28.03%

    Scent© AI

  • Properties

    XLogP3-AA
    2.4

    Molecular weight
    140.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    186°C

    Flash point est.
    58.99 ˚C

  • Synonyms

    • Thujaketone
    • 6-Methyl-5-methylene-2-heptanone
    • 6-Methyl-5-methylideneheptan-2-one
    • 2-Heptanone, 6-methyl-5-methylene-
    • 498-51-1
    • 5-Isopropyl-5-hexen-2-one #
    • SCHEMBL13255954
    • RNUYQXXGCJJIPA-UHFFFAOYSA-N
    • 5-methylene-6-methylheptan-2-one
    • DB-242822

  • Applications

    6-Methyl-5-methylene-2-heptanone (CAS 498-51-1) is a nonconjugated ketone bearing a terminal methylene, used primarily as a versatile intermediate for organic synthesis and fine-chemical R&D: the dual “alkene + carbonyl” handles enable orthogonal, selective elaborations (alkene: hydroboration–oxidation, epoxidation, ozonolysis, halogenation, cross-metathesis; carbonyl: chemoselective reductions, oxime/hydrazone formation, reductive amination, Grignard/organolithium addition to give higher-order alcohols, Baeyer–Villiger oxidation to esters/lactones, enolization/aldol for chain extension and stereocenter creation); owing to its terpenoid-like backbone, it is often leveraged as a scaffold to access fragrance candidates, specialty chemicals, and fragments in pharma/agro discovery; it also serves as a model substrate for catalyst screening (probing alkene vs carbonyl selectivity), a GC/LC–MS reference/probe due to suitable volatility and a carbonyl chromophore, and a model VOC in atmospheric studies of photochemistry/ozonolysis of unsaturated carbonyls.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1249.15
    methanol 831.69
    isopropanol 1335.99
    water 3.0
    ethyl acetate 726.63
    n-propanol 931.1
    acetone 857.47
    n-butanol 859.71
    acetonitrile 883.89
    DMF 663.48
    toluene 326.22
    isobutanol 691.75
    1,4-dioxane 1574.31
    methyl acetate 693.05
    THF 1583.42
    2-butanone 717.55
    n-pentanol 486.92
    sec-butanol 912.81
    n-hexane 132.7
    ethylene glycol 170.72
    NMP 557.25
    cyclohexane 192.63
    DMSO 535.76
    n-butyl acetate 578.11
    n-octanol 343.6
    chloroform 1921.63
    n-propyl acetate 319.01
    acetic acid 589.21
    dichloromethane 1361.29
    cyclohexanone 851.41
    propylene glycol 414.64
    isopropyl acetate 391.34
    DMAc 598.82
    2-ethoxyethanol 509.42
    isopentanol 689.93
    n-heptane 115.93
    ethyl formate 409.18
    1,2-dichloroethane 631.5
    n-hexanol 767.73
    2-methoxyethanol 895.79
    isobutyl acetate 207.33
    tetrachloromethane 345.45
    n-pentyl acetate 306.37
    transcutol 1535.63
    n-heptanol 311.4
    ethylbenzene 198.6
    MIBK 305.57
    2-propoxyethanol 785.42
    tert-butanol 1345.24
    MTBE 709.68
    2-butoxyethanol 417.13
    propionic acid 577.3
    o-xylene 215.71
    formic acid 153.37
    diethyl ether 626.38
    m-xylene 218.14
    p-xylene 271.1
    chlorobenzene 387.33
    dimethyl carbonate 124.56
    n-octane 43.15
    formamide 227.83
    cyclopentanone 870.61
    2-pentanone 524.43
    anisole 378.48
    cyclopentyl methyl ether 553.23
    gamma-butyrolactone 835.31
    1-methoxy-2-propanol 774.44
    pyridine 801.72
    3-pentanone 336.82
    furfural 738.39
    n-dodecane 34.76
    diethylene glycol 449.96
    diisopropyl ether 180.25
    tert-amyl alcohol 848.69
    acetylacetone 519.28
    n-hexadecane 38.18
    acetophenone 291.96
    methyl propionate 403.35
    isopentyl acetate 478.15
    trichloroethylene 1187.7
    n-nonanol 289.33
    cyclohexanol 711.52
    benzyl alcohol 316.13
    2-ethylhexanol 410.94
    isooctanol 235.39
    dipropyl ether 382.04
    1,2-dichlorobenzene 328.81
    ethyl lactate 161.71
    propylene carbonate 507.09
    n-methylformamide 359.23
    2-pentanol 576.58
    n-pentane 128.35
    1-propoxy-2-propanol 621.03
    1-methoxy-2-propyl acetate 450.8
    2-(2-methoxypropoxy) propanol 423.16
    mesitylene 130.29
    ε-caprolactone 759.37
    p-cymene 160.13
    epichlorohydrin 947.01
    1,1,1-trichloroethane 901.64
    2-aminoethanol 449.48
    morpholine-4-carbaldehyde 793.48
    sulfolane 660.74
    2,2,4-trimethylpentane 59.55
    2-methyltetrahydrofuran 1220.99
    n-hexyl acetate 493.72
    isooctane 46.55
    2-(2-butoxyethoxy)ethanol 562.64
    sec-butyl acetate 247.15
    tert-butyl acetate 386.67
    decalin 82.26
    glycerin 343.33
    diglyme 848.43
    acrylic acid 384.16
    isopropyl myristate 194.32
    n-butyric acid 814.29
    acetyl acetate 374.91
    di(2-ethylhexyl) phthalate 186.67
    ethyl propionate 289.68
    nitromethane 730.85
    1,2-diethoxyethane 550.24
    benzonitrile 463.8
    trioctyl phosphate 129.81
    1-bromopropane 564.02
    gamma-valerolactone 1093.24
    n-decanol 210.0
    triethyl phosphate 158.28
    4-methyl-2-pentanol 306.26
    propionitrile 621.51
    vinylene carbonate 435.65
    1,1,2-trichlorotrifluoroethane 587.99
    DMS 280.46
    cumene 144.42
    2-octanol 236.35
    2-hexanone 366.71
    octyl acetate 244.78
    limonene 261.86
    1,2-dimethoxyethane 821.24
    ethyl orthosilicate 154.58
    tributyl phosphate 163.0
    diacetone alcohol 486.37
    N,N-dimethylaniline 239.06
    acrylonitrile 575.77
    aniline 444.21
    1,3-propanediol 633.4
    bromobenzene 393.08
    dibromomethane 946.85
    1,1,2,2-tetrachloroethane 991.0
    2-methyl-cyclohexyl acetate 294.34
    tetrabutyl urea 194.08
    diisobutyl methanol 224.52
    2-phenylethanol 376.85
    styrene 236.19
    dioctyl adipate 264.02
    dimethyl sulfate 173.9
    ethyl butyrate 371.57
    methyl lactate 216.18
    butyl lactate 248.1
    diethyl carbonate 244.04
    propanediol butyl ether 432.45
    triethyl orthoformate 251.41
    p-tert-butyltoluene 170.77
    methyl 4-tert-butylbenzoate 305.02
    morpholine 1722.54
    tert-butylamine 876.28
    n-dodecanol 160.32
    dimethoxymethane 391.35
    ethylene carbonate 384.8
    cyrene 283.6
    2-ethoxyethyl acetate 396.55
    2-ethylhexyl acetate 367.93
    1,2,4-trichlorobenzene 408.66
    4-methylpyridine 805.32
    dibutyl ether 353.88
    2,6-dimethyl-4-heptanol 224.52
    DEF 447.26
    dimethyl isosorbide 608.92
    tetrachloroethylene 600.18
    eugenol 292.36
    triacetin 392.75
    span 80 428.0
    1,4-butanediol 213.34
    1,1-dichloroethane 999.28
    2-methyl-1-pentanol 388.88
    methyl formate 236.96
    2-methyl-1-butanol 596.43
    n-decane 60.35
    butyronitrile 721.47
    3,7-dimethyl-1-octanol 327.99
    1-chlorooctane 200.46
    1-chlorotetradecane 79.06
    n-nonane 60.8
    undecane 44.68
    tert-butylcyclohexane 84.66
    cyclooctane 55.82
    cyclopentanol 720.69
    tetrahydropyran 1347.95
    tert-amyl methyl ether 444.86
    2,5,8-trioxanonane 599.55
    1-hexene 365.04
    2-isopropoxyethanol 380.8
    2,2,2-trifluoroethanol 175.59
    methyl butyrate 379.16

    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
Cistus (Spain) 1 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 4.4%