2-Hydroxy-3,5,5-trimethylcyclohex-2-ene-1,4-dione

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  • Identifiers

    CAS number
    35692-98-9

    Molecular formula
    C9H12O3

    SMILES
    CC1=C(C(=O)CC(C1=O)(C)C)O

  • Odor profile

    Sweet 81.28%
    Caramellic 74.24%
    Burnt 53.2%
    Tobacco 41.44%
    Coffee 32.92%
    Woody 32.08%
    Phenolic 32.0%
    Tea 30.68%
    Hay 30.24%
    Nutty 28.16%

    Scent© AI

  • Properties

    XLogP3-AA
    0.9

    Molecular weight
    168.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    321°C

    Flash point est.
    113.84 ˚C

  • Synonyms

    • 2-Cyclohexene-1,4-dione, 2-hydroxy-3,5,5-trimethyl-
    • 35692-98-9
    • 2-Hydroxy-4-oxoisophorone
    • 2-hydroxy-3,5,5-trimethylcyclohex-2-ene-1,4-dione
    • DTXSID40189207
    • 2-Hydroxy-3,5,5-trimethyl-2-cyclohexen-1,4-dione
    • 4-Hydroxy-1,1,3-trimethyl-3-cyclohexen-2,5-dione
    • 3,5,5-Trimethyl-2-hydroxy-2-cyclohexene-1,4-dione
    • SCHEMBL3154825
    • DTXCID30111698
    • NS00029900
    • 3,5,5-trimethyl-2-hydroxy-1,4-cyclohexadion-2-ene
    • 609-164-3

  • Applications

    2-Hydroxy-3,5,5-trimethylcyclohex-2-ene-1,4-dione (CAS 35692-98-9) is a cyclic 1,4-dicarbonyl prone to enolization, commonly employed in research as a Michael acceptor and dienophile for C–C/C–N bond construction, as a precursor in Paal–Knorr-type annulations and ring-expanding condensations to access fused heterocycles, and as a versatile synthon for generating quinonoid frameworks or further functionalized isophorone derivatives; it is also used as an O,O-chelating ligand for metal complexes in catalysis or sensing, as a reference compound to study keto–enol tautomerism, photochemistry, and hydrogen-bonding, and as an R&D feedstock to tune optical properties, rigidity, and electronic polarization in polymer precursors, curing components, and performance materials.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 336.6
    methanol 585.55
    isopropanol 243.58
    water 29.1
    ethyl acetate 181.75
    n-propanol 241.24
    acetone 297.9
    n-butanol 179.93
    acetonitrile 264.94
    DMF 523.13
    toluene 86.27
    isobutanol 155.44
    1,4-dioxane 514.06
    methyl acetate 188.14
    THF 722.48
    2-butanone 181.26
    n-pentanol 136.45
    sec-butanol 177.74
    n-hexane 16.8
    ethylene glycol 177.05
    NMP 279.75
    cyclohexane 10.46
    DMSO 420.84
    n-butyl acetate 105.28
    n-octanol 93.23
    chloroform 349.48
    n-propyl acetate 105.23
    acetic acid 247.89
    dichloromethane 324.94
    cyclohexanone 200.51
    propylene glycol 111.38
    isopropyl acetate 125.49
    DMAc 223.45
    2-ethoxyethanol 285.07
    isopentanol 143.09
    n-heptane 12.41
    ethyl formate 168.52
    1,2-dichloroethane 233.93
    n-hexanol 173.64
    2-methoxyethanol 491.9
    isobutyl acetate 66.91
    tetrachloromethane 81.74
    n-pentyl acetate 82.3
    transcutol 290.42
    n-heptanol 99.28
    ethylbenzene 56.78
    MIBK 147.09
    2-propoxyethanol 321.47
    tert-butanol 298.8
    MTBE 170.89
    2-butoxyethanol 167.17
    propionic acid 144.14
    o-xylene 66.74
    formic acid 282.91
    diethyl ether 213.61
    m-xylene 87.04
    p-xylene 67.16
    chlorobenzene 104.68
    dimethyl carbonate 106.62
    n-octane 7.88
    formamide 286.53
    cyclopentanone 349.16
    2-pentanone 188.78
    anisole 128.23
    cyclopentyl methyl ether 236.88
    gamma-butyrolactone 437.69
    1-methoxy-2-propanol 348.74
    pyridine 178.18
    3-pentanone 127.16
    furfural 308.02
    n-dodecane 6.54
    diethylene glycol 310.81
    diisopropyl ether 72.52
    tert-amyl alcohol 196.52
    acetylacetone 214.61
    n-hexadecane 7.36
    acetophenone 112.73
    methyl propionate 162.04
    isopentyl acetate 93.71
    trichloroethylene 356.85
    n-nonanol 79.92
    cyclohexanol 127.86
    benzyl alcohol 110.93
    2-ethylhexanol 78.26
    isooctanol 76.13
    dipropyl ether 83.36
    1,2-dichlorobenzene 104.96
    ethyl lactate 76.39
    propylene carbonate 180.07
    n-methylformamide 350.46
    2-pentanol 133.68
    n-pentane 16.86
    1-propoxy-2-propanol 175.51
    1-methoxy-2-propyl acetate 130.54
    2-(2-methoxypropoxy) propanol 103.91
    mesitylene 55.99
    ε-caprolactone 190.44
    p-cymene 37.46
    epichlorohydrin 447.8
    1,1,1-trichloroethane 199.36
    2-aminoethanol 201.55
    morpholine-4-carbaldehyde 344.05
    sulfolane 367.55
    2,2,4-trimethylpentane 13.26
    2-methyltetrahydrofuran 324.56
    n-hexyl acetate 119.09
    isooctane 13.86
    2-(2-butoxyethoxy)ethanol 154.63
    sec-butyl acetate 76.85
    tert-butyl acetate 154.01
    decalin 13.16
    glycerin 192.01
    diglyme 268.22
    acrylic acid 139.65
    isopropyl myristate 48.08
    n-butyric acid 171.96
    acetyl acetate 115.94
    di(2-ethylhexyl) phthalate 47.87
    ethyl propionate 104.11
    nitromethane 408.94
    1,2-diethoxyethane 116.04
    benzonitrile 117.53
    trioctyl phosphate 42.85
    1-bromopropane 127.46
    gamma-valerolactone 388.54
    n-decanol 57.47
    triethyl phosphate 48.46
    4-methyl-2-pentanol 92.84
    propionitrile 170.56
    vinylene carbonate 174.92
    1,1,2-trichlorotrifluoroethane 230.92
    DMS 98.12
    cumene 45.27
    2-octanol 70.97
    2-hexanone 114.33
    octyl acetate 63.62
    limonene 46.97
    1,2-dimethoxyethane 350.73
    ethyl orthosilicate 47.04
    tributyl phosphate 43.88
    diacetone alcohol 195.1
    N,N-dimethylaniline 98.34
    acrylonitrile 218.62
    aniline 107.96
    1,3-propanediol 268.86
    bromobenzene 100.28
    dibromomethane 215.33
    1,1,2,2-tetrachloroethane 266.58
    2-methyl-cyclohexyl acetate 68.9
    tetrabutyl urea 56.48
    diisobutyl methanol 54.57
    2-phenylethanol 119.28
    styrene 58.08
    dioctyl adipate 58.28
    dimethyl sulfate 170.93
    ethyl butyrate 81.32
    methyl lactate 107.48
    butyl lactate 70.62
    diethyl carbonate 54.89
    propanediol butyl ether 131.17
    triethyl orthoformate 57.11
    p-tert-butyltoluene 41.98
    methyl 4-tert-butylbenzoate 114.8
    morpholine 452.51
    tert-butylamine 165.64
    n-dodecanol 41.8
    dimethoxymethane 411.04
    ethylene carbonate 144.96
    cyrene 124.25
    2-ethoxyethyl acetate 108.22
    2-ethylhexyl acetate 69.48
    1,2,4-trichlorobenzene 117.38
    4-methylpyridine 177.88
    dibutyl ether 59.66
    2,6-dimethyl-4-heptanol 54.57
    DEF 173.93
    dimethyl isosorbide 186.8
    tetrachloroethylene 203.52
    eugenol 116.75
    triacetin 84.45
    span 80 88.3
    1,4-butanediol 128.58
    1,1-dichloroethane 219.7
    2-methyl-1-pentanol 105.17
    methyl formate 319.91
    2-methyl-1-butanol 132.96
    n-decane 11.28
    butyronitrile 163.63
    3,7-dimethyl-1-octanol 71.79
    1-chlorooctane 49.7
    1-chlorotetradecane 18.67
    n-nonane 10.63
    undecane 8.36
    tert-butylcyclohexane 16.24
    cyclooctane 6.78
    cyclopentanol 178.05
    tetrahydropyran 284.39
    tert-amyl methyl ether 132.09
    2,5,8-trioxanonane 167.65
    1-hexene 57.0
    2-isopropoxyethanol 179.07
    2,2,2-trifluoroethanol 150.53
    methyl butyrate 126.65

    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
Saffron 1 8022-19-3 Crocus sativus L., fam. Iridaceae 1.2%
Saffron 2 8022-19-3 Crocus sativus L., fam. Iridaceae 1.08%