Wyerone epoxide

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  • Identifiers

    CAS number
    60375-16-8

    Molecular formula
    C15H14O5

    SMILES
    CC[C@H]1[C@H](O1)C#CC(=O)C2=CC=C(O2)/C=C/C(=O)OC

    Safety labels

  • Odor profile

    Fragrance
    Roasted 37.75%
    Caramellic 37.71%
    Nutty 30.41%
    Sweet 29.37%
    Meaty 26.07%
    Cooked 24.11%
    Burnt 22.97%
    Odorless 22.36%
    Spicy 22.11%
    Savory 21.87%

     

    Flavor
    Bitter 80.82%
    Odorless 30.4%
    Bland 22.98%
    Very mild 19.84%
    Sweet-like 18.62%
    Taco 18.53%
    Bread crust 18.12%
    Roasted peanuts 18.08%
    Nitrile 17.93%
    Cedarleaf 17.61%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    4.65 (weak acid)

    Molecular weight
    274.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    401°C

    Flash point

    • 168.93 ˚C est.

  • Synonyms

    • Wyerone epoxide
    • ZL3V0KUH5I
    • UNII-ZL3V0KUH5I
    • 2-Propenoic acid, 3-(5-(3-((2R,3S)-3-ethyloxiranyl)-1-oxo-2-propynyl)-2-furanyl)-, methyl ester, (2E)-rel-
    • Methyl (2Z)-3-(5-(3-(3-ethyloxiran-2-yl)prop-2-ynoyl)furan-2-yl)prop-2-enoic acid
    • Methyl (2Z)-3-{5-[3-(3-ethyloxiran-2-yl)prop-2-ynoyl]furan-2-yl}prop-2-enoic acid
    • 2-Propenoic acid, 3-[5-[3-[(2R,3S)-3-ethyloxiranyl]-1-oxo-2-propynyl]-2-furanyl]-, methyl ester, (2E)-rel-
    • RefChem:195082
    • 60375-16-8
    • CHEBI:174604
    • methyl (E)-3-[5-[3-[(2R,3S)-3-ethyloxiran-2-yl]prop-2-ynoyl]uran-2-yl]prop-2-enoate
    • 60375-16-8

  • Applications

    Wyerone epoxide (CAS 60375-16-8) is commonly used as a reactive intermediate in the synthesis of epoxy resins and related polymer systems, including composites. In coatings and inks, it serves as an epoxy-based constituent that helps confer chemical resistance and crosslink density. In industrial adhesives, it is employed to improve adhesion strength and durability of epoxy formulations. In electronics and high-tech applications, it may be used for encapsulation and insulating layers in circuit assemblies. Its use is formulation- and regulation-dependent, and outcomes depend on local regulations and processing limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.23
    methanol 18.01
    isopropanol 4.21
    water 0.03
    ethyl acetate 49.61
    n-propanol 4.91
    acetone 50.64
    n-butanol 4.3
    acetonitrile 48.15
    DMF 56.39
    toluene 13.36
    isobutanol 3.36
    1,4-dioxane 45.65
    methyl acetate 68.7
    THF 72.48
    2-butanone 44.65
    n-pentanol 5.52
    sec-butanol 5.26
    n-hexane 0.22
    ethylene glycol 6.9
    NMP 56.7
    cyclohexane 0.5
    DMSO 93.6
    n-butyl acetate 18.06
    n-octanol 1.78
    chloroform 72.37
    n-propyl acetate 29.21
    acetic acid 37.77
    dichloromethane 133.35
    cyclohexanone 34.53
    propylene glycol 4.44
    isopropyl acetate 27.13
    DMAc 161.26
    2-ethoxyethanol 44.84
    isopentanol 5.98
    n-heptane 0.27
    ethyl formate 17.61
    1,2-dichloroethane 60.28
    n-hexanol 4.17
    2-methoxyethanol 60.06
    isobutyl acetate 16.95
    tetrachloromethane 3.08
    n-pentyl acetate 8.41
    transcutol 125.17
    n-heptanol 2.42
    ethylbenzene 7.56
    MIBK 17.26
    2-propoxyethanol 29.82
    tert-butanol 8.63
    MTBE 15.74
    2-butoxyethanol 15.5
    propionic acid 16.36
    o-xylene 8.64
    formic acid 31.09
    diethyl ether 13.28
    m-xylene 6.65
    p-xylene 11.22
    chlorobenzene 18.85
    dimethyl carbonate 34.47
    n-octane 0.15
    formamide 79.81
    cyclopentanone 51.38
    2-pentanone 23.2
    anisole 34.31
    cyclopentyl methyl ether 19.12
    gamma-butyrolactone 70.85
    1-methoxy-2-propanol 29.79
    pyridine 68.78
    3-pentanone 25.34
    furfural 90.24
    n-dodecane 0.21
    diethylene glycol 36.12
    diisopropyl ether 4.2
    tert-amyl alcohol 9.86
    acetylacetone 77.03
    n-hexadecane 0.25
    acetophenone 42.5
    methyl propionate 41.36
    isopentyl acetate 19.28
    trichloroethylene 155.57
    n-nonanol 2.38
    cyclohexanol 5.96
    benzyl alcohol 23.75
    2-ethylhexanol 3.91
    isooctanol 2.67
    dipropyl ether 6.41
    1,2-dichlorobenzene 21.12
    ethyl lactate 17.75
    propylene carbonate 33.15
    n-methylformamide 31.55
    2-pentanol 3.55
    n-pentane 0.17
    1-propoxy-2-propanol 16.59
    1-methoxy-2-propyl acetate 38.55
    2-(2-methoxypropoxy) propanol 32.99
    mesitylene 3.63
    ε-caprolactone 35.48
    p-cymene 4.53
    epichlorohydrin 127.94
    1,1,1-trichloroethane 32.35
    2-aminoethanol 8.84
    morpholine-4-carbaldehyde 85.26
    sulfolane 75.24
    2,2,4-trimethylpentane 0.39
    2-methyltetrahydrofuran 33.91
    n-hexyl acetate 10.45
    isooctane 0.18
    2-(2-butoxyethoxy)ethanol 33.12
    sec-butyl acetate 22.08
    tert-butyl acetate 32.37
    decalin 0.68
    glycerin 14.59
    diglyme 85.79
    acrylic acid 23.54
    isopropyl myristate 5.89
    n-butyric acid 15.47
    acetyl acetate 47.49
    di(2-ethylhexyl) phthalate 8.95
    ethyl propionate 28.74
    nitromethane 169.04
    1,2-diethoxyethane 28.97
    benzonitrile 26.08
    trioctyl phosphate 4.03
    1-bromopropane 13.17
    gamma-valerolactone 87.14
    n-decanol 2.06
    triethyl phosphate 14.77
    4-methyl-2-pentanol 3.41
    propionitrile 21.77
    vinylene carbonate 33.51
    1,1,2-trichlorotrifluoroethane 80.91
    DMS 35.89
    cumene 5.12
    2-octanol 1.51
    2-hexanone 22.23
    octyl acetate 6.64
    limonene 4.85
    1,2-dimethoxyethane 75.61
    ethyl orthosilicate 12.58
    tributyl phosphate 6.9
    diacetone alcohol 34.18
    N,N-dimethylaniline 20.67
    acrylonitrile 42.6
    aniline 17.84
    1,3-propanediol 12.49
    bromobenzene 22.06
    dibromomethane 45.14
    1,1,2,2-tetrachloroethane 74.71
    2-methyl-cyclohexyl acetate 18.19
    tetrabutyl urea 10.38
    diisobutyl methanol 3.25
    2-phenylethanol 17.71
    styrene 11.14
    dioctyl adipate 13.67
    dimethyl sulfate 60.08
    ethyl butyrate 20.05
    methyl lactate 22.68
    butyl lactate 9.55
    diethyl carbonate 18.81
    propanediol butyl ether 10.98
    triethyl orthoformate 15.49
    p-tert-butyltoluene 3.85
    methyl 4-tert-butylbenzoate 23.78
    morpholine 45.89
    tert-butylamine 3.67
    n-dodecanol 1.74
    dimethoxymethane 57.58
    ethylene carbonate 23.62
    cyrene 39.65
    2-ethoxyethyl acetate 28.15
    2-ethylhexyl acetate 14.83
    1,2,4-trichlorobenzene 33.03
    4-methylpyridine 42.96
    dibutyl ether 4.98
    2,6-dimethyl-4-heptanol 3.25
    DEF 37.7
    dimethyl isosorbide 58.45
    tetrachloroethylene 39.71
    eugenol 25.93
    triacetin 33.72
    span 80 14.51
    1,4-butanediol 6.75
    1,1-dichloroethane 32.97
    2-methyl-1-pentanol 7.95
    methyl formate 31.26
    2-methyl-1-butanol 5.14
    n-decane 0.27
    butyronitrile 12.62
    3,7-dimethyl-1-octanol 3.72
    1-chlorooctane 1.57
    1-chlorotetradecane 1.0
    n-nonane 0.19
    undecane 0.24
    tert-butylcyclohexane 0.53
    cyclooctane 0.21
    cyclopentanol 6.25
    tetrahydropyran 19.32
    tert-amyl methyl ether 14.27
    2,5,8-trioxanonane 67.52
    1-hexene 1.69
    2-isopropoxyethanol 28.26
    2,2,2-trifluoroethanol 21.87
    methyl butyrate 31.01

    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