Oxiranecarboxylic acid, 3-methyl-3-[2-(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenyl]-, methyl ester

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  • Identifiers

    CAS number
    67905-40-2

    Molecular formula
    C16H24O3

    SMILES
    CC1=CCCC(C1C=CC2(C(O2)C(=O)OC)C)(C)C

  • Odor profile

    Fragrance
    Fruity 80.92%
    Woody 58.29%
    Berry 52.28%
    Sweet 43.55%
    Floral 41.85%
    Powdery 36.75%
    Raspberry 34.57%
    Tropical 31.31%
    Dry 30.87%
    Amber 30.84%

     

    Flavor
    Woody 44.85%
    Bitter 37.59%
    Fruity 29.87%
    Floral 26.73%
    Herbal 26.12%
    Wood 25.85%
    Tropical 24.13%
    Sweet 23.86%
    Ionone 22.31%
    Bergamot 21.07%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    6.38 (neutral)

    Molecular weight
    264.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    307°C

    Flash point

    • 130.06 ˚C est.

  • Synonyms

    • 67905-40-2
    • Oxiranecarboxylic acid, 3-methyl-3-[2-(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenyl]-, methyl ester
    • methyl 3-methyl-3-[2-(2,6,6-trimethylcyclohex-2-en-1-yl)ethenyl]oxirane-2-carboxylate
    • prune glycidate
    • DTXSID00867392
    • Methyl 3-methyl-3-(2-(2,6,6-trimethylcyclohex-2-en-1-yl)vinyl)oxirane-2-carboxylate
    • WOCOGWMEEYJGLH-UHFFFAOYSA-N
    • DB-243693

  • Applications

    Chemical name: Oxiranecarboxylic acid, 3-methyl-3-[2-(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenyl]-, methyl ester; CAS 67905-40-2. It is primarily used as a reactive intermediate and monomer in polymer chemistry, particularly as an epoxy-functional monomer for the synthesis of specialty polymers and epoxy resins. In practice it serves as a crosslinking/functional monomer for epoxy resins, coatings, and adhesives, enabling network formation and enhanced chemical resistance. It can also be used as a reactive diluent in epoxy resin formulations to reduce viscosity while participating in the polymerization. Additionally, it is an intermediate for the synthesis of terpenoid-containing polymers to tailor properties such as hydrophobicity and flexibility, and it finds application in electronics encapsulation/potting materials where epoxy functionality provides adhesion and dielectric performance.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 214.9
    methanol 164.59
    isopropanol 134.22
    water 0.06
    ethyl acetate 226.03
    n-propanol 145.38
    acetone 142.17
    n-butanol 132.94
    acetonitrile 106.6
    DMF 134.37
    toluene 151.49
    isobutanol 96.89
    1,4-dioxane 364.49
    methyl acetate 150.37
    THF 520.4
    2-butanone 154.55
    n-pentanol 96.26
    sec-butanol 109.1
    n-hexane 5.21
    ethylene glycol 22.88
    NMP 132.75
    cyclohexane 14.69
    DMSO 91.99
    n-butyl acetate 122.55
    n-octanol 36.93
    chloroform 540.4
    n-propyl acetate 110.96
    acetic acid 129.58
    dichloromethane 406.87
    cyclohexanone 187.2
    propylene glycol 56.94
    isopropyl acetate 148.01
    DMAc 163.82
    2-ethoxyethanol 189.5
    isopentanol 111.11
    n-heptane 4.52
    ethyl formate 81.11
    1,2-dichloroethane 193.2
    n-hexanol 108.02
    2-methoxyethanol 301.26
    isobutyl acetate 91.84
    tetrachloromethane 42.42
    n-pentyl acetate 73.1
    transcutol 645.7
    n-heptanol 45.59
    ethylbenzene 61.17
    MIBK 116.03
    2-propoxyethanol 249.7
    tert-butanol 151.69
    MTBE 157.37
    2-butoxyethanol 122.02
    propionic acid 76.35
    o-xylene 70.27
    formic acid 49.84
    diethyl ether 158.82
    m-xylene 94.83
    p-xylene 77.84
    chlorobenzene 134.61
    dimethyl carbonate 65.73
    n-octane 2.1
    formamide 84.03
    cyclopentanone 203.93
    2-pentanone 146.58
    anisole 138.85
    cyclopentyl methyl ether 184.78
    gamma-butyrolactone 188.07
    1-methoxy-2-propanol 237.72
    pyridine 240.9
    3-pentanone 106.82
    furfural 184.54
    n-dodecane 2.15
    diethylene glycol 187.57
    diisopropyl ether 50.4
    tert-amyl alcohol 113.93
    acetylacetone 174.86
    n-hexadecane 2.56
    acetophenone 114.49
    methyl propionate 147.66
    isopentyl acetate 131.36
    trichloroethylene 396.2
    n-nonanol 37.66
    cyclohexanol 103.58
    benzyl alcohol 105.95
    2-ethylhexanol 60.0
    isooctanol 41.36
    dipropyl ether 57.23
    1,2-dichlorobenzene 114.88
    ethyl lactate 64.35
    propylene carbonate 124.72
    n-methylformamide 76.45
    2-pentanol 88.95
    n-pentane 6.3
    1-propoxy-2-propanol 160.81
    1-methoxy-2-propyl acetate 200.97
    2-(2-methoxypropoxy) propanol 135.73
    mesitylene 51.23
    ε-caprolactone 184.07
    p-cymene 39.28
    epichlorohydrin 332.05
    1,1,1-trichloroethane 189.48
    2-aminoethanol 75.66
    morpholine-4-carbaldehyde 237.37
    sulfolane 143.84
    2,2,4-trimethylpentane 6.96
    2-methyltetrahydrofuran 276.97
    n-hexyl acetate 97.65
    isooctane 6.17
    2-(2-butoxyethoxy)ethanol 187.83
    sec-butyl acetate 100.63
    tert-butyl acetate 148.49
    decalin 10.05
    glycerin 70.88
    diglyme 292.81
    acrylic acid 59.29
    isopropyl myristate 40.04
    n-butyric acid 135.67
    acetyl acetate 135.11
    di(2-ethylhexyl) phthalate 47.88
    ethyl propionate 98.56
    nitromethane 162.9
    1,2-diethoxyethane 167.04
    benzonitrile 106.66
    trioctyl phosphate 29.52
    1-bromopropane 118.32
    gamma-valerolactone 293.29
    n-decanol 27.43
    triethyl phosphate 49.6
    4-methyl-2-pentanol 64.45
    propionitrile 96.64
    vinylene carbonate 112.89
    1,1,2-trichlorotrifluoroethane 203.97
    DMS 106.36
    cumene 42.7
    2-octanol 29.61
    2-hexanone 103.06
    octyl acetate 48.3
    limonene 46.56
    1,2-dimethoxyethane 236.59
    ethyl orthosilicate 52.04
    tributyl phosphate 36.91
    diacetone alcohol 157.86
    N,N-dimethylaniline 85.36
    acrylonitrile 99.74
    aniline 137.71
    1,3-propanediol 129.6
    bromobenzene 148.48
    dibromomethane 242.47
    1,1,2,2-tetrachloroethane 305.39
    2-methyl-cyclohexyl acetate 91.9
    tetrabutyl urea 45.52
    diisobutyl methanol 39.07
    2-phenylethanol 134.21
    styrene 70.22
    dioctyl adipate 62.06
    dimethyl sulfate 66.15
    ethyl butyrate 89.98
    methyl lactate 76.64
    butyl lactate 70.59
    diethyl carbonate 65.05
    propanediol butyl ether 108.49
    triethyl orthoformate 73.32
    p-tert-butyltoluene 39.61
    methyl 4-tert-butylbenzoate 91.02
    morpholine 432.48
    tert-butylamine 81.76
    n-dodecanol 20.39
    dimethoxymethane 222.55
    ethylene carbonate 101.56
    cyrene 126.0
    2-ethoxyethyl acetate 148.09
    2-ethylhexyl acetate 104.15
    1,2,4-trichlorobenzene 141.46
    4-methylpyridine 219.45
    dibutyl ether 41.88
    2,6-dimethyl-4-heptanol 39.07
    DEF 129.27
    dimethyl isosorbide 208.78
    tetrachloroethylene 167.46
    eugenol 96.42
    triacetin 117.42
    span 80 102.5
    1,4-butanediol 50.59
    1,1-dichloroethane 213.94
    2-methyl-1-pentanol 91.83
    methyl formate 54.24
    2-methyl-1-butanol 96.95
    n-decane 3.6
    butyronitrile 113.66
    3,7-dimethyl-1-octanol 49.35
    1-chlorooctane 23.57
    1-chlorotetradecane 9.48
    n-nonane 2.95
    undecane 2.7
    tert-butylcyclohexane 9.11
    cyclooctane 4.88
    cyclopentanol 99.88
    tetrahydropyran 279.61
    tert-amyl methyl ether 103.4
    2,5,8-trioxanonane 194.98
    1-hexene 28.06
    2-isopropoxyethanol 142.82
    2,2,2-trifluoroethanol 38.84
    methyl butyrate 110.2

    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