2-Hydroxy-3-isopropyl-6-methylcyclohex-2-enone

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  • Identifiers

    CAS number
    54783-36-7

    Molecular formula
    C10H16O2

    SMILES
    CC1CCC(=C(C1=O)O)C(C)C

    Retention indicies (RI)

    • Carbowax: 1748.0

  • Odor profile

    Sweet 58.93%
    Caramellic 58.25%
    Mint 48.14%
    Burnt 41.6%
    Phenolic 37.72%
    Herbal 35.73%
    Camphoreous 33.37%
    Woody 29.8%
    Spicy 29.73%
    Tobacco 25.78%

    Scent© AI

  • Properties

    XLogP3-AA
    2.0

    Molecular weight
    168.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    287°C

    Melting point expt.

    • 34.5 °C

    Flash point est.
    114.44 ˚C

  • Synonyms

    • 54783-36-7
    • 2-Hydroxy-3-(isopropyl)-6-methylcyclohex-2-en-1-one
    • gamma-Diosphenol
    • 2-Cyclohexen-1-one, 2-hydroxy-6-methyl-3-(1-methylethyl)-
    • 2-hydroxy-6-methyl-3-propan-2-ylcyclohex-2-en-1-one
    • Pseudodiosphenol
    • EINECS 259-345-2
    • 2-Hydroxy-3-isopropyl-6-methylcyclohex-2-enone
    • ISODIOSPHENOL
    • V71N032XUM
    • .PSI.-DIOSPHENOL
    • psi-Diosphenol
    • UNII-V71N032XUM
    • y-Diosphenol
    • 2-Hydroxy-3-isopropyl-6-methyl-2-cyclohexen-1-one
    • 3-hydroxy-p-menth-3-en-2-one
    • CHEBI:190869
    • DB-293114
    • NS00033197
    • G83816
    • 2-Hydroxy-3-isopropyl-6-methyl-2-cyclohexen-1-one #
    • Q27291615
    • 2-hydroxy-6-methyl-3-(propan-2-yl)cyclohex-2-en-1-one
    • 2-Hydroxy-6-methyl-3-(1-methylethyl)-2-Cyclohexen-1-one
    • 2-Hydroxy-6-methyl-3-(1-methylethyl)-2-cyclohexen-1-one, 9CI

  • Applications

    2-Hydroxy-3-isopropyl-6-methylcyclohex-2-enone (CAS 54783-36-7) is a cyclic enone with an enolic hydroxyl that enables rich reactivity, making it a versatile building block in fine organic synthesis; its conjugated cyclohexenone core and chelating enol form allow it to function as a Michael acceptor, a precursor in aldol/cyclization sequences, and a platform for heterocycle construction, so it is explored as an intermediate toward terpenoid-inspired fragrances and flavors, pharmaceutical and agrochemical leads, and enaminone or bicyclic derivatives; it is also studied as a ligand/ligand precursor for metal complexation in catalysis and functional materials, as a reference compound for probing keto–enol tautomerism, stereochemistry, and enone reaction kinetics, and as a scaffold to tune hydrophobicity and reactivity in selective grafting onto polymers or surfaces.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 264.9
    methanol 299.41
    isopropanol 273.34
    water 1.99
    ethyl acetate 102.49
    n-propanol 210.04
    acetone 202.76
    n-butanol 189.29
    acetonitrile 244.18
    DMF 292.27
    toluene 83.98
    isobutanol 159.2
    1,4-dioxane 439.31
    methyl acetate 170.61
    THF 393.71
    2-butanone 178.01
    n-pentanol 145.3
    sec-butanol 188.8
    n-hexane 12.71
    ethylene glycol 44.71
    NMP 236.15
    cyclohexane 27.75
    DMSO 194.88
    n-butyl acetate 159.94
    n-octanol 114.22
    chloroform 637.44
    n-propyl acetate 104.05
    acetic acid 185.69
    dichloromethane 523.56
    cyclohexanone 268.95
    propylene glycol 52.05
    isopropyl acetate 75.74
    DMAc 181.4
    2-ethoxyethanol 149.14
    isopentanol 144.31
    n-heptane 13.43
    ethyl formate 148.13
    1,2-dichloroethane 268.25
    n-hexanol 176.87
    2-methoxyethanol 221.91
    isobutyl acetate 72.35
    tetrachloromethane 111.46
    n-pentyl acetate 124.84
    transcutol 306.75
    n-heptanol 119.56
    ethylbenzene 68.85
    MIBK 85.69
    2-propoxyethanol 202.36
    tert-butanol 241.07
    MTBE 130.96
    2-butoxyethanol 160.06
    propionic acid 149.67
    o-xylene 69.14
    formic acid 84.01
    diethyl ether 121.12
    m-xylene 71.62
    p-xylene 92.72
    chlorobenzene 162.09
    dimethyl carbonate 39.54
    n-octane 10.42
    formamide 137.04
    cyclopentanone 285.76
    2-pentanone 112.78
    anisole 113.19
    cyclopentyl methyl ether 111.46
    gamma-butyrolactone 343.2
    1-methoxy-2-propanol 153.69
    pyridine 298.47
    3-pentanone 78.97
    furfural 307.17
    n-dodecane 9.59
    diethylene glycol 148.92
    diisopropyl ether 38.01
    tert-amyl alcohol 163.85
    acetylacetone 118.08
    n-hexadecane 11.22
    acetophenone 112.73
    methyl propionate 80.73
    isopentyl acetate 142.97
    trichloroethylene 531.4
    n-nonanol 97.01
    cyclohexanol 149.51
    benzyl alcohol 116.29
    2-ethylhexanol 99.88
    isooctanol 94.06
    dipropyl ether 67.96
    1,2-dichlorobenzene 155.04
    ethyl lactate 57.05
    propylene carbonate 191.35
    n-methylformamide 178.95
    2-pentanol 110.69
    n-pentane 13.19
    1-propoxy-2-propanol 153.64
    1-methoxy-2-propyl acetate 108.73
    2-(2-methoxypropoxy) propanol 115.98
    mesitylene 53.69
    ε-caprolactone 222.16
    p-cymene 59.6
    epichlorohydrin 343.0
    1,1,1-trichloroethane 258.98
    2-aminoethanol 97.11
    morpholine-4-carbaldehyde 237.89
    sulfolane 306.96
    2,2,4-trimethylpentane 11.62
    2-methyltetrahydrofuran 236.41
    n-hexyl acetate 155.37
    isooctane 10.91
    2-(2-butoxyethoxy)ethanol 162.9
    sec-butyl acetate 65.33
    tert-butyl acetate 86.86
    decalin 17.33
    glycerin 70.64
    diglyme 263.73
    acrylic acid 132.19
    isopropyl myristate 59.11
    n-butyric acid 189.01
    acetyl acetate 69.98
    di(2-ethylhexyl) phthalate 66.37
    ethyl propionate 70.83
    nitromethane 275.53
    1,2-diethoxyethane 133.56
    benzonitrile 188.92
    trioctyl phosphate 53.72
    1-bromopropane 146.05
    gamma-valerolactone 345.62
    n-decanol 72.22
    triethyl phosphate 51.52
    4-methyl-2-pentanol 72.87
    propionitrile 186.23
    vinylene carbonate 204.08
    1,1,2-trichlorotrifluoroethane 198.16
    DMS 87.58
    cumene 56.24
    2-octanol 88.51
    2-hexanone 112.97
    octyl acetate 78.19
    limonene 72.89
    1,2-dimethoxyethane 232.94
    ethyl orthosilicate 51.87
    tributyl phosphate 52.96
    diacetone alcohol 115.02
    N,N-dimethylaniline 79.44
    acrylonitrile 236.56
    aniline 120.71
    1,3-propanediol 162.16
    bromobenzene 158.62
    dibromomethane 350.44
    1,1,2,2-tetrachloroethane 370.84
    2-methyl-cyclohexyl acetate 90.37
    tetrabutyl urea 68.68
    diisobutyl methanol 64.93
    2-phenylethanol 139.38
    styrene 75.39
    dioctyl adipate 77.05
    dimethyl sulfate 67.32
    ethyl butyrate 89.52
    methyl lactate 54.24
    butyl lactate 92.8
    diethyl carbonate 69.73
    propanediol butyl ether 133.65
    triethyl orthoformate 69.16
    p-tert-butyltoluene 56.91
    methyl 4-tert-butylbenzoate 119.67
    morpholine 388.78
    tert-butylamine 145.81
    n-dodecanol 52.95
    dimethoxymethane 138.05
    ethylene carbonate 161.24
    cyrene 111.25
    2-ethoxyethyl acetate 130.39
    2-ethylhexyl acetate 109.38
    1,2,4-trichlorobenzene 172.16
    4-methylpyridine 235.19
    dibutyl ether 76.75
    2,6-dimethyl-4-heptanol 64.93
    DEF 109.08
    dimethyl isosorbide 179.67
    tetrachloroethylene 271.61
    eugenol 119.96
    triacetin 108.74
    span 80 111.39
    1,4-butanediol 74.83
    1,1-dichloroethane 284.19
    2-methyl-1-pentanol 119.58
    methyl formate 152.34
    2-methyl-1-butanol 127.78
    n-decane 16.27
    butyronitrile 196.88
    3,7-dimethyl-1-octanol 88.9
    1-chlorooctane 70.09
    1-chlorotetradecane 26.99
    n-nonane 14.71
    undecane 12.36
    tert-butylcyclohexane 17.03
    cyclooctane 8.6
    cyclopentanol 165.39
    tetrahydropyran 286.49
    tert-amyl methyl ether 81.93
    2,5,8-trioxanonane 182.89
    1-hexene 52.75
    2-isopropoxyethanol 110.66
    2,2,2-trifluoroethanol 78.38
    methyl butyrate 109.84

    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
Blackcurrant bud 1 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.1%
Buchu leaf (South Africa) 1a 84649-93-4 Agathosma betulina (Berg.) Pillans (Barosma betulina Bertl.), fam. Rutacea 18.58%
Buchu leaf (South Africa) 1c (hybrid) 84649-93-4 Agathosma betulina x crenulata, fam. Rutaceae 0.22%
Buchu leaf (South Africa) 2 84649-93-4 Agathosma betulina (Berg.) Pillans (Barosma betulina Bertl.), fam. Rutacea 13.2%