2-Cyclohexen-1-one, 6-methyl-3-(1-methylethyl)-

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  • Identifiers

    CAS number
    499-74-1

    Molecular formula
    C10H16O

    SMILES
    CC1CCC(=CC1=O)C(C)C

    Retention indicies (RI)

    • DB5: 1252.0

  • Odor profile

    Mint 64.02%
    Herbal 49.92%
    Spicy 40.43%
    Camphoreous 36.69%
    Ketonic 36.56%
    Woody 35.46%
    Caramellic 28.89%
    Tobacco 28.29%
    Phenolic 27.45%
    Burnt 25.7%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    226°C

    Flash point est.
    82.51 ˚C

  • Synonyms

    • p-Menth-3-en-2-one
    • Carvenone
    • 499-74-1
    • 2-Cyclohexen-1-one, 6-methyl-3-(1-methylethyl)-
    • 3-(Isopropyl)-6-methylcyclohex-2-en-1-one
    • 23733-68-8
    • 6-methyl-3-propan-2-ylcyclohex-2-en-1-one
    • EINECS 245-850-5
    • carvenon
    • EINECS 207-888-0
    • EINECS 245-852-6
    • AI3-27537
    • (R)-3-(Isopropyl)-6-methylcyclohex-2-en-1-one
    • (1)-3-(Isopropyl)-6-methylcyclohex-2-en-1-one
    • SCHEMBL812087
    • RLYSXAZAJUMULG-UHFFFAOYSA-
    • DTXSID00871338
    • 3-Isopropyl-6-methyl-2-cyclohexen-1-one #
    • NS00043601
    • 6-Methyl-3-(propan-2-yl)cyclohex-2-en-1-one
    • 3-ISOPROPYL-6-METHYLCYCLOHEX-2-EN-1-ONE
    • Q67879765
    • 2-Cyclohexen-1-one, 6-methyl-3-(1-methylethyl)-, (R)-(+)-
    • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h6-8H,4-5H2,1-3H3

  • Applications

    2-Cyclohexen-1-one, 6-methyl-3-(1-methylethyl)- (CAS 499-74-1) is a reactive cyclic enone used mainly as a synthetic building block to assemble cyclohexenone/cyclohexanone scaffolds in pharmaceuticals, agrochemicals, and fine chemicals; it serves as a substrate for selective transformations such as Michael addition, Robinson/aldol condensations, Diels–Alder, hydrogenation, epoxidation, and amination/alcohol formation, enabling access to terpene/monoterpene derivatives and related saturated ketones; it is also employed in flavor and fragrance work as a precursor/modifier contributing minty, herbal, or citrus facets depending on the blend, and in materials R&D where the enone handle is leveraged as an attachment or crosslinking site via Michael-type chemistry; additionally, it is used as a reference/analytical standard in studies of enone reactivity and the development of asymmetric catalysis.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 243.1
    methanol 154.26
    isopropanol 309.83
    water 0.7
    ethyl acetate 214.71
    n-propanol 257.86
    acetone 241.77
    n-butanol 259.99
    acetonitrile 328.05
    DMF 325.23
    toluene 261.99
    isobutanol 220.86
    1,4-dioxane 492.47
    methyl acetate 274.86
    THF 462.59
    2-butanone 327.32
    n-pentanol 160.54
    sec-butanol 271.22
    n-hexane 44.27
    ethylene glycol 33.84
    NMP 268.24
    cyclohexane 82.77
    DMSO 154.07
    n-butyl acetate 308.33
    n-octanol 166.42
    chloroform 1194.81
    n-propyl acetate 152.32
    acetic acid 140.98
    dichloromethane 783.62
    cyclohexanone 456.97
    propylene glycol 62.88
    isopropyl acetate 137.39
    DMAc 275.73
    2-ethoxyethanol 145.78
    isopentanol 222.26
    n-heptane 45.47
    ethyl formate 181.16
    1,2-dichloroethane 376.97
    n-hexanol 292.17
    2-methoxyethanol 229.07
    isobutyl acetate 114.35
    tetrachloromethane 201.69
    n-pentyl acetate 180.66
    transcutol 488.21
    n-heptanol 159.62
    ethylbenzene 159.54
    MIBK 145.3
    2-propoxyethanol 277.43
    tert-butanol 309.16
    MTBE 236.15
    2-butoxyethanol 198.91
    propionic acid 183.57
    o-xylene 177.02
    formic acid 35.75
    diethyl ether 204.23
    m-xylene 169.47
    p-xylene 227.78
    chlorobenzene 322.15
    dimethyl carbonate 61.44
    n-octane 24.21
    formamide 66.86
    cyclopentanone 403.07
    2-pentanone 214.33
    anisole 224.86
    cyclopentyl methyl ether 187.66
    gamma-butyrolactone 375.84
    1-methoxy-2-propanol 209.52
    pyridine 568.39
    3-pentanone 166.8
    furfural 405.64
    n-dodecane 21.58
    diethylene glycol 151.32
    diisopropyl ether 72.89
    tert-amyl alcohol 246.67
    acetylacetone 184.77
    n-hexadecane 25.23
    acetophenone 201.86
    methyl propionate 155.33
    isopentyl acetate 273.17
    trichloroethylene 800.47
    n-nonanol 137.18
    cyclohexanol 240.49
    benzyl alcohol 177.8
    2-ethylhexanol 193.19
    isooctanol 130.11
    dipropyl ether 147.99
    1,2-dichlorobenzene 278.16
    ethyl lactate 80.27
    propylene carbonate 259.02
    n-methylformamide 145.52
    2-pentanol 174.06
    n-pentane 44.08
    1-propoxy-2-propanol 244.32
    1-methoxy-2-propyl acetate 197.07
    2-(2-methoxypropoxy) propanol 189.65
    mesitylene 110.95
    ε-caprolactone 359.29
    p-cymene 130.33
    epichlorohydrin 432.86
    1,1,1-trichloroethane 511.82
    2-aminoethanol 91.8
    morpholine-4-carbaldehyde 321.94
    sulfolane 305.47
    2,2,4-trimethylpentane 27.77
    2-methyltetrahydrofuran 370.04
    n-hexyl acetate 254.58
    isooctane 25.42
    2-(2-butoxyethoxy)ethanol 231.08
    sec-butyl acetate 117.06
    tert-butyl acetate 144.88
    decalin 46.73
    glycerin 69.75
    diglyme 373.7
    acrylic acid 135.47
    isopropyl myristate 105.33
    n-butyric acid 261.66
    acetyl acetate 128.88
    di(2-ethylhexyl) phthalate 108.48
    ethyl propionate 129.15
    nitromethane 235.55
    1,2-diethoxyethane 232.59
    benzonitrile 356.42
    trioctyl phosphate 75.38
    1-bromopropane 303.07
    gamma-valerolactone 478.92
    n-decanol 101.36
    triethyl phosphate 93.64
    4-methyl-2-pentanol 113.54
    propionitrile 321.2
    vinylene carbonate 269.32
    1,1,2-trichlorotrifluoroethane 245.44
    DMS 155.28
    cumene 119.41
    2-octanol 124.63
    2-hexanone 191.28
    octyl acetate 128.94
    limonene 161.33
    1,2-dimethoxyethane 273.96
    ethyl orthosilicate 94.32
    tributyl phosphate 86.87
    diacetone alcohol 171.59
    N,N-dimethylaniline 157.16
    acrylonitrile 345.23
    aniline 250.67
    1,3-propanediol 149.23
    bromobenzene 352.91
    dibromomethane 580.18
    1,1,2,2-tetrachloroethane 621.23
    2-methyl-cyclohexyl acetate 163.94
    tetrabutyl urea 110.62
    diisobutyl methanol 112.18
    2-phenylethanol 228.12
    styrene 182.6
    dioctyl adipate 134.87
    dimethyl sulfate 86.49
    ethyl butyrate 181.18
    methyl lactate 79.77
    butyl lactate 135.97
    diethyl carbonate 134.57
    propanediol butyl ether 171.6
    triethyl orthoformate 132.92
    p-tert-butyltoluene 122.14
    methyl 4-tert-butylbenzoate 190.38
    morpholine 506.97
    tert-butylamine 221.41
    n-dodecanol 79.34
    dimethoxymethane 156.12
    ethylene carbonate 209.15
    cyrene 144.87
    2-ethoxyethyl acetate 207.0
    2-ethylhexyl acetate 222.98
    1,2,4-trichlorobenzene 321.09
    4-methylpyridine 509.05
    dibutyl ether 152.46
    2,6-dimethyl-4-heptanol 112.18
    DEF 197.16
    dimethyl isosorbide 279.95
    tetrachloroethylene 384.05
    eugenol 182.08
    triacetin 184.75
    span 80 179.16
    1,4-butanediol 63.04
    1,1-dichloroethane 533.09
    2-methyl-1-pentanol 166.91
    methyl formate 107.94
    2-methyl-1-butanol 208.42
    n-decane 34.37
    butyronitrile 348.95
    3,7-dimethyl-1-octanol 153.59
    1-chlorooctane 121.25
    1-chlorotetradecane 52.51
    n-nonane 32.72
    undecane 26.44
    tert-butylcyclohexane 46.05
    cyclooctane 28.54
    cyclopentanol 234.53
    tetrahydropyran 447.13
    tert-amyl methyl ether 161.19
    2,5,8-trioxanonane 259.3
    1-hexene 149.42
    2-isopropoxyethanol 129.61
    2,2,2-trifluoroethanol 59.8
    methyl butyrate 177.94

    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
Cascarilla 2 8007-06-5 Croton eluteria Bennett, fam. Euphorbiaceae 0.02%
Mentha spicata (Cuba) Chemotype Mentha spicata L., fam. Lamiaceae (Labiatae) 0.1%
Kewda (India) Pandanus fascicularis Lam., var. fascilarris, fam. Pandanaceae 0.15%
Eucalyptus globulus (Spain) 2c mature fruits 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.01%
Eucalyptus citriodora (Rwanda) 8008-48-4 Eucalyptus citriodora Hook. f., fam. Myrtaceae 0.06%
Calamintha nepeta (France) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 0.01%
Thymus migricus (Turkey) Thymus migricus Klokov et Des.-Shost., fam. Lamiaceae (Labiatae) 0.02%