Limonene diepoxide

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  • Identifiers

    CAS number
    96-08-2

    Molecular formula
    C10H16O2

    SMILES
    CC12CCC(CC1O2)C3(CO3)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 2059.0

  • Odor profile

    Green 53.24%
    Fresh 51.84%
    Herbal 51.02%
    Woody 49.02%
    Mint 45.75%
    Sweet 36.82%
    Camphoreous 36.16%
    Earthy 35.65%
    Cooling 34.0%
    Floral 31.58%

    Scent© AI

  • Properties

    XLogP3-AA
    1.1

    pKa est.
    6.3 (neutral)

    Molecular weight
    168.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Melting point expt.

    • FREEZING POINT: -100 °C

    Boiling point

    • 242 °C

    Flash point est.
    108.1 ˚C

    Flash point expt.

    • 118 °C
    • 118 °C OC

    Solubility expt.

    • SLIGHTLY SOL IN WATER; MISCIBLE WITH METHANOL AND BENZENE; MISCIBLE WITH CARBON TETRACHLORIDE AND HEXANE

  • Synonyms

    • Limonene dioxide
    • 96-08-2
    • Limonene diepoxide
    • Dipentene dioxide
    • Dipentene oxide
    • 1-Methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
    • Dipentene diepoxide
    • Unox epoxide 269
    • Unox 269
    • Epoxide 269
    • Unoxat epoxide 269
    • diepoxylimonene
    • 1,2,8,9-Diepoxylimonene
    • p-Menthane, 1,2:8,9-diepoxy-
    • Menthane, 1,2:8,9-diepoxy-
    • .alpha.-Limonene diepoxide
    • 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
    • 1,2:8,9-DIEPOXY-P-MENTHANE
    • M6TUW5WEJ9
    • NSC 30545
    • 1-Methyl-4-(2-methyloxiranyl)-7-oxabicyclo(4.1.0)heptane
    • 1-METHYL-4-(2-METHYLOXIRANYL)-7-OXABICYCLO[4.1.0]HEPTANE
    • HSDB 5298
    • EINECS 202-475-1
    • NSC-30545
    • NSC-54753
    • 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(2-methyloxiranyl)-
    • BRN 0107989
    • AI3-26044
    • MLS002639331
    • 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(2-methyloxiranyl)-
    • 4-(1,2-Epoxy-1-methylethyl)-1-methyl-7-oxabicyclo(4.1.0)heptane
    • 5-19-01-00324 (Beilstein Handbook Reference)
    • 7-Oxabicyclo(4.1.0)heptane, 4-(1,2-epoxy-1-methylethyl)-1-methyl-
    • 1,9-Diepoxylimonene
    • LIMONENE 1,2:8,9-DIEPOXIDE
    • 1,9-Diepoxy-p-menthane
    • 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(2-methyl-2-oxiranyl)-
    • 1,2:8,9-DIEPOXY-P-MENTHANE [HSDB]
    • Menthane,2:8,9-diepoxy-
    • p-Menthane,2:8,9-diepoxy-
    • 1,2-EPOXY-1-METHYL-4-(1-METHYLEPOXYETHYL)CYCLOHEXANE
    • 1,2-EPOXY-4-(2-METHYLOXIRANYL)-1-METHYLCYCLOHEXANE
    • WLN: T36 BOTJ A1 E- BT3OTJ B1
    • UNII-M6TUW5WEJ9
    • 1-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo(4.1.0)heptane
    • 7-Oxabicyclo[4.1.0]heptane,2-epoxy-1-methylethyl)-1-methyl-
    • 4-(1,2-Epoxy-1-methylethyl)-1-methyl-7-oxabicyclo[4.1.0]heptane
    • 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(2-methyl-2-oxiranyl)-
    • alpha-Limonene diepoxide
    • 1,2,8,9Diepoxylimonene
    • 1,2:8,9Diepoxypmenthane
    • 1,2:8,9-Diepoxylimonene
    • Menthane, 1,2:8,9diepoxy
    • pMenthane, 1,2:8,9diepoxy
    • SCHEMBL215026
    • ( not+/-)-Limonene diepoxide
    • 1,2,8,9-diepoxy-p-menthane
    • CHEMBL1880461
    • NSC30545
    • NSC54753
    • MFCD00022353
    • AKOS006272591
    • FM106422
    • NCI60_002581
    • SMR001548776
    • DB-301487
    • G77464
    • 1Methyl4(2methyloxiranyl)7oxabicyclo(4.1.0)heptane
    • Q27283565
    • 7Oxabicyclo(4.1.0)heptane, 1methyl4(2methyloxiranyl)
    • 4(1,2Epoxy1methylethyl)1methyl7oxabicyclo(4.1.0)heptane
    • 7-Oxabicyclo4.1.0heptane, 1-methyl-4-(2-methyloxiranyl)-
    • 7Oxabicyclo(4.1.0)heptane, 4(1,2epoxy1methylethyl)1methyl
    • 1-Methyl-4-(2-methyl-2-oxiranyl)-7-oxabicyclo[4.1.0]heptane #
    • 202-475-1

  • Applications

    Limonene diepoxide (CAS 96-08-2) is a bio-based difunctional epoxy monomer employed as a reactive diluent and comonomer in epoxy resins to build mechanically robust, chemically resistant, corrosion-resistant thermoset networks for coatings, inks, adhesives and sealants, electronics encapsulation, and 3D-printing resins; it performs well in cationic UV/EB-curable systems due to its strained epoxide rings and low volatility, lowering VOCs; it is also used as a building block in ring-opening polymerizations (to make polyethers and polyols), as a precursor to cyclic carbonates via CO2 fixation for non-isocyanate polyurethane synthesis, and as a grafting/surface-activation agent for cellulose, lignin, silica, or nanoparticles to enhance adhesion and compatibilization in sustainable fiber-reinforced composites.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 139.43
    methanol 172.99
    isopropanol 94.82
    water 3.25
    ethyl acetate 132.38
    n-propanol 100.34
    acetone 106.4
    n-butanol 92.36
    acetonitrile 198.8
    DMF 99.37
    toluene 85.15
    isobutanol 67.37
    1,4-dioxane 318.57
    methyl acetate 136.53
    THF 243.07
    2-butanone 96.18
    n-pentanol 59.03
    sec-butanol 60.5
    n-hexane 4.99
    ethylene glycol 49.81
    NMP 74.12
    cyclohexane 16.85
    DMSO 93.94
    n-butyl acetate 82.14
    n-octanol 40.38
    chloroform 438.52
    n-propyl acetate 69.11
    acetic acid 131.0
    dichloromethane 335.18
    cyclohexanone 119.9
    propylene glycol 54.9
    isopropyl acetate 78.63
    DMAc 108.88
    2-ethoxyethanol 128.16
    isopentanol 71.89
    n-heptane 7.11
    ethyl formate 96.71
    1,2-dichloroethane 126.4
    n-hexanol 74.57
    2-methoxyethanol 209.27
    isobutyl acetate 51.4
    tetrachloromethane 56.32
    n-pentyl acetate 49.2
    transcutol 424.61
    n-heptanol 39.77
    ethylbenzene 40.53
    MIBK 55.79
    2-propoxyethanol 164.17
    tert-butanol 84.76
    MTBE 65.04
    2-butoxyethanol 92.44
    propionic acid 88.5
    o-xylene 51.38
    formic acid 93.68
    diethyl ether 86.39
    m-xylene 53.85
    p-xylene 59.43
    chlorobenzene 97.24
    dimethyl carbonate 55.72
    n-octane 3.34
    formamide 139.07
    cyclopentanone 120.39
    2-pentanone 74.49
    anisole 93.17
    cyclopentyl methyl ether 82.52
    gamma-butyrolactone 148.88
    1-methoxy-2-propanol 134.66
    pyridine 216.34
    3-pentanone 60.45
    furfural 175.89
    n-dodecane 3.97
    diethylene glycol 149.93
    diisopropyl ether 28.42
    tert-amyl alcohol 53.36
    acetylacetone 105.93
    n-hexadecane 4.65
    acetophenone 84.83
    methyl propionate 88.01
    isopentyl acetate 75.33
    trichloroethylene 257.48
    n-nonanol 38.75
    cyclohexanol 69.33
    benzyl alcohol 82.93
    2-ethylhexanol 41.74
    isooctanol 30.7
    dipropyl ether 49.86
    1,2-dichlorobenzene 85.03
    ethyl lactate 45.12
    propylene carbonate 100.36
    n-methylformamide 98.04
    2-pentanol 49.61
    n-pentane 7.63
    1-propoxy-2-propanol 104.61
    1-methoxy-2-propyl acetate 117.27
    2-(2-methoxypropoxy) propanol 94.07
    mesitylene 32.53
    ε-caprolactone 116.56
    p-cymene 30.34
    epichlorohydrin 181.27
    1,1,1-trichloroethane 127.8
    2-aminoethanol 81.7
    morpholine-4-carbaldehyde 167.54
    sulfolane 96.13
    2,2,4-trimethylpentane 4.97
    2-methyltetrahydrofuran 128.63
    n-hexyl acetate 69.44
    isooctane 4.55
    2-(2-butoxyethoxy)ethanol 133.64
    sec-butyl acetate 53.32
    tert-butyl acetate 67.9
    decalin 8.75
    glycerin 75.61
    diglyme 237.29
    acrylic acid 80.97
    isopropyl myristate 33.16
    n-butyric acid 108.36
    acetyl acetate 112.94
    di(2-ethylhexyl) phthalate 37.39
    ethyl propionate 64.01
    nitromethane 191.62
    1,2-diethoxyethane 119.98
    benzonitrile 112.63
    trioctyl phosphate 25.45
    1-bromopropane 70.09
    gamma-valerolactone 204.22
    n-decanol 28.61
    triethyl phosphate 39.54
    4-methyl-2-pentanol 38.8
    propionitrile 135.31
    vinylene carbonate 120.29
    1,1,2-trichlorotrifluoroethane 136.0
    DMS 73.06
    cumene 29.04
    2-octanol 23.89
    2-hexanone 56.96
    octyl acetate 37.87
    limonene 33.81
    1,2-dimethoxyethane 173.64
    ethyl orthosilicate 39.51
    tributyl phosphate 32.46
    diacetone alcohol 71.8
    N,N-dimethylaniline 54.44
    acrylonitrile 155.01
    aniline 106.8
    1,3-propanediol 117.96
    bromobenzene 100.28
    dibromomethane 186.85
    1,1,2,2-tetrachloroethane 185.38
    2-methyl-cyclohexyl acetate 58.23
    tetrabutyl urea 37.32
    diisobutyl methanol 30.76
    2-phenylethanol 86.64
    styrene 51.45
    dioctyl adipate 45.92
    dimethyl sulfate 53.58
    ethyl butyrate 67.4
    methyl lactate 58.53
    butyl lactate 48.79
    diethyl carbonate 58.32
    propanediol butyl ether 78.61
    triethyl orthoformate 57.24
    p-tert-butyltoluene 28.15
    methyl 4-tert-butylbenzoate 59.87
    morpholine 274.79
    tert-butylamine 58.32
    n-dodecanol 21.85
    dimethoxymethane 130.93
    ethylene carbonate 103.89
    cyrene 75.1
    2-ethoxyethyl acetate 93.37
    2-ethylhexyl acetate 59.75
    1,2,4-trichlorobenzene 102.52
    4-methylpyridine 151.32
    dibutyl ether 42.92
    2,6-dimethyl-4-heptanol 30.76
    DEF 72.72
    dimethyl isosorbide 134.97
    tetrachloroethylene 130.12
    eugenol 66.79
    triacetin 92.14
    span 80 71.89
    1,4-butanediol 49.7
    1,1-dichloroethane 139.85
    2-methyl-1-pentanol 48.68
    methyl formate 78.28
    2-methyl-1-butanol 56.87
    n-decane 6.12
    butyronitrile 113.37
    3,7-dimethyl-1-octanol 42.27
    1-chlorooctane 22.17
    1-chlorotetradecane 10.86
    n-nonane 5.18
    undecane 4.82
    tert-butylcyclohexane 7.24
    cyclooctane 6.75
    cyclopentanol 68.7
    tetrahydropyran 170.11
    tert-amyl methyl ether 42.73
    2,5,8-trioxanonane 163.28
    1-hexene 21.07
    2-isopropoxyethanol 84.49
    2,2,2-trifluoroethanol 62.22
    methyl butyrate 72.75

    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
Orange, sweet (USA-Florida) 7 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.02%
Orange, sweet (Italy) 3 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.02%
Orange, sweet (Spain) 2 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Navel, fam. Rutaceae 0.2%
Orange, sweet (Spain) 3 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Sanguine, fam. Rutaceae 0.09%
Orange, sweet (Taiwan) 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Tankan, fam. Rutaceae 0.05%
Orange, sweet (USA) 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.03%
Orange, sweet (Mexico) 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.01%
Orange, sweet (Italy) 4 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.03%
Tangerine (USA-Florida) 2 8008-31-9 Citrus reticulata Blanco, cultivar Dancy, fam. Rutaceae 0.04%
Lemon (Japan) 2 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Grapefruit (Japan) 1 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.18%
Orange, bitter 1 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.09%
Mandarin 2 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.07%
Citron (Vietnam) peel 1a Citrus medica L., cultivar sarcodactylis (Noot.) Swingle, fam. Rutaceae 0.6%
Citron (Vietnam) peel 1b Citrus medica L., cultivar sarcodactylis (Noot.) Swingle, fam. Rutaceae 0.01%
Lime (Mexican, West Indian, Key) (Peru) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.01%
Lemon (France-Corsica) 1i Panache 84929-31-7 Citrus limon (L.) Burm. f., cultivar Panache, fam. Rutaceae 0.05%
Lime (Mexican, West Indian, Key) (Vietnam) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.02%
Yuzu (Japana) 6 Citrus junos Sieb. ex Tanaka, fam. Rutaceae 0.02%