4-Hydroxy-3,5,5-Trimethylcyclohex-2-Enone

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  • Identifiers

    CAS number
    14203-59-9

    Molecular formula
    C9H14O2

    SMILES
    CC1=CC(=O)CC(C1O)(C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Sweet 74.75%
    Woody 62.01%
    Mint 54.29%
    Camphoreous 50.68%
    Tobacco 46.07%
    Herbal 44.49%
    Tea 37.72%
    Spicy 37.26%
    Musty 36.69%
    Caramellic 35.46%

    Scent© AI

  • Properties

    XLogP3-AA
    0.5

    Molecular weight
    154.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    266°C

    Flash point est.
    101.43 ˚C

  • Synonyms

    • 4-Hydroxy-3,5,5-trimethylcyclohex-2-enone
    • 14203-59-9
    • 4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one
    • CHEMBL463102
    • 4-hydroxyisophorone
    • 4-Hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one
    • SCHEMBL6557553
    • BDBM50250532
    • 3,5,5-Trimethyl-4-hydroxycyclohexan-1-on-2-ene
    • 4-Hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one #
    • 81238-64-4

  • Applications

    4-Hydroxy-3,5,5-trimethylcyclohex-2-enone (4-hydroxyisophorone) is a reactive beta-hydroxy enone widely used as a versatile intermediate to: (i) make cycloaliphatic (meth)acrylate, carbonate, or urethane derivatives for UV/EB-curable coatings, adhesives, inks, and 3D-printing resins, imparting hardness, low yellowing, and weatherability; (ii) prepare flavor and fragrance ingredients, notably as a precursor to 4-oxoisophorone and ionone/damascone-type norisoprenoids with woody/tea/tobacco notes; and (iii) build pharmaceutical and agrochemical scaffolds via Michael/aldol reactions, O-acylation, and cyclizations to access bicyclics and heterocycles; it is also used as a model substrate in catalytic and biocatalytic studies of conjugate addition, selective enone reduction, and asymmetric transformations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 537.22
    methanol 866.86
    isopropanol 313.44
    water 15.18
    ethyl acetate 220.66
    n-propanol 351.91
    acetone 244.02
    n-butanol 287.67
    acetonitrile 300.39
    DMF 337.55
    toluene 89.51
    isobutanol 208.66
    1,4-dioxane 454.32
    methyl acetate 207.51
    THF 671.47
    2-butanone 189.33
    n-pentanol 169.61
    sec-butanol 219.97
    n-hexane 26.14
    ethylene glycol 140.02
    NMP 271.31
    cyclohexane 21.65
    DMSO 227.49
    n-butyl acetate 157.09
    n-octanol 122.72
    chloroform 404.57
    n-propyl acetate 120.06
    acetic acid 425.21
    dichloromethane 305.25
    cyclohexanone 230.8
    propylene glycol 127.45
    isopropyl acetate 146.15
    DMAc 197.21
    2-ethoxyethanol 265.31
    isopentanol 204.18
    n-heptane 22.49
    ethyl formate 183.15
    1,2-dichloroethane 179.33
    n-hexanol 275.37
    2-methoxyethanol 495.13
    isobutyl acetate 84.42
    tetrachloromethane 81.61
    n-pentyl acetate 99.45
    transcutol 582.84
    n-heptanol 118.74
    ethylbenzene 55.09
    MIBK 139.07
    2-propoxyethanol 397.51
    tert-butanol 345.87
    MTBE 211.11
    2-butoxyethanol 189.74
    propionic acid 227.15
    o-xylene 69.16
    formic acid 335.01
    diethyl ether 259.25
    m-xylene 91.22
    p-xylene 70.48
    chlorobenzene 111.08
    dimethyl carbonate 83.82
    n-octane 9.63
    formamide 278.51
    cyclopentanone 310.02
    2-pentanone 183.89
    anisole 131.24
    cyclopentyl methyl ether 246.24
    gamma-butyrolactone 397.8
    1-methoxy-2-propanol 329.88
    pyridine 189.63
    3-pentanone 123.48
    furfural 292.84
    n-dodecane 8.04
    diethylene glycol 315.59
    diisopropyl ether 85.12
    tert-amyl alcohol 230.15
    acetylacetone 181.62
    n-hexadecane 8.93
    acetophenone 106.74
    methyl propionate 153.05
    isopentyl acetate 138.42
    trichloroethylene 313.31
    n-nonanol 100.55
    cyclohexanol 166.15
    benzyl alcohol 102.88
    2-ethylhexanol 118.48
    isooctanol 86.9
    dipropyl ether 125.18
    1,2-dichlorobenzene 107.09
    ethyl lactate 78.04
    propylene carbonate 200.09
    n-methylformamide 281.81
    2-pentanol 176.74
    n-pentane 28.86
    1-propoxy-2-propanol 227.85
    1-methoxy-2-propyl acetate 174.41
    2-(2-methoxypropoxy) propanol 140.19
    mesitylene 58.36
    ε-caprolactone 222.65
    p-cymene 47.95
    epichlorohydrin 371.48
    1,1,1-trichloroethane 200.95
    2-aminoethanol 240.68
    morpholine-4-carbaldehyde 316.07
    sulfolane 297.26
    2,2,4-trimethylpentane 17.56
    2-methyltetrahydrofuran 347.58
    n-hexyl acetate 149.45
    isooctane 18.1
    2-(2-butoxyethoxy)ethanol 202.81
    sec-butyl acetate 93.84
    tert-butyl acetate 174.54
    decalin 16.8
    glycerin 181.72
    diglyme 314.31
    acrylic acid 199.16
    isopropyl myristate 59.86
    n-butyric acid 261.1
    acetyl acetate 142.78
    di(2-ethylhexyl) phthalate 58.58
    ethyl propionate 110.35
    nitromethane 442.49
    1,2-diethoxyethane 171.55
    benzonitrile 129.41
    trioctyl phosphate 49.72
    1-bromopropane 138.03
    gamma-valerolactone 371.91
    n-decanol 71.64
    triethyl phosphate 57.97
    4-methyl-2-pentanol 118.64
    propionitrile 218.4
    vinylene carbonate 181.75
    1,1,2-trichlorotrifluoroethane 233.41
    DMS 113.36
    cumene 47.5
    2-octanol 77.75
    2-hexanone 118.82
    octyl acetate 75.1
    limonene 66.56
    1,2-dimethoxyethane 326.74
    ethyl orthosilicate 58.98
    tributyl phosphate 57.84
    diacetone alcohol 194.55
    N,N-dimethylaniline 89.84
    acrylonitrile 214.71
    aniline 121.06
    1,3-propanediol 293.07
    bromobenzene 98.12
    dibromomethane 210.27
    1,1,2,2-tetrachloroethane 246.0
    2-methyl-cyclohexyl acetate 94.55
    tetrabutyl urea 64.24
    diisobutyl methanol 71.55
    2-phenylethanol 136.39
    styrene 57.73
    dioctyl adipate 74.66
    dimethyl sulfate 114.9
    ethyl butyrate 112.74
    methyl lactate 99.59
    butyl lactate 85.94
    diethyl carbonate 77.2
    propanediol butyl ether 161.92
    triethyl orthoformate 81.22
    p-tert-butyltoluene 50.13
    methyl 4-tert-butylbenzoate 118.21
    morpholine 455.25
    tert-butylamine 218.35
    n-dodecanol 51.25
    dimethoxymethane 289.02
    ethylene carbonate 157.48
    cyrene 127.29
    2-ethoxyethyl acetate 136.26
    2-ethylhexyl acetate 103.01
    1,2,4-trichlorobenzene 120.1
    4-methylpyridine 187.64
    dibutyl ether 88.12
    2,6-dimethyl-4-heptanol 71.55
    DEF 169.42
    dimethyl isosorbide 212.91
    tetrachloroethylene 179.77
    eugenol 116.9
    triacetin 114.38
    span 80 119.08
    1,4-butanediol 114.52
    1,1-dichloroethane 213.49
    2-methyl-1-pentanol 130.32
    methyl formate 235.31
    2-methyl-1-butanol 179.83
    n-decane 14.76
    butyronitrile 221.47
    3,7-dimethyl-1-octanol 103.69
    1-chlorooctane 59.17
    1-chlorotetradecane 22.52
    n-nonane 14.11
    undecane 10.48
    tert-butylcyclohexane 19.6
    cyclooctane 11.14
    cyclopentanol 197.02
    tetrahydropyran 335.93
    tert-amyl methyl ether 155.04
    2,5,8-trioxanonane 209.15
    1-hexene 83.4
    2-isopropoxyethanol 172.99
    2,2,2-trifluoroethanol 176.32
    methyl butyrate 130.73

    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 6.0%
Saffron 2 8022-19-3 Crocus sativus L., fam. Iridaceae 0.22%