Limonene-1,2-epoxide

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    1195-92-2

    Molecular formula
    C10H16O

    SMILES
    CC(=C)C1CCC2(C(C1)O2)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1134.0
    • Carbowax: 1428.0

  • Odor profile

    Herbal 83.07%
    Sweet 71.58%
    Mint 71.39%
    Green 71.12%
    Fresh 69.56%
    Citrus 63.5%
    Fruity 59.45%
    Spicy 56.04%
    Woody 53.78%
    Cooling 53.52%

    Scent© AI

  • Properties

    XLogP3-AA
    2.5

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    189°C

    Flash point est.
    72.61 ˚C

  • Synonyms

    • Limonene oxide
    • 1195-92-2
    • Limonene epoxide
    • Limonene 1,2-epoxide
    • Limonene monoxide
    • 1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
    • Limonene 1,2-oxide
    • 1,2-Epoxylimonene
    • 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-
    • 1,2-Epoxy-p-menth-8-ene
    • p-Menth-8-ene, 1,2-epoxy-
    • CCRIS 3763
    • EINECS 214-805-1
    • NSC 12045
    • 4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane
    • CHEBI:16431
    • AI3-24998
    • 1-Methyl-4-(1-methylvinyl)-7-oxabicyclo(4.1.0)heptane
    • 1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
    • 1-Methyl-4-(1-methylethenyl)-7-oxabicyclo(4.1.0)heptane
    • DTXSID50862594
    • NSC12045
    • 1-methyl-4-(1-methylvinyl)-7-oxabicyclo[4.1.0]heptane
    • 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-
    • 6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
    • 4-isopropenyl-1-methyl-7-oxabicyclo(4.1.0)heptane
    • limoxide
    • 1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo(4.1.0)heptane
    • 6-methyl-3-prop-1-en-2-yl-7-oxabicyclo(4.1.0)heptane
    • 1,2Epoxylimonene
    • (+)-TRANS-LIMONENE1,2-EPOXIDE
    • Limonene 1,2oxide
    • 1,2Epoxypmenth8ene
    • MFCD00005127
    • limonene-1,2-oxide
    • Limonene 1, 2-oxide
    • pMenth8ene, 1,2epoxy
    • a limonene-1,2-epoxide
    • a 1,2-epoxymenth-8-ene
    • p-Menth-8-ene,2-epoxy-
    • SCHEMBL93297
    • 3-isopropenyl-6-methyl-7-oxabicyclo[4.1.0]heptane
    • CHEMBL2268547
    • DTXCID40219331
    • 13837-75-7
    • BBL027497
    • MFCD00074770
    • NSC-12045
    • STK801933
    • AKOS006228851
    • SB44781
    • SY257451
    • VS-08553
    • DB-061578
    • CS-0442167
    • NS00041597
    • E83861
    • EN300-322402
    • 1Methyl4(1methylvinyl)7oxabicyclo(4.1.0)heptane
    • 1Methyl4(1methylethenyl)7oxabicyclo(4.1.0)heptane
    • 7Oxabicyclo(4.1.0)heptane, 1methyl4(1methylethenyl)
    • Q27101901
    • Z1198147214
    • 7-Oxabicyclo4.1.0heptane, 1-methyl-4-(1-methylethenyl)-
    • {7-Oxabicyclo[4.1.0]heptane,} 1-methyl-4-(1-methylethenyl)-
    • 1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, 9CI
    • 4-isopropenyl-1-methyl-7-oxa-bicyclo[4.1.0]heptane, AldrichCPR
    • 1-METHYL-4-(PROP-1-EN-2-YL)-7-OXABICYCLO[4.1.0]HEPTANE(TBC AS STABILIZER)
    • 214-805-1

  • Applications

    Limonene-1,2-epoxide (CAS 1195-92-2) is a bio-based terpene epoxide derived from limonene, used as a versatile chiral building block and intermediate: ring-opening gives diols, allylic alcohols (carveol), ketones (carvone) and other terpene derivatives; it also serves as a precursor to limonene cyclic carbonate via CO2 coupling, enabling CO2 utilization and greener materials routes. In materials science, it functions as a monomer/reactive species for ring-opening polymerization to polyethers, epoxide–CO2 copolymerization to bio-based polycarbonates, and as a reactive diluent or modifier to increase bio-content and flexibility in epoxy resins, coatings, adhesives and inks; it is also a precursor to non-isocyanate polyurethanes (polyhydroxyurethanes) via the cyclic carbonate. In catalysis and biocatalysis research, it is a standard substrate to probe enantioselective ring-opening, epoxide hydrolases and selective biotransformations to enantiopure diols or mono-epoxides; it is also employed as an analytical standard and stereochemical reference in chromatography. Additionally, it is exploited as an intermediate toward terpene-based fragrance and flavor ingredients, as a bio-based building block for surface-functional monomers, and as a potential antimicrobial coating additive under investigation; appropriate handling is required because epoxides are reactive and may be irritant/sensitizing.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 936.79
    methanol 805.31
    isopropanol 752.52
    water 2.0
    ethyl acetate 510.33
    n-propanol 660.75
    acetone 349.61
    n-butanol 600.33
    acetonitrile 587.36
    DMF 231.96
    toluene 296.77
    isobutanol 411.09
    1,4-dioxane 1466.74
    methyl acetate 447.41
    THF 956.83
    2-butanone 388.43
    n-pentanol 361.54
    sec-butanol 459.71
    n-hexane 33.15
    ethylene glycol 161.45
    NMP 117.57
    cyclohexane 84.84
    DMSO 190.13
    n-butyl acetate 331.41
    n-octanol 185.28
    chloroform 1139.69
    n-propyl acetate 218.13
    acetic acid 370.09
    dichloromethane 781.61
    cyclohexanone 327.59
    propylene glycol 262.48
    isopropyl acetate 281.33
    DMAc 246.18
    2-ethoxyethanol 571.46
    isopentanol 415.75
    n-heptane 40.2
    ethyl formate 284.12
    1,2-dichloroethane 323.0
    n-hexanol 470.2
    2-methoxyethanol 868.59
    isobutyl acetate 148.34
    tetrachloromethane 164.12
    n-pentyl acetate 164.45
    transcutol 1484.14
    n-heptanol 182.46
    ethylbenzene 127.32
    MIBK 179.0
    2-propoxyethanol 780.11
    tert-butanol 555.92
    MTBE 385.5
    2-butoxyethanol 338.2
    propionic acid 292.12
    o-xylene 135.01
    formic acid 179.09
    diethyl ether 561.91
    m-xylene 159.79
    p-xylene 159.28
    chlorobenzene 236.14
    dimethyl carbonate 110.09
    n-octane 15.38
    formamide 263.55
    cyclopentanone 279.25
    2-pentanone 287.1
    anisole 282.14
    cyclopentyl methyl ether 282.6
    gamma-butyrolactone 283.34
    1-methoxy-2-propanol 632.5
    pyridine 674.19
    3-pentanone 187.62
    furfural 326.37
    n-dodecane 14.53
    diethylene glycol 528.24
    diisopropyl ether 135.37
    tert-amyl alcohol 343.37
    acetylacetone 256.46
    n-hexadecane 16.59
    acetophenone 188.44
    methyl propionate 276.32
    isopentyl acetate 277.08
    trichloroethylene 565.52
    n-nonanol 165.02
    cyclohexanol 328.3
    benzyl alcohol 265.01
    2-ethylhexanol 198.54
    isooctanol 125.97
    dipropyl ether 248.54
    1,2-dichlorobenzene 174.11
    ethyl lactate 113.24
    propylene carbonate 198.6
    n-methylformamide 244.58
    2-pentanol 344.27
    n-pentane 51.38
    1-propoxy-2-propanol 482.17
    1-methoxy-2-propyl acetate 382.16
    2-(2-methoxypropoxy) propanol 277.72
    mesitylene 88.32
    ε-caprolactone 336.53
    p-cymene 87.68
    epichlorohydrin 494.03
    1,1,1-trichloroethane 322.6
    2-aminoethanol 356.81
    morpholine-4-carbaldehyde 403.38
    sulfolane 150.0
    2,2,4-trimethylpentane 22.58
    2-methyltetrahydrofuran 546.02
    n-hexyl acetate 240.3
    isooctane 21.32
    2-(2-butoxyethoxy)ethanol 442.41
    sec-butyl acetate 168.69
    tert-butyl acetate 213.83
    decalin 31.65
    glycerin 248.5
    diglyme 722.45
    acrylic acid 196.74
    isopropyl myristate 97.65
    n-butyric acid 436.45
    acetyl acetate 271.86
    di(2-ethylhexyl) phthalate 94.92
    ethyl propionate 188.3
    nitromethane 393.83
    1,2-diethoxyethane 530.27
    benzonitrile 306.55
    trioctyl phosphate 62.5
    1-bromopropane 278.98
    gamma-valerolactone 532.48
    n-decanol 114.75
    triethyl phosphate 88.8
    4-methyl-2-pentanol 196.48
    propionitrile 500.34
    vinylene carbonate 222.83
    1,1,2-trichlorotrifluoroethane 307.1
    DMS 180.76
    cumene 82.46
    2-octanol 110.34
    2-hexanone 200.02
    octyl acetate 118.99
    limonene 108.71
    1,2-dimethoxyethane 646.37
    ethyl orthosilicate 95.6
    tributyl phosphate 81.16
    diacetone alcohol 227.48
    N,N-dimethylaniline 150.55
    acrylonitrile 439.72
    aniline 334.76
    1,3-propanediol 543.97
    bromobenzene 246.9
    dibromomethane 533.65
    1,1,2,2-tetrachloroethane 434.76
    2-methyl-cyclohexyl acetate 150.47
    tetrabutyl urea 89.94
    diisobutyl methanol 118.61
    2-phenylethanol 314.3
    styrene 161.74
    dioctyl adipate 118.73
    dimethyl sulfate 75.97
    ethyl butyrate 208.51
    methyl lactate 147.31
    butyl lactate 133.53
    diethyl carbonate 153.78
    propanediol butyl ether 284.67
    triethyl orthoformate 168.43
    p-tert-butyltoluene 84.53
    methyl 4-tert-butylbenzoate 138.87
    morpholine 1365.79
    tert-butylamine 363.89
    n-dodecanol 83.84
    dimethoxymethane 394.56
    ethylene carbonate 212.86
    cyrene 144.19
    2-ethoxyethyl acetate 309.63
    2-ethylhexyl acetate 205.56
    1,2,4-trichlorobenzene 209.49
    4-methylpyridine 491.16
    dibutyl ether 184.64
    2,6-dimethyl-4-heptanol 118.61
    DEF 219.89
    dimethyl isosorbide 316.58
    tetrachloroethylene 291.78
    eugenol 162.31
    triacetin 226.07
    span 80 220.06
    1,4-butanediol 200.56
    1,1-dichloroethane 434.92
    2-methyl-1-pentanol 246.95
    methyl formate 157.79
    2-methyl-1-butanol 332.42
    n-decane 24.34
    butyronitrile 510.28
    3,7-dimethyl-1-octanol 181.28
    1-chlorooctane 82.27
    1-chlorotetradecane 35.33
    n-nonane 21.68
    undecane 18.01
    tert-butylcyclohexane 28.82
    cyclooctane 27.06
    cyclopentanol 282.73
    tetrahydropyran 930.48
    tert-amyl methyl ether 213.23
    2,5,8-trioxanonane 467.14
    1-hexene 130.4
    2-isopropoxyethanol 372.08
    2,2,2-trifluoroethanol 103.37
    methyl butyrate 204.69

    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
Blackcurrant bud 2 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.1%
Blackcurrant bud 3 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.1%
Lemongrass (China) 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 6.43%
Eucalyptus globulus (Algeria) 1 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.01%
Lycopersicon hirsutum leaf Lycopersicon hirsutum Humb. et Bonpl., fam Solanaceae 1.08%
Lime (Mexican, West Indian, Key) (Cameroon) leaf 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.11%